AI has made execution cheap. The first draft, the ten ad variations, the first-pass analysis: chuck it all into any AI tool and you’ll get an answer. What it doesn’t solve, at least for now, is judgement. Knowing what to make and why. Knowing which of the thousand generated answers is the one that actually matters to your customer.

Judgement sounds like something you can’t earn at the start of a career, and there is some truth in that. It takes time, and mistakes that stick. But you can start building it from your very first internship.

Here are four things I’d tell anyone starting out in their career:

1️⃣ Pick the fastest-growing team you can find, not the biggest logo. A team that is growing forces you to learn at its pace.

2️⃣ Learn how marketing shows up in the P&L. The faster you can connect your work to revenue, rather than letting it sit as a black box, the faster people will trust you with bigger decisions.

3️⃣ Get close to the customer now. Sit in on the calls, read the tickets, watch real users. Context continues to be a scarce skill, and getting in front of customers helps you build insight.

4️⃣ And the whole point about how building brands that endured was to never bet on a single channel. They built a system. I suspect careers work the same way.

The one-person marketing team is already here

That last point is worth expanding on, because it is no longer a thought experiment. It is increasingly possible to run marketing as a team of one. I recently listened to Matt Swulinski’s conversation with Harry Stebbings on 20VC, and it is the best articulation of this change that I’ve heard so far.

Matt was marketing hire #1 at Wispr Flow, and until recently the sole person running all of marketing execution. Faced with more work than any one person could do, he didn’t hire his way out. He built what he calls a marketing operating system: a set of AI agents that now handle the roughly 100 newsletter sponsorships Wispr runs every month. Drop a contract in, and the system checks the CPM, researches the audience, pushes back if the price or fit looks weak, writes the copy in Wispr’s voice, and builds the tracking links, drawing on performance data from every placement they’ve ever run. It got good enough that Wispr paused hiring for two marketing roles. He spends about US$4,500 a month on the AI behind it and calls it the cheapest hire he’s ever made.

The tooling is impressive, but his observation on how he hires made me sit up. Matt said that two years ago he would have wanted the best Meta or Google buyer in the world. Today he’d rather have someone intermediate who is a systems thinker, someone who can “understand all the moving pieces and layer in AI to 10X themselves.” His test is not whether you can use a chat window. It’s whether you can deconstruct a workflow, find the bottlenecks, and map the inputs and outputs.

If you can, you can build a system. If you can’t, you’ll just use AI to send emails faster.

And what does his system actually encode?

What a fair CPM looks like.
When an audience is the wrong fit.
What the brand sounds like.

Every one of those used to be a judgement call that humans used to make, only now that it’s been codified and fed to a machine to repeat hundreds of times a month.

While we used to say execution was what mattered, nowadays it’s more than just that. Seeing the whole board, deciding what matters, and wiring it together so it compounds: that part is still can be your differentiation2 (for now).

For now, anyway.

What’s probably more important to carry to your role (whether it’s your first internship or first full-time gig) is not “what can AI do for me?” (that’s already a given), but “what do I understand well enough to turn into a system?”

If you want to go deeper

A few episodes that shaped my thinking on systems-building, worth the listen:

• Matt Swulinski on 20VC’s 20Growth with Harry Stebbings: the interview behind this essay. How he built Wispr Flow’s growth engine as marketing hire #1, why SaaS should steal the e-commerce paid playbook, and how he hires for systems thinking.

• Matt on Profound’s Marketing Engineer podcast: the companion piece, going deeper into how the marketing OS is actually built. Skills, session logs, and the mistakes that break most AI systems.

• Elena Verna on Lenny’s Podcast: the new AI growth playbook, from her seat as Head of Growth at Lovable, which hit US$200M ARR in under a year with about 100 people. Why innovation now beats optimisation.

• Jason Lemkin on Lenny’s Podcast: what happened when SaaStr replaced a ten-person sales team with 20 AI agents run by 1.2 humans. The sales-side version of the same shift, with candour about what didn’t work.

Elaine is my cousin, and also the person who gave me my first internship and my first taste of marcomms when I was 19. I had some free time, wanted to feel helpful, so I thought why not? I learnt very quickly that behind glamorous events and press launches was a dedicated and hardworking team making it happen. I learnt how to pick up the phone to speak to strangers, arranged for press kits to be sent to the media, practiced my pitch, and learnt that disappointment was part and parcel. But that internship taught me something I’ve carried into every job since: there is no ceiling when it comes to hard work. If you’re willing to do it, there are always opportunities.

In the years after, Elaine became something of a compass for me. Her career has crossed Singapore, Hong Kong, and now Auckland, from hotel PR to founding her own agency to building a personal branding consultancy. Through all of it, she has been a testament that a good voice of reason paired with common sense always wins. And as a mum to her daughter Alexis, now 21, she has been a role model for what balancing a career and a daughter can actually look like, not in theory but across two decades of real choices.

I’ll let you read the rest of the conversation.

Who you are

Tell us a little about yourself: your work, your family, and where you are right now in both.

I’m Singaporean at heart, but Auckland has been home for the past nine years. Before that, I spent a wonderful decade living in Hong Kong.

I’m the mum of a newly minted 21-year-old university student who now has a wonderfully full life of study, work and friends. Watching her step confidently into adulthood has been one of the greatest privileges of my life.

Professionally, I’m a personal brand strategist specialising in LinkedIn content strategy, ghostwriting and community outreach. I help founders, consultants and business owners turn their expertise into stories that build credibility, trust and authority.

What sets me apart is my background in PR and FMCG marketing. I don’t just write posts - I develop a strategic content narrative that positions each client in a way that feels authentic to them. Beyond the writing, I help grow an engaged LinkedIn community that becomes a supportive audience and, ultimately, a source of meaningful business opportunities.

My career has taken a few interesting turns. I started in hotel PR at Mandarin Oriental Singapore before moving into agency life, managing lifestyle campaigns at Directions Marketing & Communications and later founding my own agency, Firefly Marketing & Communications.

A move to Hong Kong opened another unexpected chapter. I started a lifestyle blog called Simply Fabulicious, back when blogging was the social platform of the day and long before newsletters and Substack existed. That little blog introduced me to incredible brands and opportunities, including the Langham Hospitality Group. When I later moved to New Zealand, they invited me to help lead the rebranding of Auckland’s Langham Hotel into the Cordis - a project I’ll always remember fondly and proudly.

After Covid, I worked across several Auckland PR agencies before joining The Attention Seeker, where I led the personal branding team. Eventually, I left to build my own consultancy, bringing together everything I’d learnt over two decades in communications. Looking back, my career has evolved from telling company stories through the media to helping leaders build platforms and voices of their own.

These days I love the flexibility that running my own business brings. It allows me to do meaningful work while designing a life that gives me freedom and space.

Where am I right now? In many ways, I’m in the season they call the “sandwich generation”, caring for ageing parents in Singapore while cheering on a daughter who is now on her way to graduating and building her own independent life in Auckland. It can be emotionally stretching, but I don’t take for granted that I still get to do life with both my mum and my daughter. That feels like a real gift.

How old are your child or children, and who is the primary caregiver at home?

Alexis has just turned 21.

These days, we joke that we look after each other. She’s “Boo” to me, I’m “Moo” to her, although I’ve recently been promoted to “Momster” which, apparently, comes with the territory. I do miss the days of being called “Mummy.”

Our relationship has changed completely. I’ve gone from telling her what I think and will do to genuinely asking for her opinion. For many years I was her primary companion, but now I happily compete with university, her internship work, a wonderful boyfriend and a very busy social life. That’s exactly how it should be.

How you think

Was there one thing that made you change after becoming a parent?

Motherhood shifted my perspective from making decisions that were best for me to making decisions that were best for someone else.

Every choice - where to live, what jobs to take, how much to work, even how I spent my weekends - was no longer just about my own ambitions or enjoyment. It became about creating emotional security, financial stability and opportunities for my daughter. You begin to think much further ahead because your decisions ripple into someone else’s future.

Was there a moment after having children when you looked at your career and thought, this needs to change? What happened next?

Working full-time no longer felt like the right fit for me.

For many years I’d built my career around flexible, work-from-home roles - running my own agency in Singapore and later blogging and freelancing in Hong Kong which meant I was present throughout my daughter’s early years.

That changed after we moved to New Zealand. Although my role was officially part-time, it regularly stretched into full-time hours. As my daughter navigated the challenges of settling into a new country at age 11, I realised she needed more than an empty house after school.

I chose to leave that role rather than move into full-time work. It meant I could be there when she came home, welcome her friends into our house, quietly observe the friendships she was forming and create space for those everyday conversations that often reveal far more than direct questions ever do.

Looking back, I believe the pre-teen years are some of the most important. Children may look grown up on the outside, but inside they’re still figuring out who they are.

Tell me about a moment when you felt the tension between work and being present most acutely.

There wasn’t one defining moment - instead it was a series of ordinary moments that slowly became impossible to ignore.

I remember being in the office, desperately looking through school holiday programmes that ran from 9am to 5pm, simply so that I could get through another working day. And I remember asking myself a much bigger question: Why did we move here in the first place?

The answer was obvious.

We hadn’t left Hong Kong simply for another job. We moved because I wanted my daughter to experience a different kind of childhood - one with less pressure, less tuition, less chasing the next exam and more room to discover who she was. I wanted her to grow up with an Asian foundation but within the openness of a Western education.

If I wasn’t actually present for that journey, then I realised I was asking her to navigate it largely on her own.

That was the turning point. I left the role and returned to remote, flexible work. Financially it wasn’t always the easier choice, but it was the right one. Looking back now, I wouldn’t change it.

How has your parenting philosophy evolved, with age, with experience, or as your family has grown?

With a 21-year-old young adult, it’s a completely different season of parenting.

I try to tell less and listen more because I’ve learnt that adulting advice isn’t always welcome. Sometimes the greatest act of love is allowing your child to make mistakes instead of trying to prevent every disappointment.

I no longer live with a child who depends on me for everything. I live with a young adult. It’s less like parenting a child and more like sharing a home with a roommate who is finding her own way in the world and in many moments, I am grateful that I still get to be there to see things unfold.

What is the one generational pattern you are consciously trying to undo?

The idea that love is measured by achievement.

Growing up in Singapore, many of us were taught to work hard, perform well and keep striving for the next milestone. Those values have served me well, but they can also quietly become the measure of our worth.

I’ve tried to raise my daughter knowing that who she is matters more than what she achieves. All I want is that she truly knows that with everything she attempts - she has genuinely put in her best effort. Things will not always go her way, but once she knows what her best looks like, I hope she will know that she has been true to herself, and that already is a success metric.

What you built

Tell me about what you built. What made you choose this, and not something else?

If I could have chosen any career, I think I would have been a bartender because I genuinely love listening to people’s stories - especially over a good drink. Or a DJ, because music is about an era of collective memories, and I used to spin a set or two growing up so I like the idea of bringing people together to celebrate a moment. Or perhaps I would have been an interior designer, because beautiful spaces and the aesthetic are important to me and have a remarkable way of shaping how I feel.

But life doesn’t always unfold according to the plans we make.

What I realised early on was that I could write. So I combined my curiosity about people, my love of storytelling and my interest in strategy, and found my way into PR.

Today I help founders and business owners tell stories that build trust and open doors. Looking back, I think every version of my dream career had one thing in common: helping people feel seen.

Is there something in what you built that you made specifically for your child, whether she knows it yet or not?

I built a career around flexibility.

It may not always have been the fastest-growing or highest-paying path, but it allowed me to be there for school pickups, sports days, after-school conversations and the ordinary moments that often become the important ones.

One day I hope she’ll realise that many of my career decisions weren’t simply about work - and that they were about being present for her.

When your child is old enough to look back at the choices you made, what do you hope she takes from it?

I hope she sees that careers evolve. Titles change. But the people who matter most will always remember whether you were there.

Singapore specifically

Raising children in Singapore comes with its own particular pressures. What is one thing you wish you had given yourself more permission to do?

I actually raised my daughter in both Hong Kong and New Zealand and looking back, one of the greatest gifts was stepping outside the Singapore system.

Having more time and less academic pressure gave her space to discover who she was, pursue her own interests and make thoughtful decisions about her future.

Singapore offers incredible opportunities, but I’m grateful she also experienced a childhood where life wasn’t always about keeping up with everyone else.

What you have learned

What has your child taught you that no colleague, mentor or book ever did?

That people need to be loved differently at different stages of life.

The way a five-year-old needs you isn’t the way an eleven-year-old does, and it’s certainly not the way a twenty-one-year-old does. Parenting has taught me that relationships only thrive when we’re willing to keep adapting.

What is one thing you do to teach your child to be kind?

I try to model kindness rather than lecture about it.

Whether it’s remembering someone’s birthday, helping a neighbour, going out of my way for a friend or simply listening well, I hope she’s seen that kindness is found in ordinary moments, not grand gestures.

What is one piece of advice you wish someone had shared with you earlier in this season of life?

You don’t have to solve every problem.

Sometimes your child isn’t looking for advice - they’re simply looking for someone safe enough to tell the story to (minus the judgement).

And finally

What do you cook when you want to show your child you love them?

Babi Tau Yew, without question.

It somehow is comfort food for her and a reminder of home and her childhood all on one plate.

What is one thing in your bag you never fail to have on hand when you bring your child out?

These days it’s the house keys. We live in an apartment with two security keys that can’t be easily replicated and there have been occasions when either of us has thought that the other person had the keys on them and closed the door behind us.

If you had one hour to yourself this week, what would you do with it?

I have lots of hours to myself these days.

And finally, what is in your cup right now?

Coffee. Always coffee, and NZ coffee is really the best in terms of a lovely aroma and a full bodied rich flavour.

Preferably a really good Americano, enjoyed while it’s still hot if it’s in winter or on ice when it’s in summer - which, as any parent knows, is always something of a stolen luxury.

I’ve balanced this series with mothers wrangling toddlers and school runs, and those on the other side with articulate, self-aware and loving adult children, such as Elaine. When I asked what she’d do with one hour to herself this week, she said she has lots of hours to herself these days. To me, knees deep in the trenches of parenting, it’s what the school gate years eventually turn into, and it arrives sooner than any of us in the thick of it can imagine.

What she did with the years before those hours is the part I keep returning to. She built a career around flexibility, not as a compromise but as a design choice, and she made that choice again and again across three cities. Leaving a role in Auckland when Alexis was eleven so there wouldn’t be an empty house after school. Choosing to be around for the everyday conversations that reveal more than direct questions ever do. Careers evolve, titles change, but the people who matter most will always remember whether you were there.

I saw the early chapters of this up close. The cousin who put a phone in my hand and had me cold calling for press kits is the same person who spent two decades proving that hard work has no ceiling, and that common sense, applied consistently, outlasts every clever strategy. Now she’s in the sandwich years, caring for her mum in Singapore while sharing a home in Auckland with a young adult who calls her Momster.

Somewhere in between, there’s a really good Americano, still hot, finally drunk in peace.

A Cup With is a series on Cup & Weekend where I ask mothers who are building lives outside the template about what they carry, what they’ve made, and what’s in their cup. These conversations happen over text and emails, sometimes over coffee, and always between an errand run or two. If you’d like to follow along, subscribe below.

If you’d like to receive these conversations as they come out, you can subscribe here.

🍵 “More from A Cup With” ☕

Foolittle also has some books on the lower two shelves, but honestly we are perpetually running out of space for books. That being said, this is a problem I’m happy to live with. Many of our books came by as gifts or second hand. We tend to ask people to gift us books in lieu of toys especially as Foolet got older, and now that Foolet is able to independently read, it’s been wonderful introducing him books and sussing out his preferences.

A few years ago, I started chronicling his book picks, especially the Chinese books, partly for posterity, but also because quite a few friends were curious about our book choices.

Since National Day is coming up, I decided to pull out a series of children’s books written by local authors that we’ve read through the years. Here’s a 7+1 list (6 for primary schoolers, 1 for a preschooler and a bonus one for parents).

1. 《寻找》(Looking For) by Ah Guo / Lee Kow Fong was gifted by a friend years ago and as a fans of penguins - it demanded to be read. It won Best Children’s Title at the Singapore Book Awards in 2016, and reading it with Foolet, I understood why. It follows a lonely boy who wanders into the hills looking for a way to stop feeling alone, and finds instead a string of small, hard-to-name things: stillness, permanence, the particular quiet of watching a season turn. It’s officially pitched at ages ten and up (but that’s never stopped us), so I think reading it again with Foolet when he is older will introduce a different (and probably deeper) set of questions. Available in English as well.

   

2. 《这是什么呢？》(What Is This?), also by Ah Guo, turned out to be the answer to a gap I’d more or less given up on filling: something genuinely made for a two year old written by a local author. Fruits turn into animals with a few bold brushstrokes, local fruits such as papayas and rambutan included, and it comes with a sticker activity at the back that Foolittle has already half destroyed.

   

3. Chou Chou surprised me for a different reason. Foolet chose it 4 years ago at Hook on Books near Outram, and we bought it seeing that it was written and illustrated by two eleven-year-old students, their original handwriting preserved in the text. A pillow with a face and a flag and a full personality, made by children not much older than Foolet is now. I liked the idea that the shelf we’re looking for also is home to children authors. Sometimes it needs children writing to each other, and the rest of us just get to read along. In fact, Foolet’s been writing and illustrating his own stories, and I hope that this serves as a reminder to be proud of his imagination.

   

4. Superworm to the Rescue, by Weng Pixin, is the one that made my boy laugh out loud. A cape-wearing earthworm investigates a missing eye, traces it to a snake with a habit of hoarding things that aren’t his, and ends up learning that being a good friend sometimes means understanding someone before judging them, even a misunderstood thief. Great for readers eight and up, and honestly great for anyone who likes things a little funny, odd and weird. Foolet told me that he loved the humour, which is major praise coming from him.
   

   

5. Sherlock Sam was part of a series of books handed down from his cousins. I surreptitiously added it to the bookshelf (no one likes mummy to dictate what they read, right?) and discovered him reading it one day. It helped us have a conversation about my own version of ghost stories (S/O to Russell Lee’s Singapore Ghost Stories series) and detective stories (anyone remember The Bookworm Club from the 80s and 90s?). In this one, strange sounds are haunting Fort Canning, and Sam is determined to prove there’s a logical explanation, even when it doesn’t feel that way at first. There’s a small glossary tucked in the back explaining local words from duit pisang to tau huay, which also adds local texture to a mystery novel.

   

6. Oyster Girl landed differently, because Foolet actually went to the launch back in 2024. It’s Xiao Wei’s story, following her grandmother’s hawker stall and the oyster cakes she’s known for, back to a childhood in Hui’an harvesting oysters by hand, then a journey south to Singapore. Author Joyce Chng wrote it as a tribute to her own grandmother, and the real family recipe is printed at the back.

   

7. Living not too far from Geylang Serai, going for the Ramadan bazaar is an annual affair. As he got older, he started to notice customs that differ from his, and these books passed to me from a friend were a helpful opener. Comprising four books, one for each of Singapore’s major ethnic groups, each built around twenty specific questions rather than a general overview. I am very aware of our privilege and at the same time I want to teach him to have the sensitivity to explore such questions and to also encourage respectful curiosity about other races.

   

8. One more, not quite for either of them yet, but too good not to mention. Gwee Li Sui’s The Leeter Tunku takes Saint-Exupéry’s The Little Prince and translates the whole thing into Singlish, rose and fox and all. The rose becomes Ah Huay. The fox stays, rather charmingly, Fantastic Mr Fox. It’s less a children’s book than a small act of local literary mischief. Foolet loves reading The Little Prince and this is itching to be added to the bookshelf. Disclaimer: this is the only book I’ve not read yet, but if anyone wants to add it to our bookshelf, it’ll be very welcome!

If you’re hunting for any of these yourself, a few places worth starting:

• Epigram Bookshop, physical store at Robertson Quay, Singapore’s first bookshop built entirely around local titles

• Hook on Books, physical store near Outram Park, for Chinese children’s books worth browsing rather than searching for

• My Story Treasury, a online curated Chinese picture book specialist, strong on bilingual and pinyin editions

• Woods in the Books, physical stores at East Coast, New Bahru and Orchard Forum, an independent children’s bookshop that regularly hosts local author events

• Wormhole, an independent online bookstore that offers a curated selection of literary fiction, non-fiction, children’s titles, and art merchandise

• City Book Room, Joo Chiat, an independent Chinese bookstore and publisher, and where we caught the Oyster Girl launch

• Maha Yu Yi, physical store at Bras Basah Complex, a Chinese bookstore since 1969 with a dedicated children’s section

A little side project I did over the past month was to build a directory of sorts on books.cupandweekend.com to store those books I’ve read and bookmarked previously on IG. I stopped capturing them about 3 years ago, but maybe I’ll slowly start again with Foolittle, who’s also starting to read, and showing remarkably similar preferences to his brother.

I’m hoping that this becomes a small, honest record of what these two very different children are actually reaching for, rather than what I think they should be reaching for.

The shelf isn’t finished, and I hope it inspires you to pick up a book this weekend, be it for yourself, your children, and perhaps just for the love of reading.

Other related essays

S, who mans the counter and has made every one of my drinks so far, suggested a less acidic blend for my iced matcha latte today, taking the time to explain a bit more about its tasting notes.

Miura comes from the folks who gave us The Plain, Ronin, Punch, Gather and Paaru, and that lineage unlocked a whole drawer of memory I had not opened in a while. The Plain was a revelation in 2010. Located at Craig Road - it introduced the Melbourne style cafe concept to me, and I enjoyed their coffee immensely. Later on when I worked at Amazon, Punch was a short walk away. It was where I discovered what different types of coffee could actually taste like, and it was also where I had my first Reuben sandwich, and I will say plainly that the Reuben changed me. Punch was the de facto place I would go for lunch meetings and team celebratory events, and I would make the occasional trek through the years long after I left Amazon to continue meeting people there.

So I was already softened up, sitting in this small café inside a clothing shop, when I fell into conversation with S and V. Within a few minutes we were deep in a shared love of Japan’s B-side. I told S about my travels to the little cities, and that memorable hike in Kamikochi with an infant in the carrier. We talked about finding inspiration in the most nondescript places. For a while the three of us were just trading places and seasons, each name pulling up another, the way a good conversation goes.

Walking home, I kept thinking about why it had felt so good. It struck me that what made it possible was not really the setting, though the setting helped. The kopitiam uncle will talk your ear off too, if you catch him at three in the afternoon instead of the lunch rush. Mostly, though, we decline these conversations. We order at people rather than talk with them, eyes already back on our phones before the change arrives. What the conversation actually cost was time: a lull between customers on their side, an unhurried mid-morning on mine, which is not a thing my weeks hand out often. The person across the counter has been to places and has opinions about them, and will tell you, if both of you have ten minutes that belong to no one else.

But part of it was also something each of us had brought to the table without realising. A conversation like that draws on an archive. You need to have gone somewhere, read something, eaten the sandwich, made the mistake, formed the opinion. You need a certain critical eye about your own experiences, so that you are offering more than a list of places you have been. And you need to be paying attention to the person across from you, adjusting as you go, noticing what makes their eyes come up from their cup. None of this happens overnight. The archive takes years to build, and most of it gets built when you are not trying to build anything at all.

There was a copy of Dale Carnegie’s How to Win Friends and Influence People on the bookshelf of my childhood home. I’m not sure whose it was actually, but it circulated in the household. I read it more than twenty years ago and I remember almost nothing of it now. What stayed is one idea, worn smooth by time: that the heart of connection is genuine interest in other people. Let the conversation be about them. Ask about their story and be genuinely curious about the answer.

Carnegie has a complicated reputation these days, even as his words were adopted by generations of networkers. Curiosity deployed as technique can often be labeled as manipulative, artificial, fake. But nothing was being networked at that table in Miura. Nobody wanted anything from anybody. S and V were curious about the Japan of someone they knew only by her drink order, and I was curious about theirs, and the whole exchange ran on that. Which is, I suspect, what my (maybe?) grandfather’s book was actually about, underneath everything that got built on top of it.

I have been watching this same thing take shape at our own dinner table. Foolet has reached the age where he interviews us. Where did you work at last time? Was it the same office I visited? (No, it was a different place.) Why do you work from home nowadays? (There’s this thing called Covid... and there’s this another person called didi....)

He listens in on adult conversations now and interjects from time to time, wanting the parts he missed explained. His questions are not polite questions. He genuinely wants to know, and he can be persistent. If you don’t give a satisfactory answer, he’ll be at you again like a dog with a bone (or a bone to pick, I can never remember which).

I do not know what he will remember of these years. Probably not the answers. But somewhere in our house there is a shelf, and one day there will be books on it that came from somewhere, and habits at the table that came from somewhere too. Dale Carnegie hardly matters. What hopefully gets handed down is the leaning in to hear a stranger’s story at a cafe inside a clothing shop.

What’s your favourite memory of a cafe conversation? Leave a comment below.

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Foolet and Papa were on a road trip north when I wrote this and while chaotic Foolittle and me are back in Singapore, I had some empty blocks of time between work and school hours. I have learnt to treat these mornings as precious interludes, and when an opportunity arises, you grab them without thinking twice.

The two-hour nowcast on the NEA website looked promising: my corner of the island was partly cloudy, and the storms were all out at sea, sitting over the southern islands. The weather forecast can be doom and gloom for the entire week, and it might not rain at all.

The Rengas Path: the steep backdoor from Dairy Farm

Carpark B at Dairy Farm is the unglamorous entrance, which is exactly why I like it. You fill your water at the entrance, you follow the signs saying “Wallace Trail” into the trees, and almost at once the hum of the city pauses. Most people go up Bukit Timah the front way, the steep paved road from Hindhede where the brisk-walk uncles power past you with their arms swinging and their kopi waiting back at the bottom. I personally prefer going the other way via the Dairy Farm Loop.

It is quieter. It is also, for a stretch they have named the Rengas Path, a flight of steps that does not so much climb the hill as interrogate your fitness about it.

I had decided to do the hard part first, while my legs still believed in me. By the third set of steps I had stopped thinking about the weather (it really helped that with the dense foliage), the work email I had not answered, and the school form due Friday.

There was only the next step, and then the one after it, and the small doubtful voice that wants to know why you do this to yourself on a morning you could have spent lying down. It’s okay, I decided to tune it out by listening to a podcast instead.

The summit and the Devil’s Stairs

The top of Bukit Timah is a hundred and sixty-three metres, which is not a number that impresses anyone who has stood on a real mountain, and it is marked by a large rock that people queue, gently and a little sheepishly, to photograph. I did not queue. I stood off to one side and looked out at what you can see from the highest point in Singapore, which on a sunny morning is mostly more trees, and a lot of sweaty people.

The weather was still holding, and I decided to keep up the pace and continue my hike. I walked downwards this time around, taking the Devil’s Stairs, a notoriously steep flight of 184 steps located in the Bukit Timah Nature Reserve in Singapore.

The longer way: the Catchment loop to Beauty World

There is a longer loop that runs east, the Catchment Path, out into the Central Catchment where the trees close over and the people thin out and you are, by Singapore standards, properly alone.

It is easy to walk through here and assume the forest is ancient, that it was always left alone. Mostly it was not. By the middle of the nineteenth century the island had been cleared back to lalang and shrubs, and what spared this particular stretch was the need to keep our water clean. When MacRitchie was dammed in 1867, the island’s first proper reservoir, the trees around it were kept on purpose, protected as water catchment so the supply would run clean.

It’s a straight, unfussy path. It breaks out to a clear pathway, dotted by biking trails with clear KEEP OUT signage to ensure that the errant hiker doesn’t meander into a biking fracas.

Then onto a short walk alongside Rifle Range Road. The rare times I’ve been on this road, there has always been roadworks and I’ve always ended up having to walk on the edge of the road, praying that I wouldn’t get hit by the occasional speeding car.

The road name comes with a straightforward history. There was a rifle range here, built in 1924 for the colony’s volunteer soldiers to practise their aim, and by 1930 the road had simply taken the range’s name and kept it. The Singapore Gun Club came later, in the fifties, starting life in a zinc-roofed shed barely four square metres across. Before any of that, the British kept an ammunition depot on the site, which is why, every so often over the years, the ground here has turned up wartime grenades, bombs and the occasional pistol. My doomsday brain, it turns out, had the right instinct and the wrong century. Whatever there was to fear on this road, it was less the passing cars than the things once buried beside it.

Eventually, I find a little opening that guides me back onto the Rifle Range Park trail, which was then dotted with small durians and cempedaks. Of course my doomsday brain starts catastrophising, “If I’m not getting hit by a car, I’ll get hit by a falling durian.”

But of course I don’t, and I eventually find my way to a lovely sight at the Colugo deck. It’s the old site where the Sin Seng Quarry used to operate from.

The water below the deck is still and green and looks as though it has always been there, which is the opposite of true. It was one of a whole cluster of granite quarries that chewed into the foot of Bukit Timah for most of the twentieth century. The hill is granite, some of the strongest rock on the island, and for decades it was blasted out with dynamite (the periodic booms were a fact of daily life for anyone living nearby) and carted off to become roads and the HDB flats many of us grew up in.

The mainland quarries closed from the seventies onward, once it was cheaper to bring granite in from elsewhere, and the abandoned pits simply filled with rain. What I was looking at from thirty metres up was a wound that had quietly become a wetland. It takes the forest no time at all, it turns out, to make even the violent places look as though they were always meant to be peaceful.

A walk downhill brings me to an exit leading to Beauty World, crossed the overhead bridge, and found the small place there that takes its coffee seriously. I drank an iced white slowly, salt drying on my arms, the storm still holding off somewhere behind the hills. The brisk-walk uncles were long done and home.

The train home runs east under the city and out the other side, back toward the part of my life that does ask things of me, the boys and the pickups and the work I am slowly, carefully picking up again.

The morning had been mine, and I had spent all of it, generously, on nothing. In an hour or two it would be loud somewhere in the house and someone would need something, and I would be glad to be needed, mostly. For now there was only the cool carriage, and the long ache in my legs, and the radar on my phone finally, blessedly, closed.

Field Notes

Dairy Farm Nature Park (Carpark B), up the Dairy Farm Loop and the Rengas Path to the Bukit Timah summit, then the longer eastern loop out along the Catchment Path into the Central Catchment and back, coming out at Beauty World. A good half-morning walk of around 6.81km, rougher and longer than the standard summit-and-back, shaded almost the whole way.

Other Walks

I have known Ruth since junior college, when we were schoolmates at VJC. Even back then she had a certain je ne sais quoi that magically drew people to her. She did not follow a predictable path, and she has never seemed to want to. She is a free spirit in the truest sense, and somehow that has always made the people around her want to be a little braver too.

Over the years I have moved in and out of her orbit. I cheered her on when she started her first floral business, and again when she started Blessed Blooms, the brand she runs now, built around an idea she calls making love visible through flowers. What strikes me most about Ruth, though, is how much of her life is organised around kindness. She wrote a book to raise money for charity, as did her husband. She sits on the board of Child at Street 11, brings her son along to volunteer in the community, and hands flowers to the elderly in the rental flats near her home. She and her husband do not just talk about these things to their son. They live and model these principles, every day.

There is a poem I’ve associated with Ruth for a long time (she’s told me she has always loved it), and I think it comes close to a life philosophy. It is William Blake’s Auguries of Innocence:

To see a world in a grain of sand

And a heaven in a wild flower,

Hold infinity in the palm of your hand

And eternity in an hour.

It is a very Ruth thing, to build a life around finding the whole world in something small and meaningful. When I read her answers, I kept seeing the poem behind them.

I’ll let you read the rest of the conversation.

Who you are

Tell us a little about yourself: your work, your family, and where you are right now in both.

I’m Ruth, founder of Blessed Blooms, a floral brand in Singapore built around the idea of making love visible through flowers. Before this, I was a teacher but I left the profession to pursue entrepreneurship and create a life that allowed me to be more present for my family while building something meaningful.

Today, my work goes beyond just selling flowers. Through Blessed Blooms, we create everyday floral experiences for gifting, gratitude, grief, celebration and connection. I also work with corporate teams, schools and community groups through workshops and community initiatives. A big part of what drives me is the belief that small acts of care can have a real impact on people’s lives.

On the family side, I’m a mum to an 11 year old son who’s a national diver, and family remains at the centre of many of my decisions. I’m also involved in community work as a board member of Child at Street 11 and through various ground up initiatives.

Right now, I think I’m at a season where both work and family are becoming more intentional. I’m learning how to build a business that is sustainable and purpose driven, while also being fully present for the people and moments that matter most.

How old are your children, and who is the primary caregiver at home?

I’m the primary caregiver. My son is 11, foster daughter is 3 but she has just been reunited with her biological mom and they have since moved back to Malaysia.

How you think

Was there one thing that made you change after becoming a parent?

Becoming a parent changed the way I see both time and responsibility.

When my son was born, I remember looking at this tiny newborn and feeling the weight of it all. Newborns are so precious and completely dependent on the people around them. It made me realise that as parents, we are shaping someone’s world, not just keeping them alive, but shaping how safe, loved and seen they feel.

It also gave me a much deeper appreciation for my own parents. You suddenly understand the quiet sacrifices, worries and invisible labour that parents carry every single day.

More than anything, becoming a mum changed my perspective on life itself. Parenthood made me realise how fleeting time really is. The days can feel very long sometimes, especially in the exhausting seasons, but the years pass incredibly quickly. Children grow while we’re busy living ordinary days, and one day you realise those moments are gone forever.

That awareness has made me more intentional about how I spend my time and what I want to build my life around. It’s also part of why I started my business and why the idea of “making love visible” matters so much to me now. At the end of the day, achievements come and go, but the love, memories and presence we give to people are the things that truly stay.

Was there a moment after having children when you looked at your career and thought, this needs to change? What happened next?

Yes I feel that my time is so limited and whenever I’m at work I’ll be missing my son’s milestones. They grow so fast and we can’t buy back time. So I decided to focus on him and left teaching. I never looked back since and don’t regret my decision at all. He’s 11 now and I still feel I don’t have enough time with him.

Tell me about a moment when you felt the tension between work and being present most acutely. Not the general feeling, but a specific moment you still think about.

I still remember feeling very guilty once when my son was 3 and I had to leave work early to attend his kindergarten concert.

At that time, I was running the flower studio during one of our busiest periods. The concert happened to fall right during crunch time, just before we closed the day’s orders and the drivers arrived to collect the flowers. I remember standing there debating whether I should stay back to help because the team was overwhelmed. But deep down, I knew I couldn’t miss the concert for the world, so I left at the very last minute and rushed down so I wouldn’t be late.

That tension between work and being present still follows me today.

Last year, during a family trip to Japan, we were having dinner beside a beautiful waterfall in the mountains. It should have been one of those peaceful family moments. Instead, I was glued to my phone trying to firefight an emergency delivery issue back in Singapore.

I still remember my husband looking at me in frustration, almost wanting to grab my phone and throw it into the running water.

I think moments like these stay with me because they remind me how easy it is for work to quietly take over the very life we’re working so hard for in the first place.

How has your parenting philosophy evolved, with age, with experience, or as your family has grown?

When my son was a newborn, my husband and I used to joke that our main parenting philosophy was simply to make sure he doesn’t die 🤣 We were exhausted first time parents trying to survive the sleepless nights, endless diaper changes and breastfeeding schedules. Looking back, that mindset actually helped us put things into perspective. In those early days, small problems can feel enormous because you’re so tired and overwhelmed, but we kept reminding ourselves that if the baby was safe, fed and loved, the rest could be figured out.

As he grew older, our parenting philosophy evolved beyond just keeping him alive and happy. We became much more intentional about character building and the kind of person we hope he grows up to be.

More than achievements or grades, we care deeply about him having a good heart. We want him to be kind, generous and aware of people around him. One thing we often tell him is to look at other people’s plates and see how you can help fill theirs too.

At the same time, we encourage him to do hard things and to keep showing up consistently, even when he doesn’t feel like it. Whether it’s training, school, relationships or life in general, we want him to understand that growth often comes from learning to stay through discomfort instead of avoiding it. And to just keep showing up, no matter what.

I think parenthood has also made us realise that children learn far more from what we model than what we say. So a big part of parenting for us is trying to live out the values we hope he carries forward one day.

What is the one generational pattern you are consciously trying to undo?

I think our parents did the best they could with what they knew, and a lot of it came from love, survival and wanting to raise resilient children. I’ve realised that while authority can create obedience, it doesn’t always create connection or trust. With Jude, I’m trying to parent with more conversation and explanation instead of just control. Of course there are still boundaries and consequences, but I want him to feel safe expressing himself, asking questions and even disagreeing respectfully.

What you built

Tell me about what you built (in the context of your career). What made you choose this, and not something else?

I built a flower business, but more than that I think I built a way of helping people express love, care and connection through everyday moments. Before this I was a teacher and while I loved working with children, I realised I also wanted to create something of my own and build a life with more flexibility and meaning for my family.

Honestly, I didn’t enter floristry because I grew up dreaming about flowers. I was drawn to the business first, but along the way I discovered how powerful flowers can be in people’s lives. They appear in moments where words often fall short, grief, celebration, apology, gratitude, love. Over time, it became less about flowers themselves and more about what they carry between people. That’s why the idea of “making love visible” became such a big part of my work and life.

Is there something in what you built that you made specifically for your child or children, whether they know it yet or not?

I think what I’m really building for my son is not just a business, but a way of living. I want him to grow up seeing that work can be meaningful, that success is not only about money or titles and that it’s possible to build something with heart. I hope he sees that kindness, relationships and integrity matter just as much as achievement.

At the same time, I also built this life because I wanted more presence. Leaving teaching and becoming an entrepreneur gave me the flexibility to be there for school events, competitions, ordinary afternoons and the little moments that would otherwise be missed. I’m not sure he fully understands it yet but I hope one day he’ll realise that many of the decisions I made were shaped around being able to have more life with him while still building something meaningful.

When your child or children are old enough to look back at the choices you made, what do you hope they take from it?

We have the power and freedom to make our own choices. Don’t succumb to societal’s standards, we build the life we want and we put in the hard work and sacrifice to get there. Dont complain about our situation because we are where we are because of the choices we make, we are 100% responsible for both the good and bad. If we are unhappy with something, we take action to change it. If we choose not to do anything about it, then we can’t complain.

Singapore specifically

Raising children in Singapore comes with its own particular pressures. What is one thing you wish you had given yourself more permission to do?

Not to follow the crowd blindly, let Jude learn at his own pace. Sadly, we can’t run away from the PSLE system so as responsible parents, we still have to do our due diligence to make sure his studies are on track to meet the minimum standards to get to the next level. Sometimes I wish I don’t have to struggle to do 听写 with him 🤭

What you have learned

What has your child or children taught you that no colleague, mentor, or book ever did?

Love is unconditional. No matter what happens, kids don’t bear grudges and they will love us back no matter how much we scold them or “disappoint” them. They really mean what they say and their love is so pure. It’s something you have to experience yourself and it can’t be taught or learned.

What is one thing you do to teach your child or children to be kind?

We model kindness and talk about it. We will always point out situations when we can extend some kindness to others in our everyday - holding the lift door for others, greeting cleaners, guards along the way, thanking servers. When we’re overseas and meet the homeless along the streets we would talk about it and encourage him to give some money instead of pretending they don’t exist. He has since learned to notice them and always ask us for money to give them.

We also bring him along whenever we have charity events and always try to involve him, no matter how small. He joined the kids to wash cars 2 years back when the kindergarten had a fundraising event. He would also help to give out food and flowers to the elderly in rental houses near our area on occasions.

What is one piece of advice you wish someone had shared with you earlier in this season of life?

Ignore what others say, everyone’s path is different and we would know our child the best so do what we feel is right for our child and doesn’t matter what others do or say

And finally

What do you cook when you want to show your child or children you love them? Recipes welcome.

(Soupy) Mac and cheese. It’s simple: just boil the pasta, melt whatever cheese we have in the fridge, add some milk (my son likes it soupy) and bake it to get a crispy top.

What is one thing in your bag you never fail to have on hand when you bring your child or children out?

Wet wipes!

If you had one hour to yourself this week, what would you do with it?

Uninterrupted sleep with all my pillows and bolster on the whole bed to myself!

And finally, what is in your cup right now?

Pipping hot coffee and so much gratitude for what I have, who I am now and the people who are in my life.

What stays with me about this conversation is how much of Ruth is about kindness, and how deliberately she practises it.

She wants her son to have a good heart more than good grades. She tells him to look at other people’s plates and see how he can help fill theirs. She points out the cleaners and the guards and the people sleeping on the street so that he learns to notice them rather than walk past. Ruth and her husband model it daily: fundraising with their son for charity, in the books they each wrote to (also to raise money for charity), and in the flowers given to the elderly nearby. It is a life made of small acts of care, grain by grain.

This is the same Ruth I knew back then, the one who never followed the crowd and never seemed to mind. She said it plainly in her answers: don’t succumb to society’s standards, build the life you want, and take responsibility for all of it. She left teaching because she did not want to keep missing her son’s milestones, and she has never once regretted it. Ruth is a free spirit, but a deliberate one.

I think that is why Blake’s poem is so apt. Ruth has built a whole working life around the idea that a flower can hold something as large as love, and that a small act of care can change someone’s day. Making love visible is not a tagline for her. It is how she has always moved through the world.

She said her cup right now holds piping hot coffee and so much gratitude for what she has, who she is, and the people in her life. That sounds about right. Ruth has always been good at holding eternity in an hour, and a heaven in a wild flower.

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A Cup With is a series on Cup & Weekend where I ask mothers who are building lives outside the template about what they carry, what they’ve made, and what’s in their cup. These conversations happen over text and emails, sometimes over coffee, and always between an errand run or two. If you’d like to follow along, subscribe below.

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🍵 “More from A Cup With” ☕

I gave him thirty minutes to watch how-to videos on YouTube. As we neared the thirty minute mark, the living room floor was strewn in his many iterations, and he was frowning at the way the plane refused to return to him. I didn’t extend his thirty minutes and he became upset. He was convinced that the answer was inside another video but I stayed firm.

So with the TV off, he stubbornly sat at his table and continued folding. A while later, he sidled up to me and told me, “I did it, I managed to make a boomerang plane. Can I show it to you?”

Eyes soft and tired but triumphant, he threw the plane. It traced a small arc and landed neatly at his feet.

I quite enjoy watching Foolet find his way through obstacles like these. He doesn’t make it easy for himself (or the people around him), but he eventually gets it done.

Pictured: a particularly inspired plane drawn by Foolet at 5.5 years old

I’ve had a lot of conversations with fellow parents about the skills we want our kids to have growing up. The roles I did at work did not exist in my parents’ time, and I still struggle to explain them even to people my own age. Teaching our kids how to think is what every parent would say. But what does it truly mean?

We were thinking about AI, of course. The conversations in parenting circles this year all seem to circle the same anxiety, that our children will outsource their imagination, that the pursuit of knowledge is no longer a trudge to the library but an answer on a screen. They will watch the video instead of folding the plane. Generate the comic instead of drawing it. Prompt the essay instead of writing it. What if they lose the experience of the messy middle entirely?

But I had to laugh a little at myself, because I have lived through this panic before. In my own childhood we moved, within a handful of years, from looking things up in the library to Encarta 95 on a CD-ROM, and then to the world wide web itself. The trudge to the library that I am now nostalgic for was exactly what we were so happy to be rid of. I am sure the adults around us worried about what instant answers would do to our minds. And here I am, more or less fine, writing my own (I think).

So perhaps the worry is an old one wearing new clothes. And yet I couldn’t shake the niggling feeling that something wasn’t right. Naturally, I went off on a tangential spiral internally and started asking myself: what is original thought? Do any of us have a real claim to it?

The philosopher David Hume had an answer, and it was not a flattering one. All the mind ever does, he argued, is rearrange the materials that experience hands it. We can imagine a golden mountain only because we have seen gold and we have seen mountains. Nothing in the imagination is truly new. It is old furniture, moved around.

I wouldn’t call anything I have made original. My own drawings as a child were derivatives of what I read, Tintin, Asterix, the rest. I read Brigid Schulte’s essay on time confetti and I noticed her phrases turning up in my own sentences. We are all rearranging our inheritance. We always were.

AI has dragged this into the open. It has held up a mirror to what creative work has always been, and asked, reasonably enough: if this is what creation is, why is it I cannot do it? The answer is that it can. If originality means producing combinations the world has not seen before, AI is closing the gap quickly, and there is no obvious reason it should not eventually close it entirely.

Which is why the worry about outsourcing imagination is the smaller worry. If the arrangement was never the thing that made us us, because everyone rearranges and now the machines do too, then the value was never in the finished plane at all. It was in who did the folding, and in what the folding did to him.

This is the part the panic keeps missing. Hannah Arendt wrote about a capacity she called natality, her word for the human ability to begin something new, to bring into the world a thing that could not have been predicted from anything that came before. She rooted this capacity in birth itself. Each child, for her, was a beginning. A new actor on a stage where they could not previously have been calculated.

The thoughts that any of us have are borrowed, like everyone’s, like Hume’s, like mine. What matters is that they came out of a someone who was here. Foolet did not exist before he existed. Foolittle did not exist before he existed. Whatever they make, whatever comic or boomerang plan they put in front of me, will be downstream of them having arrived. AI is downstream of all the people who arrived. It has, by definition, no original arrival.

This is what I think we should be paying attention to as parents right now. The question is no longer whether our children can produce original combinations. They can, and so can the machines. What we have to protect is harder to articulate. It is that they are their own person, with a right to their own beginnings. A Saturday afternoon. A foldable table. A pile of crumpled planes nobody else will ever see.

If the goal had been a working boomerang plane, I should have let Foolet keep watching. The video would have shown him the fold. He would have copied it, and we would have had something that flew correctly before dinner.

But eventually, something else had happened. Foolet had become the boy who could make a boomerang plane. That boy did not exist at minute zero. He arrived, through the friction. The video would have arranged the room for him. Instead, he worked through each piece by himself and felt the weight of the frustration when the plane didn’t fly the way he’d intended. His hands know something now that they did not know at the start, and the next time will come a little easier, because the mover has changed.

The part parents will have to fight for in the years ahead is not against AI itself, which will be in our children’s lives whether we like it or not. It is against the seductive logic that says the friction was wasteful and inefficient.

The friction was never waste, even when it felt like it. It is how a person gets made.

I do not always know how much to let him struggle. Some afternoons it tips into a tantrum that teaches him nothing. The boundary I hold is more instinct than science.

Writing this essay is no different. So many of the phrases and words came from the writers who came before me. What I am beginning to understand, slowly, is that I was asking the wrong question. The thoughts were always going to be borrowed. What belongs to me is those snatches of time throughout the week when the sentences took the shape they did. The thoughts were passing through someone who happened to be me, and that someone is what makes them mine.

It is the same answer for Foolet, in his own way. The boomerang plane was made of things he had seen before, like the comics that live on the dining table for a week. His Saturday afternoon. The pile of crumpled paper. The boy who came back to find me with the plane in his hands. No one else was in the room for any of it. With AI everywhere, there is something comforting about him still working with his hands, figuring out problems, feeling the satisfaction of solving them. I cannot place a dollar value on it.

I do not know what the next ten years will look like for him. The pressures to skip the friction will only get heavier, and at some point he will be the one deciding whether to skip it, and I will not be in the room.

What I can do, for now, is keep the dining table available. Keep the planes on it when they pile up. Keep the screentime limit in place for (quite a few) more seasons. Keep him company in the silence after the frustration. For now, he still has to find his own way into the thirty minutes.

I got to know Jillian through her husband Kin, who I have known for years. Jillian is a third culture kid, who grew up in Australia and Indonesia as a child, followed by nine years in New York. Then next up was Hong Kong, where she met her husband, who convinced her to move to Singapore.

Two years ago, she started her own batik kidswear brand, Dots and Dribble, which she created from scratch. From the brand work, the designs, the sourcing trips to Indonesia, she does it all while raising two young kids in Singapore. Jillian has mentioned that “starting this store was also a way for my kids to connect with their Indonesian and Malaysian heritage.”

(I should mention I’m a customer. I buy her batik for my kids, and her batik painting kits too, because I love her tasteful designs and my kids are happy to wear them as well!)

Third culture kids often have a complicated relationship with the question of where they are from. Their roots are made up of many places, none of them fully. After a life of moving, Jillian is doing the work of rooting, and I think many of us feel this more urgently with children. She is giving her two children a thread back to where she and Kin came from. She is also making something personal and beautiful for them.

I’ll let you read the rest of the conversation.

Who you are

Tell us a little about yourself: your work, your family, and where you are right now in both.

I’m Jillian. I always knew I wanted to do something creative. After art school in New York, I worked in digital agencies for a decade, but when I took a break to be more present with the kids, I realised I wanted to make something that was entirely mine. Two years ago, I started Dots and Dribble, an online store specialising in batik kidswear. It was a way to blend my design background with my kids’ heritage—and it’s been a whole learning process.

How old are your children, and who is the primary caregiver at home?

My kids are seven and four, and I’m the primary caregiver. My husband’s work involves quite a bit of travel and client dinners, so he pitches in when he can. We also have a wonderful helper who assists with cleaning, cooking, and childcare.

How you think

Was there one thing that made you change after becoming a parent?

You’re always split. In school, anything less than an A is a failure. As a parent, I’ve had to unlearn that getting C’s across everything like work, kids, myself beats an A in one thing and nothing else.

Was there a moment after having children when you looked at your career and thought, this needs to change? What happened next?

I was one month into a new job when I found out I was pregnant. Hiding it while feeling sick at a job I hated was miserable. But it made me ask: why am I doing this to myself just so my employer doesn’t feel bad? I quit six months later. I was privileged to have options such as my partner’s support and the ability to freelance again. At that point the realization was clear: I couldn’t keep sacrificing my family for a job I didn’t love.

Tell me about a moment when you felt the tension between work and being present most acutely. Not the general feeling, but a specific moment you still think about.

Parenting made me examine my people-pleasing. My dream job at an ad agency came at ten months postpartum. Working until 1–2am, waking at 3am with a baby, then starting at 7am wasn’t sustainable. Nobody talks about this. I was up at 2am sweating, stressed and miserable, wondering why. Then I looked around: no mothers in core roles. During COVID, with everything falling apart and still pitching, it was clear I had no future there. I had to leave.

How has your parenting philosophy evolved, with age, with experience, or with each subsequent child if you have more than one?

I realised how neurotic I am as a parent. Before kids, I was a go-with-the-flow type of person, but parenting changed that completely. I am not a planner but having kids is 90% logistics and 10% the craziness that comes with it. A set schedule with an early bedtime allows both the children and me to thrive. With my second child, I had less time to be neurotic and just aimed to enjoy the chaos…to a certain extent!

What is the one generational pattern you are consciously trying to undo?

Emotional awareness. Being aware of your own emotions and naming them is such a powerful tool. After a long day, I catch myself scolding the kids for little things and have to consciously step back and ask: Is it because I’m tired? 99% of the time, the answer is yes.

What you built

Tell me about what you built. What made you choose this, and not something else?

I launched a modern batik shop for kids to blend my design background with my Southeast Asian roots. My kids don’t speak Bahasa or Malay, so this was a way to give them that connection. It felt like the right combination of everything I cared about.

Is there something in what you built that you made specifically for your children, whether they know it yet or not?

It started with my son’s preschool dress-up days. All the cultural outfits were cheap, fast fashion junk. I set up the shop to solve that problem for him. But then I discovered something unexpected: I loved building this. It showed me what fulfilling work could be manageable—spending as little as ten minutes a day or long hours over a weekend working on your project. But I’ve learned to be ruthless about what matters and prioritize. Over time, it compounds into something meaningful.

When your children are old enough to look back at the choices you made, what do you hope they take from it?

That your self-worth is not tied to your productivity or achievements. Being a good person is about building your confidence, nurturing relationships, finding meaning in your work and trying new things. Not everything in life has to have a measurable outcome.

Singapore specifically

Raising children in Singapore comes with its own particular pressures. What is one thing you wish you had given yourself more permission to do?

Let them be kids. The only results you should measure is: were they better than they were last year? That’s the only result that should matter but unfortunately that’s now how it works here. Raising kids in Singapore is different from how I was raised in Australia. We had no homework. I didn’t have exams until I was in grade 9 and I turned out ok (I hope). For this generation on social media it’s chaos. There’s too much literature out there. I get FOMO watching other kids hit milestones mine haven’t. But I’ve learned: just try things and see what works. You can always change your mind. And as much as I love them, honestly, my kids are extremely average. And that’s okay.

What you have learned

What has your child taught you that no colleague, mentor, or book ever did?

To love someone so unconditionally that it hurts. Before you become a parent, you’re the centre of your own universe. But the minute a child grows inside you, your life and choices become bigger than yourself. Your kids can be absolute sh*ts and you’ll still worship them. Parents, you understand this dilemma.

What is one thing you do to teach your child to be kind?

My son is seven and pushes boundaries at the playground. Boys have a lot of physical energy and use rough play to socialise. Nothing wrong with that. We just guide it, teaching acceptable behaviour and how to manage emotions when things get intense.

My daughter is the opposite. She’s extremely sensitive and shy. She doesn’t need reminding to be kind to others. She needs reminding to be kind to herself, to stand up for herself.

You can’t force kindness into kids. You can only model it and hope they see it. Slowly, they start taking your lessons into consideration when you least expect it.

What is one piece of advice you wish someone had shared with you earlier in this season of life?

Oh, so many. I feel like there’s too much advice being thrown around. Sometimes the best thing you can do is just be. Just do. Then learn from it.

And finally

What do you cook when you want to show your child you love them? Recipes welcome.

Korean seaweed soup is the ultimate comfort food in our house.

What is one thing in your bag you never fail to have on hand when you bring your children out?

Water bottles and tissues! Singapore is so hot.

If you had one hour to yourself this week, what would you do with it?

A massage and a meal with my husband! One hour well spent to recharge and come out a better person.

And finally, what is in your cup right now?

A hot latte. Or three lattes. After becoming a parent I can have 3-4 coffees a day and I still conk out at night.

What stays with me about this conversation is that Jillian is doing two things at the same time.

She is giving her kids a way to reach back to where she and Kin came from, and she is also showing them what it looks like to build something of your own.

She said she hopes they learn that self-worth is not tied to productivity. I’ve been caught up in the 996 narrative working in startups for years, and I have to admit that as a parent now, it’s just not possible to sustain that. She also realised a very real and painful truth, no one doing the core work of that agency was a mother. You can replace “agency” with many other industries, and that’s the hard truth. And that’s what I admire about Jillian and other mums I’ve interviewed, after they came to that realisation, they’ve taken things into their own hands, literally.

People who grew up rooted in one place tend to inherit their heritage almost without noticing it (ie me). People who grew up between places have to choose theirs. Jillian is choosing batik. She wants it to be something her kids can hold, and something she can build with her own hands and turn her design eye to. She is making it between school runs and sourcing trips, in pieces. It’s growing because she kept showing up to the next ten orders, then the next fifty.

Jillian said she needs a hot latte to get through the day. Underneath that latte is something quieter, the conviction of a third culture kid who took the long way to Singapore and is using everything she gathered along the way to give her children, and herself, something beautiful to belong to.

A Cup With is a series on Cup & Weekend where I ask mothers who are building lives outside the template about what they carry, what they’ve made, and what’s in their cup. These conversations happen over text and emails, sometimes over coffee, and always between an errand run or two. If you’d like to follow along, subscribe below.

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What does it take to have a full-time career as a founder and to raise 4 children?

I met Elena many years ago when she tried to hire me. There was an up-and-coming startup, a role being shaped, and a conversation about whether I would be the right fit. I wasn’t, in the end. But Elena made an impression on me. She ran that conversation with an attentiveness that lingers and also a keen hustle. She was one of the first recruiters I met that seemed to actually care about her candidates’ careers (not to mention the first who actually focused on recruiting for startups in those very early days).

Years later, I learnt that not only did Elena not come from a HR and Recruitment background, she was building her company while raising 4 children! It was a thread that I picked up, and I genuinely got curious. What does it take to do what Elena did?

The more I read her responses, the more it comes down to one instinct. Elena sees what’s in front of her, trusts her read, and acts. About ConnectOne, she writes almost in passing: “It was not intentional, I never thought I’d start a HR and Recruitment company but when you see a problem in front of you and you know the solution, you go plug that gap.” Fifteen years in corporate watching how great companies build great teams, and when she saw the gap nobody was filling for VC-backed startups in Singapore, she went and plugged it.

The same instinct showed up in how she raised her four. While her friends were sending their kids to Learning Lab to learn European history, Elena sent her daughter to art class and got chided by a friend for being a bad mum. On teaching kindness, she shrugs: “I never did intentionally. But if anything, I brought them with me on multiple overseas social mission trips from a young age, and I think that experience has inculcated a sense of empathy that no lecture or textbook can impart.” Elena was remarkably consistent: she sees what matters, chooses that, and ignores the consensus.

Elena is in a pivoting season now. The question she keeps asking has shifted from “How do I build more?” to “What is worth building next?” Like Sam, she’s further along the journey, with children mostly grown. Talking to Elena reminded me that the wisdom from this stage of parenting sounds different. It’s less hurried, more circumspect, and I appreciate seeing it from her angle.

Here is our conversation.

Who you are

Tell us a little about yourself: your work, your family, and where you are right now in both.

I would say I’m in a pivoting season.

For many years, my focus was very much on building — building my family of 4 kids, building a HR and executive search practice, building networks within the startup ecosystem, and building teams for high-growth companies. That season was energising because everything felt like forward momentum.

But over the past year or two, I’ve started asking different questions. Instead of “How do I build more?”, the question has become “What is worth building next?”

That shift has led me to explore several new directions - supporting fractional leaders or portfolio careerists, rethinking the kinds of organisations and leaders I want to work with and venturing into a new space that I am currently in a discovery/research phase. In many ways, the pivot is less about abandoning the past and more about reframing how the past experience can be used in a different way.

How old are your child or children, and who is the primary caregiver at home?

My kids are between the ages of 28 to 18 haha. They don’t need a caregiver anymore.

How you think

Was there one thing that made you change after becoming a parent?

My ambition at work was no longer the same. Before that I was always gunning for the promotion, I remember crying as I was the 2nd fastest to be promoted in my cohort and not the fastest! After becoming a parent, my priority was to rush home as fast as I could from work.

Was there a moment after having children when you looked at your career and thought, this needs to change? What happened next?

I was in a meeting and had more than 10 missed calls right after a one hour meeting. I remember that occasion (although there were many of the same before but this was one that as they say “ the bucket overflowed”) because it was one of the triggers that told me,” Hey, I think it’s about time that I spend more time with the kids, right?”

Also my second son who was super challenging to handle (he had ADD and was constantly distracted) was going to P1 and I knew I would have to be around more for him.

Tell me about a moment when you felt the tension between work and being present most acutely. Not the general feeling, but a specific moment you still think about.

That meeting as described above - while it was not anything dramatic but it was a build up that culminated in a seemingly innocent ordinary meeting triggering that thought.

How has your parenting philosophy evolved, with age, with experience, or as your family has grown?

I was a lot more involved, even fanatic to the point of counting the hours I spend with my kid vs my helper at home - to one of “I have done my best to impart the best foundation for you and hence I trust that all decisions that you make are well thought through and values based”. Especially with 4 kids, you apply the way you raise consistently (principles, values etc) and let them base off that to grow.

What is the one generational pattern you are consciously trying to undo?

Some members of my husband’s family have severe anxiety and I am always on the look out for manifestation in my kids and pay special care to helping them with it. My family has a short temper and in the same way, I recognise them in my kids. Awareness is the foundation of the resolution.

What you built

Tell me about what you built (in the context of your career). What made you choose this, and not something else?

My first 15 years was in corporate and I did not build anything for myself other than the knowledge of how great companies approach building great teams. I took that knowledge and first hand experience to start ConnectOne, which I built to help tech startups build great teams. It was not intentional, I never thought I’d start a HR and Recruitment company but when you see a problem in front of you and you know the solution, you go plug that gap! Hence I am pretty proud of being (one of) the first HR company that specializes in helping VC backed startups. Many have jumped in since then but it is still nice to be recognized as the first.

Is there something in what you built that you made specifically for your child or children, whether they know it yet or not?

No none haha. But if any of them come up to me and say “Mum, let me take over your business and grow it”, I would definitely think hard!

When your child or children are old enough to look back at the choices you made, what do you hope they take from it?

From a career standpoint - start by working in corporate but always aim to build your own before you are 40! And if possible build for an exit :) which I did not of course.

Singapore specifically

Raising children in Singapore comes with its own particular pressures. What is one thing you wish you had given yourself more permission to do?

Can I answer it in the context of what I gave myself permission to do? :)

Not be FOMO and send them to enrichment classes and tuition after tuition! While my friends’ kids were going to the Learning Lab to learn about European History, I sent my daughter to art class (this is a true story as a friend chided me for being a bad mum for doing this). I also did not send them to music classes but they picked up guitar on their own and played beautifully :)

What you have learned

What has your child or children taught you that no colleague, mentor, or book ever did?

Boys can be mum’s best friends! Contrary to what most will say that have girls as they are your best companion. But I truly enjoy spending time with my boys and while they were so difficult to raise (naughty and disruptive!) but they are the sweetest now

What is one thing you do to teach your child or children to be kind?

Hmm, I never did intentionally. But if anything, I brought them with me on multiple overseas social mission trips from a young age and I think that experience has inculcated a sense of empathy that no lecture or textbook can impart.

What is one piece of advice you wish someone had shared with you earlier in this season of life?

On parenthood? That raising 4 kids is very expensive and that I should have been wiser with investing my money when I was younger haha. Funny that no one ever told me that - they were concerned more about our capacity than money (or maybe they were too paiseh to articulate it).

And finally

What do you cook when you want to show your child or children you love them?

I am very fortunate that I never had to cook at home as my husband/helper does all the cooking. But what they appreciate is my making of Mum’s jelly cheese cake on their birthday!

What is one thing in your bag you never fail to have on hand when you bring your child or children out?

My kids are grown but they still ask me for tissue paper haha.

If you had one hour to yourself this week, what would you do with it?

I have many more hours now that my kids have grown but if I had that extra hour, I would like to join this iphone photography thing that a friend has launched, finish my chinese landscape art and double down on some AI automation.

And finally, what is in your cup right now?

A cup full of joy and gratitude for the blessings of energy and optimism even as i stand at the verge of the next third of my life (I think of life in thirds)

In Elena’s responses, she carries a wonderful sense of energy and positivity that I admire. She has made many tough choices building her company while bringing up her children, and while many of them were not easy, I sense a strong conviction in her choices, where she knew what she wanted and went all out to get it.

That conviction reshaped her as a mum. In the early years she was, in her own words, fanatic, counting the hours she spent with her kids against the hours her helper did. Years later, with four kids 28 to 18, she trusts what she put down: “I have done my best to impart the best foundation for you and hence I trust that all decisions that you make are well thought through and values based.”

And you can see what they got. They picked up guitar on their own, and came home from her overseas mission trips with empathy no textbook would have given them. Elena raised them on principles and values rather than schedules, and the foundation has held.

And now, she’s pivoting to think about what’s worth building next.

It’s a question I wouldn’t have known to ask in my twenties, although it was something I already did start working on after I had my first child and got hit by the shock that was Covid. Elena is much further along her journey, and is sizing up the materials for the next play. But underneath it all, she doesn’t sound like someone in a hurry, and the joy in her voice is the part I really admire.

I would like to carry that gratitude in my cup too.

A Cup With is a series on Cup & Weekend where I ask mothers who are building lives outside the template about what they carry, what they’ve made, and what’s in their cup. These conversations happen over text and emails, sometimes over coffee, and always between an errand run or two. If you’d like to follow along, subscribe below.

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I’ve known Cass for years. Singapore is small enough that paths cross more than once if you stay in the same orbit, and ours did, going back to her Foodpanda days. Later, when she was made redundant from a tech role in 2023 and started her own fractional marketing agency, I had the chance to work with her team on a few campaigns. That’s where I really saw it up close: her hustle, optimism, and the relentless energy that doesn’t seem to run out. If you ask me whether someone is hungry, Cass is.

But I’ve also seen the other side of her. The way she is with her two girls. The way she is actively thinking about the kind of environment they are growing up in, and the version of her they are watching. I’ve been a little curious about the person beneath all that drive, so I asked her to share more.

What follows is our conversation.

Who you are

Tell us a little about yourself: your work, your family, and where you are right now in both.

I’m Cassandra, founder of OtterHalf (www.otterhalf.co), an award-winning fractional marketing agency based in Singapore. We work with tech startups and SMEs as their part-time marketing team, jumping in, helping them grow, and sometimes making ourselves redundant in the best way possible. I have 14 years of experience across companies like foodpanda, Chope, and Tripadvisor before a tech layoff in 2023 became the unlikely catalyst for everything I’m building now.

At home, I’m a mum to two girls. I grew up in a fairly chaotic household, so peace at home isn’t something I take for granted. Right now in both work and family, I’d say I’m in a good place. Still building, still doing work that feels meaningful, and genuinely happy with where things are, stress and all.

How old are your children, and who is the primary caregiver at home?

My girls are 5 and 8. It really does take a village, and I’m lucky to have mine. My husband, our helper, and my in-laws all play a big part in keeping things running. That said, I’m very much in the thick of it too, and yes, I still co-sleep with both girls. One of the gifts of founding OtterHalf and going remote is that I get to be around for the ordinary moments. My daughters literally peel me away from my workstation to remind me to eat dinner or go bathe. Some days, that’s the most grounding part of my day.

How you think

Was there one thing that made you change after becoming a parent?

Before kids, I’ll admit I was pretty superficial about my career choices. I made decisions based on what I personally liked. I love food, so I told myself to join a food company. I joined an FMCG because it was THE company every marketer wanted on their CV, not because I was passionate about their products or what they stand for. I just went where people went.

After having my girls, I started thinking a lot more about what I actually wanted to contribute, and why. It made me ask harder questions, like what can I do that would positively influence the environment my daughters grow up in? That question affects a lot of what I do, from the clients I choose to work with, to the card game I built, to the workshops I now run for kids. It gave my work a reason beyond myself.

Was there a moment after having children when you looked at your career and thought, this needs to change? What happened next?

Yes, it was the layoff in 2023. I was Head of Marketing at a B2B SaaS company when almost the entire marketing function was made redundant. At that moment, I had two young daughters at home and no job. I could have spiralled.

But something in me went very still, the thought about starting my own venture. I thought: if not now, when? I called two trusted ex-colleagues, we put our heads together, and within a month we’d launched OtterHalf as the first fractional marketing agency in Singapore. We closed the year with six-figure revenue. But more than the numbers, I remember thinking: I don’t want my daughters to ever feel that a setback is the end of the story. So I decided to write a different one.

Tell me about a moment when you felt the tension between work and being present most acutely. Not the general feeling, but a specific moment you still think about.

The one that stays with me happened in the early days of building OtterHalf. We were out as a family on a weekend, but I had my phone out the whole time. Replying to messages, checking in on work, one eye on the girls and one eye on the screen. My husband turned to me at some point and said, “Going out with you is like going out with a teenager.”

To a certain extent, it was true. I was physically there and completely elsewhere. That comment has stuck with me and I start being more intentional about putting the phone down, especially on weekends. I’m still working on it, but I think about that line more than I’d like to admit.

How has your parenting philosophy evolved, with age, with experience, or as your family has grown?

When my eldest was born, I was inexperienced and pretty anxious. Parenting to me was ensuring that she sleeps through the night, cries less, and is well fed. I would also google every little thing, and even send her to A&E at the slightest fall.

By the time my second came along, I’d loosened up quite a bit. I think she got a more relaxed version of me, and she probably benefited from that.

Then starting my own business made me rethink about how both my girls grow up. I want them to see that life doesn’t always go to plan, and that’s okay. That you can lose something and build something better from it. I want them to grow up with confidence that they can figure things out, having watched someone they love navigate the hard parts and keep going.

What is the one generational pattern you are consciously trying to undo?

Growing up, there was an unspoken rule that parents were the authority and you didn’t question them. You just complied. I understand why that generation parented that way, but I saw what it cost — in communication, in closeness, in the things left unsaid.

I’m consciously trying to undo that. I want my girls to feel like they can come to me with anything. The moment they’re afraid to tell me something is the moment I’ve lost the most important part of being their mum. I’d rather be the person they run towards than the one they hide things from.

What you built

Tell me about what you built (in the context of your career). What made you choose this, and not something else?

I started OtterHalf because the agencies I kept interacting with were focused on brand building — impressions, reach, awareness. But as someone who had spent years working at startups, I couldn’t justify marketing spend on brand impressions alone. The environment I was in was cutthroat enough that my team could have been asked to leave if I spent a lot of money driving impressions that led to little conversions. So at some point I thought: maybe I could just be the agency I had been searching for all along.

As I built the agency, one thing stayed consistent: the belief that businesses have the power to contribute to a better world. That shaped who we work with, why we created Ottie’s Fishy Business, a card game that teaches kids the fundamentals of marketing, and why I care so much about using the skills I have to better the environment my girls grow up in.

These days, my weeks look a little like this: running the agency from Monday to Friday, and on weekends, stepping into a room full of kids to teach them about marketing through play. Two very different rooms, but the same thread running through both. I’m building things I actually believe in, and that feels like the point.

Is there something in what you built that you made specifically for your child or children, whether they know it yet or not?

Ottie’s Fishy Business was made because of them and for them, and they know that. My daughters asked me one day: “Mama, what do you do at work?” I tried explaining marketing and quickly realised how abstract it all sounded. So I made a card game. It took eight months to develop and test. They were my harshest critics and my loudest cheerleaders. But beyond the game, I think everything I’ve built at OtterHalf is for them too. I want them to grow up knowing their mum built something from scratch, after a setback, and that it worked. That’s the version of female leadership I want them to grow up watching.

When your child or children are old enough to look back at the choices you made, what do you hope they take from it?

That you can always forge your own path. That a closed door isn’t the end, sometimes it’s the thing that sends you in the right direction. I also hope they take from it that work doesn’t have to swallow you whole. That you can build something meaningful and still show up for dinner. I haven’t always gotten the balance right, but the intention has always been there. I hope that counts for something.

Singapore specifically

Raising children in Singapore comes with its own particular pressures. What is one thing you wish you had given yourself more permission to do?

What I wish I had given myself more permission to do was to be kinder to my younger self. To accept that failing is part of it, and that what matters most is whether you get back up and try again.

Singapore can make that hard. There’s a certain pressure to have it together, get good grades, get good careers, and look like you’re moving in the right direction and not let people see you stumble. I internalised that more than I realised. The layoff I experienced forced me to sit with the uncertainty, and then to get up anyway. And somewhere in that process, I stopped being so afraid of getting things wrong.

I wish I’d learned that earlier (so much wasted tears on bad grades), mostly for my girls to grow up watching a mum who isn’t afraid to fail, and who shows them what it looks like to keep going regardless.

What you have learned

What has your child or children taught you that no colleague, mentor, or book ever did?

That happiness is not about the things that you have but how present you are for the life that’s already in front of you. Kids have no interest in your achievements or your title. They just want you, fully, right now.

What is one thing you do to teach your child or children to be kind?

Every night when we wind down, we play a little game called “tell me three things you like about today.” It’s become our ritual. And whenever I can, I pull out a moment from the day when one of my girls was kind to someone, and I name it out loud.

Like the time my daughter gave up her scooter for another child who really wanted to scoot and was crying for it, even though she really wanted to scoot too. I made sure she knew I saw that. That it mattered.

I think kindness grows when it’s noticed. Kids do more of what gets reflected back to them. So I try to be the one who catches it, calls it out, and makes it feel like something worth repeating.

What is one piece of advice you wish someone had shared with you earlier in this season of life?

Give yourself some grace. When I started OtterHalf, I was catastrophising constantly. What if this doesn’t work, what if I lose a client, what if I’m not enough. No one sat me down and said: you’re going to feel like you’re failing even when you’re not. The discomfort is part of the growth. I wish someone had told me that. I’d have spent a lot less energy on dread.

And finally

What do you cook when you want to show your child or children you love them? Recipes welcome.

My girls’ favourite is spaghetti bolognese baked pasta.

What is one thing in your bag you never fail to have on hand when you bring your child or children out?

Wet tissues.

If you had one hour to yourself this week, what would you do with it?

Body massage.

And finally, what is in your cup right now?

Water.

What stays with me about Cass’s answers is how often the things that happen to her gain a new sense of purpose for her and for her daughters. The layoff became a company. The questions her girls asked about her work became a card game. Even her husband’s comment that going out with her was like going out with a teenager became a reason to put the phone down on weekends.

Underneath all of that is something Cass names plainly: the belief that businesses have the power to contribute to a better world. That belief is what shapes the clients she takes on, the card game she spent eight months building, and the environment she’s actively trying to set for her girls.

She told me she doesn’t want her daughters to feel that a setback is the end of the story. So she decided to write a different one. That takes a whole lot of courage.

And at this q&a’s heart is her answer to the question about teaching kindness. This question tends to shine a light on a softer side of a person, the part of them that sits closer to who they are at their core. When Cass described how kids do more of what gets reflected back to them, and how that kindness needs to be caught and named out loud to take root, I get it.

A Cup With is a series on Cup & Weekend where I ask mothers who are building lives outside the template about what they carry, what they’ve made, and what’s in their cup. These conversations happen over text and emails, sometimes over coffee, and always between an errand run or two. If you’d like to follow along, subscribe below.

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I met Sam in 2019, when I was a new mum still finding my feet. I had reached out to her looking for a coach, without being fully sure what I was actually looking for. I just knew I felt off. The work self I used to recognise had got wrapped around a very small person, and I couldn’t work out who I was inside the new shape.

What I remember from those early sessions is how little she needed me to perform. She asked questions, listened, asked more. She was in no hurry. Coming out of my big tech role, where every conversation had an agenda, the pace took getting used to.

We worked together over the next few years. Somewhere along the way the professional relationship softened into something warmer. I have since graduated from coaching, as these things go, but Sam has stayed. She is a friend whose perspective I still reach for on the days that need it.

Reading her answers for this interview, I kept coming back to her response about control. About realising she needed to heal herself in order to parent differently. About still undoing and doing. Most of us could recognise some version of that in ourselves if we sat with it long enough. What stayed with me was how patient she is with her own language. She doesn’t claim to be finished with any of it. She is in the middle of the work, and says so.

A Cup With is a series where I sit down (usually over text, sometimes over coffee, always between an errand or two) with mothers who are building lives and work that look nothing like what they left behind. Sam’s children are in their twenties, so her picture is further along than some of the women I am speaking to. Reading her responses from where I am, with a toddler and a seven-year-old, feels like encouragement.

I’ll let her tell you the rest.

Who she is

Tell us a little about yourself: your work, your family, and where you are right now in both.

I am an executive coach. I had 2 career transitions from pharmacist to a regional sales executive and then to becoming a professional coach. My kids are between 19-27 and they are all on their way into the world. I am enjoying this stage of life with more freedom and space for myself.

How old are your children, and who is the primary caregiver at home?

My kids are mostly grown and need little physical care. My role as a primary caregiver has shifted to more of a mentor and advisor.

How she thinks

Was there one thing that made you change after becoming a parent?

The great responsibility of looking after my babies made me think deeper and further about who I am. As they are now older, I am thinking about my new roles and adjusting to new boundaries with them.

Was there a moment after having children when you looked at your career and thought, this needs to change? What happened next?

Interestingly, I was a pioneer in working from home. 3 months after giving birth to my eldest, the Singapore branch office went fully virtual. That went on for a long time and I lived in a way that was a dream for many of my friends at that time. As the kids grew, I realised I needed to as well. So once my office moved back into being in person, I relished the personal contact with others. I grew a lot in that middle stage of my career.

Tell me about a moment when you felt the tension between work and being present most acutely. Not the general feeling, but a specific moment you still think about.

The moment I felt the tension was many years after. I was in a much more senior role. Large country size client accounts, long hours and the increased complexity of the workplace started to wear me down. I was completing a large tender response at 3am and that tension was clanging in my head and heart. I was not present for my family and everyday was just a big rush. I hear myself say I can’t do this for too long more. There must be something else.

How has your parenting philosophy evolved, with age, with experience, or as your family has grown?

With age, with experience, and as my family has grown, our relationships and roles changed. It moved from being a caregiver to a coach to a mentor and now as a supporter.

What is the one generational pattern you are consciously trying to undo?

Control. I grew up in an extremely strict household with parents who had their own generational trauma. Luckily working in a more westernised environment helped me to see another way of parenting. I struggled with control as a child and as a parent. With experience I learn to parent differently. It was late in my life that I realised I do not need to live like this. As the kids grew, I also realised I needed to heal myself to have better relationships with them. So I sought therapy and made great strides in finding a better way to be a parent and a person. I am still undoing and doing.

What she built

Tell me about what you built (in the context of your career). What made you choose this, and not something else?

My top value has always been service to others. You can see it in the roles I excel in. It became clearer working with a coach and I was able to move towards a profession that is even more aligned with my values, my natural gift of intuition and a lifestyle that I desired. Thus, being an independent coach was the best way for me. For the last 10 years, I worked hard and now I have a thriving coaching practice and a life that is filled with meaning and freedom.

Is there something in what you built that you made specifically for your child or children, whether they know it yet or not?

Rather than build something, I wanted my children to see that there are many ways to live a life. I am the example of how they can design their lives if they are convinced in what they want and to be willing to do the hard work of building it. I want them to be free.

When your child or children are old enough to look back at the choices you made, what do you hope they take from it?

I hope they never limit themselves and their imagination of what they can do for themselves and others. That they know they can choose how they are, their attitudes, their values even in the worst circumstances that are beyond their control. To learn to trust God and trust themselves.

Singapore specifically

Raising children in Singapore comes with its own particular pressures. What is one thing you wish you had given yourself more permission to do?

I wished I was less influenced by the environment and be more present with my children. I wished I had given myself the permission to have grace for myself, to enjoy the moment and to truly feel the joy of having kids.

What she has learned

What has your child or children taught you that no colleague, mentor, or book ever did?

That children are unique and they come knowing what they want. They possessed their own unique set of features. That I am privileged to be chosen to be their caretakers. That my role is to love, support and help them become who they really are. That I too, can be who I really am.

What is one thing you do to teach your child or children to be kind?

I demonstrate kindness to others. There is nothing more powerful as a lesson to see your own parents do it.

What is one piece of advice you wish someone had shared with you earlier in this season of life?

In the end you only have your children for a season. Cherish the time you have, be present and let go of the rest.

And finally

What do you cook when you want to show your child or children you love them?

I love to cook so I cook based on their preferences. The challenge is that they all like different foods! So they push my creativity in cooking to my limits. I make them up based on what I have in the fridge and what they like to eat.

What is one thing in your bag you never fail to have on hand when you bring your child or children out?

Money, tissue paper and a power bank 😅

If you had one hour to yourself this week, what would you do with it?

I will draw, paint, write, walk or read.

And finally, what is in your cup right now?

There is a lot of space in my cup right now. I am designing and working on the next stage of life. I have been thinking about what I would want to do given the space, time and resources I have now; things I can pursue now that I could not have when my kids were young. So I have applied to do the Executive Masters of Change with INSEAD, specially designed for coaches and leaders who want to develop themselves to the next level. Interestingly, this desire to go for further education is inspired by my kids going for theirs. Other than the program, in the next 5-6 years, I want to get my MCC credential, the highest level for ICF Certified coaches, explore being a coach supervisor to help other coaches, grow my practice and travel the world as far as my curiosity takes me. I am currently learning Korean and am eager to be able to speak like a native. Then, I will eagerly await my next role - becoming a grandmother!

One of Sam’s answers stuck with me. The one where she wrote that children come knowing what they want, and that a parent’s role is to love and support them into who they really are. And then, almost as an aside, she wrote that she too can be who she really is. It’s a good reminder that this runs in both directions.

I will always be grateful for the role Sam played in my life when I was at a loss. She was the person I sat with when I was new to being a mother and couldn’t quite find the shape of who I was turning into. On difficult days, her voice is still somewhere in the background of how I think. Reading her answers, I see more of the life that shaped that voice. The three-month-old at home while the office went virtual. The 3am tender response when something in her said enough. The therapy she sought later, first for herself and then for her children. The years of building quietly towards this. A cup, eventually, with space in it.

A mother whose children are nearly grown sees the season differently. She has the softness of hindsight, and a clearer sense of which of her own worries turned out to matter and which did not. When Sam writes that you only have your children for a season, she is writing from the other side of it. This line settles differently when someone has traveled the path.

A Cup With is a series on Cup & Weekend where I ask mothers who are building lives outside the template about what they carry, what they’ve made, and what’s in their cup. These conversations happen over text and emails, sometimes over coffee, and always between an errand run or two. If you’d like to follow along, subscribe below.

🍵 “More from A Cup With” ☕

In our conversation, the lamp came across as a record. A way of saying: you arrived, and you changed how we see light. Their studio is a way to keep their hands moving, and to stay connected to the part of themselves that needs to bring concepts to life.

Xinnie calls herself a recovering workaholic. When the kids came, saying no to projects got easier. She still has the late-night calls sometimes, and she still feels guilty when her daughter walks up and asks if she can help so they can play. But the direction of travel is clear: she is showing up for family.

What follows is our conversation.

Who you are

Tell us a little about yourself: your work, your family, and where you are right now in both.

I’m Xinnie and I’m an illustrative designer. I come from a big family, have my own little family now and it’s been a journey of rediscovering myself as both a human and a parent.

How old are your child or children, and who is the primary caregiver at home?

They are 4 and 2, my husband and I both care for them while they aren’t in infant care. We’re also grateful for grandparents and our siblings who help us create a loving environment for them when we have our hands full.

How you think

Was there one thing that made you change after becoming a parent?

Learning to regulate my own emotional needs.

Alot of parenting now runs on what’s out there, the latest parenting hack, advice, pedagogy. These are great but when you’re parenting your kid, you’re actually re-connecting with your inner child and unresolved issues as well.

It’s not easy to face but being honest with myself on certain issues has helped me to confront them and show up as a more whole and authentic person to my kids.

Was there a moment after having children when you looked at your career and thought, this needs to change? What happened next?

Yes, I am a recovering workaholic! My brain is always thinking about something life or work-related and when my kids came along, suddenly it was easier to say no to things, turn down projects that I knew would be draining my time away from them. I am still learning how to prioritise things, but balancing career/work with kids means something’s gotta give, and I’d rather give up certain aspects of my career in order to show up for them more.

Tell me about a moment when you felt the tension between work and being present most acutely. Not the general feeling, but a specific moment you still think about.

I was having a late night call and my daughter came up to ask if she could help me at work so I can play with her.

Those meetings don’t happen very often but still I felt really bad.

How has your parenting philosophy evolved, with age, with experience, or as your family has grown?

I don’t think it’s been that long enough to evolve but my husband and I often discuss how to better meet our kids’ needs and be present with them.

What is the one generational pattern you are consciously trying to undo?

Using shame or taking away of privileges as a form of getting them to comply.

What you built

Tell me about what you built (in the context of your career). What made you choose this, and not something else?

My husband and I run a design studio of sorts together, as a way to still carve out time for our passion projects and doing what we love which is to create and bring our concepts to life.

We both come from an Industrial Design background, so it’s a natural course to still want to build something and explore different mediums.

Is there something in what you built that you made specifically for your child or children, whether they know it yet or not?

We didn’t build anything specifically for them, but we did make a lamp inspired by my son when he was born.

When your child or children are old enough to look back at the choices you made, what do you hope they take from it?

I hope they learn how to take chances, but also have wisdom to seek advice from those from different walks of life.

Singapore specifically

Raising children in Singapore comes with its own particular pressures. What is one thing you wish you had given yourself more permission to do?

That’s a tough one (only choosing one thing). I wish I had stood my ground in my wish to go abroad to live and study in my formative years. I’m too much of a scaredy-cat now!

What you have learned

What has your child or children taught you that no colleague, mentor, or book ever did?

To “just do it lah.” They’re just so unabashed and go with the flow. Mistake, what mistake?

What is one thing you do to teach your child or children to be kind?

To do unto others what you’d wish was done to you. Gentle hands and words reflect a gentle heart for others as well.

What is one piece of advice you wish someone had shared with you earlier in this season of life?

That life is going to be hard but it’s going to be ok too.

And finally

What do you cook when you want to show your child or children you love them? Recipes welcome.

Cheese toast.

What is one thing in your bag you never fail to have on hand when you bring your child or children out?

Myself! And of course my phone (to navigate, pay for meals, show them photos of past memories).

If you had one hour to yourself this week, what would you do with it?

Go to a very quiet cafe, drink good coffee and read/sketch.

And finally, what is in your cup right now?

Thinking how to fill their cup.

What I love about Xinnie's answers is how unvarnished they are.

“That life is going to be hard but it’s going to be ok too.”

“Just do it lah.”

“Gentle hands and words reflect a gentle heart for others as well.”

She made a lamp inspired by her son. Not for him, inspired by him. I wonder if more of parenting is like that than we admit. Not just building things for our kids, but letting their arrival rearrange the things we were already making.

A Cup With is a series on Cup & Weekend where I ask mothers who are building lives outside the template about what they carry, what they’ve made, and what’s in their cup. These conversations happen over text and emails, sometimes over coffee, and always between an errand run or two. If you’d like to follow along, subscribe below.

🍵 “More from A Cup With” ☕

Entering Wei Ting’s home, you’d spot a coffee corner. For someone like me, whose utilitarian tastes meant that coffee was just at best a Nespresso machine (it still is!), her coffee corner was a revelation, a proper espresso machine with nice glasses and cups, all neatly arranged. Of course, we all wanted to have a nice cuppa.

Wei Ting was on my team at Entrepreneurs First, where we worked on scaling our growth during COVID. During the Covid period of 8-person meeting limits, our team would assemble at each other’s homes while dialing into Zoom. Wei Ting generously opened her doors a few times and I would recall how her eyes lit up as she walked us through her kitchen, pointing things out the way someone does when the space is genuinely theirs and they have thought about every part of it. The living room was spacious in a way that felt deliberate, a home designed to be lived in by every member of the family. I remember thinking that the care she put into that space said something about how she sees the world.

When Wei Ting later told me she was thinking of striking out on her own, building a business around children’s products, I felt excited for her. It felt like a courageous and natural next step, one that spoke directly to her strengths and also her stage in life. I’d like to believe that as a mother myself, I acutely felt her own tension of balancing career and motherhood.

Reading her responses to these questions, what stayed with me was her answer about the weight of words. She wrote about growing up with labels that stuck quietly and shaped how she saw herself. And when she describes the work she is doing now, with her own children, to focus on guiding behaviour rather than defining who they are, it is a slow, deliberate redirection, and I think that is harder than a clean rupture. You have to keep choosing it, day after day, in the small moments when the old words are right there.

This is the first conversation in a series called A Cup With, where I sit down (usually over text, sometimes over coffee, always between someone’s school run and someone else’s nap window) with mothers who are building lives and work that look nothing like what they left behind. Wei Ting is the right person to begin with. She builds from what is real and in front of her, from her children’s enthusiasms, from the materials of her actual life.

I will let her tell you the rest.

Who she is

Tell us a little about yourself: your work, your family, and where you are right now in both.

I run a small kids’ e-commerce store where I curate and design products for children and families. Alongside that, I’m also a content creator, sharing snippets of family life, kids’ meals, and little things that make everyday life easier.

I’m a mum of two young kids, 7 and 3. I’m the primary caregiver, but my husband is very involved too. Right now I’m focusing more on them, with one transitioning into primary school and the other still very little, while juggling work that I genuinely enjoy and that also brings in some side income.

How she thinks

Was there one thing that made you change after becoming a parent?

My priorities shifted. I no longer dwell on trivial things or unnecessary concerns. My kids’ wellbeing comes first.

Was there a moment after having children when you looked at your career and thought, this needs to change? What happened next?

I realised I didn’t want a career that constantly pulled me away from my kids or made me feel like I had to choose between the two.

That was what pushed me to build something of my own. I wanted flexibility, and also something I enjoy and find meaningful.

Tell me about a moment when you felt the tension between work and being present most acutely. Not the general feeling, but a specific moment you still think about.

I remember during the COVID lockdown, I was working from home while my one-year-old was playing nearby. At one point, he pulled on the wooden playpen and it fell on him. He was okay, but I felt a deep sense of guilt.

How has your parenting philosophy evolved, with age, with experience, or as your family has grown?

With my first child, I did a lot of research, reading books, joining parenting groups, and trying to follow what I thought was the “right” way, from sleep training to BLW.

With my second, I’m much more relaxed. I’ve learned there isn’t just one way to raise a child, and it’s more important to tune in and respond to their cues.

What is the one generational pattern you are consciously trying to undo?

The pattern I’m consciously trying to undo is the way words were used to define me. Comments about my body, my character, my worth, often without realising the weight they carried.

Children absorb everything. Those words became the voice in my own head, shaping how I saw myself for years.

So with my child, I want to be intentional. I want them to feel valued for who they are, not how they look or what they achieve. When a child knows their worth isn’t conditional, they carry that confidence for life.

What she built

Tell me about what you built (in the context of your career). What made you choose this, and not something else?

I built a kids’ retail brand that really came from my own life as a mum. I was already searching for more sustainable options for my kids, and realised there was space to curate products that are fun, thoughtfully designed, and eco-friendly.

Along the way, I also built an online community. It started from creating content for my brand, and I realised I genuinely enjoyed it. I began sharing things that work for me, as well as things I personally find comforting or inspiring. I didn’t expect it, but people started to resonate with it and follow along.

I didn’t set out choosing this over something else. It was more of it’s what I genuinely enjoyed and kept coming back to.

Is there something in what you built that you made specifically for your child or children, whether they know it yet or not?

My online store is actually named after my son, Big Head haha. So in a way, it already started with him.

A lot of what I bring into the store or create is influenced by my kids: what they enjoy, what keeps them engaged, and what makes play more meaningful. We even developed our own bubble toys because he loved them so much, and it eventually became something we sold in the store.

When your child or children are old enough to look back at the choices you made, what do you hope they take from it?

That it’s okay to try different things and not be afraid of failing. I hope they see that you don’t always have to follow the usual path, it’s okay to do something different, and to figure things out along the way.

Singapore specifically

Raising children in Singapore comes with its own particular pressures. What is one thing you wish you had given yourself more permission to do?

To slow down and not feel like I have to optimise everything, enrichment, milestones, schedules. Kids don’t need a perfectly planned childhood.

What she has learned

What has your child or children taught you that no colleague, mentor, or book ever did?

Finding joy in small ordinary moments.

What is one thing you do to teach your child or children to be kind?

I try to model it, in how I speak to them, to others, and in small everyday situations.

What is one piece of advice you wish someone had shared with you earlier in this season of life?

To prioritise my own wellbeing. You can only truly pour into others when your own cup is full.

And finally

What do you cook when you want to show your child or children you love them?

ABC soup. It’s something my mum always made for us when we were kids, and her soups are unforgettable. I hope my kids will remember my soups the same way. It’s easy to put together, colourful, comforting, and nourishing.

What is one thing in your bag you never fail to have on hand when you bring your child or children out?

Snacks!

If you had one hour to yourself this week, what would you do with it?

I would go to a cafe to enjoy some pastries and a good cup of coffee.

And finally, what is in your cup right now?

Iced Matcha Latte.

I asked Wei Ting about generational patterns because I wanted to understand what she carries from her own childhood into the one she is building for her kids. Her answer is one I keep coming back to. The idea that words can stay with you and quietly shape how you see yourself is something most parents would recognise, if they sat with it long enough. What I find remarkable is the precision of her redirect. She is choosing, with her own kids, to guide behaviour rather than define who they are. That distinction sounds simple when you read it. Living it, in the tired hours when patience is thinnest, is another thing entirely.

The store, Big Head, is named after her son. The bubble toys that exist because he loved bubbles. Her home has a spacious living room. There is a consistency to how Wei Ting builds, and it starts with paying attention to what the people around her actually need.

I think that is what I keep finding in these conversations. Building and caring are not separate activities. They grow from the same place, and they look like each other if you know where to look.

A Cup With is a series on Cup & Weekend where I ask mothers who are building lives outside the template about what they carry, what they’ve made, and what’s in their cup. These conversations happen over text and emails, sometimes over coffee, and always between an errand run or two. If you'd like to follow along, subscribe below.

🍵 “More from A Cup With” ☕

And then I had children, and the hours didn’t multiply. They just started belonging to more people at once. My days had a choreography: I’d rush to pick up my then only son at 5pm, answer a “hey, have you got a minute?” call at five-thirty while standing at the edge of a playground with one eye on the slide and one hand pressing my earpiece into my ear trying to hear over the shrieking (and always hoping that when I unmuted I didn’t sound like I was in the most chaotic situation ever and deafening everyone’s eardrums). Dinner was fast and bath was faster. I’d hand reading duties to my husband and disappear into a string of back-to-back calls that ran until I couldn’t tell whether it was late evening or early morning. Some evenings we swapped: he had his US calls, and I was the one doing bedtime, reading Goodnight Moon while mentally running through the deck I hadn’t finished.

At some point, and I couldn’t tell you exactly when, I remember thinking: is this what life is? This wasn’t work-life integration, and it most certainly wasn’t work-life balance. This was the relentless demands of a high-performing role steamrolling over family time and everything else, and we were all just running fast enough to pretend we were managing.

I’ve been reading Teo You Yenn’s new book, Unease: Life in Singapore Families. An ethnographic study of the lives of ordinary, middle-class Singaporean families, the ones navigating enrichment schedules and mortgage payments and the silent arithmetic of how much is enough, sure feels like something that has been a long time coming. So much of the discourse in Singapore focuses on either the very top or the very bottom, and the vast anxious middle, the one most of us are living in, rarely gets examined with this kind of care.

There’s a passage early on that I haven’t been able to shake. She spent three years interviewing ninety-two parents in Singapore, asking them to describe their typical days, from the time they woke to the time they went to bed. What she noticed was that their speech often quickened as they ran through the lists, as if the time pressure of their lives had seeped into the way they talked about them. Wake up, prepare breakfast, wake children up, bring them to school, get dressed for work, commute, work, sneak in errands at lunchtime, back to work, commute home, pick children up from childcare or the parents’ place, go home if not already there, supervise homework, check and pack schoolbag, dishes, laundry, minor cleaning, social media, sleep. Repeat.

That breathlessness is the one that many parents live in day-to-day.

But the thing that really made my pause was what she found missing. In all those conversations about daily life, if she didn’t ask about it directly, leisure would not come up at all. Parents simply did not mention it. And when it did surface, it was almost never something separate from the children. Leisure, for most parents of young kids, meant going to the playground or the library or the mall. It meant doing something that interested the children, in a place designed for children. Adult non-work time gets folded into children’s play. One father listed everything he used to enjoy before he became a parent, the pool, the movies, going out with friends, and finished with something like: basically once you’re a responsible parent, everything stops. He said it very matter-of-factly, without a trace self-pity. It was pretty much expected as a trade-off.

Reading that, I found myself in a strange position. Because the truth is, I didn’t want to let everything stop. I’ve held onto my hobbies (albeit in a highly reduced capacity) with a stubbornness that sometimes borders on the absurd. I hiked through the Japanese countryside with Foolittle strapped to my chest at nine months old. I’ve brought Foolet on little sojourns to small towns in Japan where we spent entire afternoons doing nothing but visiting playgrounds and watching trains. I read, I cycle, I drag my family to museums. I am brimming with a thousand things I want to do and I squeeze them fiercely into days that sometimes run completely dry.

But I also know that this fierceness is itself a kind of resistance that the system doesn’t make easy. It takes planning and stubbornness and a certain financial margin. And I think about the parents in Teo You Yenn’s interviews who didn’t mention leisure at all, and I wonder whether the difference between us is really about personality, or whether it’s about the structural conditions that make it possible for some of us to hold on and impossible for others. Which is, again, maybe exactly her point.

There’s something else she found that I keep thinking about. Every parent she spoke to reached for the same rhetoric: family is the highest priority. It’s the instinctive answer, the one that feels true, and I believe them when they say it because I would say it too. But when she listened to how their days actually unfolded, the picture was more complicated. In practice, the demands of work ended up taking first place, not as a conscious decision but as a matter of habit and norm. Some talked about feeling guilt toward their colleagues and bosses on the weekends when they chose family over work. Guilt was flowing toward the office, not away from it. The night calls weren’t overtime but proof of commitment, and nobody talked about what they were giving up to be on them, because acknowledging the cost would have meant questioning the entire arrangement.

And underneath all of it, a discomforting hum that I think any parent in Singapore would recognise: you never really know if you’re doing enough, whether you’re making the right decisions, and whether your children will be okay in the long run. That’s the unease she’s naming, found in every calculation and every compromise.

Which brings her to money, and the way money and family are wrapped around each other so tightly you can’t pull them apart. Parents of children are always calculating: food, clothing, healthcare, enrichment, tuition, childcare, transport, mortgage, insurance. The list is relentless and it grows as children grow. When I decided to step away from full-time work, the cost wasn’t just the salary I was giving up in the moment. It was the compounding I’d lose over the years, the trajectory interrupted, the gap on the CV that would raise questions I’d have to answer carefully. The maths never quite resolves, because the variables keep changing.

Teo You Yenn has a term for what happens to women who shift their priorities toward caregiving. She calls it “folding down.” When mothers pivot, they don’t just reorganise their time and activities. They rearrange their worldviews and the value they place on different parts of themselves. Ambition, aspiration, curiosity, engagement with the world outside the family: these get made smaller, turned down in volume, to create space for the new version of who they’re becoming. In the process, they give up things they valued, including the autonomy and sense of worth that comes with wage work.

One of her interviewees, a finance analyst on a temporary break, put it in a way that made me laugh and then made me ache. She talked about how her colleagues discuss work while she can only contribute her expertise on which Daiso product is best for cleaning toilets. The worlds she moves between have shrunk and shifted, and she’s aware of the gap even as she’s living inside it.

What Teo You Yenn doesn’t quite get to, because her book is rightly focused on the structural diagnosis, is what happens after the folding. Or more precisely, what can happen if the circumstances allow it. Because for me, somewhere in the margins, in the scraps of time between feeds and school pickups and the long afternoons where Foolittle napped and Foolet was at school, I started building again.

I am absolutely terrified of my world and knowledge shrinking, which is why I choose the uncomfortable and difficult path of continuing to work, read and write, all while continuing to spend time with the children. Finding my way back to work on terms that bend around the life instead of demanding the life bend around them. It’s fractional, selective, and often squeezed into hours that don’t technically exist. But it’s mine, and it’s growing, and it doesn’t look like anything the system would recognise as a career.

When I walk past the many kids inside the enrichment centres, no windows, fluorescent lights, and the anxious parents milling outside, eyes glued to their phones, I ponder about something else Teo You Yenn found. The attention parents give to education is paradoxically deep yet narrow. Enrichment isn’t pursued as something valuable for its own sake, it’s a means to keep children afloat in the system. Children’s natural tendencies to dawdle, to daydream, to prefer play over structured work, these are treated as problems to be managed.

After spending enough time in technology, you start to notice that the qualities this system optimises for in children, discipline, predictability, the ability to perform well on standardised assessments, are becoming less and less differentiated in a world where AI can do all of those things faster and cheaper. The enrichment treadmill is preparing children, at enormous cost to families and to childhoods, for a version of the working world that may look very different by the time they step into it. And the things that might matter most in whatever comes next, the ability to sit with ambiguity, to make meaning out of noise, to create something that didn’t exist before, to think sideways, those are exactly what gets squeezed out when every hour is optimised.

Teo You Yenn asks: what kind of pro-family regime is this, really? What kind of pro-future regime is this? What happens to the ones who want to dance, or paint, or build strange things out of cardboard? A friend and I ended up talking about what it actually costs a family to go against the mainstream. Think about what it took for Joseph Schooling’s family to send him to the US to train, or Chloe Kim’s father leaving his job entirely to support her snowboarding career. These are extraordinary stories that required extraordinary financial sacrifice. Most middle-class families in Singapore don’t have that margin. The system prices out divergent dreams before a child even knows they have them. Teo You Yenn writes, in one of her most potent lines, that care cannot be designated as a realm outside the reach of market and state. She’s right. The dreams that survive are the ones the system already knows how to reward.

In an interview before the book’s release, Teo You Yenn said something that I keep coming back to:

“I hope, when people read it, they feel an ache. Parenting shouldn’t feel that way and childhood shouldn’t feel that way. That is one of the big costs of having society be structured the way it is.”

I felt that ache. I think I’ve been feeling it for years. It’s there in the five-thirty playground call with one eye on the slide, in the guilt that flows toward the office instead of away from it, in the fluorescent-lit enrichment centres I walk past every afternoon, in the quiet dread of not knowing whether I’m doing enough. It’s the feeling that something about all of this is off, even when you’re doing everything the system asks of you. Especially when you’re doing everything the system asks of you.

Teo You Yenn gets to something near the end of the book that I think about what unease means to me. She writes that a more equal society is one where the possibilities for flourishing lives are more evenly distributed, where workers in all types of jobs have time and money to do things they might like to do, to learn new things, start businesses, pursue leisure, spend time with people they care about. When I read that, I recognised the life I’m trying to build. And I also recognised that the fact it requires so much fight and so much margin tells us something about how far we are from the society she’s describing. The fierce protection of leisure, the building in the margins, the choosing of a different path for your children, these shouldn’t feel like acts of resistance. In a more equal society, they’d just be what life looks like.

Once in a while I’ll ask Foolet what he wants to be when he grows up. For the longest time the answer was fighter pilot, delivered with the conviction that only a six-year-old can muster. But recently, he told me he wants to be an engineer. When I asked why, he said it’s because he loves to build things.

Foolet wakes up at 7am on Saturday mornings and quietly assembles his solar-powered robot before anyone else is up. He folds paper planes by the dozens, and there was a stretch where he spent time watching the same YouTube video over and over, trying to produce a boomerang plane that would actually come back. It didn’t work, and it didn’t work, and it didn’t work, and then somewhere around the hundredth build, it did. Nobody told him to do any of this. Nobody scheduled it. He just wanted to make something fly and he kept going until it did.

He’s seven, so the career answer will probably change half a dozen more times before it matters. But I find myself hoping he holds onto the thing underneath it, the love of building for its own sake. Because the system Teo You Yenn describes in Unease is very good at taking that kind of love and narrowing it into something instrumental, turning “I build because I love it” into “I build because it’s a viable career path.” And maybe that narrowing is just what growing up looks like in a society that measures worth by output. But I’d like to think a good society would protect the first version for as long as possible.

He doesn’t know any of this, of course. He just wants to build things. And I hope he still does.

Over the coming weeks, I’ll be publishing a series of conversations called “A Cup With,” featuring mothers who are swimming against this current in their own quiet ways: building businesses around school pickups, choosing unconventional paths for their families, and figuring out what it looks like to want more from life without wanting less for their children. If Teo You Yenn’s book gave me the language for the ache, these women are showing me what it looks like to live with it honestly. The first conversation arrives on 4th May. I invite you to share my publication with more readers that might be inspired by these conversations.

We played football in the living room among things that could definitely break. We dragged a Garfield cushion to the top of the stairs and flung ourselves off them, seeing who could drift furthest down the landing. My mother, who probably heard the commotion, definitely knew and wisely chose not to look.

Foolet has recently discovered that Brazilian jiu-jitsu is basically wrestling with rules, which he finds enormously appealing. Foolittle is eighteen months and at a stage where his entire body is a hypothesis he is constantly testing against the nearest available surface, which is usually his father or brother. Most weekends we are out, moving, loud. I have become, by necessity, a mother who plans around motion.

Stuart Brown, who spent years researching play, found that rough-and-tumble play builds something that quieter play doesn’t quite reach: the capacity to hold aggression and affection at the same time, to read when things have tipped from fun into too much, to stay in the discomfort of someone pushing back and not immediately collapse or retaliate1. There’s a social intelligence that gets built in the tumble of it. Which to me, sounds like a tidy way of explaining something I mostly experience as two children ricocheting off every surface of my home on a Saturday morning. (The doorframe of my bedroom has opinions about this. So does the fan.)

I am also a person of contradictions. I am constitutionally, the kind of person who owns crochet hooks and has strong feelings about yarn weight. I am also someone who would happily play Civ V from Friday to Sunday without leaving the home. That gamer version of me has been on hold for a good many years (Yes PM Lawrence Wong, I heed your call on less screen time!)

But growing up with two brothers, I didn’t grow up thinking the roughhousing was off-limits for me; it just was, the way siblings are, physical and loud and without much ceremony. Even the quieter moments with my brothers weren’t quite quiet. Sitting down with my eldest brother to watch TV meant hours of skateboarding and snowboarding videos, the camera following someone down a half-pipe or off a ledge, both of us leaning slightly forward as if we might fall with them. Rest, in our house, looked a lot like watching motion.

So maybe I came into this more prepared than I realised. When Foolet started BJJ, I didn’t flinch at the part where children are taught to fall properly, not brace, not flinch, just let the fall happen and roll through it and come back up. His coach had him do it over and over and he laughed and found it fun. To me, this is how you learn what your body can take, and build the confidence to try something that might not go well and get up anyway. Stuart Brown calls it the capacity to stay in the discomfort of someone pushing back, but what I was watching was just Foolet, at seven, finding out that falling isn’t the end of the thing.

That’s what the roughhousing is doing, underneath all the noise. Teaching them that their bodies are capable, that aggression and affection can live in the same moment, that you can crash into someone, really crash into them, and still come out okay on the other side.

My own body has been teaching me similar things, more slowly and with less crashing. Years of yoga will do that, if you pay attention. I discovered at some point that my left leg is significantly more developed than my right, that all those years of unconscious compensation had created an imbalance I hadn’t noticed because nothing had asked me to notice it. Warrior Three on the right side made it impossible to ignore. Your body accumulates a history, and it takes something that demands real balance to show you what’s actually there (or not there for that matter).

I think about this when I watch Foolet fall and get back up at BJJ, and when Foolittle uses his whole body to communicate something he doesn’t have words for yet. In all this noise and motion and physical negotiation comes the capacity to know what they’re feeling by what their body is doing, and eventually, to use movement as a way back to themselves when things get hard. To go for a run when the feelings won’t organise themselves into thoughts. To know that the body can metabolise what the mind can’t yet process.

There is a statistic that stays with me: children today spend less time in unstructured outdoor play than any previous generation, and the age at which they stop playing outside altogether keeps dropping. I think about this sometimes when I watch Foolet and his friends tear around the estate in the evening, excited, loud and completely absorbed. I hope they are among the ones who don't stop. I hope the habit gets into their bones early enough that it becomes something they return to rather than something they grow out of.

It won’t look like this forever. The ricocheting off doorframes will give way to something more intentional as they get older. Skateboards might get traded for keyboards. But the relationship with motion, with using the body as a tool for regulation rather than just a vehicle for getting through the day, that’s what I’m hoping takes root now, in these loud, chaotic, cushion-flinging years.

Maybe this is what it means to be a mother of boys whose bodies are always slightly ahead of their words: you stop trying to be the still point in all of it, and you become something more like a fellow traveller. Someone who already knows, from a long time ago, that the cushions need to come off the stairs eventually.

I know this because I’m inside that gap.

After I had my second child, I stepped away from work to be the primary caregiver for my kids. I had already started fractional work a few years ago, finding the work that fit my life, the ones that could bend around school pickups and fevers and the general unpredictability of small children. But while I rebuilt my career and myself, there was something nagging at the back of my head.

It was only natural that I wanted to find others who traveled the same path. Maybe it was for reassurance, that I wasn’t crazy to choose this. Instead, I found that I rarely read about mothers going fractional, and for mothers that rebuilt themselves and built businesses, the messy middle was glossed over. I wanted to read about mothers who had stepped away and come back on different terms. The version with the doubt still in it, the four-year pause. I wanted the version where the woman is still figuring it out and building anyway (because we’re strong and tenacious!).

The pieces I found had been polished into something aspirational, which made them harder to trust and harder to learn from. The mess had been edited out, but the mess was the part I needed to see.

At the same time, I also received many well-intentioned questions, “so when are you going back full-time?” As if my life is measured in productivity and contribution to society. As if after childbirth, it’s back to status quo. Any parent that has gone through it knows it changes you irrevocably, right down to identity. And yet the expectation is that you come back the same.

So I started asking women directly. I wanted to know what happened when mothers build their work around their lives. The meaningful work that happened between someone’s school run and someone else’s nap window.

In my conversations, I saw new shoots that grew. One built a business from the materials of her life. Another lost her job and instead rebuilt a new business on her own terms. And another continued to lean into her passions, moulding her life gently around her family. For many, I learnt about how they build clarity inside a life that seemed to be rearranging itself around the needs of others. It’s about holding onto the thread of what you’re building when your whole day folds in on itself and the thing you were working on has to wait another week. And that’s where most of it lives.

Building in the margins is not easy, and the hardest part, for me at least, was the professional isolation. The infrastructure for community is built for a different life. Meetups are in the evenings (bedtime). Conferences are on weekdays (school). Networking events assume you can turn up at 7pm, which is exactly when you’re negotiating pyjamas and reading one more chapter of the same book for the eleventh night running. You lose the shorthand. You lose the casual “how’s your project going” that used to happen in an office kitchen. Even coffee with a friend falls apart when your kid wakes up with a fever and your whole day rearranges itself around a thermometer. And yet these women keep deciding, over and over again, that what they’re building is worth continuing. That’s the part that gets me.

What I’ve found, now that I’ve been asking, is that the women inside this gap are already building. Quietly, stubbornly, from living room floors and kitchen tables, between drop-off and laundry and the eleventh reading of the same bedtime book. And when you ask them about it, they describe it as being almost surprising. As if the building happened while they were paying attention to something else.

That’s what I want to make visible. The thing that’s already happening, in the lives of women who are doing it without a stage to tell it from. That was enough to keep going. And enough to start asking.

I’m still working on it, so I can’t share more than what I have already, but I hope you’ll continue with me as I explore life outside the salaried 9 to 6.

There is an HDB block near Foolet’s school that is numbered 67. I noticed it for a few weeks, and then one afternoon, walking him home, I casually mentioned that the block across the overhead bridge was Block 67. He stopped and looked at me before bursting out, “sixxxxxxxx seeeeeven~”, before calmly informing me that he was well aware, thank you very much, and how was I so late to the party? In a short span of time, I went from hopeful connection to being crushed, yes, it is really hard to be cool in front of your child.

If you don’t have a child between the ages of six and ten, 67 requires some explanation, and even with explanation it resists full translation. It is a number that became funny on the internet, absorbed into what people call brainrot humor — the aesthetic of deliberate nonsense elevated to in-group currency. The joke is not really the number. The joke is knowing that the number is the joke. Us fellow parents figured it out by asking each other and checking the biggest meme folder, ie the Internet. Because asking our children what 67 meant would be destroying any remaining self-respect they had for us (if we even had any left!)

I’ve realised that while being funny helps considerably, parenting a child’s humour requires you to learn the system well enough to play inside it with them.

Foolet is not, strictly speaking, a humorous kid in the way I used to imagine funny children to be. He does not perform. He does not do voices. What he likes is Mark Rober, who is enormously satisfying to watch because every video is a mechanism behaving exactly as planned, or more usually, slightly more spectacularly than planned. He likes science kits and magic sets, the same instinct in a different box. He likes riddles, knock knock jokes, and the humour found in Dog Man and Diary of a Wimpy Kid. We also play a guessing game together — one of us thinks of an object, anywhere in the world, and the other has to find it through questions alone. It can go on for a very long time.

I spent some time wondering what these things had in common before I realised the thread was obvious. They are all systems with a reveal built in. The riddle has a correct answer. The magic trick has a mechanism. Mark Rober’s big truck obstacle course often ends explosively. Dog Man’s plots have internal logic even when absurd. The humour comes from the gap between what you expect the system to do and what it actually does. Foolet is not looking for randomness. He is looking for a specific kind of surprise, the kind that retrospectively makes sense.

Growing up, Conan O’Brien always made sense to me, even when I couldn’t have articulated why. The Clueless Gamer sketches work because Conan is genuinely, horrendously bad at video games and finds this completely hilarious. He is not performing incompetence. He is actually incompetent, and his willingness to be so, loudly, in front of cameras, is what makes it funny. His trip to South Korea with Steven Yeun might be the purest version of this, two people being conspicuously foreign and finding it wonderful rather than mortifying. Humour as a way of being a stranger somewhere, gracefully.

(Of course, Conan traveling all the way to film a kpop video with TWICE when years later other late night hosts were just feeling their way around the kpop music scene…hilarious.)

Children respond to this immediately because they live in incompetence. They are new at most things. An adult who can be bad at something and laugh about it without embarrassment is communicating something important. Something like: this is allowed. Being in the middle of figuring something out is a fine place to be.

Mr Bean is perhaps the most extreme version of this principle. Fourteen episodes, which almost nobody believes when they first hear it. It felt like a whole childhood’s worth because each episode was so completely committed, so densely itself, that memory expanded it the way you expand things that mattered. No dialogue, no cultural interpretation, just a man being aggressively, inconveniently himself in situations that don’t quite have room for him. He was found in hospital waiting rooms in Singapore, and in living rooms where none of the older folks spoke English once upon a time. The joke required nothing except watching someone refuse to behave normally, with complete conviction.

And yet some of the most remembered moments in comedy come from exactly the opposite position, the performance that couldn’t hold. SNL built an entire mythology around this. The sketches people remember aren’t always the ones that landed cleanly. They’re the ones where Ryan Gosling or Harry Styles keeps losing it, you saw the cast dissolved in laughter before the punchline, where the joke escaped the person telling it. Breaking character at SNL isn’t treated as failure. It’s celebrated. The curtain doesn’t just part, it falls completely, and the audience cheers.

What both things share is contact with something real. The fully committed performance and the one that breaks open are two different paths to the same place.

Foolet understands this intuitively, which is probably why he gravitates toward the reveal in all its forms. The magic trick whose mechanism becomes visible. The riddle whose answer was hiding in plain sight. The SNL cast losing it because the joke got to them first. He is not just watching the joke. He is watching for the moment when something real escapes.

My parents’ generation had a complicated relationship with this kind of humour. Slapstick read as low, as embarrassing, something to be tolerated in children and quietly grown out of. Wit was acceptable. Wordplay was acceptable. Physical comedy and dialect humour occupied a different register, one that polite company acknowledged without quite endorsing.

Singapore has always had this tension with its own humour. Liang Po Po, Kumar, Under One Roof, the whole ecosystem of Singaporean comedy that found its audience anyway, through television sets in living rooms, through community centres, through the specific recognition that happens when someone is being funny in your actual idiom. The establishment was never quite sure what to do with any of it.

And then there is Phua Chu Kang, the most memorable example I can recall. Crass, broad, lampooned cheerfully from Singapore to JB, built from everything aspirational Singapore kept at a careful distance. The yellow boots. The syntax. The gleeful refusal to be respectable. When HPB needed to reach people during Covid, they called him. Because he had done what polished official communication almost never manages: lodged himself somewhere real in people’s memories. You cannot manufacture that. You can only earn it by being fully yourself, even when yourself is a man in yellow boots.

Children are natural connoisseurs of commitment. They can tell, with an accuracy I find slightly unnerving, when an adult is performing silliness versus actually inhabiting it. When I drop 67 into conversation and mean it, when I engage fully with the guessing game rather than running a background thread of my own thoughts while technically playing, something shifts. We are inside the same system together. That is different from tolerating the system while waiting to redirect him toward something more improving.

This is what my parents’ generation sometimes missed. Not because they were wrong exactly, but because the instinct to elevate — to pull children up toward what counted as serious — can crowd out the other instinct. The one that says: go to where they are. See what they see. Mean it.

Foolet has no idea that I clocked that HDB block weeks before I said anything. That I filed it away for the right moment. That it felt like a minor act of translation, one system to another, a small piece of evidence that I am paying attention to what makes him laugh and why.

He just knows I said 67 and he stopped and looked at me, before reminding me exactly how late I was. Still. That brief spark of recognition, before the roasting began, was enough.

A week ago, I joined another mothers’ walk along the Rail Corridor from Hillview to Ulu Pandan. 7km of greenery, movement, and conversation. But this time, Foolittle was not on my chest. He was at school, learning to pay attention, to socialise, to exist in a room without me. And I was on a trail, arms swinging free, learning something similar.

There is a particular kind of lightness that comes when a weight you have carried for years lifts. It is not the lightness of relief, exactly. It is more uncertain than that. You have held the shape of something for so long that when it goes, you feel the outline it leaves behind. Your arms remember, and your centre of gravity has not caught up.

I kept reaching for him subconsciously in the small adjustments. Hugging my front and then remembering his solid weight was not there, not being able to stand still but instead, gently swaying side to side. The body remembers a task longer than the task requires it to, and I think that is its own kind of tenderness.

We introduced ourselves in pairs and threes as we walked.

Many of the women had never done this stretch of the Rail Corridor before. When it was my turn, I mentioned walking parts of it more than ten years ago. Back then, I was training with the intention of summiting Mount Fuji and Mount Kinabalu. Since the topic of the upcoming school holidays came up, I mentioned solo trips I had taken with my children.

One woman said she had never met someone who had actually done solo trips with young children and had questions about why I did it. I appreciated their curiosity. But I could eventually feel the conversation reaching a natural wall, the point where interest becomes something closer to anthropology, and I found myself editing down, making the trips sound smaller than they were.

Another exhale, and a slight shift in the air before conversation returned to familiar ground. School closures. Calendar coordination. The difficulty of aligning children’s schedules with spouses’ work.

I have felt this before.

I have felt this most of my life.

I have rarely fit neatly into whatever template was dominant in the room. In tech, it was trying to find my voice in a room dominated by men, many 15-20 years ahead of me. In motherhood, I still talk about mountains. I orbit many groups, and in most of them I am adjacent. A little off-centre. Present, but angled.

Even here, in a self-selected group of women who had chosen green, I was still slightly to one side. The forest does not automatically gather your people.

Most of the women came from the public sector or were running their own businesses. Many had stepped back during their caregiving years. The hours alone filter who can come, because a Friday morning walk at 9am narrows the field by default. I only met two ladies who came from places where I was close enough to recognise the pace, but different enough to confirm the distance.

As I fill my plate with work once more, the strange thing is how easy it feels. The shift back into that mode is almost pleasurable, like discovering you can still read in a language you thought you had forgotten. The words come back. The syntax is yours, has always been yours, and you feel it return not with effort but with recognition. The pleasure of a fast problem, of thinking alongside adults, of being myself in a room rather than only someone’s mother.

What catches me off guard is the other direction. The session ends, and I have forty minutes before pickup, and I cannot quite find the gear that takes me from strategy and timelines back to “shoot, we’re late.” It is not that the work is hard to enter. It is that the work is hard to leave. The mind wants to keep going, and instead you are cutting grapes in half and answering questions about why birds have different-shaped beaks.

Foolet asked why I am back at work.

“Well, I get to earn money,” I said. “And I enjoy it.” (He’s currently a bit more conscious about money since he’s been counting his red packet money and thinking how he can persuade me to let him buy something he likes with a portion of it.)

“I remember your old office. I liked labeling things.”

“You were a great help.”

“But Daddy’s office is nicer.”

I am reminded that my children are watching this transition too. They are forming their own understanding of what it means that I am slowly becoming a little more mine again.

Full-time is not possible right now. This is still a caregiving season, with its own shape and demands. My current work fits because it bends around pickups and decompression hours and the emotional weather of the household. Nothing gets handed back when you return to work as a primary caregiver. You quietly add.

I think about adjacency more than I used to.

It is not the same as loneliness, though they share a border. Loneliness is the absence of connection. Adjacency is connection at a slight angle. You are there, you are in the room, you are part of the conversation, but your centre of gravity sits somewhere the group does not quite reach. You participate genuinely and still head home feeling like you spent the morning standing one step to the left.

The world I spent a lot of time in before does not naturally produce people who spend their mornings walking slowly through green. It produces runners tracking splits. And the world I am in now, of caregiving mothers finding their way back, does not quite know what to do with someone who once trained for altitude.

It’s difficult to fully share a transition that others have not taken the same shape of. You find companionship in pieces, in temperament rather than demographic, in the occasional person who has also measured their life in trails and the particular solitude of going against the grain.

They are fewer, and more dispersed. But they exist. And you find them the way you find anything real, slowly, without a map, one honest conversation at a time.

There is something about walking that makes all of this lighter. It does not resolve it completely, but I end up carrying it differently. Maybe it is the rhythm, or maybe it is that the forest does not require explanation. You are either there or you are not, and it does not ask you to account for the distance between where you stand and where the group expects you to be.

I keep returning to komorebi. Light does not force its way through leaves. It finds the gaps, the spaces that have opened, that were not there before. It does not mourn the closed places. It just moves toward whatever is available.

Foolittle is finding his gaps at school. I am finding mine on Friday mornings, in work calls, in essays written at the edges of the day. Foolet is watching all of it, forming conclusions I will not know about for years.

I used to wonder if adjacency was something to solve, a problem of fit. Maybe it is just what happens when you have spent your life not quite on the beaten path. Not lost, not wandering, just walking to the beat of your own drum.

The gaps may keep changing, but the light is patient.

Have you been in a season of recalibration? I would love to hear where you have been finding your people.

I recently read an article about AI porting SimCity in four days without reading the code. It made me wonder: could I build a game?

I’ve always loved the old Sierra Online and LucasArts adventures. Loom, Day of the Tentacle (and tons more). The kind of point-and-click logic where combining a rubber chicken with a pulley is somehow correct. The magic you felt hearing the low humming sounds of Loom’s gameplay on your Creative speakers for the first time. So if I was going to try, it had to be something my son would actually want to play. Something we could finish in fifteen focused minutes.

Then the angle clicked: science experiments. He’s a huge Mark Rober fan. So I thought, can I go kaboom?

On the second morning of Chinese New Year, in between cooking lunch for the family and prepping for more visitations, I opened Claude and started describing what I wanted.

My Excel formulas and dated Objective-C knowledge were useless here. I didn’t write a single line of code. Everything happened through conversation.

Level One: The Cursed Island With Drainage Issues

Before going full kaboom, I started smaller. Squid Ink Isle was the proof of concept.

A cursed island. A grumpy toad named Gerald. Three spell-shards hidden across a haunted forest and pirate cove. The parent reads the story and clicks through choices. The child solves multiplication puzzles to unlock doors and break curses. Sierra Online meets the seven-times table.

From first prompt to deployed game took about four hours. The focused build time was closer to an hour, wedged between entertaining visiting relatives. I still re-read that in mild disbelief.

The workflow was simple. I described a scene. Claude wrote code. I said what was wrong. It fixed things. Back and forth, like collaborating with someone very fast, very literal, occasionally in need of the same instruction three times.

Gerald, for the record, has strong opinions about drainage policy. That part was mine.

Level Two: The Octopus With a Volcano Problem

The second game came from the confidence, possibly overconfidence, of the first working. This time: science.

An octopus in a lab coat accidentally blasts five Science Crystals across the neighbourhood with his Anything-O-Blaster. You visit four scientists to retrieve them. A lightning-enthusiastic Benjamin Franklin. A suspiciously familiar man in an orange bow tie who says “SO COOL!” about everything. A magnet-obsessed engineer who used to work at NASA. Newton, grumpy under a tree.

My son liked the Mike MagnetoRober reference immediately.

Each scientist has a quest. Find an item. Help with a problem. Answer two science questions woven into dialogue. Wrong answers trigger explanations in character. Right answers move the story forward.

And with ambition I guess, came the breaking of things.

Things I Learned While Breaking Everything

Describing what you want is the skill. “Make it more fun” got me nowhere. “Make it feel like a Day of the Tentacle screenshot, with portraits and speech bubbles” worked. “Give MagnetoRober the cadence of someone who genuinely believes magnets are the most exciting thing in the universe” produced dialogue better than I’d written myself. Vague got me vague. Specific got me Gerald.

Tone transfers surprisingly well. Cue irreverent humour. A doomsday device labelled “POINT AWAY FROM FACE (I mean it this time).” The AI wouldn’t just replicate it. It would riff. A chalkboard equation including a sandwich. A magnet engineer stuck to a fridge insisting “this is fine.” I didn’t feel like I was barking instructions with the precision of a drill sergeant. Instead, I felt like I was jamming with someone who shares your sense of humour.

You will break things. At one point, only four of five crystals were obtainable. The volcano required all five. The fifth was inside the volcano. A perfect deadlock. Claude didn’t catch it. I found it by playing through. Images loaded in preview but not deployment. Dialogue referenced renamed devices. The AI is the hands. The quality control is still yours.

Tools have opinions. Some of them are good. Lovable turns React code into live websites. I learned early to say explicitly: replace the entire contents of App.jsx, do not refactor. Left alone, it would helpfully reorganise things into breakage.

But once the game was deployed, Lovable surprised me. I could talk to it directly. “Add sound effects using the Web Audio API.” Done. Synthesised chimes for correct answers, buzzer for wrong ones, a dramatic rumble when you start the game. All procedurally generated, no audio files. “Add animated room illustrations using CSS or SVG.” Done. Professor Squiddleton’s lab got bubbling beakers and a glowing Anything-O-Blaster. The junkyard got floating spoons magnetically attracted to MagnetoRober. Newton’s orchard got apples falling on loop.

I also asked Lovable to playtest the game end-to-end. It clicked through every screen, every puzzle, every inventory interaction, and came back with a full test report. Crystal counters updating. Item dependencies working. Cross-location puzzle chains functioning. The kind of QA I might’ve have done systematically on my own, but with crossed eyes after an hour of playthrough.

Claude built the game. Lovable made it feel like one, right down to fixing a glitchy Mark Rober portrait illustration I’d been wrestling with.

Enter: The Eight-Year-Old UX Consultant

After dinner, I told my son he was going to try playing a game I created, a game about science. He was incredulous, but game.

No surprises, he got stuck immediately. Not on puzzles. On navigation. He didn’t know he needed to go back to the lab. He’d finish a puzzle and sit there, waiting.

You cannot catch this abstractly. You catch it by watching a child express his frustration, “what am I supposed to do next?”

These changes transformed the game. The next action button glows green. “Back to Lab” became “Back to other scientists.” Puzzle flow became automatic. Answer the first question, dialogue continues, second question appears, crystal earned, return to hub.

All of this came from him.

The penguin-toast bit got three repeat laughs. Dr Squiddleton powering things with lava was, apparently, peak comedy. He said it was pretty cool. That’s the only review that matters.

The Bill (Surprisingly Modest)

Roughly $10 in Claude Pro and Lovable credits. The real cost was attention. About six hours across two days. But the alternative would have cost more in money, time, or compromise.

I can BUIDL?

Something has shifted in what’s possible for people like me. A year ago, building a custom educational game meant learning to code, hiring someone, or settling for templates. Now I can describe what I want, iterate in conversation, and hand my child a link. In a day.

I use Claude and ChatGPT for actual work. Lovable too. Home optimisation, scheduling, content. But this was different. This was a labour of love that started with a simple question: can I build something fun?

It turns out the answer is yes. And the building was the fun part.

When I was six, I built houses out of cardboard boxes. Floor plans taped at improbable angles. I wrote stories about Egyptian pharaohs in lined exercise books, complete with invented hieroglyphs only I could decipher. If I wanted a world, I made it slowly. With glue. With a satay stick dipped into paint, because I knew pencils in ancient Egypt didn’t exist.

The world expanded at the speed of my hands. Now I can build worlds for my son by bedtime.

I do worry about how fast things happen nowadays though. Today’s speed is not neutral. It can remove the pause where imagination stretches. I do wonder what that does over years.

But I did pause between iterations.

As I edited the game, changing the button glow, fixing spelling, adjusting dialogue, my son watched. He saw the changes appear. He saw me describing what should happen next.

He looked at me and asked, in wonder, “You’re actually making this game for me?”

The magic wasn’t that it was fast or that I’m coding with the help of AI. In the chat box, he could see me make it happen over text.

When I built cardboard houses, I wasn’t consuming. I was directing. Choosing rooms. Deciding who lived there. Shaping a world to fit my imagination.

In my childhood, I built those worlds for myself. Now I can build them with him.

Directing, it turns out, is its own kind of making.

And before I knew it, Foolet and me are co-creating our own game. We’ve already got the prototype and he’s going to go down the journey of “bigger, better weapons”. Not bad, not bad at all.

Onto the Games…

Oh. My. Gooseberry. I made a game. Two, actually. For kids aged 7-9. About 15mins of gameplay with an adult.

Squid Ink Isle (for some simple maths)

Professor Squiddleton’s Magnificent Mess (for some slightly more advanced science)

Best on laptop or iPads, it’s a tad tiny for the phone since it’s pretty text heavy.

Here’s your schedule for today.
8:30am: School drop-off.
9:15am: F45.
11am: Call with client.
4:30pm: Pickup for swim class.

I didn’t open a calendar. I didn’t tap through three screens to check which kid had what. The information just arrived, like a quiet tap on the shoulder from someone who already knew what I needed.

A week ago, this same morning would have gone differently. I would have remembered, maybe, to check the family calendar while brushing my teeth. Or I would have forgotten entirely, and the swimming slot would have surfaced in my brain at 3:15pm in a flush of panic. The information was always there. I just had to go find it. And on most mornings, with two boys competing for every scrap of my attention, I wouldn’t have the bandwidth to look.

There’s a term for this. Push versus pull. Pull is when you go to the information. Open the app, navigate to the right screen, parse what’s relevant. Push is when the information comes to you. It’s a huge distinction. For anyone running on depleted reserves, the difference between push and pull is often the difference between a system that works and one that quietly collapses because nobody had the spare energy to go check.

This is not a new obsession for our household.

My husband and I have been chasing the frictionless household for the better part of fifteen years. Splitwise, BillPin, YNAB, spreadsheets, portfolio trackers. Shared grocery lists on Evernote, shared family calendars… the list went on and on. We were the kind of people who got excited about a budgeting app. I still remember the big ah-ha moment when we discovered YNAB aka You Need A Budget app. We tracked every dollar. We planned ahead. It was satisfying in the way that good systems are. You could feel the gears turning smoothly.

And then life changed shape.

By the time my second boy arrived, there came the kind of fullness that doesn’t leave room for spreadsheet maintenance (at least for me, my husband doggedly continued to stick to it). The system didn’t break dramatically for me. It just faded. I stopped opening the app and the spreadsheets went stale. The friction of maintaining the system, the pull it required from me every single day, no longer made sense in the broader scheme of things.

I think a lot of parents know this feeling especially. You build a good system. You believe in it. And then the system asks more of you than you can give, and quietly, without anyone announcing it, the system stops.

My husband, who has always been the one driving our household towards what I’d call operational elegance, took last weekend as a sprint1. He set up an AI assistant that automates a variety of household tasks including calendaring, reminders, and expense tracking. We’re still working through the kinks, still adjusting how it categorises things, still figuring out what to ask it and what to handle ourselves. But it’s running. And the fact that “still figuring it out” doesn’t feel stressful is part of the point. The cost of experimentation has dropped so low that imperfection is fine. You tinker on a Saturday, fix something the next day. The shift went from “too costly to try” to “easy enough to iterate.”

Now, when our kids’ school messages us through the school apps (yes, plural, even for one child gosh!), we take a screenshot and drop it into one of our messaging apps. It’s routed into calendars and reminders. When we buy things for the family, I take a photo of the receipt and send it there too. The bot reads it, categorises the expense, and populates our shared spreadsheet. I can ask: what’s coming up this week? And it tells me.

The killer app, really, is the conversation flow that comes with it. Every previous tool had its own logic you had to learn. YNAB had categories and reconciliation flows. Spreadsheets had formulas. The school apps each have their own navigation. But talking is something you already know how to do. That’s what I mean when I say it humanises the interaction. The bot doesn’t have a personality, but it now speaks your language instead of asking you to speak its. The interaction feels less like using software and more like asking someone who’s been paying attention.

And there’s something else worth noticing. Since the bot started pushing my schedule every morning, I’ve stopped checking the calendar myself. It’s convenient, but it means I’m placing trust in a system I didn’t fully build and don’t fully control. Some mornings the chat notification arrives and I think of HAL 9000. Except in our house it’s less “I’m sorry, Dave, I’m afraid I can’t do that” and more “I’m sorry, Yi Ning, I’m afraid you have a dental appointment at two.” The horror isn’t rogue AI. The horror is that it’s right and I forgot. That said, the kinks are real, a miscategorised expense here, a missed detail there, and the friction we removed was also, in its own way, a form of staying engaged with the details of your own life. That’s a trade-off worth noticing, even if it’s one I’d still make.

What’s disappearing isn’t the need for systems. It’s how much attention they require to keep running.

Perhaps we might want to frame all of this as a natural endpoint. A household that finally runs with minimal friction. But I think the more honest truth is that it’s just another iteration. We’ll tinker with Clawdia next weekend, and the weekend after that. Something will break and we’ll fix it. And on some Tuesday morning, the phone will buzz, and I’ll read my schedule, and I’ll think: we’re not done yet.

But we’re closer. Technology is catching up with life.

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