I loathe prediction markets.

For lots of rational reasons and one irrational one: I don’t like how they make me feel. They’re like a siren to my mind, calling to me with probabilities and odds. Subtle insights and unlocks at the edges where my brain craves voraciously consuming the knowable.

But the deeper me knows better. Because ultimately, these markets pray on an obsession with certainty. They push to spend more time in the land of bounded odds instead of the land of unbounded possibility.

And I hate that in less than two years they’ve become so widespread. Because they’re clever and seemingly “efficient” and of course: they make a lot of money.

But what worries me most: between prediction markets and AI, our lives are becoming dominated by probabilities. Which, by definition, exist within bounds and therefore, left unchecked, bind and tether our minds and our lives to boxes we don’t ultimately control.

parenthood is just anxietyhood.

We are vulnerable bodies of soft flesh and cosmically temporary existence. We are bred to hate uncertainty because usually, it means death.

Anxiety, logic, prediction, technology - all of it stems ultimately from our desire to know more, so that we might die less.

And yet. The great irony is that the more that I’ve used gadgets of certainty like wearable trackers or GPS or nanny cams, the less alive I feel.

The numbers and predictions and prognostications stand like a gauzy shield between the discomfort of living and a false cocoon of comfort.

No where has this been more apparent than my life as a parent.

It’s impossible to explain how much anxiety comes to reside in your body the moment you bring a whole human being forth. How, as soon as that helpless wriggling form is placed in your arms, the weight you carry far exceeds the mass of the baby.

There’s quote that says being parent is learning to live with a part of your heart walking outside of your body. I think it best explains how becoming a mother was a brutally torturous experience for me. Already an anxious personality, it so filled me with uncertainty that I founded not one, but three startups aimed at trying to lesson it, even by a bit.

Of course I can tell you I wanted to solve for childcare or the crushing and uneven load of family logistics. But if we’re going to be honest on these pages, I’ve since realized it was all to be able to exert some kind of control in the face of the uncontrollable.

For 15 years I’ve felt this tug of war. Wanting to bathe myself in certainty while knowing it doesn’t work that way. It’s why I refused to have our Poppy caregivers travel with nanny cams to bookings. Because I wanted to build a modern village where we had to trust each other, not an purely efficient marketplace to pick up a false sense of certainty.

Life in general, and parenthood in particular, are endless exercises in uncertainty than I thought it deceptive to cater to the base illusion of knowing.

learning to live with the unlivable.

Back to the prediction markets. That’s why I think they’re deceiving and cowardly, not clever. Praying on the pocketbooks of the masses under a guise of freeing local knowledge, when the data clearly shows it’s a small number of insiders doing the winning.

I equally loathe the rush to embrace them at every turn - just this morning I click the More menu to find a poetry block, and was greeted by a Prediction market option.

What does it do? I don’t know, and honestly, I don’t care to.

I realize that makes me judgey and not curious but in this case, I’m okay with that.

Because I can feel my anxious mind gravitating towards the logic and thin comfort of these figures. I can already feel the delicious oblivion of sinking into the rabbit hole of odds and data points.

Instead, I’m trying to do the opposite. I’m trying to sit with poetry that teaches me how to be an imperfect human with no real control over any of this.

So I’ll return to the Poetry block and share this. A provocation and not a prediction.

Because what do any of us really know?

And anyway, I’d rather spend my minutes in the stinging brine of the unknowing than the fickle warmth of the knowing.

I shouted “boba!” out into the house and immediately I had feet scampering towards me, eyes wide with delight - a rare unanimous agreement among siblings.

But as perfect as boba sounded, as I looked up all the boba shops within walking or biking distance - they were all closed for the holidays (ways the quaint boundaries of Canada still catches me off guard after the”anytime, anywhere” wild west of the US.)

The three of us sat on our front stoop, head in hands, a comically dejected picture of womp-womp, when S, in all of her 14 year old wisdom goes - we can take the bus!

We immediately hopped up, excited at the idea of an unknown adventure in our known hometown, and walked a block away to the bus stop J and I had been telling the girls would be the source of their preteen/teen freedom.

Still - I don’t think I had ridden a bus in Vancouver since undergrad, but honestly, how different could it be?

The bus stop listed the routes that stoped there - the 9 and the 14. Now just to figure out where these numbered paths actually led. Because neither of the girls have a phone I wanted to limit how much I also used mine - so I searched for a poster mapping the options but alas, only a number to text.

A quick exception for a route check on Google Maps showed us that the 14 would take us right to our favourite donut and ice cream shop, with the added bonus of Aritzia, a real plus for teen girls. And so five minutes later, when the number 14 unceremoniously pulled up, we excitedly got on.

I tapped my phone to pay the fare, but then I put my phone away - determined to do the rest of this adventure the way I’d be asking the girls to - without a device.

Quickly I remembered how much attention you need to pay to your surroundings when you’re riding a route the first couple of times and if you shun the safety blanket of your phone.

The bus didn’t list all the stops inside either, but we saw it sort of took a doglegged route from 10th Ave up to 4th Ave as it travelled east. I had the girls point out landmarks they knew to help them place themselves in the neighborhood as we passed places they knew.

I was surprised though: without a phone or GPS to be tethered to, I felt shockingly exposed and vulnerable - this feeling of not knowing, for certain.

It brought to mind this article I had just read called “G.P.S. and the Lost Art of Getting Lost”. It dug beautifully into the question of how our relationship to places and “knowing” have changed, the more we constantly rely on the constant data streams of devices like a GPS.

One sentence in particular has stayed with me:

Do we lose something when we no longer get lost?

This riding of a bus - so simple, so mundane. And yet. It felt alarmingly uncomfortable - existing in this liminal space of little unknowns.

In a city I know thoroughly with the literal worst that could happen being that we undershoot or overshoot our destination by a block or two.

But it felt so foreign - not constantly having a stream of exactness to tether my attention, and frankly, my responsibility, to.

Instead, I had to rely on me. My sense of where we were and my judgement of what to do. I’ve been slowly losing my ability to know a place, this place, on an instinctual level.

How can I teach my kids to know and trust themselves when I’ve ceded that myself? Bit by bit in the interest of convenience and “safety” and efficiency. It’s so easy to justify, especially when you’re with your kids, not wanting to deal with unexpected surprises.

But if we’re not willing to deal with surprises, then how do we grow through the unexpected? Don’t we doom ourselves to live in a box made over and over of what is expected?

If you ask me why we haven’t given our girls a phone and still won’t be, is that I believe, in my deepest heart of hearts, that until they know who they are and how they connect to the world, these swiss army devices of distraction and ease are too easy a crutch to escape the sheer discomfort of the world. And they encourage a false sense of constant knowing.

Instead of sitting in a cafe, alone and feeling awkward, forced to notice the little dramas of the day…

Instead of learning to live with the wonderings and doubts of the voices in one’s head…

Instead of learning to daydream the mundanity of life away - in those long stretches of time your body is required to be in a place but your mind wants to escape…

Instead of tuning your attention to your neighbours and cafes and community….

Instead of feeling how your body is feeling today…

… we can escape so easily to the comforts of our devices. To the allure of “knowing” without the discomfort of feeling.

I struggle everyday with how much I use GPS/health trackers/messages - devices intended to give us more ease and more data, but in my mind serve to separate us from the original data tracker - ourselves.

At least I had nearly 30 years to develop myself before being handed a smart phone. Thirty years to develop a sense of self to return to.

The girls are 11 and 14. They don’t know who they are and won’t for decades. This journey is only starting.

But only if we let it.

Hence the no phones. Not because they’re evil. But because they encourage a sort of orientation in the world that makes it hard to feel connected to yourself and to the people and the world around you.

And what they’re losing in digital connection, I have belief that building analogue connection will more than make up for.

Because a chance at knowing themselves - it’s the single most important thing I want my girls (but also every other young person I know) to develop over these treacherous but oh-so-formative middle/high school years.

A connection to, an intuition about, and a responsibility to, the world around them.

And a deep respect and thirst for a different kind of knowing - not the intellectual kind, but the gut, instinctual kind.

Because it's clear that the facts and the logic of the intellectual kind will be heavily supplied and subsidized by innovations borne of explicit data, like AI. But the gut. That's where things like discernment and taste and judgement spring from.

For my girls, how to teach it? And for me, how to return to it?

I've been trying to answer this for years and the only thread of an answer I’ve been able to arrive at is: a lot of inconvenience.

Like this bus. It makes no sense. We could have Ubered. Soon we'll be back to having a second car.

But as we sat on the bus and cackled at little observations and A, my youngest, classically fretted over when the precisely right time was to pull that line or push the button, I felt a freedom and a lightness. I didn’t have to worry about traffic or the way there. The expense was trivial. And I watched blocks go by as a logged the stops in my mind, relearning my city in a completely new way. I saw shops that I had never noticed before. I measured the paces of the distance we were traversing as a feeling as much as a knowing.

When we got to our stop we hopped out, all proud and excited - thrilled at this little achievement.

And when it came time to head back, I gleefully held out my transfer ticket so we didn’t have to pay again. Ridiculous delight in the idea of saving $3.50.

Ready to level up our challenge level, we decided to stop at the grocery store to pick up ingredients for dinner. I started to fret about the logistics of two kids, groceries and public transport, so when J texted to say he could pick us up on his way home, I was really tempted to say yes.

I've done the whole groceries on the bus thing in my youth and it's a level of inconvenience I feel okay with not fully embracing.

But again the girls surprised me. S sagely pointed out: We need to finish this adventure with the bus. And so I agreed, declining the offer of ease and we grabbed the rest of things for dinner - checking out and organizing the goods in equally balanced bags made for carrying.

Of course, in any hero’s journey, there’s the part of sobering reality where things go awry. Because of construction, the bus stop had been moved (of course it had) and I wan't quite sure how far away it was. But we had made our proverbial bed, there was nothing for it but to sleep in it, hauling our bags of eggs and bread and milk (why did we get the gallon??)

Kids are the most amazing thing though - if you let them, they have this infinite spirit of adventure and possibility. And so this was just all more adventure.

While I manically kept looking back to see if I could see the bus, ready to start sprinting, transfer in hand, the girls didn’t have this anxiety in their heads and so kept chattering and walking with the most casual "que sera, sera".

It made me realize just how low the stakes were here. It was a gorgeous sunny day in a super urban area. If we missed one bus, we'd catch the next. Or have J pick us up, or 20 other options. There was no reason for me to be so wound up about this. And yet. Most of my days are so tightly packed that I've made that my default. No breathing room. No room for mistakes or serendipity or life.

But with this slower option, we had no option. Like biking the girls to school - there can’t be speeding or frantic yelling to hurry up - we have to leave a certain time ahead and there’s only so fast you can pedal. You say hi to the neighbours and wave to the dog walkers because what else is there to do?

I realize it’s probably just me so wound up tightly, trying to control the world so closely, but it’s why these moments are so meaningful to me. They force me to see and really feel the big picture. To have faith in the universe, and more importantly, in me.

Of course we eventually found the bus stop. And the 14 inevitably came. And we had more lessons to learn - pushing the button too early and shouting out to the driver "next one!". And then at our stop, I waited patiently for the doors to open, just for the women behind us to kindly say "oh, you need to push the bar for it to open".

I laughed, embarrassed, and got off but we had a shared moment - this stranger and us. Her sharing a small kindness, us receiving it.

Of course, “knowing” which stop or how to exit would have made it all so much smoother. But also textureless.

So yeah, we rode the bus. And while we're lucky that soon we wont strictly have to, I've seen how much I want to.

It's freedom. But not the kind that I thought.

No matter how small and how mundane, riding the bus on this sunny day was a bit of rebellion. Of hurling myself into a little bit of the unknown. To invite serendipity into my days again.

And to teach my girls a lesson life used to just teach us, but that we now have to work at:

Not knowing isn’t all that bad. And sometimes that’s the only way to get the real knowing.

Look for what you notice
but no one else sees.

***

The ability to look deeply
is the root of creativity.
To see past the ordinary and mundane
and get to what might otherwise be invisible.

- The Creative Act: Rick Rubin

A couple weeks ago, we took a much needed vacation and landed at a friend of a friends's place in the south of Italy. I don’t know what I was expecting, but where we ended up wasn't it.

Rural as rural gets. Towns shuttered on Sunday and Monday so it felt like a ghost town and we had no choice but to go to the local Lidl to get groceries and cook dinner.

By the fourth morning I had finally settled into the slow rhythm of the land to really write.

***
Here, time doesn’t so much march as it flows, languidly. The thick air moves around us with a swish and a rumble. It’s taken a day or two, but now the chorus of the cicadas don’t grate at me but instead feel like a reassuring presence. The constant flies and wasps and other assorted insects don’t annoy, but rather feel like a part of the intricate tapestry we’ve been invited into.

Perhaps unsurprisingly, as soon as we got to the masseria, I immediately went to the book shelves and started scanning. My eyes fell upon Rick Rubin's The Creative Act. I felt both delight and a recognition. I had bought the book years and years ago when it came out and eagerly dove in. But force it as I might, it wasn’t the time for this book and I. I couldn’t hear the truths it was trying to tell me. So I placed it back on my bookshelf, in wait for when it might be time.

But this week? I've been carrying it around like a bible, a tarot, a blankie. Reading it both in order and also randomly opening it up to a passage and seeking its message.

The noticing. That's what I've been missing. My writing is about seeing the little things that often get missed, and yet I’ve been living my life at a speed and a frequency that doesn’t lend itself to good, careful, insightful noticing.

The kind you get where there are no phones. No screens. No schedules. But that's easy here, where everyone I know is asleep when I wake up, and I have until the late afternoon to live life languidly.

It's the perfect place to practice. In this 35 degree weather there is no moving quickly.

And so we siesta and we linger and we savour. All words that don’t usually have a place in my daily lexicon.

It's hard. Harder than it seems. To let go of the busywork of motion. To sit in the discomfort of true intention.

When you can't distract yourself through motion or consumption there is no place for all of those thoughts to go but up and out. To sweat them out.

I wonder if the heat is necessary to this process? To get good and hot and sweaty and just sit in it. Let the bugs swirl around. Let the hot wind make my hair dance and tickle my cheeks. Force me to endure all of the discomfort so that I an dip lower and lower in the the noticing.

Still until the creamy butterfly approaches haltingly, surely, questioningly, calmly.

See the wasp as it skims the surface of the pool trying to evade death by dehydration as it flirts with death by drowning.

And I can’t help but think: isn’t that true of all of us? Constantly flirting with a death of one sort or another?

Which make me then think: ensconced in all of the physical optimizations and comforts, I'm living a sterile, disconnected life that feels like a different kind of death. A sleep of my soul that precedes the sleep of my organs.

This place jolts me from that slumber. It's not comfortable. I don’t like this kind of heat. These bugs. This isolation. I've fought it for 3 days. But today. This morning, I've allowed a tentative truce.

This morning - this hot, sticky, still morning - I am noticing all the things I usually let fly past - the cactus in its pot, placed just so. The curve and speckled texture of the umbrella stand. The sweetness carried on the stingy breezes when they deign to blow.

I’ve sat still for so long that I’ve become a part of the landscape. The butterfly will land next to me. The fly will buzz and fly off.

I can see what the true work of noticing looks like. With a full bodied kind of listening as Mr. Rick Rubin speaks of. Feeling the vibrations of the cicadas in my chest, sensing the vastness of the blue sky with some part that lives inside of me.

Life. in other words. In the here and now.

It’s funny, the truths we run away from our whole lives but can’t escape.

The good ones don’t chase, but they also don’t abandon.

My relationship to writing is one of those truths.

I’m still not sure I consider myself a writer. The writing that brings me the most joy and meaning and flow I don’t do for public consumption, but rather for personal understanding. But being a founder complicates that. Especially in our age of “founder-led” comms.

And I’m thinking, maybe that’s when all the trouble started.

I. I am a writer.

Six years out from the terrifying first months of Covid, it all feels like a fever dream. Like: did we actually stay 6 feet away from each other and drop our kids off to school outside and hang masks from our rearview mirrors and isolate ourselves in our homes with only the made up rituals of zoom calls and weekly clapping to mark the time?

Yes, yes we did. I still feel the dissonance of those months. It was some of the hardest, but also some of the most intimate time I’ve spent with my kids and my husband. And through all that, I found myself turning inwards, with nowhere to put all the thoughts that would have otherwise gotten out through idle chitchat with friends and my team and strangers.

Needing a hobby to distract, I decided that I would invest more time in something that I’ve always wanted to do: being a Writer (note I didn’t saying: Writing).

And so I got a writing coach and I joined a writing group. I started penning essays.

I think they were pretty good.

There was just one problem: I never published them.

Why? I don’t know - I would write them and then share for feedback and the feedback would be good but then I would lose steam on wanting to spend the time necessary to properly edit. So it would languish in that unspace of possible and published.

But still I persisted - I figured that’s what being a writer was - penning pieces that gave some insight to my reader. And I just wasn’t good enough yet. As I moved more fully from my own blog to Substack, I felt the pressure to publish “something worthy of reading” mount even more.

I had never felt pressure around my writing. Vulnerability, release, joy. But never pressure. I didn’t know what I was doing wrong.

II. Maybe I’m not a writer.

My first writing was always for myself - in my journal. A deeply lonely kid, I had my books and my thoughts. But I needed them to go somewhere. Because I see now that I was actually not a quiet kid - just one with a lot of big thoughts and questions and no place to really ask and explore them.

So I built myself an outlet and taught myself how to reason through all the messy as I poured it onto a page.

I also learned that by voicing the worries and the anxieties, I could see them and render them less viscous.

My writing was a refuge. Simple the act of writing was meditative in a way that I was simply drawn to do.

But I also loved words - learning new ones, playing with unfamiliar ones. I loved learning them in other languages and forms, like sign language or code.

And I would look on reverently at Authors. People who had been so blessed as to have been asked to commit their insights to eternity within a book.

I see now that I was worshiping the wrong idols. The love was pure and true. The object was not.

III. Every hero’s journey needs a reckoning.

It's the hero finally admitting what they already half-knew and had organized their life around not-knowing.

I don’t do transitions well. I’d like to think I’m getting better, but I am at my core, an obsessive personality who needs a focal point. While I intellectually understand the wisdom of “taking time” between things, I struggle deeply with the reality of it. My skin feels itchy and my mind races and my body just sighs in resignation.

Purpose fuels my sails. And right now my sails have been hanging slack - a state I’ve learned is “being becalmed”.

I know I need to be patient. To really understand what direction this next chapter will go in. And to do that, I’ve needed to learn how to sit, dead in the water, and listen. And wait.

And it’s here that I found the thread that has always been with me. The one that I’ve realized I’ve been gripping just as strongly now at 46, as I did when I was 8.

I thought my thread was my mission for equity and for building. It’s not. It’s seeing the truth in what is, imagining what might be, and building a bridge that connects the two.

That’s the real thread that binds all that I’ve done before, and all that I hope to do in the future.

IV. Bearing witness.

Just the act of writing this piece has uncovered truths that I’ve not been able to see clearly.

What I know: I’ve been using my writing for the wrong thing for me - I’ve been trying to construct arguments and persuade. My writing is not how I do that. That’s conversations for me.

My writing is for resonance. For seeing everyday truths and pointing them out. My writing is for noticing. And bearing witness.

And for that, I don’t need to write for anyone else but me. But I publish because I think one of the most powerful things in the world is shared experience. Shared wisdom. Shared insight.

Sharing joys and sorrows and truths make them resonate in way that they never could, locked away inside.

So I publish. I don’t know if I’m a Writer or not.

I actually don’t care anymore, I realize.

But I do care if I’m sharing truths honestly and frequently enough. Not caring about the process or the result.

My only imperative:

Never let go of that thread.

Share 10,000 ways

This week, as I gear up to share the next chapter of 10,000 Ways, I’m going to share the posts that have most meaningful to me. Being a founder is a personal journey above all else, one where you meet your angels and your demons. And instead of battling them so hard, you have to learn to live with them. So what better place to start than this piece, ripped from my heart, a bit more than 4 years ago.

I’ve been thinking a lot about “kintsugi” over the past couple of days. It's the Japanese art of putting together broken shards of pottery -  only instead of using a clear glue, you use a lacquer dusted with gold. More than a form of art though, it's a philosophy - a way of viewing the world. It asks - what happens when we celebrate the piece’s history of imperfection, of brokenness, rather than try to "fix" or disguise or ignore it.

What’s more, it’s a recognition that this beauty and extraordinariness does not exist without the broken. That it is a fundamental part of the piece’s existence that must be celebrated equally as the “good stuff”. 

I wish this was how we thought about humans and particularly how we truly view mental health.

This week, when Naomi Osaka made the decision to pull out of the French Open, what we really saw was exactly how far we are from a kintsugi mindset.

We are a society that lives to idolize our heroes but we can’t stand to examine what forges the steel that lies beneath. We love to marvel at how she’s the highest paid athlete but we have no stomach for her possible fallibility; a people primed for consumption without caring about the price. 

Our heroes’ stories must be wholesome and whole. Cracks are always seen as weakness never as a history to more. A history of persistence and survival and that grit we all love to talk about.

We need to change that.

Because otherwise, we’re relying on empathy to do the heavy lifting in making mental health more widely acceptable and understood.  

But in the same way it's hard to understand physical pain or being drunk or altitude sickness unless you too have experienced it, it’s nearly impossible to really understand what a day trapped in the cold fog of anxiety feels like. Or how terrifying the utter lack of will in depression is like. And while I could wish for everyone to experience just one day of it, the truth is, I wouldn’t wish that on my worst enemy.

I say this as someone who otherwise would be considered all the admirable words –– accomplished, successful and the worst of them all–– happy. 

But I find myself desperate to make people understand: Very rarely is there beauty without the broken.

Almost 3 years ago to this day, I hit publish on a piece I was terrified to put out into the world. Because it made me feel weak and broken and damaged. It was the first time I put words to the Dementor-like fog that would engulf me for days and weeks but that I have learned how to become bigger than. I didn't want to open myself up to doubt and question and worst of all - pity. After all, all my life I've been taught to never appear "weak". 

But the world had just lost Kate Spade and Anthony Bordain and we were all talking in surfacey devastated terms that completely glossed over the devious efficacy of mental illnesses. 

"Oh how could she do this to her daughter?", or, "...but he had the best job in the world!". 

And today, we’re back at it, with Naomi Osaka’s decision to pull out of the French Open because of her mental health. Thankfully it’s not to talk about a death but a life that someone is trying desperately to save for herself. 

When she couldn't be more brave and clear and upfront about the demons she's battling, it seems all we can find ourselves talking about are the sponsorships she willingly took or the rules she understood she needed to abide by before coming. All rational, valid points if that’s actually what mattered. 

But those are matters of obligation and optimization. 

We’re talking about survival. 

Of waking up and constantly feeling threatened and under attack from all directions, and scariest of all, from within. 

And of course I can only speak to the ways that this shows up in my life, which is to say it could be completely different for others. But every morning, I wake up and test the waters of my thoughts. I reach a bit further and bolder to see if they shoot out in bold, colorful jets of confidence and creativity or if they get bounced back off of a dark forbidding wall, ricocheting around my brain, making me feel small and brittle. 

From there, I take stock of what must be done. If it’s a good day, I do everything I can to keep it like that. I limit alcohol, I try to be outside and active, I only surround myself with people that make me feel good about myself.

If it’s some degree of a challenging day then I go into protection mode. I push everything else out - meetings, plans, to-do’s and I go do what needs to be done. Often it's a hard workout. Sometimes it's a cafe and a book (the past year I've had to find other go-tos). Inch by inch - and I'm being quite literal here - it feels as grinding and as grueling to go inch by inch, I work to get myself back into the headspace I need to then do the rest of life - work and parenting and being. 

But other days it’s not enough. And it just gets worse. Every thought, every moment can be a threat, making it all worse until it threatens to consume me completely. 

On those days I can’t do anything but try to survive. I’ll make excuses to my team. I’ll cancel meetings I’ve been looking forward to for days. Not in a self preservation way. In a destructive - "I’m a failure, why would anyone want to talk to me or work with me or even be around me" kind of way. 

And here’s the part I wish others could understand. Here, there is no choice. There are actions I can take but it’s terrifying here. Because it truly seems like you’ll feel like this forever. That this is all there is. 

Just as lucidly as I can tell you today, on a good day, that I'm certain it always passes, at those other times, I’m just as certain it won’t. That actually, that is the true me. The other is just an imposter. A happy facade.

I make destructive choices in those moments because I think that’s what’s best not for me, but for everyone else - why would they want to be around me when I can’t give them what they need and deserve. So in business school I hid in my dorm instead of joining parties and study sessions and new ventures. Today, I'll bail on meetings or I won't hit publish on something I've been working hard on (like this piece).

It doesn’t make me proud or feel strong to admit this. 

But just as I felt compelled to talk openly about what failure was like with Poppy, I feel compelled to bring every ugly, dark reality of this, out into the light. So we can talk about it and render it powerless. 

Even though I don’t know Naomi’s pain or struggle, it connects back to mine. Every time someone says, "it’s just a little press conference", what’s the big deal? I want to rage against the lack of understanding. 

I'm not surprised press conferences are a source of extreme stress.  Her sister has even said: Naomi has insecurities about the French Open and every time the press digs into it, it makes her doubt herself.

Reading that struck me in my heart. Because this is me every time I go out to raise a new round of funding. Full of scrutiny and criticism and poking and prodding to break through to the “real story”.

Imagine a day filled with meeting with really smart, engaging people that you would love to work with - whose POVs you respect on Twitter, who are just really good at what they do, who quite literally make their names on “picking the right bets”. Then imagine meeting with all of them and having them tell you why it won’t work, second guess your decisions, your choices, your view of the world. And ultimately: No. You’re great and all, but this is not a thing we’re excited about getting behind. 

And listen, I get it. It's all a part of what I signed up to build a “venture scale” company that can have the biggest, broadest impact possible. I know that finding the right investors is critical to this ambition and I’ve been so fortunate to work with so many of the best (the ones that immediately get it and it feels like collaboration rather than interrogation). So naturally I completely, rationally understand and accept this part of my job. 

But what’s harder to understand from the outside is that what I actually signed up for was to solve people's problems. To make their lives easier. Not to split my heart open and share my life’s work for others to judge it and find it wanting. Over and over again. 

Knowing that the constant scrutiny and rejection is a painful but necessary part of my mission doesn't make it any easier. I understand we’re all just doing our jobs - that it is theirs to figure out all the ways my venture is and isn’t a good bet. I know I could and should do it differently - care less, be more removed. But I can’t. That’s just not me. 

So all there’s left is to figure out how to do it on my terms that doesn't constantly destroy me and therefore, ironically, my company.

Because on this side of the table, underneath the glib advice of “for every 99 nos you only need 1 yes” is a person hearing all the ways that she’s inadequate and that she’s not enough. That she’s destined to be a failure. 

I say all this not for pity. I say this so you can see another more human and more complete reality of what gets glossed over. Of being more careful the next time you say, "but they signed up for this willingly." or, "It doesn't look like she's having issues on her Instagram on that fancy photo shoot."

These are complex, messy lives being lived every day as we all know how. Every single person trying to figure their shit out as much as the next. 

And as we work to figure it out, we understand our boundaries and our limitations. You see, though it might seem it with what looks like callous action on the outside, I am not trying to be reckless or inconsiderate. Rather the opposite. Each day I’m meticulously trying to figure out what might break me and avoid those things as much as possible. 

On a regular day I've got battles to fight. But on days that I know I'm going to be putting myself out there for particularly intense scrutiny and criticism? Well those days I’m just trying to figure out my armor. The force field I can put up around me before I go in. 

And sometimes the force field holds, and sometimes it doesn't. Like a great scene out of Star Wars, there comes a time when the shield didn't start out strong enough or you end up taking too many hits. And in those times you have to get yourself out before you're destroyed. You're not thinking about anything other than survival. 

For me, it has always been coming back to my users and why I'm doing the thing in the first place. I have a doc that holds out user feedback. And I go back to that to remind me ultimately of how worth is measured. I’ll schedule to pick up my daughters from school so I remember the fierce love that lies within me. I go for a walk with a friend so I remember that life is more than anyone else's estimations. 

I do what I have to to protect myself and my peace and my grace. 

It might look cold from the outside when I decline to do a coffee chat or to respond to the hundreds of LinkedIn or Twitter outreaches. 

But it’s not about you. It’s about survival and me doing what I need to not only get through the day, but thrive in my way. 

So I’ll be damned if I sit idly by and let people judge me for that. 

It’s not pretty. It’s not perfect. 

In fact it’s messy and downright ugly.

But you - you have two choices. You can just leave us be. Leave the judgment, the commentary, the consideration. Just completely ignore our imperfect existence. But then you don't get to marvel at our wins, our achievements, our extraordinary. 

Or you can accept us for our messy selves -  witness and celebrate the brilliance alongside the wreckage. 

So yeah, I'm thinking about kintsugi a lot right now. I’m tired of using the clear crazy glue that does nothing but make me feel broken and, well, crazy. 

It’s nothing but gold for me from here on out - celebrating the broken bits along with the whole. Because every single time that I break a little, I figure out how to build myself back - more beautiful and valuable than ever. 

And that’s worth something more, I think.

(last note 😅 : while the title of the talk was the “UI of trust” (because I think of where AI products interface with our lives especially with increasingly agentic services) it really covers the UX or the full user experience/promise of the product.)

I'm going to be talking about building for trust. It's a little more salient for those who are building agentic experiences but I think it applies to all products because trust is at the heart of any relationship between a user and a product.

So take a look that this set of considerations and think on where your product falls in the continuum of each. Do you work with your user on a browser interface that they're actively engaged in the whole time? Or do you have something that runs in the background and collaboratively volleys interactions back and forth? We’ll come back to this at the end.

I build for parents. The kind of help I need in my life - things like childcare when my nanny calls in sick, or help dealing with the firehose of information and logistics to keep a modern family running. That just means that I'm building for the things that I need in my life.

And ultimately, that means I’m building for trust. Things like privacy and security are definitely table-stakes, but for the purposes of this conversation, I mean: trust you can count on it to be there when you need it, and trust for it to do the thing you need it to.

Specifically I've been building for this.

This is just a sample of the kind of information I get hit with on a daily basis. My girls are 10 and 13 so for the better part of a decade, I and millions of parents have had to handle this. Read it, process it and action it. Oh and then remember and tell the other people about it, when it's relevant.

Let's take the birthday party invite.

For the majority of families, what happens is they get an invite by email or text message. Then they need to get it into the family calendar, manually checking for conflicts, remembering to buy a birthday present and mentally rearranging the shape of that whole weekend with this new event.

With software, we can get a bit better. We can use OCR and write a program to extract the relevant info and create the calendar event, within some narrow parameters. But it doesn’t understand that this is a "birthday party" and can’t do downstream actions without a lot of brittle if/thens.

But with LLMs, this changes dramatically. Not only can we build a system that understands the semantic meaning of an American child’s birthday party, it can do the reasoning we need - check for conflicts with the soccer game (not the gardeners coming by), remind me to buy a bday present (and oh btw we like to give books and here’s a couple of great books for a 7yo). It can also help me think through rearranging the weekend ("Let's do the farmers market on Sunday instead - there's one in Menlo Park instead of the one in Palo Alto).

AI has been the missing piece of a puzzle I've spent years trying to solve. Finally, we can build not just a tool, but the actual collaborator that I need to actually be helpful.

More than an assistant that books dentist appointments or researches vacations, I need a forcefield I can trust to handle the logistics firehose and make space for me to show up and do the parenting things. Something I can just throw things to and know it’ll do what I need it to. On the go, at bedtime, heading into a meeting.

It's easy enough to say it and even easier to imagine it, but what does it mean to build it?

Before we can start building to take on the right actions for those dentist appointments or vacations, we need complete, accurate data and nuanced context first.

There's just one, massive wrinkle: before we get to the challenges of putting good context to work, we have our work cut out for us with the data. We have to start with a really good, fairly complete, data representation of the family, in digital form.

That doesn’t really exist. Most of it lies in IRL or as unstructured information - in our minds, on pdfs or in emails.

Let's take some examples. This first event seems pretty straightforward - has all the info, clearly formatted. This next one is a bit more complex - we need to make sure we have 5 events with right info to remember, so my kids doesn’t show up wearing pajamas on Retro day. And with the last one, we're starting to strain OCR and even current vision models but still doable.

What about this baseball schedule or now, we're getting to the heart of the matter - this school calendar or this kindergarten staggered start date doc - where families with odd home address have one schedule, and those with even have an other.

This is what parents across the country are dealing with. And if we're going to build them a forcefield to help, it's kind of all or nothing.

I can't hold some info in my head and other not. Or more importantly, my AI can't actually be helpful if it only ever has 50% of the info - and the easy half at that. But it’s also the reality that our existing AI models and capabilities just can’t get all of that right (yet).

So how do we build trust with a product that does what it needs to, has a reasonable failure path and communicates the the difference in a way that feels actionable, not frustrating.

Oh and wait, we’re running into a growing tension: for Milo to get as much of the info as possible, we need to lower the friction of reflexively sending it over. That means SMS, voice, emails - increasingly invisible, mindless and habitual paths (pay less attention).

But the work Milo takes on gets more complex and personal, with stakes getting higher (pay more attention to make sure it’s being done right).

So the question is: how do we make it increasingly easier for users to share the things they're being hit with, but in a way that makes it really clear what's been done and what they can do about it.

Well, I think about 4 things, from the POV of a user:

1. Transparency - what are you going to do or what happened?

2. Control - what can I do? How can I intervene? What are the points of check-in?

3. Consistency - Can I expect the same thing each time so that it’s easy for me to see if it’s right and so that I can relax checking over time?

4. Bounds - What can and can’t you do, and how do you teach me that over time, not just at "onboarding"?

What does this matter? Well, as one of my users said early on: You need to understand: I'm the only thing standing between a week that mostly works and total chaos.

If I'm handing that off to Milo, it had better do it right. I take the responsibility seriously, also because that's how I think about my role with my family.

So here are some ways we've thought about it with Milo.

First, for any given input, have a really standard, transparent output over SMS - because this is where 90% of our users use Milo.

For this reminder, there is a clear output of what kind of item, how many and the details added to it. If for some reason the user wants to dig further or edit something, we've given them a link. Then can go in and see exactly what's been sent in and what's been done with it. If they want to edit it, they can.

Next, consistency is under-appreciated but it's critical if we're going to really build trust that doesn’t chip away over time with minute frictions.

Take this rundown. It's pretty good at telling me what's happening and for who. But there are inconsistencies in how the kid in question is communicated - sometimes in parentheses and sometimes in the title. This is a shockingly hard problem to get right 100% of the time with current models and software rules, even though it seems like it should be trivial. And it sounds like a silly, small thing to get get hung up on, but these things add up (and with AI, they actually multiply up).

And lastly, we’ve built in deterministic ways for users to interact with Milo using “@ commands” - little, knowable ways for them to understand what they can and can’t do, starting with “@milo”.

To close, I come back to: What kind of product are you building and therefore what kind of experience are you going to need to design to give users transparency, control, consistency and clear bounds?

Today, most products tend to be on the left - chatbots or code editors; creative writing or image generation - things that have lots of UI and margin of error with single turn requests and responses.

What we're trying to do lies on the other end - a forcefield that runs in the background, with high stakes information and minimal UI, meant for actions on the users behalf in a collaborative, back and forth manner.

So our focus has been:

1. How do you take 100% unstructured data and get it to be consistent, accurate, predictable structured output?

2. How do we communicate clearly and simply what happened, and make it easy for the user to intervene and change?

3. How do we fix issues quickly with reasonable expectations of what Milo can and can’t do?

A last note then - what does graceful failure look like? I think true trust is built when things don’t go the way they need to. So how can we own it, fix it and communicate it? Here is just one example where even ChatGPT hasn’t really figured it out - promising things it can't do and doubling down when called out. But then, maybe with a chat bot - “use at your own risk” is acceptable.

But it’s also undeniable that it's burning through trust in very real ways with regular consumers. So each of us has a choice on where we want to burden of failure to lie.

For Milo, we choose to be conservative - if something is off (at either the model or software level), we let the users know and we've build a human review system in to fix and communicate it. Because that's the only way I'm okay with trusting Milo with my family's details.

As the technology gets more sophisticated, I'm certain that we'll get even more nuanced ways to catch and communicate misses.

But the point is: how we design for trust needs to be thought about and built in from the very beginning. Users feel the impacts of these choices subconsciously at the tiniest level - at the level of the formatting of a single line of an SMS.

AI is opening up incredible ways to solve problems and I’m so excited to see what everyone here will have a hand in bringing to life.

But what doesn’t change is that at the end of the day, each of us is ultimately building and selling trust. And by being intentional and thoughtful with the trade-offs we can create delight both with incredible features but also dependable reliability.

This is probably the number one question I get asked - whether it's undergrads considering first jobs or MBAs looking for internships; people weighing how to leave a job and others figuring out how to take a big leap on a new endeavour. All looking for data, a sign, tidy wayfinders pointing them to the “right” decision.

Well, after 20 years of navigating increasingly complex decisions with bigger and bigger stakes, I’ve realized two things.

1. That data that makes the uncertainty bearable doesn’t exist. Not in the way that would actually lessen the uncertainty.

2. In the face of needing to embrace that uncertainty, I have one guide:

Maximize slope.

Meaning: which option is going to give me the most learning and growth?

I think it's really hard to predict if you're going to like something or if you'll be successful at it. But it's usually pretty clear which option you'll end up learning the most in.

When plotting options on a graph like this, it’s easy to see how the more known option (the dotted blue line) could feel better because today, I know a lot more about it or it sticks to areas of my past expertise.

The other option (the green line) likely feels really scary because I know so little about it and in the beginning it might even feel like I’m going backwards. But the slope of the learning of the latter is clearly much steeper than the former.

😎 You don’t have to love it for it to be the right choice.

When I was 21, I had to choose between doing another internship in Vancouver at a lab I had been at the summer before, or doing a Pharma Sales internship at P&G in Toronto. I had no idea what Pharma Sales even was (or really what P&G was 😵), and I’d never even been to Toronto, so I definitely didn’t know I was getting myself into (and I'm glad I didn’t because honestly, 21 year old me likely would have chickened out) but I knew that one way or another I would learn a lot, even if I didn't love it.

Nearly 10 years later when J and I were presented with the option of moving to Shanghai and needing to decide over a long weekend - we decided that the experience we would get with a couple years in China would beat another couple in the US. From learning Mandarin to really understanding what it’s like to not live in a democracy but a Communist state to learning how to manage businesses where a 40% yoy growth rate is tame.

And that experience provided a great foundation when I decided to step off the corporate ladder and start a company - where the only thing I felt confident in was my belief that even if it didn't work, I would have learned more in that year than staying in my corporate job.

⤴Learn your way through the uncertainty to the frontier of your life.

Over time though, it's become second nature to optimize for my rate of learning over anything else - it's also what's allowed me - a non technical solo founder - to build multiple tech startups.

Because the superpower I’ve honed in my life has been to be great at learning. From the sciences to CPG to startups to AI. The what and the where and the how has shifted dramatically and often.

So that by the time I was building tech startups and even though it was daunting, I was able to become technical enough to learn what I needed about software and now AI.

Maximizing slope at every point also has the added bonus that you’ll be able to get yourself to the unique space where you and you alone occupy in the world. Where your unique set of talents exist to do something that no one (I’d argue even AI) is able to.

🙅🏽‍♀️ There are no absolutes of experience.

It’s probably no surprise that I get frustrated by people who offer definitives - ‘big companies are where talent goes to wither away” or that “every young person should start a startup”.

I think that misses the bigger picture - there are ways to learn in big companies - just ask me. And there are ways to stagnate at startups - again, just ask me.

In the absence of a crystal ball, it's really hard to know what choice is right for you. Though even if I had that crystal ball, I'm not sure I'd want to use it - because I'd have seen how hard I found cold-calling doctors for that first internship and I'd have fixated on how miserable I was in Shanghai 3 months in - and given that “data” I very well might not have taken either leap.

Worse, I'd have missed the point. That for me, the "right" decision was or is less about some objective marker of success, but an internal one of growth and resilience.

😰 Get comfortable with being uncomfortable.

A warning though: maximizing slope also means maximizing discomfort. Because it will often mean changing many things at the same time or jumping into a completely unknown areas.

In these times, I think of the 6 month rule one of my earliest mentors - Jeff Davis - taught me when he promoted me and encouraged me to move from Toronto to Cincinnati.

He said: the first 6 months of anything hard is going to suck and feel terrible. It’s when you’re having to deal with the sheer volume of new things. You're not allowed to reconsider this decision for 6 months. Instead, your job is to embrace and fully experience it. Then, at the 6 month mark, if you're still miserable, I'll bring you back myself.

What a gift - to be encouraged to do something that certainly maximized slope for me, but in a way that I felt supported. And yes, that happened in one of the biggest, most corporate companies in the world. The place where I learned how to be not just a great business manager but a great people one too.

Of course at 4 months I was looking forward to taking him up on the offer, but by 6 I couldn’t imagine what I had been so worried about.

So take a look at that decision staring you in the face. Pick a timeframe - a year or two is usually great. I truly believe there will rarely be a time you regret choosing the thing where you learned and grew and stretched yourself.

🤓 Learning is growth, not hustle or achievement.

There will be times though that you need to juggle where the learning is happening. When we had young kids and we each were getting a company off the ground, we moved back to Vancouver where we could have stability, while the learning came from building a family and a company at the same time.

There will be chapters when the slope you're maximizing isn't at work but in your relationship or on a project. And learning doesn’t have to be about “achieving” endless milestones. Learning is simply growth. In our emotional or spiritual or physical selves.

But I believe now more than ever it's important to exercise our instincts to maximize learning. To teach our kids to orient towards that and to be okay with the inevitable natural discomfort. Because increasingly, success isn’t going to look like a collection of “right jobs” but of occupying unique spaces that only I can.

🌱 Start small.

This, like anything, is a practice. Of tuning into that feeling of discomfort and making friends with it. Of acknowledging as it grows each time you do something even more bold but not letting it overwhelm so that it starts making the calls. Because to really maximize slope you have to work with that feeling and keeping it on the right side of productive for you.

But start today. With big things or little - even choosing to walk home a different way or to bike when you usually drive is learning in a small way.

All of it practice for when the biggie decisions show up at your door. So that when that question inevitably comes - “how do I decide?”

You’ll know which way to turn.

I've started reading poetry.

I’ve always wanted to be the kind of person who did that. As if a goal to pursue, I've collected books like wishes that sit on my bookshelves, waiting to share their secrets.

But poems are not meant to be consumed in bite sized flashes - like reels or tweets. You can't summarize them into tidy snippets or easily pop them into your ear running errands.

No - poetry calls for presence.

To make space in your day and your mind to hear its wisdom.

It's patient - I'l give you that much. It doesn’t demand, but nor does it ask.

And so, while I've wanted to be the kind of person who read poetry regularly, the closest I've ever gotten was a couple years ago, listening to Pádraig Ó Tuama’s beautiful Irish lilt read me poems while I made dinner every Wednesday. Kids at piano lessons, house blissfully quiet. Holiness in my ears.

Like most things, it didn’t last.

But this last summer I picked up a Mary Oliver anthology. The only reason I know who she is is because I once wrote an essay in my 20s to the question:

Her question has stayed with me since. The plainness of language with the bigness of question. So like before, I bought the book and promptly added it to the pile.

But recently I've started meditating and writing in the mornings. A way to find an hour of myself, to myself, to be myself. And I grabbed these poems and put it with my journal (which also held Mary Oliver quotes) because it felt like the kind of things that went together.

So each morning I just started opening to a random page and started reading. At first it felt uncomfortable and awkward - the subtle turn of phrases and incomplete thoughts. Suggesting, opening but not telling or completing.

It felt unsatisfying and frustrating. Irritated, I'd put the book away, feeling good that I checked some box but knowing it wasn’t the one I had wanted to check.

But poetry is sneaky that way. It'll wait for you to be ready for it. Slowly the quotes in the journal drew me in. Little bite sized versions that made think and stayed with me.

This one I thought about all weekend as I tried to notice and appreciate the times I felt joy in all the big ways, but especially in all the small.

And then today, I came across the full version. As I read it I sank into it, I started reading it out loud, to myself, really feeling her words, letting them embrace me.

The thing about poetry is that there are no extra words. Every single one chosen with intention. There is a message in the word choice as much as there is in the composition and the message.

I find that fascinating but in this moment of reading, I let all of that assessment and analysis go. I sat in the feeling of it all.

I've always wanted to be the kind of person who read poetry.

I realized today that I already am.

I just had to sit still enough to hear the words - held on a frequency too low for everyday life. Slow and flowing. Needing me to drop down into it, to hear it.

“Start-ups die, not because they starve, but because they drown.”

I keep this adage front and center in my mind because I believe it speaks to the leading killer of start-ups: slow progress, solving the wrong things (or the right things but that are too small to move the needle, which still makes them the wrong things).

It’s actually pretty easy to come up with ideas on how to improve your product or your landing page or your sales plan. When you know your product and space as well as most founders/teams do, ideas abound. Speed improvements, feature adds, messaging changes, onboarding fixes.

The question is not what, but which one?

The hard part is figuring out which one idea has outsized impact. Which one thing built or changed or ventured would amount to the next 4 combined.

Now that’s hard. If we do this, we can’t do that. And that doesn’t feel great when the odds are so bad and there’s so much progress that needs to be made in such little time.

There are 2 ways to get this wrong:

1. Pick too many of incremental ideas - none of which actually move the needle. The ol’ “motion not progress” problem. The siren of shipping lots of small, surface-levels things calls out. She’s alluring but she needs to be ignored.

2. Picking, but then spending too long building out the one idea - once you have the One idea, you can also fail to scope the critical v1 things and spend the next month working on this one thing.

Both are sure ways that lead in one direction: death.

The first, because you’re spreading your limited resources too thinly and the second because you might actually be wrong in that being the One thing and now, not only have you spent a month building a thing, it’s going to be harder to kill it and move to the next thing.

Here’s what I try to do (I say try, because this is what I struggle with the most as a founder).

1. 🧘🏻‍♀️Meditate on the problem. It can be literally or figuratively, but step away from the computer, the whiteboard and even your users. Go for a walk or actually meditate for 10 minutes. But chill.
   
   Think about it: what one thing thing is most preventing us from growing faster?
   
   Write down the first thing that comes to mind instinctually. But don’t stop there. Keep asking: what’s causing that, until you get to truly the first principles version of the most critical problem
   
   Too often we’ll get to: we need more users. But if you ask why that’s a problem, you learn it’s because the ones you do add churn after 2 weeks. Why? Because they don’t figure out the core value in the first session. Why? Because we’re asking them to do too many things. Why? Because we don’t know the one thing users want us for most. Well already that last thing is a much more solvable thing with concrete ideas.
   

2. 🤔 Now, ask: if we wanted to solve that problem this week, what ideas would we explore? Which will make the biggest dent or give us the most learning?
   

   If you’ve dug deep enough into the core issue you should be able to come up with small hypothesis that can be quickly scoped and test.
   
   Write all this up a brief doc:

   1. ⚡️What is the most urgent problem to solve.

   2. 💡 What are the boldest ideas to solve it.

   3. ☝🏽What is the 1-2 ideas to rule them all.
      

3. 🚢 Build, ship, see. Get to work building and shipping that hypothesis. Make sure measurement is included in the scoping. See - did it have the impact you expected? What else did you learn? Now take this learning and get go back and do it all again.
   
   This is also, btw, why it’s a good practice to start fresh sprints every week. Okay to have a backlog to see from, but the most urgent problem shifts if you’re solving the right thing the week prior. It changes the backlog projects’ scope and design. Also, one week sprints keep you really honest in that beginning when you’re just trying to get to PMF. There is only so much that can be built in one week. So it forces you to really ruthlessly prioritize and ship. Plus there’s only so much you can get attached to your darlings. You only had a week to obsess about them.

   
   After you’ve done this process a couple of weeks in a row you’ll start feeling the momentum of the process and the intuition of the whole team working to prioritize and pick.

I’m convinced that speed of learning and improvement is a founder’s only true advantage in a game played with limited resources, information and a default resistance to anything new.

Systematizing focus and speed, and weaving it into the team’s DNA is how the best founding teams I’ve watched actually build game changing products and companies. Here’s just one suggestion on how that I’ve learned along the way.

1. Only two things matter: how well you know your users and can solve their frictions, and the speed of your learning and building loops.

2. Anyone can be a founder. Truly. It's just harder for those who don't have easy access to early unlocks (technical skill, $$, users). So you have to do double duty - solving for those while also making progress on traction.

3. High growth means some kind of leverage - distribution, patent, tech. For most of us, software/AI makes it possible for the "little guy" to get leverage. That's why the focus on technical. It’s the path to high growth.

4. Don't outsource your leverage/source of growth. If it's tech, don't outsource dev. Yes it's incredibly hard to find a technical lead. Welcome to the work.

5. Build in the place that welcomes your weirdness and is lousy with the people who've done the reps in your chosen field. For renaissance painters that was Northern Italy. For fantasy series writers (CS Lewis, JRR Tolkien) that was Oxford. For tech founders that's the Bay area. Move here or don't. But find a way to spend a lot of time here because it's one of the easiest ways to increase slope and speed of learning. You have to live somewhere. If you’ve chosen to build a start-up as your life’s work, welcome to the hard choices.

6. Few hurdles are unsurmountable for true founders if you're really here to do the work. You really can reach anyone, do any thing - it might just take longer and require more resourcefulness than you ever thought. But that it’s possible? That’s all I’ve ever needed to hear.

7. You can absolutely have a family and a startup. Just be prepared to do both things on hard mode and follow no one else's playbook. Ruthless prioritization, leading by values and constant communication with your partner/team is the only way to make both work.

8. Most startup things are noise and ego and vanity - act accordingly. PR, conferences, networking events - they feel like progress but are only surface motion. Unless something will directly get you users, team or $$, don't do it. Anchor on your users, the problem and your team, not the product or press or investors. Obsess about the first three and the other three will follow.

9. It's the sacrifices that make it hard, not the work.

10. Guard your cap table like a fiend. No advisor shares or easy early party rounds. Build like you'll be doing many rounds and bridge financing. Don't lose before you’ve really even started because you gave away 50% of your equity before Series A. And choose your investors wisely - they’re like a team member only it’s very hard to fire them. Values matter more than you think.

11. No one can teach you entrepreneurship. When you're building the future, no one has ever done it before - there are no experts. Use accelerators and incubators cautiously - only if they unlock speed, access to deep technical expertise, access to $$ or hiring. Make sure you’re not doing them because it feels like a comfortable way to “do start-ups”. Ultimately not is not school or even a job. This is your vision, your company, your call. The only thing that matters is: how did you make your users’ lives better this week and how fast did you grow?

12. Ultimately, just find a way to stay alive. Ask yourself: what’s the thing that’s going to kill us next. And just solve that. Over and over and over.
    
    Find a problem you’d doing anything to keep getting the chance to solve for and then find a way each day to not die.

My form of building the future relies heavily on engineering - this seemingly scientific process of designing, building, testing to gets us the machines for the problems that plague us.

But if there’s one thing I’ve been forced to learn, when solving for human problems: I can’t just will a thing into existence. I can’t logic it. I can’t brute force it. Especially as my calling is to lessen the everyday frictions of parents, in all of its plain mundanity and irrational complexity.

Instead, I’ve learned to sit in the pain of the problems. To come to love the very contours and grooves that define them.

To see them through every angle and every wavelength.

Until all that data lives within me as puzzle pieces, as signals, as sirens.

I’ve had to sit quietly and patiently for more days and months and now years than I care to count.

But here, in the hush and the quiet, I can hear that hum. The hum of hope. Of potential. Of progress.

I keep my eyes closed and use my fingers to trace the path - to feel the grit and the grooves. To let the light and warmth guide my way forward.

It’s slow going, but what is time when progress is clear? When answers are near?

To engineer the future, I’ve had to let my curiosity take the lead - more artist than scientist. To feel the data in my gut over crunching it in my mind.

I know what that psst sounds like now.

It’s soft and insistent but it won’t go out of its way to shout or get my attention.

It’ll keep waiting. For that someone who will choose to sit. Choose to listen. Quietly. Patiently. Persistently.

The best way to predict the future is to invent it, yes. But the future also has a say on how it wishes to be invented.

Call it destiny or any other name.

If you find yourself stuck - go towards the friction, the pain, the feelings.

That’s where you’ll find the most interesting bits.

That’s where you’ll start hearing those pssts.

And that’s where my kind of engineering begins.

There is a lot I love about life right now. And a lot I hate.

Endless, sunny summer days extending into September, kind, social neighbors, long bike rides, a casita for our projects and games, baristas who remember your name already…. love.

Watching your kids go through the hell of new everything… seeing the panic in your 9yos eyes as you have to firmly disentangle your hands from her hands and walk away - arming her only with the words “you are brave, you are strong” - hate. Like reallyreally hate. Seeing your 12 year old get sucked into the masses of a 1000 kid middle school with nothing more than “Good luck!” and “I love you!” - hate.

Seeing the kindness of kids reaching out to befriend mine - tentative smiles, little jokes, time spent together - the beginnings of new bonds - love. Hearing stories of recess and lunch adventures even as they facetime their friends at home - seeing the new start to weave into the old - love.

Feeling completely overwhelmed by the sheer number of new things to be on top of - emails upon emails - volleyball assessments, musical auditions, math homework to help decipher (7th grade kids doing 9th grade math 🙃), textbooks to order, pictures to print, french to help conjugate (qu'est-ce que c’est beau-fille?) - hate.

Breathe.

I tell myself the same thing I tell my 9 year old: one thing at a time and we’ll do it together.

The past three weeks have been a grinder on top of a past three months that have been challenging, on top of a year that has been nonstop.

But this morning: my sassy middle schooler grabbed her things and walked into school stilling reciting the monologue she’ll be auditioning with later today, after flag football try-outs. And my kind, big-hearted 5th grader showed us what bravery really is, by walking away from me and up those stairs by herself for the first time - still not loving it but doing it anyway.

Yes we can do hard things. But fuck - it’s hard for a reason.

Every fiber of our being is telling us no. Danger. Don’t do it.

And for kids it’s just that much harder - they haven’t built up the muscle memory, the intuition, the tools to know it’ll be okay and how to make it be all okay. Of course these experiences will teach them this.

But it is quite literally the worst thing in the world as a parent to be the reason they’re going through it. To see the pain and know that not only is there only so much you can do, that you are the reason behind it.

Two things can be true: that you know it’ll be okay/ they’ll be the better for it AND you hate that you made your family go through this and you want to just grab them and make a run for it.

Life is not predictable and feeling comfortable and surety - it’s messy and heartbreaking and uneven.

But: as my little firecracker showed me this morning: one foot in front of the other.

We’ve got this.

It feels like everyone has the answers - how can that be?

Everywhere I look - my email inbox, my Instagram feed, my LinkedIn… everyone is crushing it. From their breezy summer adventures to their work milestones. Solutions to my parenting woes or answers to my productivity. Reporting on all fancy parties in Paris or adventures at the lake. Even vulnerability posts that feel weirdly performative.

Of course I know that’s not reality - I know everyone’s lives are messy and imperfect.

But it’s getting really hard to find a place where I can see any of that. Or share it.

Where did my space go for the insecurity, the indecision, the messiness of it all?

It’s why I’ve always loved blogging … and OG Twitter. Those were two places where I could toss out imperfect thoughts and ideas and find my people. People who were also striving to just figure it all out too. Even Substack now is a machine filled with more people and more answers.

It’s not wrong or bad - I love seeing all of the ways people’s passions and talents and expertise are find a way to the world without intermediaries. But nor is it really the thing that fits the need of an old school blog.

And so, for the past couple of years, I’ve struggled to find my voice, because I don’t know where to share it. I live in the mess. In the in-between of neat and tidy. It’s what I’ve always written about.

Perfect has never been my muse. I find equilibrium boring (also, as we learn in science, it’s an illusion).

I am a deeply imperfect human. I am short with my parents and I get frustrated with my daughters and I snipe at my husband. I don’t call my friends nearly enough and even though I want to live according to these values I say are so important, most days I’m too exhausted to do anything but crawl into bed and pick up a book I’ve already read 4 times.

I am constantly terrified that I’m a failure and a fraud at this founder thing - that I should have tossed in the towel years ago and gotten a well paying job so I wasn’t so constantly worried about money. I worry my family gets the worst bits of me at the end of the day. I worry that I’m doing all of this wrong.

But where does the messy live these days? Where we ask questions without fear of judgement, where we offer no definitive answers, but support and suggestions.

It’s worse because when you’re a builder, you’re also its Chief Cheerleader. The person telling all the people why your thing is quite literally the best thing since sliced bread.

But my way is not to tell, but to show. To build products that do the talking for me. But what do when you find yourself building in a space where, for every answer you discover there are 3 deeper questions behind it?

For me, you keep digging. You keep asking. You keep building.

Only now, that’s not enough because suddenly, after building in a wide open space for 5 years that no one wanted to acknowledge let alone touch, it is now one of the hottest/competitive markets.

Which ultimately is fantastic for everyone - because finally we have a market and consumers will have choice.

But in the moment - all I can see are Instagram ads, emails, press… all confidently saying how this thing solves all the things.

So I find myself needing to find my voice again. Yes for the company, but more just for me.

Because I believe in messy and I think a lot of others do too.

I want to find a space where messy is okay. Where it’s celebrated. Where we don’t try to sweep the chaos under the rug and reach for a glass of wine. Or worse: where we think we can successfully solve it.

Again, maybe it’s the scientist in me, but chaos is just the beautiful reality of life. It’s the striving for the equilibrium … the making it seem like that’s the goal, that’s giving me heartburn.

Even this post should probably be edited or cut down and cleaned up.

But lesson one of Club Messy: real is better than perfect.

Allez.

But earlier this year I had exactly that experience and that moment.

Back in March I was asked if I could choreograph the Big Kid dance for our Indian community’s annual show. I might have let out an involuntary laugh - it was such a ludicrous idea. To take on choreographing a dance on top of traveling every week, launching a new product and coordinating a move was beyond laughable, it was a clear and understandable “no”.

I quickly and emphatically said I'd love to, but I really and truly can’t. A week later though, no one else had volunteered and it looked like the big kid dance was on the chopping block. I was devastated for the girls. Some of my most cherished memories from being 10 - 16 years old was doing dance with friends across the community. It extended into my 20s with competitions and even recently, coming back to dance with women I danced with when I was a teen.

It was bad enough that Covid stole 3 years of shows, of the community gathering, of culture being passed down - if I had the ability to change the outcome of this year, I had to do it.

And so, against all the better judgement of my mind, my heart and I volunteered.

Cue the panic and the “what-have-I-done” for weeks following. I've danced for more years that I can count, but I’ve never choreographed. Not once. I am great at memorizing and executing complex sequences but never have I been called to conjure the movement that tells the story of the music.

I watched YouTube videos and tried to find shortcuts but that was almost worse - there were professionals with moves that would never work or small kids with steps too simple for what I knew these kids could do.

By Easter Sunday I was about to message to say, I'm so sorry I made a terrible mistake and I need to quit. I think people, including myself, would have been disappointed, but no one would have blamed me.

But, deep down, I didn’t want to quit. This mattered. As I reflected on all the things I was dedicating time and energy to in my life, this easily fell into the top of what was important to me - not only personally, but for what I wanted to pass on to the girls, for what I want my life and contribution to my community to be.

So I told myself I'd give it one week - if I couldn’t make progress I was happy with, I'd hand it back.

I then sat down and came what felt natural to me - I took a scientific, first principles approach to the task at hand. I have no idea if this is the way proper choreographers do it or not, but I broke the whole song down to the component 8 and 16 counts. I saw where the chorus repeated and where the instrumental parts came in. I listened to what the lyrics were. I basically nerded the shit out of the problem.

And then I committed to doing ~30-60 seconds at a time - just 2-3 sections. I closed my eyes and just listened to the music, let formations and movement come together.

Once I had the frame of something, I roped the girls into it all and we all tried it out. What I didn’t know when I started was that I would have incredible co-collaborators in my girls. Trying moves out, giving notes, suggesting other options. It became a thing we would do every Saturday morning, together. Before I knew it, we had over half of the song done and within a couple of weeks the whole thing.

At dress rehearsal yesterday, it all came together for the first time in a way that brought me nearly to tears.

I saw before my eyes why I loved it. Because dance is so much more than moving your body to some music; it tells an age old story of culture and celebration and resistance and triumph. Because dance makes us, for a couple minutes, exist in our bodies and shut out this noisy world. Because dance can be passed down from generation to generation and even as the music and steps evolve, the heart remains the same.

And for the first time, I felt this joy not because I'm on that stage. But because my daughters are. It’s impossible to share what that feeling is exactly, other than to say it’s heart-bursting.

In the work that I do in the everyday, I spend so much time worrying about the details of our home lives. The logistics behind all the meaningful things. Ironically, it’s taken a toll in my own life, because I've had to focus on the most pressing things, the most immediate and practical.

But today … today, we danced. We told a generational story on a stage, in front of our kids and our parents and our grandparents. And after my daughters danced, we all watched my mum dance, celebrating her 70th birthday on that stage that I grew up.

That matters. A lot. In the every day frenzy, this is what I want to hold to. Commit to. Honour.

It doesn’t matter if it was perfect or even if it was good. It was.

And for that, I will always be grateful to the part of me that said yes to something so very scary and daunting but that I knew would build something even more important than what I build in the everyday.

So, as the timeless Leanne Womack puts it:

…when you get the choice to sit it out or dance,

… I hope you dance.

5.5 years. It’s been five and a half years since I’ve had an office.

How is it that possible? And yet.

Shutting Poppy and “taking time”, and then Covid and then not having a team and then not warranting a whole space for only 2 people… one way or another it’s been too many years since I’ve occupied one of my favorite spaces - a sacred place that holds the fierce people and the audacious ideas within its 4 walls. Where we can be as bold and curious and tenacious as we need to be.

It’s not much - a beautiful box that holds some desks, crazy comfy IKEA chairs and a little conference table. Some plants make the place feel homey and we’ll get to the fun wallpaper and art.

But the most important thing went up first - my whiteboard. A whiteboard that doesn’t need to be erased at the end of the day. A whiteboard that holds context and keeps us in our Future Distortion Field. Where conversations can extend from one day into the next. Where we can put a pin into something hard and come back to it later.

And the location? I’m in love. We chose it for its proximity to the very buzz of Palo Alto. Realizing that it mattered more that we could walk out into the energy of the place anytime we needed than the fanciness of the actual space. And while we wanted to stay in the city, we had to be practical: minimizing commute and maximizing time in here.

I didn’t realize how much I needed this until this very moment. When I unlocked the door at 7am, first to the quiet hush. Setting my coffee on my desk and clearing my thoughts for the work ahead, just as I used to. This ritual I had honed and then had had to set aside.

I’m tired of debated in person vs. remote. Different things work for different people, different companies, different challenges.

All I know is that given our realities and context - that we’re choosing to build a big bold audacious thing while both founders are also parents of young children and have partners with big crazy jobs of their own - this is what’s right for us.

I feel the thrill of electricity in my veins as I stand at this desk. Rooted to a place, this place, for now, for however long this is what we need.

I’m so happy to be back, to a here.

Newton’s first law states that a body will remain at rest (or keep moving at its constant speed) unless acted upon by an outside force.

Said another way: Things like to keep doing what they're doing unless something else makes them change.

Inertia.

As I’ve moved from physics to the world of solving people problems, I’ve realized this law still very much applies.

People hate to change unless some force moves them to.

That force can be joy or convenience. Connection or fear. At our core, we are a species driven by our emotions, far from acting perfectly rationally.

I love it. It’s why I fell in love with building consumer businesses. What a puzzle - people act in a certain way and they’ll continue to act that way unless you build them something that compels them to act otherwise.

I got a taste of that with Poppy - that’s what product-market fit is. That moment when you figured some number of things out, such that you’ve exerted a force successfully to move people to sustained action.

So I know exactly how hard it is to move people off of their status quo and exactly how powerful it can be when you do (especially in something as hard and tricky as childcare).

But it turns out that childcare is a broken market…. the raveworthy product we had built, that moved people to change wasn’t scaleable. As much as I hated this fact, I had a choice: I could keep talking about what should be. Or I could take what was, and solve for that.

And so I turned to a problem where I thought software could create delight-filled, affordable solution at scale: the overwhelm of the behind the scenes logistics for families.

But if childcare is a hard problem to solve operationally, the invisible load is mind-bogglingly hard to “see” and untangle product-ly.

Believing as I do that it is hard to get people to change behavior, you can’t build a thing and tell them to use it. You need to painstakingly map existing behavior and meet them where they already are.

Take school emails: people will ask why I don’t build software for schools to send out more sane communication. I could. Others are. But I’d rather assume that at least for the next while, humans are going to human. And schools and sports teams and other parents are going to keep sending communication at the speed of thought - papers and text messages and emails galore. Inertia again - defaulting to the easiest thing will always win over a theoretically “better” thing.

In the matter of the invisible load, this has been a 4+ year of mapping and measuring and making. But the principles of inertia dictate that that’s what’s necessary - to understand what is and solve for that vs. building something people “should” use and expecting them to. Build people a forcefield that filters the noise. That accommodates the millions of ways we are pinged in a day and turn that into some sort of sanity.

So if you want to know why I build the way I build it really comes down to this:

People hate to change.

So don’t make them.

Last week I was invited to my daughters' school to speak to the high schoolers for Career Day.

Talking to 15-18 year olds about a career is a fascinating experience - now seen both through the lens of my 12 yo who will soon be there, but also vividly remembering those years for myself as a kid in Vancouver.

I took them through the chronology of my life - from the sciences to brand management to my MBA to consulting to China to babies to venture backed tech startups to now, AI.

The point was not to suggest the specifics of my life as any kind of roadmap, but rather give a guidebook of the lessons that they might apply to theirs.

They boiled down to these 5 first principles:

1. 🔵 Dots not ladders. I was a really great ladder-climber. I had to be, to go from the my family's modest immigrant background, to some of the most amazing company and educational opportunities. And I had to build my own safety net along the way before I could really start taking leaps. So I focused on companies and education that allowed me to leap into successively new categories of future opportunities and backstop further leaps. But once I had a sufficient safety net, I realized that further ladder climbing was not going to serve my life. Instead, I started to focus on "dots”.

My favorite Steve Job’s quote says: “You can only connect the dots looking backwards". I stopped obsessing over the next rung of the ladder - this Director role or that project and started focusing on the dots that might serve me. Moving to Shanghai was the start of the approach - taking a massive leap that we believed would be a life experience no matter what, still supported by the safety net of a big company. Choosing dots over ladders became increasingly easier after that.

2. 📈 Choose the "dot" that maximizes the slope of your learning curve. How do you know if a “dot” is the one to pursue? Forever a student of science, I don’t think in terms of absolute values, but the rate of a thing. I’ve always focused less on the specific milestones and accomplishments to gather but rather on maximizing the steepness of the learning. Ironically, this approach usually ends up getting to the milestones and accomplishments but not because I aimed for it. It’s the approach that had me knowing nothing of brand management but saying yes to P&G in Toronto at 21, nothing nothing about the US but saying yes to Cincinnati at 24, all the way to knowing little about tech or AI originally, but saying yes to YC and OpenAI most recently.

The only decisions I re-litigate in my mind are the times I didn’t follow this rule for myself- the times I took the safer or seemingly "sexier" path. Each time I regretted it but found my way to quickly jump back. There was a period after graduating from my MBA where it seemed like I couldn’t stay at a place longer than 2 years. Turns out it wasn’t bc of my ability to commit, but my inability to find a sustainable place where my learning curve stayed steep.

When you have the option, choose thing (or the person) that will teach you the most in the shortest amount of time. That might be at a big company or a small. It might be across the world or in your backyard. The specifics matter way less than people make them out to be. Focus on the learning. Then if you stay for 6 months (the minimum I think for anything new, but more on that in minute) or 6 years.

3. 📆 The 6-month rule. If you're going to take leaps on the things that maximize your learning, then it's going to feel scary and sometimes you're going to get it wrong. So how do you deal with that? With something my first manager and mentor taught me as I considered the momentous decision of taking an international assignment in Geneva or Cincinnati. 23-year old me thought Switzerland was a no brainer. Jeff wasn’t so sure. He said, "Go learn how to run a US business and compete at that level - then any door will be open to you. And don’t take my word for it. Try it for 6 months. If it's not the thing you want, I'll personally pull you back and send you to Geneva."

That was (and remains) the most powerful thing someone could do for me- to not only honor my ambition and give me a big opportunity with a nudge, but a create a built-in safety net to make it feel safe and doable, especially so early in my career.

The 6 month rule words like this: Doing anything new feels scary. Add in something really hard and you're going to second guess yourself inside of the first couple of weeks. The natural reaction is going to be that you made the wrong decision and to quit. But the 6 month rule says you have to commit to 6 months of doing your all. Throw yourself into the full experience without reconsidering or waffling. Then at the 6 month (or even 12 months if you can) you can take stock and assess how its going. Most times you'll have gotten over the hardest bits and be excited about all the new that lies before you. But there will be times when you realize you've learned a lot and its actually shed light on the thing you're more interested in doing. And so you choose that.

In any case, this is a map for progress made of big leaps, made safe with practical safety nets.

4. 🤔 Learn how to think, not what to think. Anytime I get to speak to high schoolers or undergrads, I'll get the question - “what do you think I should study?”. I personally think it's the wrong questions to be asking, especially in our quickly evolving world. I rather think we need to focus on learning how to think not what to think.

Choose the thing that develops robust and complete mental models from which to evaluate the world. And if you can, choose multiple schools of thought - the sciences are fantastic to teach you about first principles and hypotheses or choose economics to learn about markets or psychology to learn about biases or philosophy or…. And then go travel. Go live in another culture and learn a completely new language. That will teach you more than an entire major might.

And finally, learn to be a lifelong learner - picking up more mental modals and testing them against the data of the world as you come across it. It’s the only way I know we’ll all be able to “compete” and keep up in this quickly changing world.

5. 👯‍♀️ Focus on the people not ideas. The other most common question I'll get is: “how do you get your startup ideas?” Again I think that's the wrong question to be asking.

This is also the one thing I wished I had been told or had learned earlier in my career:

In the early years, my job was not to focus on ideas but rather to collect two things - insights and people. The living and the learning from the previous point will lead to the ideas. But then you'll need the people to make it a reality. And truth be told - this is actually the harder part. When it comes time to work on something big and ambitious - who will be beside you? So as early as you can, start noticing who are not only the most intimidatingly talented people around you, but all the most fun to work with (for you). Start finding ways to work with them and test that out in practice.

The idea is to always have a shortlist of people you'd call up if you ever decide to do something - and by then it wont be a theoretical test, but a continuation of previous collaborations. And on the other side, you wont be a totally unknown quantity to them. That friend will know you and what you’re capable of.

There is so much more that I could probably impart but these are the 5 that I think are the most relevant and actually useful, especially for folks earlier in their career (or for anyone restarting in a new space).

Focus on the dots that maximize learning - commit to at least 6 months in gathering insights, mental models and amazing people.

The rest is trusting and living life in all in messy wonder.

I’m sitting on the Acela right now, enroute to Boston. But because I’m here, I’m not at either of my daughters’ Music Sharing sessions. Luckily my husband is going to our youngest’s and my mum is going to our eldest’s (because of course why put them at the same time for working parents when you could do one at 11am and the other at 2:30pm).

But this is actually a good day. I feel a pang anytime I miss something, but this is the reality of our lives and our choices. With two companies and two kids, “good” looks like a week when we know everything we need to do, we’re able to divide and conquer well and the big things don’t get missed.

Today is a day that everyone knew to wear the formal uniform and to bring the instruments. We knew it was happening early enough that we could talk over on Sunday who would take which shift. And today, we’re all doing the things we’re supposed to be.

Today is a good day. But they’re not all - missed reminders, last minute dashes, unintended shouting matches and tears.

Too many moments when I wonder: how are we meant to make this all work?

***

I did school when I was supposed to. Got married when I was supposed to. Had kids when I was supposed to. Kept going in being just as ambitious at 40 as I was at 20.

Because isn’t that what I was supposed to do? Pay my dues in my 20s, invest and build expertise in my 30s, to really hit my stride of my 40s?

And so I did. Along the way I was lucky enough to meet and marry my partner-in-crime at 29, after graduating from my MBA. We welcomed our first daughter at 31 as we wrapped a stint in Shanghai, and our second daughter at 34, a tidy 2 and 1/2 years later.

All so very average when looking backwards at the timestamps of my life.

I figured my 30s would those messy years with really young kids but it was okay because I was still building my career. Surely by the time I hit my 40s, things would start feeling less hard. Less crunched. Less frantic.

I always thought that the hardest part of parenting was while the kids were young. Like under-5 young. Sleepless nights, constant care, steep learning curve on all the things. And they certainly were. Hard enough.

But then my girls started school. And ushered in what really does feel like a “harder” phase.

We have less childcare help - where we once had our amazing Rosa and we handed the kids off to her each morning, we now have to cobble together drop-offs, pick-ups and after school care in what feels like a constantly hodgepodge way.

To say the “information” is like a daily firehose wouldn’t actually be so much of an exaggeration. Library book reminders, crazy sock days, basketball team reminders, late start, early dismissal… the joke goes it takes a full time job to just read the school emails. It would be funny if it weren’t so tragically true.

Then there are our schedules. I don’t know if it’s a post-covid thing or just the age of my kids thing but everyday feels like it’s scheduled to the gills. Even fun and spontaneity have to take a ticket and get on the calendar. Extracurriculars, social things, errands, work things… all fighting for billing, all jostling for attention. It doesn’t help that the kids’ commitments out number my husband and mine - all requiring a trusted driving adult to fulfill them. To say nothing of the fact our schedules are made harder for my frequent travel, a necessity because the locations that feed my ambition don’t match up with the place that fuels my family.

And topping it all off - it turns out I’d say our girls need us more now than they did when the were younger. I thought that my traveling for work when they were 4 and 2 was the complicated bit. But no. At that age, they just needed someone who loved them and could do all of the care things - feeding, playing, bathing. Those were the years of Care. Now? They’re the years of Character. At 9 and 11, it matters that it’s me or my husband hearing their little stories about the French test or the classmate who was unkind or the amazing shot they hit in tennis. That connection on the little things is what matters and I need to be there and present. To help them understand how to navigate this complicated world with the values and mental models of our family’s making.

So if you take all of that - more things with less help while being even more important, how is this all supposed to work? And worse, why does it feel like such a surprise? Hard I can do. It’s the unexpected and unending hard I’m struggling with.

We did what we were supposed to - what we love to do. My husband and I have found ourselves to each building companies we believe in deeply. We’re trying to be the partners to each other through all of the work and the life. And we have been so incredibly blessed to have these two lights in our life. These sparks who are bundles of joy and ideas and energy and feelings.

We worked hard to get to this point and we work hard everyday. But no matter how hard I work, it just doesn’t feel like it’ll ever add up.

Maybe I should have known to do the math. That having a kid at 31 would mean feeling the greatest crunch in my 40s.

But I never did that math and no one ever told me. Maybe because there were so few to do the telling and maybe because parenthood has changed so much in the last 15 years that the tale has changed irrevocably.

All I know is that it’s not just me. Everywhere I turn I see and hear the same.

The thing is: I think it’s possible. To have the career I love and the partner I can support and be supported by, and be the parent who can be present for the little stories and the big lessons (both ways). Because there are moments of it in my life today. Enough of them that I’m just greedy for them to make up the majority.

I think it takes people we trust and who love our kids as we do, I think it takes help that is built acknowledging modern realities and I think it take policies that see families as the core unit of society, not the individual.

All I know is that I did what I was supposed to. Every day I try to keep doing what I’m supposed to. And while I feel my fortune every morning and every night, I don’t accept that it should be so hard.

I’m not asking for easy. I don’t want easy. I never have.

I love our full, messy, imperfect life. I already know I will look back on these days with nostalgia.

But modern parenting should not be a paradox.

I am no stranger to the concept - after all, there is no doing anything outside of parenthood without having a little niggling voice saying "but you could be cuddled up to them right now." Especially for women raised under the socialization of fairly traditional family roles.

But it’s been especially acute because for the past 9 years - the entirety of my youngest’s life and nearly that of my eldest - I have found myself pulled in two directions - one that loves being in the home, making a home with these incredible lights. Cooking up a storm in the kitchen, exploring our community with our neighbors, teaching the girls to see the wonder in the world in every big and small way. The other? Out there in the world and in my computer, imagining futures that don’t yet exist but that I need to exist.  

And so instead of choosing One or the Other, I, like so many others, chose to attempt to do the Both.

The cost? Beyond my sleep and sanity is surely the guilt. That I’m not doing either justice.

My head knows the guilt is fairly useless.

My heart says otherwise - when I slip into their rooms at 5am before an early flight. Or when I’m working through a challenging problem with the team instead of attending a school assembly. Or when I need to respond to a user in the middle of Uno.

My life and my choices mean that our life and our choices look different than most families.

I've struggled with this a lot, especially as I wonder "is it worth it?" The ambiguous somedays of solving this problem vs. the very real todays with my girls.

But this year changed my thinking on this.

One weekend in particular.

This time last year, we were one of 10 teams to be funded by OpenAI and invited to spend 8 weeks with their researchers and teams. I spent most of December and January in SF, learning, experimenting, building with GPT4 - still under wraps but expected to be launched in weeks.

Then March 9 happened - on this Thursday, I was flying back from SF to Vancouver and at the airport I learned: GPT-4 was to be launched in 5 days. And at the same time - something was going on with SVB the bank that held all of our company's money.

We went into divide and conquer - my cofounder was to figure out the product for Tuesday and I was to make sure we had a company making payroll. To make things worse, my girls got off on Spring Break that day and I was without childcare for the next week as my husband left for a work trip.

That Friday, I decided I needed to be back in SF so we could work through the weekend together.

My instinct was to do what I would usually do: call my parents and say I needed to drop them off for the next 4 or 5 days. But boy did the mom guilt rear its head.

It was my eldest's birthday in days, it was Spring Break and I already hadn't seen them in a week.

In flash of madness I thought: why don't I bring them?

And so I did - I booked a last minute flight for all of us to head to SF and over the next 4 days, over room service, trips to the Exploratorium and a little corner in the office for them, I managed to find my version of doing both.

We built the product and figured out all launch details while miraculously making sure our money was safe over a rollercoaster weekend. They were there when our design team introduced the “Milo Monster”, after which my youngest started drawing her own renditions. They were there as we debated how certain parts of the beta product should work, to which my eldest offered up her thoughts on emoji choices.

And when GPT4 launched that Tuesday, we ended up going a little bit viral. But by then, that was so far from the point.

As I look back on 2023, it’s one of my favorite memories. It took an insanely stressful 5 days and made it fun and meaningful.

But the true learning from this weekend didn’t sink in until later this year when I had another stint of back to back travel and mom guilt was raring its head again. Work was going really well but I was feeling terrible about home.

I came home to this sitting on my desk:

And I might have teared up.

My girls, my hearts, see my heart.

They are not damaged or deprived because I pursue my calling. They only ask to be a part of it.

That’s not to say this is all nice and tidy. The days are incredibly hard and messy. But they see I’m doing the best I can. They give me the grace and the will to do the best that I can.

It’s a conversation I’ve had to have with the girls this year- when I inevitably disappoint on the times I’m not there, I try to focus on the times I am there.

I tell them: you’re not going to be the kid who has a mama who makes every school assembly. But you’ll always be the kid who’s invited to be a part of these crazy life adventures. Invited in to this other side of what makes me, me.

They are always welcome in our office, in our meetings, into our mess. Just as my team sees and hears and lives it all too.

And ultimately what I’m taking into next year?

The guilt happens not because I’m trying to do two hard things well. It happens when I try to do them on someone else’s terms - whether it’s the other families at our school, my friends or society in general.

This is the year I said goodbye to this Mom Guilt. Not because I won’t keep feeling this tension. But because I’ll use it to find the wild options I could never have seen otherwise.

Persistence is a critical factor in most successes, but particularly in start-ups.

“If you can just avoid dying, you get rich.” is one of my favourite expressions of the idea. There are many examples to prove this point - from Twitch to Airbnb to Canva to Pinterst - really more the rule than the exception of the Instagrams.

It’s easier said than done. I am increasingly asked - what makes you persist? After all, it’s been nearly 9 years on this crusade to use technology to make the every day experience of parenting today easier.

Having considered it, I’d say it’s 3 things:

1. I see my work as a scientist, not as a business person. My job is to “imagine and future and build what’s missing.” That sounds awfully like: have an overarching theory and test individual hypothesis until you can figure out if the theory holds or not. It’s why I don’t see Poppy as a failure - sure, in start-up terms it failed. But in scientific terms it was a tremendous success - the number of variables and hypotheses tested have led to not only insight in the critical sector of childcare, but in shedding light on the next problem to work on which doesn’t even have a category. It pushed me to a frontier I couldn’t previous see, standing in the distance. Success in science is measured in advancing the frontier of knowledge and understanding, not in the outcome of any one experiment. Getting something for 0-1 (eg until there is a viable business to grow), the work is more of science than business.

2. Obsess about rate, not time. Most ambitious projects - whether in films and books or satellites and medicine - take years if not decades to come to successful fruition. There is a false expectation that start-ups should be measured in months. The true question to ask is not one of time but rate. What distance is being covered over a given unit of time? If that rate is reasonable, then the matter of time is simply a by-product of the work. Each year over the past 9 years I have personally experienced a higher learning curve than my previous years and I’ve created valuable insights in the category in which I work. As long as we’re achieving progress, earned by serving our users and held to the discipline of runway, it’s quite easy to watch years slip by, working on something endlessly fascinating and impactful.

3. Persistence chooses you. It’s so much easier to keep going on something that you find endlessly fascinating and can keep finding threads to pull on. But the surprising thing is how often people are surprised by what that thing ends up being. Many founders, artists, scientists will say “it’s a calling” - as if the topic of study or work wasn’t really a choice but a call to answer. Similarly, I never imagined becoming obsessed with matters of care and the work of the home, especially when so much of my interests lay in other places. And yet - it’s the only thing that has ever held my attention past a year.

Know when to hold and when to fold.
Still, there is a difference between persisting in promise vs in vain. In any arduous hike, you need to make sure you’re persisting in the right direction - blindly walking in the wrong direction out of stubbornness is not persistence, it’s a waste and worse, can kill you.

The easiest way to know the difference is to:

• Have the right core metric and focus on it relentlessly. The only way to know you’re on the right path is to have the one core metric that tells you your hypotheses is bearing out. If you have the right metric and you can grow it consistently 10% week on week, then persistence is just a matter of time and compounding doing its thing. If you can’t get it to grow consistently by that much, ask the question: what is single thing keeping me from growing that number by that much. Then go solve for that. Over and over. Said best in the The Martian: “You just begin. You do the math. You solve one problem... and you solve the next one... and then the next. And If you solve enough problems, you get to come home.” Persistence lies in the blinders of solving what lies in front of you.

• Know what are unbreakable walls or immovable hurdles. In some categories, there are factors that will lead to failure no matter the resolve or even the money. You’ll start to get a sense of them when the growth rate of your core metric doesn’t budge no matter the focus on controllable levers. For Poppy, it was the fact that childcare is in many cases is a broken market and trying to apply market principles was destined to fail. There wasn’t enough money in the system to make it work sustainably. Quality workers didn’t get paid enough, parents couldn’t afford more and there wasn’t enough for the intermediary in the middle (us) to uphold the necessary level of quality and trust. Moreover, costs like taxes pushed any scale solution out of the possible to the improbable. Realizing it was a math problem would require me to: 1. lower quality 2. turn a blind eye to laws (paying taxes) or 3. entirely change the product into something that didn’t solve the problem. Instead, I had to acknowledge this wall I couldn’t bust through and I chose to move on from the conclusion of this hypothesis.

• Have a board of reality mirrors. Founders have to believe in something so ludicrous that few others attempt to try it. Over the years it becomes a very present version of reality to live in. Every founder needs a small number of individuals who can kindly but firmly hold a “truth mirror” up to them. To ask the questions and hold to timelines. When it’s time to call it, they’ll be the ones sounding the alarm first. And if you don’t have the people, you will have the reality check of runway. The money never waffles. But by then, you’ll likely be out of options.
  
  And finally, a personal reflection - persistence rarely happens in a vacuum. There is a whole network of support people and circumstances that have to be in place for the will to do its thing. If you’re like me and started doing this with a partner and kids in the picture, that support extends to quite the village of people that have to not only help but be on the ride for the long haul. Too many people don’t have access to the kinds of support systems - people, time, money - to even attempt this kind of work.
  
  [One of the most depressing findings of my time has been how women in particular are not systematically enabled to attempt work that requires persistence, especially after they have a family. Matters of care, risk and finances mean that while many men continue to pursue this work with a supporting spouse and society, very rarely is it done the other way around. In my research, it’s not just entrepreneurship but anything that requires this kind of persistence and obsession - composers, artists, chefs, scientists, politicians… the frontiers are lined with men (especially with wives that played critical roles as “research assistants” vs. named collaborators) in good part because the conditions of persistence are not as readily available for women with a family. While the Motherhood Penalty has been well measured (“mothers experience a 60% drop in earnings compared to fathers in the decade following the birth of a first child”), the effects on the frontiers of disciplines are less discussed.

I attach this insight here because I think it’s just as important to share the behind the scenes factors as much as the more obvious ones. Today I really don’t think most people realize just how much supporting conditions have to be right for this kind of work to continue for years and decades and how unevenly distributed those conditions are. So if we’re going to talk about will, we’re going to talk about village.]

In the end, persistence is a measure of progress and time. If you have enough progress, persisting is actually quite easy, spending time on a frontier of your choosing and skills. If you don’t have enough progress, then you’ll find persistence is actually out of your hands - through runway, will, or mutiny.

Focus on the progress. The persistence will come.