In the process, I picked up An Odyssey by Daniel Mendelsohn, a memoir that describes what happens when Daniel’s 81-year-old father, Jay, signs up for his undergraduate college seminar analysing the poem.

It’s a unique book — cleverly disguising textual analysis of Homer’s work within stories of Jay and Daniel’s own father-son relationship (much like a certain Trojan Horse).

In An Odyssey, Mendelsohn points out a fact that surprised me: Homer’s poem doesn’t actually feature Odysseus for its four books.

Instead, the subject of the first ~15% of The Odyssey is Odysseus’ son Telemachus, as he seeks out stories of his father and tries to figure out if he’s still alive.

Mendelsohn compares this literary sleight-of-hand to the works of Renaissance Dutch artists.

“It is hard not to feel that Homer’s decision to obscure and blur and postpone our view of the epic’s main character is designed to pique our curiosity about this shadowy figure, who, in these crucial first pages, seems to lurk at the far edges of his own story, curiously small and difficult to make out, like one of those tiny figures in a Dutch painting you risk not noticing at all because your eye is drawn to the painting’s ostensible subject, the figure in the foreground”

The most famous example of this type of painting is Landscape with the Fall of Icarus by Pieter Brueghel. It draws upon another famous father-son myth of the great inventor Daedalus and his son Icarus, who break free from a prison by flying away on artificial wings made out of feathers bound by wax.

Daedalus warns Icarus not to fly too close to the sun because the warmth will melt the wax. But Icarus gets carried away, ignores his father’s warning, loses his wings and crashes into the sea.

Brueghel’s painting (see below) captures the moment just after Icarus has fallen.

I’ll be honest, I’m not usually a paintings kind of guy. I can appreciate the beauty of The Last Supper or Starry Night, but don’t find that they linger in my mind.

But something about this painting spoke to me. It reminded me of two things.

The first is that what can feel hugely significant to you is usually very insignificant in the grand scheme of things. The original myth of Icarus is one about humility — not to fly too close to the sun. The painting is about a different, more cosmic form of humility. A legendary tragedy is reduced to an innocuous splash off the coast as life goes on around it. Often this year, as I’ve been experimenting with making videos and podcasts, I’ve worried about what other people will think. This was a good reminder that no one actually cares that much, and that I will always be my harshest critic.

A second (and somewhat contrary) way of looking at it is not to mistake the foreground for the whole picture. Most of the painting is taken up by the shore and the three peasants going about their business. But what is of deeper interest only becomes apparent after more careful observation. The same thinking applies to problem-solving or research — you need to sit with things for a while before leaping to conclusions. I’ve found this to be true when researching videos for my YouTube channel. The broad-strokes AI-summary style research is interesting enough. But the true colour only comes out when I listen to full-length interviews with founders or read existing in-depth essays or books.

Last week, I was reading Stoner, a novel by John Williams.

It follows the seemingly unremarkable life of an English Literature professor in 20th-century Missouri, but is tinged with a deep, universal sadness.

One passage stood out to me. It describes Stoner starting his research for a book he is writing:

“He was in that stage of planning his study, and it was that stage which gave him the most pleasure — the selection among alternative approaches, the rejection of certain strategies, the mysteries and uncertainties that lay in unexplored possibilities, the consequences of choice.”

For any work that I do, I’ve noticed that these initial phases are also what give me the most joy.

This was true in my consulting career. I often had to go from ‘zero to one’ on a new industry, ranging from dairy producers to mining software to private hospitals. I always had a blast getting up to speed. This is also true for my current media projects, where I happily go down rabbit holes researching companies for my YouTube videos or researching guests for my podcast. Every choice at this initial stage feels full of meaning and can greatly change the direction of what I’m doing.

So, I wanted to write this piece as an ode to the research process, and encourage anyone reading to take on a research project.

What is research?

Our view of research is often grounded in what we did at school or university — topics that we didn’t really care about, rigidly formatted essays, pages of bibliographies (and no Wikipedia!).

While this is definitely a form of research, it is a narrow conception of what research can be. A broader definition might look like this:

• Research answers a specific question. There is usually some hypothesis at the core of any research task. This can be scientific, like “how does a virus reproduce?”, or “why does a prism split light into separate colours?”. Or it can be more grounded in the arts or culture, like “did the poet Homer actually exist?”, or “why do dragons appear in so many different mythologies?” By definition, this means that curiosity is an essential component of research.

• Research is based on evidence. To answer the hypothesis, you need to commit to finding or at least getting closer to some objective ‘truth’. The only way to do that is by finding evidence to prove or disprove your hypothesis. This can be quantitative evidence, searching for meaning and patterns in data. Or it can be qualitative evidence, involving deep investigation of primary and secondary sources.

• Research is outcome-oriented. What separates research from more casual reading is working towards an output. The form of the output can look very different — a video essay, a 10-page report, a speech at a conference or a 30-second TikTok video. Simply having this end goal gives you a framework to hang everything off and ensures you’re not just consuming information for the sake of it.

• Research has timelessness. Most research is grounded in a question that is relevant to contemporary concerns. But often, the fruits of research look very different from its initial intentions and aren’t discovered until much later. For example, the drug rapamycin was discovered by accident in a soil sample from Easter Island. It was initially used as an anti-fungal treatment. But later, researchers realised that rapamycin also suppresses immune system cells, and it is now a critical component of organ transplants.

What does a more playful form of research look like?

The above definition of research still misses a key ingredient — fun.

In her wonderful essay, research as a leisure activity, nix puts forward a conception of research that is done for joy:

“Research as a leisure activity…is fundamentally about play. It seems to describe a life where it’s just fun to be reading, learning, writing, and collaborating on ideas”

I believe that this is the type of research that John Williams was describing in Stoner. And there are a few more ingredients you need for this:

• Passion. You need to enjoy learning about a topic and peeling back the layers. What is interesting to you is a deeply personal question. But it’s always easy to detect someone’s genuine passion for a topic.

• Loose structures. For me, the part of the traditional research process that feels most draining is the rigid structures around it. In my brief foray into law school, I found one of the most annoying things was footnoting and referencing in a very specific way, and losing marks for even a comma out of place. I recognise that appropriate crediting is important - a) so that a reader can see where you got your information from and b) to acknowledge that you are standing on the shoulders of previous work. But research for fun relaxes the rigour a bit, so you focus more on the joy of discovery and learning.

• Self-driven nature. When you start researching something, you initially develop more questions than answers. You might need to dabble in adjacent fields or change the course of your argument. This requires a high degree of agency and a willingness to drive your own process. But I think exercising this agency is where the magic of research lies. I often wonder about the psychological impacts of living in a world where the map has already been fully explored — there’s no physical ‘frontier’ left. Research functions as a substitute for the physical frontier by allowing us to expand the boundaries of our knowledge.

How do you do good research?

So let’s assume I’ve convinced you to take on a research project. What does good research actually look like?

• Talk to people. Desktop research and reading can only take you so far. The true contours of a subject come out most clearly when you talk to people who’ve been immersed in the field and thinking about the question far longer than you have. I learned this when I would do ‘expert interviews’ at Bain for due diligence projects. Asking the right questions in a 30-min call to a 20-year industry veteran would be 1000x more useful than a day of Googling. This skill is getting more important in the age of AI — so much useful knowledge is tacit, meaning it can’t be sucked up by LLMs.

• Bring your expertise. This relates to the passion point I made earlier. The best research often comes from people who have insider knowledge on a topic. This might be because they have spent their whole careers in the field (for example, the guys behind Acquired are Silicon Valley insiders). Or it could be earned by reporting on a topic for a long time, like Ronan Farrow reporting on Sam Altman or Karen Hao writing about the AI race.

• But don’t underestimate an outsider perspective. Some of the best research and journalism comes from bringing an outsider’s view to a specialised topic. This is especially powerful when this outsider has expertise in a different field. One example that comes to mind is ’s NYT article on Chinese peptides. Sun doesn’t have experience in biology, but does know about the tech-bro self-optimisation culture in San Francisco.

• Have an audience in mind. Whenever I’m struggling with writing scripts for my videos, I imagine that I’m explaining the topic to one person. The persona I have in mind is an informed layman - someone who is sharp and well-read, but just hasn’t heard of the topic I’m researching. This helps me communicate at the right level.

• Don’t fret about originality. One thing I’ve been pondering with my YouTube videos is that they are not truly investigative. I am mostly consuming a bunch of information from podcasts, books, news articles and essays and repackaging them into a digestible video format. I think where I’m landing is that this is still a valuable research task because it provides access to existing information to a new audience.

I’d be keen to hear from any of you if there’s a research project you’re currently doing! I love hearing what makes people excited to get out of bed in the morning.

I just published an interview with Jessy Wu, a former VC and communications agency founder who has just released her debut novel, Good Intentions.

Below are 8 lessons from my conversation with Jessy. You can listen to the full episode here:

1. Identify your personal superpower. Writing has always been the throughline of Jessy’s career. As a consultant and VC, she consistently received good feedback on her clean, logical slides and investment memos. Writing a novel was an extension of this existing strength.

2. Publishing lives at the intersection of art and commerce. The writer controls what goes in the book. Everything else (cover design, blurbs, positioning, pricing) is shaped by the commercial engine of the publishing house. Jessy was able to lean on the business instincts she built as a VC and founder to help drive this process.

3. Craft without art is hollow; art without craft is illegible. Good art answers a question the author couldn’t answer any other way. Good craft makes that answer accessible to someone else.

4. The medium is the message. A novel lets you get a message across that an essay or tweet simply can’t, by letting you take readers on an emotional journey over 80,000 words.

5. Writing can be therapeutic. One of the first pieces of feedback Jessy got from her editors was that she was too hard on her protagonist, Nadia. Nadia has a lot of the traits that Jessy herself has struggled with. She’s pragmatic, self-protective and willing to look away at times. Rewriting Nadia’s character with real sympathy was “very therapeutic” and made the book better.

6. Having beta readers pushes you as a writer. Many authors treat writing as a solitary pursuit. Jessy went the opposite way, sharing her first chapters with three friends who “started hounding her for more”. Having a cheer squad gave her the momentum to finish and calibrated what people would respond positively to.

7. An artistic career is hard work. To make writing financially sustainable, she estimates she needs a book roughly every one to two years, strong advances across territories, translation rights, and TV/film options. To finish Good Intentions, she reread her own manuscript “a hundred times” and had to deprioritise her relationships and business at times.

8. Your vibe attracts your tribe. Jessy has been intentional about building her ‘personal brand’ on LinkedIn, vocally standing up for things she believes in. There’s more to gain than to lose from posting online, as so many people will open doors for you if they trust you and back you.

At one end, you have AI optimism (“this technology will be the best and most important thing we’ve ever built”). On the other end, you have AI populism (“this technology is destroying our environment, society and culture”)

I land more on the optimist side. But I still have a healthy dose of trepidation about what the future will bring. I think this will be another example of Amara's Law — we overestimate what technology can do in one year but underestimate what it can do in ten.

But putting philosophical musings aside, I wanted to write a more practical article about how I use AI day-to-day, what I think it’s great at, and where it’s not quite there yet.

The 4 ‘AI personas’ I use

My current work is primarily in media, both audio and video.

I make business explainer videos on my YouTube channel (Playbook), host an interview podcast and work as a producer and editor at a video agency making content for startups and tech companies. I’ve also been dabbling in building personal apps and software that make my life easier or more fun.

Over the past 6 months, Claude (both the chatbot and Claude Code) have become integral to my work. I’ve found 4 ‘modes’ or ‘personas’ that I keep coming back to:

1. Research Assistant

2. Tutor

3. Executor

4. Engineer

Let’s look at each of these more closely.

1. Research Assistant

The first thing I do when I’m researching a topic for Playbook is to ask Claude to create a consulting-style report for me.

From my days at Bain, I know that good due diligence reports typically contain the following:

• Business definition: What does this business actually do? How do they make money? How has this changed over time?

• Market size and growth: What market does this business play in? How can we size this? Is this market growing? How quickly and why?

• Competitive landscape/unique advantage: Who else plays in this space? What is it about this company that gives it the right to win?

• Next steps: How can this business create further value in the future? What does the roadmap look like? What are potential risks?

In my prompt, I ask for the report to be structured like this. Given the more narrative-driven structure of my videos, I also ask for a timeline of events, background on key characters, and an executive summary with 3-4 key takeaways.

I look at this report as a useful map of the terrain, rather than the end of the research process. I also always ask for links to source material to double-check key statements and figures (more on this later).

Zooming out, this persona feels more like a supercharged version of Googling, rather than a completely new way of working.

2. Tutor

I made a pretty sharp pivot into the media space this year, and have had to be comfortable being a beginner again.

That being said, it’s probably the best time ever to be learning new skills (at least of the keyboard warrior variety). At its best, AI functions as a tailored 1:1 tutor with a deep and broad knowledge base (particularly for widely adopted tools and programs).

This has greatly sped up my process of learning DaVinci Resolve for video editing and After Effects for motion graphics. The best part is the responsive nature — I can ask Claude to check the latest documentation, provide screenshots when I’m stuck and engage in a back-and-forth dialogue as I would with a human coach.

I’ve also (re)learned the power of clearly defining what I’m trying to solve. A Bain partner I worked with once said, “A problem well-framed is a problem half-solved”. If you don’t ask AI the right question, it will lead you down the wrong path or make incorrect assumptions. And often, doing the work of articulating the problem actually helps me think of the solution too.

3. Executor

I use the ‘executor’ term here broadly, referring to any time that Claude carries out a task that I previously would have. A few specific instances:

• Design. I’m still a relative newbie to graphic design, which is becoming more important for my work. So I was excited to try Claude Design, which promises to help build polished prototypes and animations. It blew my mind the first few times I used it. I started by asking for simple animations to use in my Playbook videos, such as a map showing all the Uniqlo stores opening in Japan. My expectations were low, but it produced a pretty slick graphic that I was able to drop straight into the final video.

• Slide-making. One thing I’m not a newbie at is making slides — this was my bread and butter as a consultant. But I underestimated how much heavy lifting Bain’s custom presets and formatting were doing (the ‘Toolbox’ as we called it). So, I’ve started using Claude to do this prep work for me. When I was recently making a podcast analytics dashboard for a client, I sketched out what I wanted the slide to look like on paper and fed a picture to Claude. It then gave me a PowerPoint file that was pretty close to what I wanted.

  

  

• Video editing: This is the use case I’ve used least so far, but the one I’m most excited about. It’s made possible by a Claude skill in this open-source GitHub repo. It transcribes your video file into text using the ElevenLabs API. It then reads the text to work out what to keep and what to cut. At each cut, it runs a self-evaluation by taking screenshots to check whether it’s messing anything up. The best part is the flexibility of both inputs and outputs.

  • Inputs: You simply point Claude Code to your raw video file(s) and give it instructions. These can range from just cutting out filler words to colour grading, adding subtitles and motion graphics. If your video is based on a script, you can also feed it a PDF and say, “assemble all the best takes”.

  • Outputs: You can ask Claude Code to render a fully colour-graded .mp4 file without opening a video editor. Or you can ask for what’s called an ‘Edit Decision List’, which you can then import into a video editor like DaVinci Resolve as a starting point. This is how I’ve been using it - feeding it my Playbook scripts and raw videos and working with Claude to create a table of what it will keep and what it will take out. After I review and approve, I then import the Edit Decision List and have an ‘assembly edit’ ready in DaVinci that I can build on.

• Podcast editing. This uses the same Claude skill as above, but in a slightly different way. I ask it to transcribe the episode and build a table of what to keep and cut and why. I also ask Claude for 3-4 ‘hook-y’ moments from the conversation that would make good shortform clips. After you’ve been in the weeds of editing for a while, you can lose sight of what is interesting or insightful. So I treat this as a useful second opinion, while still keeping my judgment in the loop. I’m not yet confident enough to hand over the reins entirely (and don’t know I ever will be).

4. Engineer

This has some overlap with the executor persona.

But here, I am referring more specifically to writing code to build websites or apps — something I’ve never been able to do in the past.

I’ve tried many times to learn programming. I’d always get through the first few lessons of Python or JavaScript, but then give up.

I think the main issue was not having a near enough goal to work towards. I would know that learning all the basic building blocks was important, but I was frustrated by how far away building a final product felt. Thanks to Claude Code, that gap has collapsed.

I can explain the product I want to build and why, create a Product Requirements Document and make collaborative design and engineering choices. For now, this has just been for fun side projects, like a daily journaling app where I note down one story I want to remember from each day. This was simple but helped me understand basics like database structure, authorisation/login flows and simple frontend design.

I’ve also built simpler automations, such as a way to highlight something I want to note down on my phone and add it automatically to a dedicated Notion page.

‘Vibe coding’ feels like a video game. I understand the level I want to complete, it’s just about finding the right way to get there. I’ve only scratched the surface here, but I’m now always on the lookout for what problems feel ‘software-shaped’ — basically anything in my work that is routine and low-risk.

What I think AI is great at

Stepping back, I see three main benefits of using AI.

1. Speed to output.

This is the most obvious one. Things that would have taken me much longer (e.g. building an animated graphic from scratch) take at least an order of magnitude less time. This has enabled me to experiment with a bunch of different projects that I probably wouldn’t have been able to juggle 2 years ago.

2. Unlocking new possibilities

Using AI has expanded the frontier of what is possible for me.

It’s hard to maintain the facade of AI as a simple ‘next-word’ predictor when you see it take complex, multi-part problems, break them apart and produce high-quality output.

I’ve had many “whoa” moments over the last few months:

• For my World Cup video, I had a very specific animation in my head of a World Cup ticket, with the price counting up and down to illustrate dynamic pricing. I struggled to build something that looked right in After Effects. Claude Design was able to produce it in just one prompt.

• When building the Story of the Day app, the first time I linked up my Supabase database and enabled sign-in with Google felt so cool. It’s probably trivial for a software engineer, but it felt like magic to me.

• While video editing, I’ve been surprised by how adeptly Claude can understand the context and objective of what I’m trying to make. It’s also produced some hilarious bloopers, like the time a fly kept coming into my shot and pushed me to the breaking point:

  

3. Effective learning

AI’s ‘tutor’ persona is extremely powerful. But it also depends a lot on how you use it.

In the article below, Ethan Mollick writes about new research that illustrates the difference between using AI to shortcut learning and to help learning.

One Useful Thing

Choosing to Stay Human

If you go to your favorite social media site, you will find it full of posts that start to look suspiciously similar to each other…

Read more

3 months ago · 1175 likes · 154 comments · Ethan Mollick

The first paper split mathematics students into two groups. One had no AI access, while the other used ChatGPT. The ChatGPT group did their homework better and thought they were learning more, but at test time, they underperformed the no-AI group. They were doing the equivalent of checking the answer key at the back of the textbook, without actually putting in the effort to learn.

The second paper (from many of the same authors) ran a five-month Python course across a thousand students in Taiwan. One group of students was given a personalised sequence of problems by an AI tutor. This group scored 0.15 standard deviations higher than the other group on a final exam taken without AI help (the equivalent of 6-9 months of schooling).

The takeaway is that how you use AI can lead to massive differences in outcomes. You need to not just let AI solve the problem for you, but use it as a tool that enables you to solve the problem yourself.

What I think it’s (currently) bad at

There are plenty of watchouts when it comes to using AI.

1. Writing.

Writing is probably the most widely adopted use of AI. It’s so much easier to dump half-formed thoughts into a chatbot than to do the work of articulating yourself.

On the surface, the outputs are good. Clear, to the point and with no typos. And with the right harness, you can make it sound like you.

But the writing lacks soul and always reverts to the mean. That can be fine for admin tasks and routine emails, but not for truly meaningful writing. If you’re feeling a sense of fatigue from all the AI slop on social media, the article below from Sam Kriss is for you.

Numb at the Lodge

If you let AI do your writing, I will come to your house and kill you

It’s none of your business why, but I’ve been planning a party. The idea was to get some caterers in to cook something over live coals, so I went online to see what was available. The first company I found described itself like this: ‘We don’t just provide food—we create meaningful experiences. Our passion for traditional fire cooking allows us to offer…

Read more

3 months ago · Sam Kriss

2. Hallucinations.

Although this is becoming less of an issue, I’m finding that AI can still make stuff up with confidence.

This has been particularly problematic in the ‘research assistant’ persona. For example, when looking into FIFA’s sponsorship structure for my World Cup video, Claude mentioned that Starbucks and New Balance couldn’t sponsor local fan events in Seattle and Massachusetts because this would have clashed with FIFA’s deals with Coca-Cola and Adidas.

Sounds realistic. But when I asked for sources, there was no actual evidence for this — it was just an inference that Claude had made. It was a good reminder to thoroughly fact-check everything I get back from AI.

3. Overenthusiasm

A good piece of advice I got was to treat AI like a skilled and enthusiastic intern, who will do a great job but needs the right guardrails. If you don’t provide appropriate direction, it will happily go off doing the wrong thing.

This means that you still need to have a strong thesis (call it taste, judgment, opinion, whatever you want) on what you’re building and why.

For example, for my Playbook video animations, I need to be able to clearly articulate the graphic I want and explain to myself why I shouldn’t build it from scratch in After Effects.

4. Polished video edits.

While the video editing skill is promising, I think there’s a way to go here. It’s currently great for removing the grunt work of finding the right takes and removing dead air. But the real skill of post-production still requires a human touch — identifying the right story beats, building the right graphics and knowing what music fits where and why.

That being said, the (short-lived) launch of Anthropic’s latest Fable 5 model might be a turning point. Interestingly, Fable edited its own launch video, which you can learn more about here.

5. Creating a bias to overcomplication

This is more of a skill issue on my part than a pitfall of AI. I’ve noticed that I’ve started to overcomplicate my work, because I know that so much more is possible.

For example, for that podcast analytics slide I mentioned above, my initial instinct was to create a website that would pull in all the data from the YouTube and Spotify APIs to create a live dashboard.

I burned a couple of hours trying to architect this, and soon realised that it would be much faster to use the native Spotify and YouTube dashboards and export CSVs to manually update a static artefact now and then. The below meme sums it up perfectly.

Thanks for reading! I’d love to know if/how you’ve been using AI and any moments that felt like magic to you.

A quick note

I’ve turned on the option for paid subscribers. This is for two main reasons:

• If you’re enjoying the writing and want a way to support me, this is the best way to do so.

• The Substack algo seems to reward writers with paid subs on with more reach (which makes sense, given their business model is taking a % share of subscriptions).

For now, all posts will remain free to read. In the future, I plan to publish more long-form articles and guides like this, which I may put behind the paywall.

As I wrote about here, I’m exploring a more ‘portfolio career’ this year, largely in the media and storytelling space.

I felt a ton of nerves and uncertainty when leaving my consulting job. Regardless of all the planning and thinking, taking the leap still felt like a huge risk.

So, as part of the process, I wanted to have conversations with people who’ve made similar bets and found success and fulfilment on more winding paths. By making these conversations public, I hope to inspire listeners who are considering taking a similar leap.

The first episode with Franko Ali is now live on Spotify, Apple Podcasts and YouTube. We chatted about Build Australia, his default optimism, the perks of growing up internet-native, his experience moving from the US to Australia and his recent sabbatical.

If you have any suggestions for future guests, reply to this email or drop me a note at saurav@nonlinear.fm.

I have a collection of pages on Notion called “Notecards”.

Anytime I come across a concept or quote I resonate with, I write it down here, along with any personal reflections or why I agree or disagree.

As you can see below, it’s loosely split into subcategories like “Life”, “Writing”, “Learning”, and “Interpersonal”.

It’s my digital version of a ‘commonplace book’. I often find myself flicking through it to remind me of ideas and observations I consider valuable.

Then, this week, I listened to this podcast episode with and writer .

In it, Celine talks about how she used to be an obsessive note-taker, but now barely touches her notes app. Instead, she goes directly to the page — all her ideas end up contained in her published work.

This inspired me to take ten ideas out of my Notecards and onto Substack. Here they are:

1. Randomness is as much a part of success as failure.

I’ve recently started a YouTube channel. My first video on the history of the IPL was an outlier success, getting my channel monetised straight away.

I then came back down to Earth with my second and third videos. I thought they were better products in terms of storytelling and video editing quality, but I got a fraction of the engagement.

I can’t lie, this sucked. I knew they probably wouldn’t land in the same way as the first video, but it was still deflating.

However, it’s made me realise how much is out of my control when posting content to algorithmic platforms like YouTube. As Nicholas Taleb writes, “Nobody accepts randomness in his success, only his failures”.

What is in my control is to keep making high-quality videos that feel interesting and alive to me. By continuing to build a portfolio of work that I’m proud of, my surface area of luck will continue to expand.

2. Great writing is often very precise writing

I often struggle to articulate what good writing is. I guess that’s part of the beauty of it — art is subjective.

But one common pattern I’ve noticed about good writing is that it is precise.

A good writer can observe an object or experience in such high resolution that they make a comparison or have an insight that is unique.

A few examples I’ve come across recently:

• “What is choice but a branch of the future grafting itself onto the stem of the present?” — from Trust by Hernan Diaz

• “The Hebrew word ruach, the Chinese word chi, the English word spirit, and the Inuit word Sila all derive from words meaning breath or breathing. Breath is life — to inspire is to breathe in; to expire is to breathe all the way out” — from Everything is Tuberculosis by John Green

• “A charming person is not one that glimmers but holds a mirror to your glow. A conversation with them makes you fall for them by making you fall for yourself” — from how to be life’s personality hire

• “There is luxury in self-reproach. When we blame ourselves, we feel that no one else has a right to blame us. It is the confession, not the priest, that gives us absolution” — from The Picture of Dorian Grey by Oscar Wilde

3. AI writing is dangerous in its frictionlessness

We’ve reached a point in society where generating words has become free. Anyone can put a half-baked thought into an LLM and get a polished output that looks intelligent on the surface.

And the quality of the outputs will only get better. Even if Claude Opus 4.7 isn’t quite there yet in producing writing that doesn’t sound “AI-fied”, I’m sure Opus 14.7 will be.

What are the consequences of this?

Well, firstly, the simple fact that a person has published writing is no longer a signal that they are a writer. This means that you have to think a bit harder about who’s writing you can trust and put weight in.

Secondly, I worry for the young student who has an easy way to avoid writing an essay. The friction of finding the right words and articulating yourself is where the value of writing lies, not the final output.

One of the reasons I pulled back on writing weekly here is that it tempted me to run my fuzzy thoughts through AI to get to a final product more quickly. At first, I naively thought “this is great!”. But I’ve come to realise how dangerous this is and how quickly my thinking and writing muscles would atrophy if this became a habit.

There is a more optimistic, abundance-focused perspective on LLM writing, though. It goes like this: LLMs will enable people who’ve had fascinating experiences but can’t effectively articulate them to get their perspectives out there. Ultimately, we’ll have a richer tapestry of voices.

I’m more cynical. I believe the amount of slop generated will far outweigh the potential unearthed gems. The value of thoughtful, human writing will only increase.

4. Long-term friendships are invaluable

I feel lucky to have several friendships that are more than a decade old. The shared history and memories mean that conversations always flow with comfort and ease.

This passage from Italo Calvino’s If On A Winter’s Night A Traveller captures it beautifully:

“Their speech is half in dialect; these are people used to seeing one another daily, year after year; everything they say is the continuation of things already said.”

5. But, it’s still important to keep expanding your social circles

I was chatting to a friend recently who immigrated to Australia from the US. He commented on the ‘cliqueyness’ of Sydney social circles, and how people tend not to go out of their way to make new friends.

This is the flip side of having long-term friendship groups. They became the default setting for social time, which is great in a lot of ways, but can also close you off.

I’ve found two effective ways to meet more people. The first is by getting involved in local activities and sports. I’ve recently started swimming lessons, and given the timing (11:30 am on a Monday), I’m generally in a class with parents who’ve taken an hour out of chasing their kids around to do something for themselves. It’s been nice to strike up conversations between laps, discussing topics I wouldn’t normally discuss.

I’ve also recently started boxing classes with my girlfriend at our local gym. One of our trainers is a professional actor and stuntman — the type of person I likely wouldn’t have met otherwise.

The second way is travel. When I was in South America last year, I encountered people from all walks of life — theoretical physicists, food truck owners, marine biologists and full-time writers. It was a humbling reminder that there are many ways in which you can live a rich and fulfilling life.

6. Action produces so much information.

I’m guilty of massively overanalysing decisions before making them. The best example of this has been my recent effort to launch a podcast (coming soon!). I spent a long time thinking about the right format, questions and guests. Because of this, it’s taken a lot longer to launch than I would have liked.

I’ve now recorded my first three episodes and gotten so much information from just doing the thing instead of thinking about it:

• I now know that I say “like” and “kind of” much more than I realised

• I should leave some buffer time to set up all the tech pre-episode

• As a host, it’s better to ask short, pointed questions and let the guest shine, instead of trying to flex my own knowledge all the time

I’m sure I’ll learn even more as I launch the first episode (in the next 2 weeks!).

7. You become the stories you tell about yourself

I have a tendency to downplay my work, especially as I’ve started down a less legible path this year. I find it easy to say I “just” make videos, or “I write here and there”.

But framing has a lot of power, and I’ve now started thinking about what I’m doing as building a media company. This may sound pretentious, and may just be words, but for me, it adds an important layer of legitimacy.

A while ago, I wrote about the Pygmalion Effect, which makes a similar point. Optimism and high expectations can often be a self-fulfilling prophecy, because they influence how we act.

8. Every day is easier than often.

Making something part of your daily life reduces the mental load of scheduling it in. You just automatically do the thing — like brushing your teeth.

For example, I’ve found the best way to force myself to go outside first thing in the morning is by getting a dog. Having another living being rely on you is quite the forcing function.

I’ve struggled to make things non-negotiable in a lower-stakes way. For example, I’ve tried to do more stretching and yoga this year and I have streaks where I’m consistent with it every day. But when it falls off, it falls off completely. Open to any advice in the comments.

9. Tell your favourite creators that you like their work.

I came across this post on LinkedIn from Brad Stulberg.

It was a great reminder for me to DM or comment on work online that I resonate with. It’s led to some fun conversations, and I’d recommend lowering the bar for what you think is worth sliding into your favourite writer/creator’s DMs for.

10. Know what’s on the back of your shirt.

An early mentor at Bain introduced me to this concept. Your ‘spikes’ (both negative and positive) will be the shorthand that people use to talk about you and can define your next set of opportunities.

You need to be conscious of what these things are and ensure that they are positive. Reputations take a long time to build and can take seconds to destroy. In finance parlance, the bull climbs up the stairs, but the bear jumps out the window.

On the whole, it’s been a fun and energising experience.

I’ve been able to work on projects that excite me, make more time for my hobbies and still earn enough money to cover most of my expenses through contracting work.

I wanted to write a Q1 2026 update to cover 3 things:

1. What I’ve been up to

2. A few reflections and challenges

3. What I’m prioritising (and deprioritising) going forward

1. What I’ve been up to

This has been an exploratory phase for me, with a few different balls in the air. A quick summary:

• Launched a YouTube channel (Playbook). I’ve posted 3 videos centred on the ‘business of sport’ — one on the history of the IPL, one on the financial struggles of Manchester United and one short-form video on the recent sale of 2 IPL franchises. It’s been a nice surprise to reach ~2.3K subscribers and ~340K views (mostly from the first video, to be fair).

• Started contracting at a video agency. I’ve been working part-time at Encour since January as a video producer/editor. It’s been fun to learn the video production toolkit from Harry and meet more people in Sydney’s startup and tech scene.

• In the process of launching a podcast. I’ve filmed the first episode of nonlinear, a podcast where I interview people who've found success on unconventional/creative career paths. I’m building out the guest pipeline for the next few episodes before formally launching.

• Experimenting with ‘vibe coding’. Like many people, I’ve been working with Claude Code to build websites and apps. My first attempt was Who’s The Liar — a super buggy (lol) party game. I had recently downgraded the backend server, because I wasn’t really using it, but then got a DM from someone who played and enjoyed it, which was a thrill. The more robust vibe-coded app I’m using is a personal journaling app that prompts me every night to write down one story from the day.

• Experimented with service work. I worked with a small business owner to develop a social media strategy and designs for their fitness studio.

• And of course, writing this weekly newsletter. It’s been nice to write for a small but engaged group of subscribers — thanks, as always, for reading.

Two notable things outside of work:

• Travelled to New Zealand. I just got back from a week-long boys’ trip in the South Island of NZ. It was my first time travelling in a campervan, which was a super fun adventure.

  

  

• Ran a half-marathon. Last weekend, I ran my second half-marathon. Training was not optimal, with some knee/shin pain cutting my training program short by a few weeks. But the relatively flat Canberra course and cool weather helped me run a PB!

2. A few reflections and challenges

Stepping away from the corporate career path has not always been easy. I’m planning to write a longer piece on the challenges/learnings from this journey after I’ve spent a bit more time on it. But three things I’ve felt so far:

• Loss of identity. I touched on this a bit in my earlier article, but one of the trickiest things has been explaining what I do to others. I had a moment on my recent NZ trip where I wasn’t sure what to put under ‘occupation’ on my immigration card. I think this will get a bit easier with time, as my work starts to take a more legible form (current hunch is that it will be focused in the media space).

• Limited external validation. In consulting, after a well-run client meeting or a tricky piece of analysis, I’d get a ‘well done’ from my manager, which would motivate me to do the next thing. My current work doesn’t have the same set of rails, and I need to get validation and encouragement from other places - mainly intrinsically.

• Uncertainty. The feedback loops for the work I’m doing can be long. I can spend many hours making a video or writing an article, but I don’t really know what the reward will be until I hit publish. This is in direct contrast to the consulting world, where there were always fixed deliverables and promotions happened on a pretty fixed timeline. This has naturally led to moments where I’ve questioned myself — is this really the best use of my skills? Would it be a smarter decision to go all-in on one startup idea instead of a bunch of scattered things? But the not-knowing is also part of the fun.

3. What I’m prioritising (and deprioritising) going forward

Q1 was about trying many different things. I now want to narrow my focus on what’s giving me energy and where I can see a path to long-term financial viability.

For now, that’s mainly doubling down on Playbook. I’ve greatly enjoyed the process of researching and making videos. The lens I use is content that I would like to consume — business breakdowns, centred on sport and tech. And I can’t lie, it’s been nice to get the external validation of views and likes, and already start earning income through YouTube ads.

I want to up the frequency of long-form videos (ideally 2x a month in steady state), continue trying short-form content and experiment with launching written content through a newsletter that is focused on more topical sports/business news. I would love to build this into a full-fledged media company.

I’m also keen to get nonlinear off the ground and continue building my video toolkit at Encour.

This will mean I have to deprioritise a few things:

• Sadly, I will pull back on weekly newsletter writing. While I do really enjoy writing here, I’ve found the weekly pace to be unsustainable with everything else going on. I’m keen to still keep writing, but less frequently. These will likely be more in-depth updates on my creator journey, as well as any learnings that I feel compelled to share.

• Say ‘no’ to other contracting work that comes up. While it was a good experience to do more agency-style work, I’ve learned that the digital marketing space is not where I’d love to spend my time.

• Spend less time building apps. I’m still keen to continue using AI coding tools and try to find ‘software-shaped’ problems in my current processes. But I don’t think it’s the best use of my time to be tinkering away with SaaS-style apps.

I recently saw a clip from his interview with Austin Butler, where he says the following (please try to ignore the overly emotional background music in the clip below).

Somebody very close to me…I was at a party once, and I was dancing…and they said ‘embarrassment is an underexplored emotion. Go out and make a fool of yourself'.

This struck a chord with me.

Either consciously or unconsciously, I try to minimise embarrassment as much as possible in my life, sticking to things I know I’m good at.

This is particularly the case when it comes to physical activities. There are some things that just come easier to me, generally anything involving hand-eye coordination. I think a lot of this comes from the fact that I mostly played ball sports like cricket and tennis when I was a kid.

But if there’s anything that requires balance or flexibility (think: skiing, swimming, ice skating, dancing, rock climbing), it takes me a long time to pick up the basics.

This frustration manifests as moody silences as I try to figure it out, and often leads me to give up the activity before I even have the chance to get good at it. Maybe it’s a male thing. There’s always an underlying sense of competition, and I hate the idea of not being a natural at something.

On the other end of the spectrum, you have my girlfriend, Vaidehi, who will leap into new hobbies with the same level of enthusiasm, regardless of her initial skill level, whether that’s ocean swimming, surfing, pilates or tennis. Even if she gets thrown off the horse, she dusts herself off and hops back on instantly. Her attitude has inspired me to try to commit to new hobbies like yoga and swimming, even though I still suck at them.

This concept extends beyond just physical activities. Cate Hall has a great term for this. She calls it the “moat of low status”.

Any goal that is worth achieving has a natural barrier to entry (a moat), where you will undoubtedly be bad at the thing you’re trying to achieve. It happens on the micro scale, say when no one wants to start the dance floor at a party, all the way to the macro scale, say when a potentially very talented musician never picks up an instrument because they don’t want to confront their current lack of skill.

The moat is powerful because the embarrassment is so short-term and visceral, whereas the eventual rewards feel far away and theoretical.

This year, I’m trying out a lot of new things - writing more regularly, posting on YouTube (see below!), podcasting, and more. I’m trying to get more comfortable splashing around in the moat and seeing that life goes on regardless.

Update Log

• ▶️ Published my second YouTube video! The latest episode of Playbook is live, exploring the business of Manchester United. Check it out below:

Recommendation Zone

This week’s recommendation is Lauryn Hill’s 1998 album The Miseducation of Lauryn Hill.

It’s an album I’ve heard so much about — she famously never released another album again, despite the massive critical and commercial success of this one, selling over 20 million albums and winning a Grammy for Album of the Year (the first hip-hop artist to do so).

And I can see why. It’s a vulnerable, emotional record that helped start the trend of mixing melodic RnB with rap.

I was also shocked by how much sounded familiar to me, with several songs sampled in newer hits like Nice For What by Drake and Famous by Kanye.

In Everything Is Tuberculosis by John Green, he shares a poem from Kurt Vonnegut’s Cat’s Cradle that captures this more poignantly.

Vonnegut reminds us that we are both inclined to question the world and inclined towards arriving at some kind of comprehensive conclusion.

You’ll see this narrative instinct in a lot of different places. Even for random processes, we conjure up stories to predict outcomes. Some examples:

• The gambler’s fallacy. “After five heads in a row, tails is due to come up”. This is clearly not true. There is still a 50% chance of tossing a head. But our brains need to make sense of our chaotic world by attributing cause and effect relationships to our knowledge of the past.

• The rags-to-riches company story. “X company used Y strategy to get Z result. If you have a company, all you have to do is follow this same strategy to be guaranteed success”. Such stories benefit from the power of hindsight. It’s super easy to connect the dots looking backwards; finding the real causal connections is a lot harder.

• Market explanations. “Last year’s recession was caused by X”. When there’s any sort of economic shock, there’s an immediate rush to explain it, whether it’s productivity loss, investor overexuberance or government missteps. In reality, the real answers are complex and interrelated. But often the simplest stories rise to the top. There’s a famous quote from an MIT economist Paul Samuelson — “the stock market has predicted nine out of the last five recessions”

There’s a theory that this narrative instinct is part of how we’ve evolved. Our ancestors who responded to a rustle in the grass as if it were a dangerous predator were more likely to survive than their braver peers, even if it was merely the wind.

This is because the cost of being wrong about the predator is very small, while the cost of not responding is fatal. Those who assigned meaning to potentially meaningless events were more likely to survive and pass on their genes, hardwiring the narrative instinct into our DNA.

I think simple awareness of the narrative instinct is useful. Be willing to question neat stories and assign a healthy chunk of credit to luck and randomness.

Update Log

• 🎥 Two client shoots this week at Encour. With my colleague Harry, we filmed a CEO intro video for a mental health app and a YouTube video for a men’s health company. I’m slowly getting more comfortable with being behind the camera and producing scripts for clients. It’s a new skillset but one that still leverages a lot of the soft skills I picked up in consulting.

Recommendation Zone

I finally watched Marty Supreme at the cinema this week with Vaidehi, and we both really enjoyed it.

Set in the 1950s, it follows table tennis player Marty Mauser (Timothée Chalamet) on his quest to become world champion (amongst many other things).

We looked up the person the movie was loosely based on, Marty Reisman, and saw him described as “living in a perpetual state of forward motion”.

I think this is also a great way to describe the movie - SO much stuff happens within what felt like a short 2.5 hours.

While Timmy missed out on the Oscar, I think he put in an amazing performance and is probably set for more accolades with Dune Part Three coming out in December.

If you haven’t seen it, it’s a play on the standard distribution you would have seen in any Stats 101 course.

The two tails of the distribution (‘the idiot’ and ‘the genius’) share the same opinion, though (it’s implied) for different reasons. The ‘midwits’ in the middle come to some sort of complicated conclusion through elaborate reasoning or ideology.

Some of my favourite examples:

A few takeaways:

• Complex ≠ smart. I’ve often fallen into the trap of overengineering analysis - building a complicated Excel model with multiple tabs and scenarios, when a 10-line model would have suited. I think it’s because adding complexity feels like productivity. But this level of overanalysis is often a waste of time and energy. I think this is why the midwit meme often applies in finance and economics settings (see the index fund and housing examples above). These are fields with very complicated problems, so it feels like the solutions also have to be equally complicated.

• Simplicity can be a hallmark of deep thinking. If you’ve ever written a speech or presentation, you’ll know that making it 2 minutes long is way harder than making it 10 minutes long. When someone deeply understands a topic, they can distil it down to its core elements. As Mark Twain once said, “I didn’t have time to write a short letter, so I wrote a long one instead”

• Youth and naivety can be assets when doing something risky. If you don’t know much about a problem, your approach can actually look very similar to that of an experienced operator. Many startup founders just go out and do things that incumbents wouldn’t dream of. The Airbnb guys just started to rent out air mattresses in apartments to strangers. Any hotel industry insider would have immediately listed dozens of reasons it couldn't work (liability, regulation, trust, safety…) and not even tried. The worst place to be is when you know just enough about something to know that it’s going to be hard, which stops you from doing it at all.

Update Log

• I’m deep into my next Playbook video on Manchester United. After my first video on the IPL did surprisingly well, I wanted to stay in the ‘business of sports’ niche for my second video. For this one, I’m trying to raise my motion graphics game. It’s been super fun trying to make charts and explainer diagrams. I hope to get the video out in ~2 weeks.

Recommendation Zone

Amidst all the AI doomerism about unemployment and economic collapse, I found this article from David Oks to be a breath of fresh air.

It’s a response to the viral article you might have seen from Matt Shumer, which argues that we’re in a moment just like February 2020, watching COVID infections go exponential.

Oks’ argument is simple yet effective - you need to think about comparative advantage when it comes to AI and the labour market. That is, the question isn’t just about whether AI can do specific tasks better than humans do (a lot of tasks now fall under this category).

It’s whether the aggregate output of humans working with AI is inferior to what AI can produce alone. If there is any way that the addition of a human to the production process can improve that process, then jobs will exist.

One of my favourite podcasts is No One Saw It Coming with Marc Fenell. Each episode dives into a product or event that changed the world in a way that, as the name suggests, no one saw coming.

This concept of accidental discovery has fascinated me for years. Christopher Columbus’ journey to America is the archetypal example — you search for what you know (India) and find something you didn’t know was there (America). A few more examples:

• Botox: The cosmetic use of Botox was accidentally discovered when Canadian scientists were trying to treat eye spasms in the 1980s. Not only did injecting with botulinum toxin help with these eye conditions, but patients also noticed that their frown lines disappeared.

• LSD: In 1938, Alfred Hoffman was working for the pharmaceutical company Sandoz, trying to synthesise a respiratory stimulant from the ergot fungus. It didn’t really work. But five years later, Hoffman decided to tinker with it again. As he worked, he suddenly felt really strange and had to go home, where he found himself entering a pleasant dreamlike state. He had accidentally ingested some of the chemical through his fingertips and had just gone on the first LSD trip in history. His dedicated research after that paved the path to LSD being a counterculture touchstone.

• Post-it notes: The ubiquitous yellow notes were invented by accident in 1968 by 3M scientist Dr Spencer Silver, who was attempting to create a super-strong adhesive for the aerospace industry. Instead, he created "microspheres" that stuck to surfaces but could be easily removed without leaving residue.

• Chemotherapy: The use of chemotherapy in cancer has a dark history. During WWII, researchers investigating the effects of mustard gas as a chemical weapon noticed its tumour-suppressing properties, leading to the first successful treatment of lymphoma in 1942.

These discoveries are an argument for science for the sake of science. You might have heard the phrase “necessity is the mother of invention”. It implies that when humanity faces critical problems like war or famine, we come up with creative solutions like computers and fertilisers.

But I actually think the more interesting way to look at it is “invention is the mother of necessity”. Inventors and scientists create cool stuff because they want to, and then society finds a use for it. As Henry Ford (apocryphally) said, “If I’d asked people what they wanted, they would have asked for faster horses”.

I was reminded of this concept when listening to the Rolex episode of the Acquired podcast. They told the story of Jean Aegler, who ended up being the sole supplier of movements (the underlying mechanism that powers watches) to Rolex. Aegler was tinkering away in his workshop in the Swiss mountains and was the only person making miniature movements that were still accurate.

But importantly, Aegler was making these miniature movements in the early 1900s, before there was even a market for them. He was just doing it because it was the hardest thing he could think of. Without his love of the craft, Rolex wristwatches may never have been a thing.

In terms of the practical takeaways of this for you and me, I keep coming back to something I’ve heard Ed Sheeran say. He compares songwriting to a clogged-up tap. When you start the tap, a bunch of dirt, rocks and stones will come out. But if you keep it open long enough, clean water will eventually flow.

If you want to create something meaningful, useful, or even just fun, you have to be comfortable making errors. Along the way, you increase your surface area of luck and could stumble on something that ends up being transformative.

Update Log

• 🏃🏽Heavy running week. I’ve been dealing with a minor leg injury that’s only just gotten better, so this was one of my first weeks of full-load running. I’ve got a half-marathon in early April, which I feel pretty undercooked for, so I need to lock in with my training for the next couple of weeks.

• 🏊‍♂️I also did my first swimming lesson! It had been a while since I’d been in the pool, so I was a bit nervous. But it ended up being a lot of fun, and I’m excited to get properly stuck into swimming.

Recommendation Zone

This week’s recommendation is for the football nerds out there. It breaks down why some footballers pass “the eye test” while others don’t. It goes surprisingly deep, covering the theory of aesthetics in general, graphing the acceleration of different players, and even analysing the types of knee-slides after scoring.

Even after posting just one YouTube video (and starting to work on my second one), I have a much greater appreciation of how hard it is to create aesthetically pleasing motion graphics that sit alongside a compelling story. Watching this has inspired me to keep working on the craft.

As much as they can be ridiculed, they are a powerful way to look at 2 dimensions simultaneously and bucket things into quadrants.

Here are 5 matrices I think about more often than I should.

1. The meaning matrix

The first matrix comes from writer and technologist — with consuming/creating on one axis and alone/together on the other.

A lot of meaning and progress is created by people who live in Quadrant 4 — creating together — whether it’s organising community movements, starting a company or making a movie. I’ve been consciously trying to push myself more into this quadrant. Over the last 2 months, I’ve spent a lot of time in the bottom-left quadrant - working on my YouTube videos, apps and writing. But I’ve found that the time I’ve spent in a co-working space at Encour has helped immensely by allowing me to bounce ideas off people and speak to others about what they’re building.

The power of Quadrant 4 is also illustrated by the types of content that become popular. One of my favourite TV genres is comedy panel shows like Would I Lie To You or Have You Been Paying Attention. There’s something magnetic about seeing groups of people reacting differently to the same content and riffing off each other to create something unique. The same concept applies when you watch bands jamming out or dance troupes improvising. People are just drawn to watching others create something together.

The rise of social media has made Quadrant 1 - consuming alone — much bigger. With the amount of information at our fingertips today, it’s very easy to get stuck in an endless cycle of scrolling and passively watching things. However, I don’t agree that everything in this quadrant is bad. Sometimes there’s nothing better than curling up with a book or movie by yourself.

2. The happiness matrix

Happiness is not an objective reality, but a function of our expectations.

On the horizontal axis is what we have, and on the vertical axis is what we want. We are only really unhappy when we have what we don’t want, or we want what we don’t have.

The issue is that our wants are not static. They increase as things get better. This is known as ‘hedonic adaptation’. A famous example of this is lottery winners, who experience a brief spike in joy due to their new wealth, but end up returning to a baseline level of happiness.

Hedonic adaptation also means that the bottom-left quadrant (want and don’t have) continues to get bigger even when our circumstances objectively improve. We want a fancier car, a bigger house and more expensive clothes.

However, we rarely think about the top-left quadrant - the universe of things that we don’t want and don’t have.

The key lever you can pull to expand this quadrant is the ‘want’ axis - reducing our desire for more. This can be tricky as our wants are shaped by societal expectations. If everyone around you wants luxury goods and the latest gadgets, it is natural to want them too.

But it is important to remember that not wanting something is as good as having it.

3. The Eisenhower matrix

This is the system that President Eisenhower (and Commander of the Allied Forces during World War II) used to manage the overwhelming amount of tasks on his plate.

All his tasks were sorted by two dimensions - urgency and importance. It is easy to conflate these two terms, because things that are urgent (i.e., that need to be done now) often feel very important. But not all things that need to be done now move the needle on your objectives.

By assessing your tasks along each dimension, you can choose one of four actions: do, delegate, decide or delete.

The quadrant that is often overlooked is the bottom-left one — important but not urgent. These are things like exercise, sleep and social time that are easy to deprioritise because they don’t show immediate results.

4. The self-knowledge matrix

I came across this 2x2 from writer .

You have access to Quadrants 3 and 4 in this matrix - your public self and your hidden self. Quadrants 1 and 2 are more interesting - these are things that are either blind spots (that are obvious to others) or truly unconscious truths about yourself.

If you have a conversation with someone who is actively engaged, things can start moving from Quadrant 4 and 1 into Quadrant 3. You might reveal something about yourself to them (e.g., that you actually really dislike EDM music), or they can highlight some of your blind spots for you (e.g., how you are uncomfortable with silences).

But what’s really interesting is when things start seeping out of Quadrant 2 — your unconscious. As Karlsson writes:

“The other person says something, and it works as a kind of prompt: it reaches into the place where experience hasn’t been articulated yet and pulls something up into the light…The other person doesn’t know what’s in that quadrant. Neither do you. But their words, because they come from a mind shaped differently from yours, illuminate corners of you that your own attention skips past”

Both reading and writing can also prompt things to seep out of Quadrants 1 and 2 into Quadrants 3 and 4. Through language and ideas, books can prompt you to reflect and view yourself in a new light. And often, if you have a lot of thoughts swimming around in your head, the simple act of articulating your thoughts on the page can crystallise what you actually believe to be true.

5. The appearances matrix

This is a more fun one, and a good way to spend 10 minutes with your friends, categorising everyone in the group.

It’s the looks scary / is scary matrix, with some helpful marine animal labels.

People who don’t look scary and are not scary are goldfish, people who don’t look scary but are scary are dolphins, people who look scary but are not scary are stingrays, and people who look scary and are scary are sharks.

Update Log

• 🎙️Filmed the first episode of my podcast! I’m in the process of launching a new interview podcast called nonlinear, where I interview people who’ve found success on unconventional career paths — think founders, writers, artists and athletes. It was super fun to film my first episode with Jessy Wu, who I’ve been working with at Encour (see a sneak peek below). Stay tuned for the episode launch!

Recommendation Zone

This week’s recommendation is Modern Love — the Amazon Prime TV show. It’s based on the New York Times column of the same name, with each episode following a couple of characters in New York navigating love in all its various forms.

I recently watched the first season and really enjoyed it. I was surprised by how big some of the names were on the show, including Dev Patel, Anne Hathaway and Tina Fey.

The definition of creation is broad here — I’m including the act of writing this newsletter every week, scripting and filming YouTube videos, and working with Claude Code to build websites and micro-apps.

But pretty much everything I’m working on is mediated through a screen.

In contrast, I had one experience over the holidays that made me realise the power of doing something more physical and tactile. I was at a birthday lunch for one of my friends, and she had set up a craft corner where we could make hand-carved linoleum stamps. Given some of my historical struggles with fine motor skills, I expected this to be a pretty frustrating activity.

But I ended up loving it.

Carving smooth curves in the lino was so satisfying and required such intense focus that time seemed to fly by. And even though the end product looked hilariously misshapen, I was proud of my little stamp.

I’ve found a similar joy in learning physical skills — whether it’s getting incrementally better at a yoga pose, or the brief period last year when my girlfriend and I took salsa dancing classes. There is something extremely rewarding about understanding how your body is meant to move in space, and working on it until it finally clicks.

The stamp-carving afternoon was a good reminder to keep learning physical skills. The next thing on my agenda is to get better at swimming. I’ve signed up for lessons at the local pool and will keep you posted…

Update log

• ⚽️ Started scripting the next episode of Playbook. I’ve been blown away by the response to my first video on the history of the IPL - with 150,000 views and counting in a week! It’s inspired me to start on my next video straight away, which will be on the business of Manchester United and how they’ve got themselves into a financial hole.

• 🌿 Went for a lovely walk in Royal National Park. For Valentine’s Day, Vaidehi and I did the Wattamolla to Eagle Rock walk - a beautiful coastal trail surrounded by bushland. We just managed to beat the rain and stay dry!

  

Recommendation Zone

This week’s recommendation is Everything is Tuberculosis by John Green. It’s an exploration of how one disease has shaped our society and culture more than most people realise.

Tuberculosis (or ‘consumption’ as it was previously known) is a disease I had vaguely heard of, but never understood the true scale and impact of. Since its discovery in 1882, over 1 billion people have died of tuberculosis, more than malaria, smallpox, HIV/AIDS, cholera and the plague combined.

It’s also been associated with many world events, at least tangentially. You might know that the catalyst for World War I was the assassination of Archduke Franz Ferdinand in modern-day Bosnia. But what you might not know is that the group of young men who went after him were all consumptives who had nothing to lose because of how advanced their disease was.

Or take the acceptance of New Mexico as a state in the US. For decades, Congress resisted granting statehood to a territory it viewed as too Mexican and too Indigenous. So, New Mexico actively encouraged thousands of white consumptives to migrate west for the desert air. It worked — the influx reshaped the territory's demographics, and Congress allowed New Mexico to become a state in 1912.

What has been particularly interesting to learn about is how intertwined the disease is with social norms, particularly class and beauty. TB was once seen as a disease of poets and the nobility, with the pale skin, thin bodies and rosy cheeks of consumptives shaping beauty standards that persist today. But over time, it has come to be seen as a disease of poverty and industrialisation, where crowding in huge cities with packed tenements and factories allows the disease to spread. This shift happened swiftly, after Robert Koch showed that TB was caused by a bacterium, changing the previous belief that it was purely genetic or caused by a lifestyle of excess.

Over the last few months, I’ve seen a lot more people talking about ‘taste’, particularly in the tech scene. It might be one of those buzzwords that come and go in the startup space, like “community” and “growth hacking”. But I think taste has a few more layers that are worth exploring.

In this piece, I’ll try to answer 3 questions:

1. What is ‘taste’?

2. Why does it matter now more than ever?

3. How does one develop ‘taste’?

1. What is taste?

‘Taste’ is a hard concept to define succinctly. The dictionary definition is the ability to discern what is of good quality or of a high aesthetic standard.

But as Brie Wolfson wrote in her seminal piece Notes on Taste, this definition can feel limited.

Words like taste are hard to pin down, perhaps because they describe a sensibility more than any particular quality, a particular thing. We’re inclined to leave them unencumbered by a definition, to preserve their ability to shift shapes…The form of jottings, rather than an essay (with its claim to a linear, consecutive argument), seem more appropriate for getting down something of this particular fugitive sensibility.”

And so, below are a few jottings on what resonates most with me when I think about taste.

• Taste is often talked about in binaries. We don’t often think of taste as a spectrum. Someone or something either has taste or doesn’t.

• You have an intuitive sense about who has taste. You can probably immediately name 2-3 people in your life who you go to for book recommendations or fashion inspiration. These ‘tastemakers’ don’t follow trends blindly, but are still in touch with what’s in vogue.

• Taste is intertwined with creation. Some people can have good taste without actually creating the thing they are experts in — movie critics who don’t own a camera, music nerds who can’t play an instrument and food critics who can’t cook. But I think this is the exception that proves the rule. Pretty much every world-class creator of something has good taste when it comes to consuming it.

• Taste is often built from combining disparate disciplines. The classic example of this is Steve Jobs taking what he learned from a calligraphy class in college and applying it to the beautiful typography and minimalist design of Apple products.

• There is a difference between tasteful and expensive. There is an overlap between these two concepts, because expensive things can be high-quality. But taste doesn’t conform to the same laws of supply and demand as price. A $20 art print can be tastefully placed in your house, even if it’s a mass-produced work.

• Taste is a blend of the subjective and the objective. The things you find tasteful can be deeply personal. But there is also an objective element of taste - the things we as a collective agree are beautiful, good and true. The real challenge is discerning what is merely trendy and what is enduring. This challenge is made harder by how much our interests are shaped by algorithms today. I like to think I have good and fairly diverse taste in music. But how much of this can I take credit for, and how much is me just listening to what my Spotify algorithm recommends to me?

2. Why does it matter now more than ever?

I believe there are three forces contributing to why taste is becoming more popular.

1. The rise of AI and its impacts on knowledge work. There is a growing feeling that a lot of white-collar work today is getting automated away, spanning the spectrum from the basics like writing emails to high-level tasks like graphic design and writing software. When everyone can ship high-quality code faster, differentiation moves upstream to judgment and curation. Or as Anu puts it below - in a world of scarcity, we treasure tools. In a world of abundance, we treasure taste.

2. The rise of lifestyle products. Over the last few decades, there’s been a shift in how products are marketed. Features used to be the headline, but now identity is.

   Take Rolex. One of their first major ads celebrated Mercedes Gleitze being the first woman to swim the English Channel. But the copy focused on functionality —mostly the watch’s waterproof nature. Now, Rolex’s ads rarely speak about the features and instead speak to the kind of person who wears one. This shift has happened across almost every consumer category. And taste becomes the filter through which every purchasing decision passes. Not “is this good?” but “does this say what I want it to say about me?”

   

   

3. A natural reaction to information overload. When everything becomes so accessible, the value lies in knowing what is worth your attention. And so ‘tastemakers’ become ever more valuable. Interestingly, we seemed to have moved away from institutions like the Oscars and print magazines as gatekeepers of taste. Even though these big organisations still have cultural clout, taste is now often intermediated through individual influencers or curated newsletters.

3. How does one develop taste?

As I talked about earlier, taste is intertwined with creation. If you want to develop taste in any craft, you need to get enough reps to understand how things are built from the ground up. You can read as much about colour theory as you want, but you only start to understand what good lighting and composition look like after taking hundreds of photos.

But active consumption can also be a pathway to good taste. If you read enough books, you understand what good writing looks and feels like. If you spend enough time studying what good websites look like, you probably know enough about frontend design to articulate it.

However, when you are developing taste through consumption, you need to force yourself to be specific about why you like or dislike something. This doesn’t have to be a super formal process — just talking about your reaction to a book with your friends can build this muscle.

What’s great about taste is that it can cross over into adjacent domains. For example, if you recognise what good compositions look like when taking a photo or video, it will transfer over into how you think about interior design. One hack that leverages this — if you’re trying to develop taste in a particular field, look at what people in adjacent fields do. For example, if you’re trying to be more fashionable, instead of looking at fashion influencers, look at what musicians, painters or authors wear. They aren’t directly thinking about what they have to wear for new sponsored content this week — but they still have a knack for aesthetics.

Update log

• ▶️ Launched my first YouTube video! Excited to share the first episode of Playbook - a channel where I break down the stories behind some of the most iconic brands and businesses in the world. The first video is on the history of the IPL, and how Lalit Modi turned cricket into a multi-billion dollar sport.

Recommendation Zone

Over the last week, I dipped my toe into the fantasy genre, reading Ursula Le Guin’s The Earthsea Quartet. I have just finished the first book in the series and really enjoyed it. It took me a second to get into the world, but Le Guin’s succinct yet evocative writing style kept me hooked.

The term nostalgia comes from the Greek words nostos (”return home”) and algos (”pain or grief”). It was initially used to refer to the homesickness that sailors would feel when they were away at sea.

But over time, it has evolved into its use today as a psychological, wistful longing for the past.

Maybe it’s just a function of getting a bit older and into my mid-late twenties, but I’ve started feeling nostalgia more often and more frequently. It will often be jogged by small things like seeing an old clip from Avatar: The Last Airbender or my phone throwing up an ‘On this day’ photo memory from 8 years ago.

But it also feels like nostalgia is becoming a bigger part of the culture. A few examples I’ve been seeing:

• The 2016 trend. Only a couple of weeks into 2026, everyone (including celebrities) started posting throwback photos from 2016 on Instagram. It started as a glow-up thing, showing off how much someone has changed. But there seemed to be an underlying tone of melancholy — that life and pop culture peaked 10 years ago.

• The comeback of digital flash photography. Cheap digital cameras are cool again, and it’s a trend I’ve unashamedly jumped on. The photos they take are objectively lower-quality than smartphone photos. But something about the faded colours, soft edges and harsh flash reminds me of the photos my parents would take on family trips, or the blurry shots I took at my Year 6 Farewell. I thought I was being cool and edgy when I took my digital camera on my recent trip to Vietnam and Cambodia. But that feeling was quickly shut down when I saw ~8 other people with the exact same camera on the Ha Giang Loop.

  

• A return of the Y2k maximalist aesthetic. Artists like Zara Larsson and PinkPantheress are bringing back the early 2000s look - low-rise jeans, butterfly clips, frosted lip gloss. What’s interesting is that most of Gen Z who are driving this trend weren't even alive during the actual Y2K era. It’s nostalgia by proxy.

I’ve also noticed that nostalgia for me is strongly tied to music. If I ever re-listen to an album or an artist that featured heavily at a particular period in my life, I find myself instantly transported back to that time.

I spent a winter working and studying in Washington, D.C. when I was in university. At this time, I had a lot of hip-hop like Big Sean, GoldLink and Kendrick Lamar in heavy rotation. One thing I’ll never forget is when I was playing some of these tunes while we had a plumber fixing the shower in our dorm. I could see him nodding his head along as he was working, and before he left, he asked me if I was a DJ. I don’t think I’ve ever come off that high.

Another song that instantly brings back memories is Tubthumping by Chumbawamba. It was the title song to a ‘Sensational Sachin’ highlights compilation of Sachin Tendulkar in the 2003 Cricket World Cup. I vividly remember camping in front of the TV with my brother as we watched that DVD for countless hours after school, to the point where we memorised the commentary word-for-word.

I looked a bit more into why nostalgia is so in vogue, including listening to this excellent podcast from my new colleagues Jessy and Danny.

I think a few things are going on:

• There are more things to miss. The explosion of algorithmic short-form content makes trends rise and fall faster than ever before, compressing the timeline for when something is considered ‘old’. Going back to Zara Larsson - her song Lush Life, which was already a global hit in 2015, is once again climbing the charts in 2026. And even when things feel like huge cultural moments, like Tiger King or Squid Game, the hype fizzles out after a few weeks as something else new and shiny comes along.

• Digital preservation makes the past very accessible. Ever since cameras started being embedded in smartphones, we’ve been able to document every aspect of our lives. While this can be great to remember important life events, we have stopped letting things slip. Historically, only a few moments remained prominent from our pasts, but now we have more opportunities to reminisce.

• The present feels harder to romanticise. Nostalgia runs on the sentiment that things were simpler ‘back then’, and this narrative is easy to tell right now. This is again a function of social media and the attention economy. Bad news stories get more clicks and become more prevalent, making it easier to get into echo chambers that reinforce pessimism about the future. The economic and existential uncertainty that AI is causing also makes it harder to be optimistic about the future.

• Companies are taking advantage of the trend. We are currently saturated with sequels, reboots and throwback content. The 80s sound has been recently repopularised by artists like Dua Lipa and The Weeknd. Kate Bush is also charting again, thanks to Running Up That Hill featuring in Stranger Things. The Avengers franchise created a cultural moment in 2019, when they seemingly culminated a 10-year saga. But just 7 years later, they are bringing all the characters back again, purely because nostalgia will sell tickets.

I’m interested to hear if you’re feeling the same way and whether it’s tied to your lifestage or just the state of the culture in general.

Update log

• 🏃🏽 Ran the Sun Run 10K in the Northern Beaches. For the second year in a row, I did the Sun Run from Dee Why to Manly. I got a bit carried away by the hype of the event at the start and ended up gassing myself out by kilometre 4. But I was able to rein it in and finish in 59 minutes — under my goal time of an hour. It was an absolute day for it, and hopefully the start of an annual tradition!

Recommendation Zone

This week’s recommendation is The Punchline episode from one of my favourite podcasts, Radiolab.

It tells the story of John Scott, a 6’8’’ professional ice hockey player whose role was to be the ‘enforcer’ on his team. As a joke, fans voted him into the NHL All-Star Game in 2016, and this ended up having far-reaching impacts on his life and career.

It’s a super interesting episode that explores the power of the internet and the psychological impact that seemingly harmless pranks can have.

I have deep respect for stand-up comedians.

Firstly, I think it takes immense courage to get on stage with the goal of making people laugh. Public speaking is hard enough already, but trying to be intentionally funny is immeasurably harder.

But I think what really stands out is the degree of casualness. Even though they are performing to a crowd, the best comedians speak like they are telling an off-the-cuff story to a friend over dinner. There’s both a sense of authenticity and a degree of risk, as you have no idea what they are going to say next.

This is the same feeling you get when you see someone give a speech at a wedding without any notes in their hand. You know that there is some degree of improvisation, which keeps you on the edge of your seat, compared to someone reading from a page word-for-word.

But in comedy, this authenticity is often constructed.

As Elliot Kalan (former head writer of The Daily Show) writes in Joke Farming, there is a difference between being a naturally funny person and being a comedy professional. Behind great comedy is a process and lots of craft, whether or not the audience sees it. Comedians test material at small clubs dozens of times, refining a single joke's wording and timing until it seems effortless.

You see a similar pattern in music. Improvisation is a key element of genres like jazz and Indian classical music. When you see maestros at work, it looks like they are just effortlessly jamming and making things up on the spot. But the ability to do this is built on years and decades of practising the foundations until they become muscle memory.

I also noticed this ‘unconscious competence’ when I was working at Bain. The best partners could command rooms and weave narratives through complex data, even if they were only seeing it for the first time. We used to call it "slide karaoke" — presenting slides that you’d never seen before, but making it look like weeks of clear thinking. But they weren’t just winging it. They'd spent years doing the same type of analysis and gradually honed their pattern recognition.

What connects all these examples is the value of focus and compounding in one discipline. If you become ridiculously good at the basics in any one field, you start to understand what rules you can and can’t break. True mastery is invisible.

Update log

• 📚 Built v1 of the Story of the Day app. This is a personal project I’ve been working on — a daily journalling app that asks you at the end of every day, “If you had to get on stage and tell a 5-minute story from today, what would that story be”? It’s a way to document and remember the ‘storyworthy’ moments in your life, which can help stop all your days from blurring into one big mess. I’m looking for 1-2 beta testers to test the UX and functionality. If you’re interested in helping out, please reach out at sauravrisbud11@gmail.com.

• 🎥 Training day at Encour. Spent a day learning about how to set up a successful video shoot, including lighting, camera rigging and pre-production client preparation. Video production and filmmaking can be a slightly overwhelming field — so this was a super useful 101 for me.

Recommendation zone

This week’s recommendation is this video from Johnny Harris on Greenland.

It was released 2 years ago, when Trump first made comments about taking over Greenland from Denmark. But it’s become more relevant than ever with the small island again becoming a geopolitical focus point.

Thanks to global warming, much of Greenland's ice is melting, opening up shipping lanes that make strategic and economic sense for the US, Canada, China and Russia to control. And the melting ice is also revealing critical mineral deposits that are crucial for powering electric vehicles, smartphones and data centres.

A good watch if you’re looking to learn more about the context behind today’s situation, as well as hear the native population’s perspective.

As someone newly self-employed, I have realised that deep focus and self-motivation have become more important than ever. There are no hard deadlines, and no one is looking over my shoulder, pushing me to get my work done.

The biggest obstacle to my focus is, unsurprisingly, my phone. Any time I feel like I’ve hit a mental wall, my first instinct is to reach for my phone and scroll through social media. And often, I’m not even using my phone for a specific purpose. It’s just something to do to avoid boredom or letting my mind wander.

If you’re also struggling to put your phone down, it’s not your fault.

Below is a screenshot of the top 10 biggest companies in the world by market capitalisation. Apart from Saudi Aramco, they are all software companies (or semiconductor companies that provide the chips that power these software companies).

A lot of this value (particularly for companies like Google and Meta) is built on advertising. The business model of these tech giants is to convert user time, engagement, and data into billions of dollars in advertising revenue. The longer a user stays on a platform, the more ads they see, and the more valuable data they provide for targeting.

And so, some of the smartest minds in the world have worked on algorithms that hijack our deepest psychological impulses to keep us engaged. Short-form vertical scroll content like TikTok and Instagram Reels is probably the most addictive form of media ever created.

Over the last few years, there has been a growing movement to return to a more analog life and “touch grass”. The market for ‘dumb’ phones and ‘Bricks’ continues to grow rapidly. It’s an understandable reaction to feeling like our phones are sucking up more of our time than we are consciously giving them.

To be clear, I still think the Internet and phones provide tremendous value — but it’s important to use them intentionally as tools rather than traps.

Here are a couple of things I’m trying to be more intentional with my phone use:

1. Adding a screen time widget to my home screen. I never used to look at my screen time stats (out of fear). But I recently bit the bullet and was shocked to see that I was averaging 4+ hours of daily screen time, with YouTube the key offender. I’ve now added the screen time widget to my home screen, and it’s been a good reminder to put my phone down when the number gets too high. What gets measured gets managed.

2. Buying an alarm clock for the bedroom. One of the worst habits I developed over the last couple of years is scrolling in bed first thing in the morning and last thing at night. It started during work, when I would wake up and instantly open Outlook and Teams to see if there were any updates. So, I recently bought an old-fashioned digital alarm clock and leave my phone out of the bedroom when I sleep. I’ve instantly found it to be a nicer way to wake up.

3. Putting my phone in a different room. On a similar note, any time I want to lock in, I will put my phone far away from me. Even if I feel the urge to quickly check my notifications, the physical barrier of walking to another room usually stops me from doing this. It’s like Odysseus tying himself to the mast of his ship to thwart the Sirens.

4. Deleting the Instagram app (and using the Chrome version when I want to). Instagram is my social media of choice, with Reels being the most dangerous black hole of time. I’ve tried deactivating my account a few times, but found that I missed keeping in touch with my friends, particularly those who live overseas. A middle ground I’ve used for a while now is to uninstall the app and only access Instagram through my mobile browser. The experience on Chrome is so suboptimal that I don’t find myself getting sucked in.

5. Activating bedtime mode at 8:30 pm. My phone has a feature where I can turn off all notifications and make the screen go greyscale at a certain time. This kicks in at 8:30 pm and immediately makes it less visually enticing to use my phone.

Update log

• 🎥 Learned motion graphics in Adobe After Effects for the first time. As part of my contract work at Encour, I’ve started to learn some basic video animation in After Effects. It’s been cool to learn about layers, motion curves and making animated graphs. It also made me realise how janky some of the animations were in the IPL video that I’ve been working on, forcing me to go back to the drawing board on a few scenes.

• 🍚 Hosted some friends for a small dinner party over the weekend. I really enjoy cooking and hosting, and plan to do a lot more of it this year. I made some baked cheese and San Choy Bow (lettuce wraps), thanks to the GOAT recipe website RecipeTin Eats.

Recommendation zone

I recently picked up Daniel Yergin’s The Prize — a history of oil and how it has shaped global capitalism, world politics and modern society. I’m only about 100 pages into this 900-page book, but it’s already been fascinating.

It opens with the story of John D. Rockefeller and the founding of Standard Oil.

To be honest, I didn’t even know that Rockefeller made his fortune in oil. So, it was super interesting to learn about how he essentially built the playbook for modern capitalism (both the good and the bad) by monopolising the oil refinery and distribution business in the US.

A quote I often think about is “the opposite of love is not hate, it is indifference”.

When you hate something, whether it’s your rival sports team or a popular movie that everyone else raves about, you still care deeply. Apathy is the true opposite, because it’s a sign that something doesn’t matter to you at all.

This can be difficult to navigate when, in the culture, putting in visible effort is not cool. ‘Tryhard’ was one of the most cutting insults you could deliver on the playground. Even if you succeed at something, you need to appear casual and effortless, particularly in Australia, where ‘tall poppy syndrome’ is so prevalent.

I definitely used to subscribe to this way of thinking. But it’s something I’ve changed my mind on.

I think excitability is a virtue. I love watching people get worked up about their passions, whether it’s the pitfalls of the medical system, the complexity of wine tasting or why historical fiction is the best book genre in the world. It doesn’t necessarily have to be something I’m deeply interested in, but there’s a magic to seeing someone’s eyes light up when they talk about something they love.

I find it particularly refreshing when I talk to people who are truly engaged in their work. It’s a feeling that eluded me in my last few months as a consultant, when I felt I was mostly just going through the motions. I think the best predictor of how long someone stays at a job is how much fun and energy they get from it (even if it’s not an easy job).

An environment of apathy can be particularly dangerous in a professional setting. In her interview with , talks about a friend who is struggling with the LGTM (‘looks good to me’) culture of their new workplace. When people don’t give you feedback on your work (even small things like pointing out typos), it’s hard to stay motivated and produce your best output.

I was lucky to have my first full-time job be in a non-LGTM culture at Bain. My supervisors were deeply engaged in the work all the way down to slide design and formatting. At first, my reaction to getting feedback on seemingly small things like chart axes and footnote alignment was — Does it really matter that much?

But as I got further into my career, I realised this obsession was a signal of care. If two slides have the same message, but one is formatted far better, it’s an indicator that that person cares more about the work.

Staying on the work theme, another area where apathy could be detrimental was coaching and feedback. The best managers I worked with always pointed out what I could do better. I knew that any criticism actually showed they were more invested in my development than someone who said that I’d done everything perfectly.

To be fair, giving feedback is something that didn’t come naturally to me, particularly upward feedback to managers. I felt that it was a tricky line to navigate between helping your supervisors improve without coming across as speaking out of turn.

One practical thing I did here was to ask my managers, “what’s one thing you are trying to improve on”? I got a range of responses to this question - such as giving my team more space, slowing down in client meetings and being more organised with weekly workplanning. This gave me a useful frame to view our interactions through and permission to criticise without surprise.

Update log

• ⚒️ Started building a personal website using Claude Code. This is something I’ve tried to do for years, using low or no-code tools like Webflow and Wix. I’ve always found these tools to be either too clunky or expensive. But within just a few hours of working with Claude, I built the bones of a website that explains who I am and links out to work I’m proud of. I’m still tinkering with it, but hope to launch it in the coming weeks

• 🍻Caught up with my brother and his wife. My brother and sister-in-law live in San Francisco. They are visiting Sydney for a couple of weeks, and it was lovely to grab a drink with them and their friends last weekend!

Recommendation zone

This week’s recommendation is the Acquired podcast’s 10th anniversary special, hosted by Michael Lewis (author of Moneyball, Liar’s Poker and The Big Short).

Acquired is a long-form podcast hosted by two Silicon Valley insiders - David Rosenthal and Ben Gilbert. Each episode is a 3-4 hour deep dive into a generational company, such as Costco, Coca-Cola, Hermes and NVIDIA.

The 10th anniversary episode is a reflection on what makes their product work when, on the surface, it shouldn’t. Episodes are released infrequently, can be the length of an audiobook and generally don’t have video or guests. And yet, they’ve developed an engaged audience of over a million people and a thriving, high-margin business.

A few key takeaways:

• Scarcity creates value. Most podcasts pump out daily or weekly episodes to stay relevant. Acquired has taken the opposite strategy, producing 8-12 high-quality episodes annually. Note: This strategy really only works if you have already built up an audience and/or have another source of income. Someone starting a podcast from scratch wouldn’t be able to spend months researching one topic and release it ‘cold’ with zero subscribers.

• Stay in your circle of competence. Ben and David are very conscious about opportunity cost and do not hesitate to put things in the “too hard” pile. For example, they turn down Hollywood deals repeatedly because it makes more financial sense to just make another episode. They focus on telling the stories that keep them engaged and excited (you can’t compete with someone having fun!)

• Podcasts are designed for compounding. The direct audience relationship of podcasts (versus algorithmic platforms like Instagram and TikTok) is a supercharger for growth. Whenever they hook a new listener, that listener is likely to continue listening to new episodes.

• Emotion and improvisation drive storytelling. Michael Lewis observed that the first few Acquired episodes sounded ‘affectless’ and there was no drama. Ben and David reflected that this was because they were essentially just reading from a script. But now, the hosts don’t share their notes on the company before recording the episode. So you end up getting actual disagreements and genuine excitement for the first time on recording day.

• Founder control and involvement. Over the entire 10 years, it’s just been David and Ben running the show. They haven’t taken on any outside funding or tried to expand into other verticals. In their eyes, they are already living the dream and don’t feel the need to build a bigger enterprise.

‘Luck’ is a concept I have been thinking and reading about for many years. What interests me is how binary and contradictory perspectives on luck can be.

One end of the spectrum is nihilistic — most of life’s outcomes, good or bad, are out of your hands. It’s a view that removes scope for personal agency and leaves it all up to fate.

The other end of the spectrum is the classic self-help mantra that you can overcome any obstacle through dedication and sheer force of will. It’s captured in this saying by Ralph Waldo Emerson, often quoted by entrepreneur Peter Thiel:

"Shallow people believe in luck...Strong people believe in cause and effect".

As with most things, the reality is more nuanced and lies somewhere in the middle.

Given how broad this topic can be, I’ve adopted the form of notes or ‘jottings’ on luck, combining different things I’ve read and experiences I’ve had.

Here they are:

1. There are two types of luck: 1) blind luck (e.g., where you’re born, who your family is, getting in a freak car accident) and 2) luck you earn.

2. Blind luck can be very powerful. In particular, the country, time period and socioeconomic background you are born into account for a lot. As Malcolm Gladwell writes in Outliers, computing pioneer Bill Joy benefited heavily from circumstance. He was born at exactly the right time (the mid-1950s) at the dawn of personal computing. He also went to the University of Michigan, one of the few colleges in the US with a time-sharing computing system. This enabled him to spend countless hours programming before most people even had access to a computer. When combined with his talent and hard work, Joy made many foundational contributions to computing, including the Unix operating system and the early protocols for the Internet.

3. The luck you earn has a ‘surface area’. Think of it like catching rain. You can’t control when or how much it rains, but you can control the size of your bucket. Baseball executive Branch Rickey famously said, "luck is the residue of design”. When intelligence and effort combine, you can manufacture a lot more good fortune.

4. There are a few ways to increase your surface area of luck. The first is simply to make more contact with the real world. This can look like having conversations with strangers (often, the most cutting-edge information in any field is not written down anywhere), building things in public or hosting events that connect quite disparate groups of friends. And the most important factor to increase your surface area of luck is to simply take more shots on goal. A musician who makes hundreds of songs a year is more likely to get lucky and produce a hit than one who painstakingly creates one ‘perfect’ composition. Your rate of experimentation is the key variable, not the percentage of successes.

5. Seek asymmetric bets. Look for opportunities with capped downside (e.g., minimal financial outlay or that build ‘no regrets’ skills) and uncapped and non-linear upside (h/t to my friend Ben for this framing). This reduces the impact of bad luck and amplifies the impact of good luck. This is one of the reasons I’m planning to pursue more media projects over the course of this year — writing, hosting a podcast and making YouTube videos. They have a capped downside — I get to meet interesting people and build a storytelling and video production skillset. And by posting them on the internet, they also have the potential for non-linear and uncapped success.

6. Leave space for flexibility and spontaneity. If the right opportunity comes up, you need to have enough time and mental energy to capitalise on it. If you fill up every minute of every day with plans, you won’t have enough slack to take risks and take advantage of serendipity. This also applies financially. One of the reasons I’ve held off on getting a mortgage over the last couple of years (apart from Sydney’s ridiculous house prices) is that it would greatly reduce my degrees of freedom. It would stop me from taking any material risks in my career that could actually have an even higher upside than getting on to the bottom rungs of the property ladder.

7. Just increasing your surface area of luck is not enough. You still need to get a return on your luck. The best recent example of this is Jensen Huang and NVIDIA. NVIDIA’s chips and data centres are the ‘picks and shovels’ of the current AI revolution. But the company undoubtedly got lucky. Their graphics cards, originally developed for gaming, happened to be exactly what was needed for the parallel processing requirements of training neural networks and transformers. No one could have seen that coming. But NVIDIA’s meteoric rise also wasn’t pure chance. Its recent success is underpinned by CUDA - the programming platform that lets developers use NVIDIA’s GPUs for general-purpose computing. Jensen started investing in this platform in 2006, when it was a niche and unprofitable product searching for a market (and was punished by the stock market for it). But when he recognised just how perfectly it worked for AI, he doubled down massively, transforming Nvidia into the most valuable company in the world. Jensen calls it “luck founded by vision.”

8. Be wary of self-serving bias. This is the mindset that any good things that happen to you are due to your skills, and any bad things that happen to you are due to bad luck. This flips when looking at other people's successes and failures. It’s important to recognise when you simply had good fortune, as well as appreciate others’ skills and talent.

   "We must believe in luck. For how else can we explain the success of those we don't like?" — Jean Cocteau

9. ‘Who luck’ is extremely powerful. So much of life comes down to who you know. People in your orbit, like ex-colleagues, mentors and friends, will often open doors for you. Interestingly, Stanford research from the 1970s showed that ‘weak ties’ (casual acquaintances) are more powerful than ‘strong ties’ (close friends) in finding a new job. This is because your close friends tend to have the same information as you, while weak ties have access to opportunities and worlds you might never have heard of. So, it is important to treat everyone with humility and not see everything as a transaction. Be willing to give generously without expecting anything in return.

10. Process over outcomes. We often judge the quality of a decision based on its result. A good outcome means you made a good decision. But this is a dangerous way of thinking, because life is like poker, not chess. You can make the best decision possible at every point in a game of poker, but still lose because you don’t know what cards will be dealt and revealed. Or you can make a series of wrong decisions and still get lucky. Life is much the same. The takeaway from this is to focus on your process rather than your results. A bad outcome doesn’t make our decision wrong if we thought about the alternatives and probabilities in advance and allocated our resources accordingly. It just means that one event in a set of possible futures occurred. If you keep this in mind, you can better diagnose why something did or didn’t work out.

11. Expect to be lucky. If you believe that good outcomes are possible, you are more likely to be alert to opportunities and stay persistent. This can start a self-reinforcing cycle where you more easily recover from setbacks, have more success and strengthen your belief in good luck and optimism.

12. Geographical luck likely shaped world history. In Guns, Germs and Steel, Jared Diamond argues that the reason ‘Western’ powers have come to dominate the world is geographical luck, compounded over time. This applies in two ways. The first is that there were simply more species of animals and plants that could be domesticated in Europe, making it easier to practice agriculture and live in cities. Living in cities meant that people could better spread ideas and technology, as well as support larger armies. Living with animals also created immunity to diseases like smallpox, which ravaged native populations during colonisation. The second is the continental-axis hypothesis. If you look at a map, you’ll notice that the Americas and Africa are lined up North–South, while Europe and Asia are lined up East-West. It’s easier to spread societies east-west, because the climate doesn't change. This allowed Eurasian crops, animals and innovations to spread more rapidly, starting a prosperous snowball effect.

13. ‘Serendipity’ has a fun etymology. British politician and writer Horace Walpole used it for the first time in 1754. The word comes from an old Persian fairy tale about three princes from Serendip (the ancient name for Sri Lanka) who were always making discoveries "by accidents and sagacity" of things they weren't looking for. What's interesting again here is the combination: accidents and sagacity. Not just stumbling into good fortune, but having the awareness to recognise it and capitalise on it when it appears.

14. I couldn’t have a post about luck have 13 points. So here is an extra one.

Some resources I relied on for this piece:

• How to increase your surface area for luck by :

Useful Fictions

How to increase your surface area for luck

This post is an excerpt from my forthcoming book (and builds on a couple of paragraphs in my original post on agency). I’ll be running a few excerpts here in the coming months, in hopes of getting feedback on the kinds of content people are excited to see in the book (which is a signal about what to expand or scale back…

Read more

a year ago · 1892 likes · 109 comments · Cate Hall

• The Luck Field Manual by

• The 4 Types of Luck by

• Where Good Ideas Come From by

• Thinking in Bets by

Update Log

• I’m excited to join and her team at Encour, a strategic communications agency that helps founders and companies command the narrative. I had a blast meeting the team this week and will be working at Encour a couple of days a week, helping out with their video productions.

Recommendation Zone

This week’s recommendation is Barbara Kingsolver’s Demon Copperhead (another banger recommendation from my girlfriend, Vaidehi).

It’s a reimagining of Charles Dickens’ David Copperfield, but set against the backdrop of rural Virginia and the opioid crisis. It follows the titular character from birth and the unrelenting challenges he faces with the foster-care system, high school and, eventually, addiction.

It’s a fairly large book, and it took me a while to really get into it. But for me, around the 60% mark, a lot of threads started to come together, and I became totally absorbed.

A great read if you want to learn more about the opioid crisis in America, the brutal economic realities of the decline of the US coal industry and the power of resilience in the face of it all.

One must wait until the evening to see how splendid the day has been — Sophocles

It’s a reminder that you can’t judge anything you do while you’re still in the messy middle. Everything looks like a failure while it’s still in progress.

This resonated with me, particularly in a professional setting. At Bain, I often worked on business transformation projects that were designed to lay the foundations for success over multiple years. But ultimately, corporations are judged on quarterly reports and short-term milestones. It was always tricky to engineer ‘quick wins’ without just creating artificial sugar hits that didn’t lead to long-term success.

This concept is also something I’ve been trying to keep in mind as I embark on a more unconventional career path this year. There will be days when I feel more uncertainty or a lack of progress. But I won’t be able to truly judge the success or failure of this pathway until I spend enough time navigating it.

One practical takeaway from this idea is to ship more completed projects. This is something I’ve discovered while pursuing creative projects, like writing or music production.

I find it easy to be inspired by an idea, such as a blog topic or a short 10-second musical loop. But after an initial burst of inspiration, I can get frustrated or bored and never end up finishing. I still have a long backlog of unfinished newsletter ideas and Ableton project files like “drum loop 2.”

But whenever I push through this period and actually end up shipping a complete product, it is always worth it. Some of my newsletters that have got the most engagement were sitting in the drafts pile for months or years before I finally got enough conviction to hit publish. It’s why I’m committing to publishing weekly on this Substack.

I found Sophocles’ quote to also literally hold true during my travels last year. Particularly when I was solo travelling, there would be times when I would feel unmotivated and that I had wasted the day. But small moments or decisions could completely change this.

One day in Medellin, I had a meh day, until I bumped into my Swiss roommate at the hostel. It was his first night in the city, and so he invited me to dinner with his friend. I initially said no, just planning to do some grocery shopping and go to bed early. But he eventually persuaded me to come out.

We ended up having a delicious dinner and a long chat ranging from how farcical Swiss compulsory military service can be to the challenges of PhD theoretical physics program across Europe. It was one of my most memorable nights on the trip and completely turned my day around.

Update log:

• 🎄Spent the festive period with friends and family. It’s been lovely to share meals, celebrate birthdays and just spend time with those closest to me

• 🌞 Enjoyed summer in Sydney. I find summer to be the best time to be in Sydney. The days are long, everyone is (even) more laid back, and you get sunsets like the one below at Maroubra Beach.

• 🏏 Continued working on my first YouTube video idea. I am planning to release a ~15-minute documentary on the rise of IPL cricket in the next couple of weeks. It’s been fun to try my hand at storytelling and video editing in Final Cut Pro.

Recommendation zone:

I really enjoy history podcasts. But my undisputed favourite is the Conflicted podcast, hosted by Zach Cornwell. Each episode goes in-depth into one historical controversy, struggle or conflict that raises difficult questions and challenges our assumptions about the past.

Cornwell is an incredible storyteller, taking just enough poetic license with things like characters’ internal dialogue to keep things interesting and exciting, without becoming unbelievable.

Some personal favourite episodes:

• The Partition of India

• The Gulf War 1991

• The 1967 6-Day War

• The Prophet’s Dilemma