Hi there,

At the end of 2023, after spending almost my entire adult life building Venture for Canada, I decided to leave. Alongside that choice came a less obvious one: not to immediately decide what would follow.

Several enticing job opportunities offered an easy solution. Each came with a salary, a title, colleagues, and a straightforward answer when people asked about my plans. But part of their appeal, I began to suspect, was simply that having an answer felt better than not having one. Living with uncertainty for a while seemed better than choosing something merely to end it.

After giving myself time to explore while taking on some consulting projects, I now have an answer I believe in. Beginning today, I am searching full time through Carrying Place Holdings for a Canadian business to acquire, operate, and steward for the long term. The company is named after the carrying places that connected waterways on portage routes. I am energized by the idea of taking responsibility for something that already exists and helping carry it forward.

I want to share some context on how I arrived here. I certainly do not have career transitions figured out, but reflecting on my own transition helped me make sense of my own decision, and I hope some of it is useful to others considering a change.

I first became sure that I wanted to leave Venture for Canada while David and I were away on our honeymoon at the end of 2023. Being removed from my normal routines gave me space to think about what I wanted the next chapter of my life to look like. Venture for Canada was also entering a different stage, and many of the challenges that had energized me in its early years were becoming less central as it matured. I told the VFC board that I expected to leave in roughly two years.

After leaving at the end of 2025, I was fortunate to spend two and a half months travelling outside Canada. That time helped me disconnect after more than a decade of building Venture for Canada, but it also gave me a genuine pause before diving into whatever came next.

Over the past seven months, I have also consulted with several exceptional organizations, principally the Shorefast Institute. The work has been deeply rewarding, especially the opportunity to lead the process through which the Institute developed its strategic vision and plan. Alongside that work, I explored housing policy and philanthropy, tested startup ideas, and spoke with people whose work I found interesting.

One idea kept coming back. Entrepreneurship through acquisition, usually called ETA, means becoming an entrepreneur by buying and operating an existing business. I first encountered the model thirteen years ago in an entrepreneurship class at Georgetown. I later read the HBR Guide to Buying a Small Business, and years after that, Venture for Canada launched an ETA program. While developing it with my colleagues, I spoke with more than 120 people involved in buying, operating, financing, and advising businesses.

None of those moments felt like the beginning of a plan. Only in retrospect can I see how they gradually shaped what I wanted. We often talk about passions as though they are fixed things waiting to be discovered, but I think they evolve through what we learn, the choices we make, and the possibilities we encounter. Sometimes it takes years to understand why an earlier interest mattered.

My interest in ETA did not develop in a straight line either. I fell in love with the idea, fell out of love with it, and eventually came back to it. Entrepreneurs often tell me that ideas develop this way: they question them, set them aside, and sometimes return to them later. It similarly took me almost a year while working at Goldman Sachs to decide whether Venture for Canada was the right path. The more alternatives I explored this time, the clearer ETA’s appeal became.

I want to spend my time with customers, team members, and operations. I like leading teams, selling, solving problems, and taking something with momentum and trying to make it stronger. Growing up in Dartmouth, Nova Scotia, also showed me how much a good local business can matter to the people who work there and the community around it.

By May, ETA no longer felt like one interesting possibility among many. It felt like what I actually wanted to do and the possibility started to fill me with energy. I also realized that I would regret never trying to own and operate a business myself. I am grateful to have the support of an exceptional group of advisors as I begin the search.

For much of the past year, I gave fairly vague answers when people asked what I was doing next. Those answers sometimes elicited confusion and, occasionally, a little judgment. A recognizable employer and title are easy to explain. Exploring several paths and changing your mind can look indecisive, especially to people who think careers should move in a straight line.

I have come to think that part of taking risks is becoming more comfortable when your choices do not produce the most conventional or socially acceptable answer. A nonlinear career rarely looks coherent while you are living it. Taking more time does not guarantee clarity, and sometimes you just stay confused for longer. But if I had optimized for having a crisp answer to “What are you doing next?”, I might have ended up with the wrong one.

Articles I Enjoyed Reading

How to use your career to reduce risks from AI: If I were not launching a search to acquire a business, AI safety is one field I would seriously consider working in. AI presents enormous opportunities, but I am not convinced we are taking all of its risks seriously enough. This is a practical guide for people, particularly those with technical backgrounds, who are interested in working on AI safety.

How did the English build such beautiful villages: There is a reason people keep flocking to the Cotswolds. One thing I found interesting in this piece is that much of what makes old English villages beautiful was never centrally planned. Roads, homes, gardens, churches, and public spaces accumulated gradually over centuries. The irregularity that planners might eliminate today is part of what makes these places so appealing.

What should the future look like? Inside the tech funded program to create a new aesthetic: We can recognize Art Deco or midcentury modern almost instantly. I have been wondering what people fifty years from now will recognize as distinctly ours. Too much of what we build today seems optimized for cost and speed rather than beauty. This piece looks at people trying to create a more ambitious aesthetic for the present.

The Uncertainty Advantage Turns One

The Uncertainty Advantage turned one this month. Since then, it has sold about 2,500 copies, reached readers through roughly 100 libraries across Canada and the United States, and taken me into rooms and conversations I never expected when I started writing it. I wrote down some of the things I wish I had known before writing my first book, including lessons about publishing, distribution, promotion, and what I would do differently next time.

Books I Enjoyed Reading

Lost Japan by Alex Kerr: Kerr moved to Japan shortly after graduating from university and has spent decades observing the country as both an outsider and a long term resident. Much of the book is about what Japan lost in its rush toward modernization, particularly traditional buildings, communities, and ways of living. After spending five weeks there myself, I found myself recognizing many of the contradictions he describes. He clearly loves Japan, which makes his criticism more interesting rather than less.

The Things We Never Say by Elizabeth Strout: I picked this up after seeing it on the Booker Prize longlist. Strout is very good at showing how seemingly ordinary family relationships can contain secrets, loneliness, and old wounds that never entirely disappear. I also liked how the book captures the way larger events and pressures of our time filter down into individual lives. I could imagine someone reading it decades from now and getting a surprisingly good sense of what it felt like to live through this period. Quiet rather than dramatic, but it stayed with me. I am excited to read more of Strout’s work.

Wanting by Luke Burgis: Before reading this book, I knew almost nothing about mimetic desire, the idea that we often learn what to want by watching what other people want. Once you start looking for it, you see it everywhere: careers, consumption, status, social media, even the people we choose to compare ourselves with. It made me think more carefully about how many of our ambitions are actually our own.

Closing Thoughts

I am glad I gave myself some time to explore. I am also ready to stop exploring quite so much and embrace entrepreneurship again.

Thanks to everyone who replied to last month’s newsletter. It was great to reconnect and hear more about your summers. If you are starting something new, or seriously considering it, I would love to hear more about it.

Until next time,

Scott

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During COVID, I counted the calories in everything I ate. I logged meals before I had finished them. I would sit down to dinner with people I loved and spend it doing arithmetic. On paper I was in great shape. I could not tell you what any of my meals tasted like.

That is why I do not track my sleep. Not because the data is useless, but because I know myself. I would spend more time worrying about my sleep score than actually improving my sleep. Something intended to improve my health would become another source of anxiety.

We have never had more ways to optimize our health. Wearable devices track our sleep, heart rate, stress, and recovery. Podcasts promise another supplement, another protocol, another way to add years to our lives. The pursuit of longevity has become an industry.

Much of this is a good thing. Living a longer, healthier life is worth pursuing. Take care of your body. Exercise. Sleep. Eat well. Do what you reasonably can to increase your chances of a long life.

But I worry that we are becoming experts at extending life without getting much better at living it. Habits meant to improve my life were shrinking it. No amount of data or discipline can eliminate illness, loss, or accident. We can reduce risk, but we cannot remove uncertainty.

In Norwegian Wood, the Japanese novelist Haruki Murakami writes, “Death exists, not as the opposite, but as a part of life.” Mortality gives today its urgency. If we believed we had endless time, nothing would feel pressing. There would be no reason to call an old friend or start the business.

I do not know how much time I have. Neither do you. That is not a problem to solve.

Articles I’ve Been Reading:

How do you ask good questions?: Practical tips on asking better questions. Cowen treats it as a skill you can get better at with practice.

Mini Cities: For most children, playing “city” means cardboard storefronts and imaginary money. But in Germany and Austria, thousands of children spend part of their summer running something much closer to a real economy. They elect mayors, open businesses, and pay taxes. These temporary child-run communities, modelled on real civic life, started with Mini Munich in 1979, which is still operating today. They remain almost unknown beyond those countries. This article is an excellent overview.

Books I’ve Been Reading:

No Great Mischief (Alistair MacLeod): I spent the beginning of July in Cape Breton and read MacLeod’s book when I was there. There’s something special about reading a book about a place while you’re in it. Even though I grew up in Nova Scotia, I wasn’t aware of the extent of Gaelic history in the Maritimes. By the late 1800s there were roughly 100,000 Gaelic speakers in Nova Scotia. The novel does a great job capturing how the place you’re from never really leaves you, even when you move away.

The Horde (Marie Favereau): A history of the Golden Horde, the western part of the Mongol empire. The Horde lasted three centuries, and it did it by absorbing local rulers and leaving them mostly in place, taxing and trading rather than governing directly. The nomadic nature of the horde ended up being more of a feature than a bug. What I found interesting is how badly the direct approach tends to work by comparison. Rome ran into a version of the same lesson, and so have most of the empires since.

10:04 (Ben Lerner): I’ve written about Lerner in some of my other newsletters. He is probably my favourite living novelist, and one of the writers who best captures what it feels like to be a millennial. What drew me back to this one is hard to describe. So much of what the book grapples with is uncertainty. The narrator is deciding whether to help a close friend have a child while carrying a diagnosis that might end his own life, and he can’t resolve either question.

Idea I’ve Been Thinking About:

In his newsletter, Derek Thompson recently wrote about the concept of uni-context. In the past, we adjusted how we acted based on the setting we were in. We acted differently at work than we did with friends. The theory of uni-context is that as our online lives become more important, we increasingly show up the same way to everyone.

This one hit close to home. This newsletter goes out to about 2,200 people. People I know from work, high school, and university, and a lot of people I have never met. I’m sensitive about what I put out, because it’s going to all of them at once and I don’t want to offend anyone. The effect is that I sometimes make this newsletter more generic than it should be. I don’t think I’m unusual in this. But uni-context doesn’t just make comparison harder to escape. It makes everyone a bit blander, including me.

I’m trying to write more of the things I would say to one person rather than to 2,200.

What Fills a Life:

This summer, I spent about a month in the Maritime provinces, where most of my family lives.

I fly fished in Cape Breton with my husband and my dad. I visited lighthouses on Grand Manan with my in laws. And I had dinner at our family cottage in Nova Scotia with my mom, my aunt, and my ninety four year old grandparents.

Spending that time with family was a reminder that a longer life matters mostly because of what fills it.

I do not know how many more summers I will get with the people I love. None of us do. But I know I want to spend less time trying to control that fact, and more time paying attention while I am here.

I also have some exciting personal news that I am not quite ready to share. More on that next month.

Until then, I would love to hear about the highlight of your summer. Just hit reply.

Best,

Scott

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Hi there,

The map above is worth a second look. The countries shaded red, the most pessimistic about where the world is heading, include some of the wealthiest, safest, and places with the longest life expectancies on earth. At first, that seems strange. But maybe it should not. In countries where life has improved dramatically within living memory, optimism may come more naturally. Progress is visible. Parents and grandparents remember how much harder life used to be.

In wealthier countries, the story is different. The gains are often less visible, expectations are higher, and people are more aware of what could be lost. If you grow up assuming stability, prosperity, and progress, even modest decline can feel like collapse.

That is the contradiction I have been thinking about. We are living through real problems, but also in a period of extraordinary human progress. And yet many of us, especially in rich countries, find it easier to believe in decline than improvement.

I notice this in myself. I can read the news for ten minutes and come away feeling like decline is the only honest position.

Some of that feeling is justified. War, climate risk, political instability, loneliness, and economic anxiety are not imaginary problems. If you are reading the news, there is plenty to worry about.

But there is a difference between taking those problems seriously and letting pessimism become your worldview.

Recently, I read Steven Pinker’s Enlightenment Now. The book makes a strong case that human progress is real, measurable, and easy to forget. World life expectancy rose from 46 years in 1950 to 73 years in 2023. Two hundred years ago, roughly 80 percent of humanity lived in extreme poverty. Today, that figure is closer to 9 percent.

None of this means everything is fine. Some of these trends are genuinely alarming. For instance, the number of active military conflicts just reached the highest level since WWII, with global peacefulness declining for the 12th straight year. In short, the march of progress is rarely a straight line and often we can slide backwards. As Martin Luther King Jr. once said, “the arc of the moral universe is long, but it bends toward justice.”

Research suggests we often see pessimistic people as smarter. They sound more serious because they notice risks, flaws, and failure points. But noticing what is broken is only the first step. Optimism is what asks what can be repaired, built, or invented.

Optimism does not mean pretending the world is better than it is. It is a posture toward action.The future is not automatically good. It has to be built.

That feels especially important right now. The news gives us a steady stream of collapse. Social media rewards outrage. Quiet progress rarely travels as fast as disaster, but it is still happening, often without much attention.

Consider just the last few months. A study found that the malaria vaccine, now reaching millions of children across Africa, averted roughly one in eight child deaths among eligible children in the first countries to offer it. Guinea worm, a parasite that afflicted millions of people in the 1980s, is down to 10 human cases worldwide. And for the first time in a century, renewable energy overtook coal, supplying more than a third of the world’s electricity. None of this got much media attention.

I spent more than a decade at Venture for Canada watching young people start companies, projects, and careers. The ones who got somewhere were rarely the ones who felt most sure it would work. They started anyway, fixed what broke, and let a small result give them the nerve to try a bigger thing. Hope did not come first. It accumulated.

Pick one problem you care about and do one useful thing about it. Support an organization. Build a product. Mentor someone. Write something. Volunteer or invest. What matters is that you start.

Optimism is not believing everything will work out. It is believing that your actions still matter.

Articles I’m Reading

You Are Not a Horse: An excellent piece that pushes back against the idea that AI will simply automate most jobs. A job is more than a task list. It is also judgment, trust, relationships, context, and accountability. Useful reading for anyone trying to understand how AI may reshape the labour market without flattening the human parts of work.

35 Rules for Living an Excellent Life in a Crazy World: Last month, I shared my own list of 35 reflections on turning 35. I was a fan of this list from Brad Stulberg. It is practical, grounded, and full of reminders that sound simple until you actually try to live them.

How to Enter Side Doors: Practical advice on how to get hired outside the traditional application process. Increasingly, people land opportunities through informal paths, warm introductions, visible work, and well timed outreach. Learning how to find the side door matters more than ever.

Books I’m Reading

Island: Alistair MacLeod may be the greatest Atlantic Canadian novelist. This collection of short stories captures the beauty, hardship, pride, and melancholy of Cape Breton. His writing makes ordinary lives feel enormous.

Transcription: This novel is slim, sharp, and packed with observations about technology, attention, language, and how modern life changes the way we experience ourselves.

The Box: A fascinating history of the shipping container and how it transformed global trade. It is easy to forget that much of the modern economy depends on boring infrastructure. This book is a reminder that some of the most important innovations are not flashy. They simply make the world work differently.

Closing Thoughts

Thanks for your replies to last month’s post on 35 reflections on turning 35. I loved hearing your learnings as well.

What makes you optimistic about the future? And do you think we are too pessimistic, or am I being too optimistic?

I would love to hear from you either way.

Until next time,

Scott

Hi there,

This past weekend I turned 35.

Your mid thirties are strange. You are not old, but you are no longer pretending adulthood is something happening later. For the first time, I can look in the mirror and see the outline of my middle aged self.

That has me thinking about what I’ve learned, what I keep relearning, and what I wish I could tell my younger self.

Here are 35 reflections from my first 35 years.

1. At twenty two, I was sure leaving Goldman Sachs was the risky decision. I had it backwards. Staying still carried its own risk. A prestigious path becomes dangerous the moment it rewards you for ignoring yourself.

2. No one is ever ready to start the thing they’re meant to start. When I began Venture for Canada I was curious, ambitious, persistent, and willing to learn in public. That was enough to begin, and beginning is most of it.

3. Coming out taught me that honesty tends to feel most frightening right before life gets freer.

4. The person you marry sets the climate of your life. David has made mine calmer, funnier, and more grounded. That has mattered more than almost any decision I’ve made about work.

5. Love is mostly ordinary, in the best way: walking the neighbourhood, cooking dinner, laughing at something stupid, building a home with someone who makes the daily stuff better.

6. Home is not the thing you return to after the interesting part of life. For a long time, I treated movement as proof that I was growing: another trip, meeting, event, proposal, or project. But some of the best parts of my life have been quieter: reading on the couch, hosting dinner, going for a walk, and realizing that stability can be its own kind of adventure.

7. A meaningful life is not the same as an easy one. If you care about things, you will feel pressure. The goal isn’t to escape pressure. It’s to choose pressure attached to something worthwhile.

8. Energy is not unlimited just because your ambition is. I have often acted like I could travel constantly, work intensely, read everything, write on the side, and still feel fine. Eventually your body sends the invoice. Sleep, exercise, quiet, and pleasure reading are not indulgences. They are maintenance.

9. Belief can start an organization; systems are what let it scale and endure. Early success hid how much of Venture for Canada was underbuilt, and growth exposed all of it. Scale doesn’t just demand more effort. It demands clearer roles, better processes, and stronger habits.

10. Leadership isn’t proven when things go well. It’s tested when people are tired, resources are thin, and the right call is the uncomfortable one.

11. Composure is a skill. It doesn’t mean feeling calm; it means staying useful when the room gets tense.

12. Managing people teaches you about yourself as much as about them. Your impatience, your conflict avoidance, your need to be liked, your need for control. All of it gets harder to ignore.

13. You can care about people and still hold clear expectations. Kindness and accountability are not opposites.

14. The most lasting thing you build is rarely the organization itself. It is the people who go on to do things you may never fully see.

15. There’s a difference between moving quickly and rushing. I’ve forced fast decisions just because waiting made me uncomfortable. Some choices get better when you let the process do its work.

16. Assertiveness is not the same as forcefulness. Competitive debate taught me how to make a point clearly, and early leadership rewarded decisiveness. But over time I learned that pushing harder does not always make you more effective. Real assertiveness clarifies what matters, says the hard thing directly, and leaves the other person with their dignity intact.

17. Comparison is a race with no finish line. I’ve measured myself against classmates, founders, and writers who seemed further ahead. It never once made me happier or wiser.

18. Ambition is useful but it needs supervision. Left unchecked, mine turns everything into a scoreboard.

19. Money matters because it buys freedom, not because it proves your worth. Wanting security is healthy. Confusing money with meaning is where things go wrong.

20. Breadth is useful, but only if you eventually choose depth. I have always been interested in many things: politics, entrepreneurship, travel, writing, public service, real estate, history, and whatever new idea grabbed my attention that week. Curiosity has opened a lot of doors for me, but the work that matters most has required staying with something long after the novelty wore off.

21. Entrepreneurship is rarely inventing something from nothing. More often it’s noticing a problem, adapting an idea that already works, selling the vision, and staying with the work longer than most people will. Venture for Canada was never a lightning bolt. It was a Canadian answer to a model I admired, shaped by local needs and a lot of persistence.

22. Productivity can quietly become a way to avoid living. I love getting things done, but not every hour needs to be turned into output.

23. My brain works better after a walk. Some of my clearest thinking has come on hikes, beside water, or while wandering through a place I do not know well. When I stay inside my own head too long, my problems get louder than they deserve.

24. A good trip interrupts the habits I’ve mistaken for personality. It’s amazing what a change of pace can do.

25. Keep a diary. You’ll forget what earlier versions of you feared, wanted, and got wrong. Reading old entries is the clearest way I know to see your own patterns.

26. Writing isn’t only communication; it’s how I find out what I think. Some things only become clear once I make myself put them in a sentence.

27. Reading has been one of the main ways I have built a larger life than my own schedule. Fiction, history, memoir, travel writing, and political biography have all changed how I understand people. The books that stay with me usually make me less certain and more humane.

28. You do not need to turn every interest into a project. I have a habit of getting excited about something, researching it intensely, building a plan, and imagining what it could become. Sometimes that has served me well. Other times, the better move is to let an interest stay an interest. Not every curiosity needs a business model, strategy document, or five year plan.

29. You can love people deeply without making their feelings your responsibility. Learning that made me both calmer and kinder.

30. Listening to understand is harder than listening to win. Competitive debate trained me to find the weak point in an argument. Life has slowly taught me that people are not arguments to defeat. Some conversations get better the moment you stop preparing your rebuttal.

31. Feedback hurts most when some part of you knows it’s true, but you’ve been suppressing it. That’s usually the part worth examining.

32. The line between persistence and stubbornness is thinner than I’d like to admit. Persistence built most of the good things in my life; stubbornness made me slow to adapt more than once.

33. Influence is less glamorous up close. When I was younger, I wanted success, power, and impact. Building VFC taught me that influence often means more responsibility, more tradeoffs, and more uncomfortable decisions. The point is not to chase importance. The point is to make sure the responsibility is worth carrying.

34. If every week is urgent, you stop being strategic. Some of my worst decisions came when I was reacting to the next email, meeting, trip, or fire. Some of my best thinking came when I had enough quiet to notice what I had been avoiding.

35. At thirty five I feel less certain than I did at twenty five, but a lot less afraid of not knowing. That might be the real lesson. Life doesn’t get cleaner; you just get better at walking through the fog.

Which lesson did you have to learn the hard way? I’d love to hear it.

Until next time,
Scott

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And yet, like most overused phrases, it is pointing at something real. Founders use it about employees. Employers use it about candidates. Educators use it about students. They mean someone who sees a problem and moves, who takes initiative without endless permission. In a world that feels less stable by the year, that quality has been elevated into something close to a personal virtue.

I want to make a different argument. Agency is not really a trait. It is closer to weather. It forms in particular conditions, and disperses when those conditions are absent. The people we call “high agency” are usually people who have spent their lives standing in the right kind of weather, with access to rooms where initiative was expected of them.

If that is right, the most important question is not how to identify high-agency individuals. It is how to give more people access to those rooms.

What Environments Actually Do

Years ago, I heard the phrase “high possibility environment,” and it has stayed with me. Some rooms make action feel obvious. Some make it feel unimaginable.

Over eleven and a half years building Venture for Canada, I watched this happen thousands of times. A student would arrive at a startup internship in week one quiet, deferential, asking permission for everything. By week six, they were proposing changes to the product. Nothing about them had changed. The room had given them a different sense of what was theirs to touch.

Agency is a current that runs through certain rooms and not others, and you keep it as long as you stay plugged in.

On the Outside

There is no good word for what happens to people who never get access to those rooms. They are surrounded, every day, by signals that initiative is not for them, that the people who act are a different category of person, that the safe move is to wait.

By the time a young person is old enough to seek out a high-possibility environment, they have already spent fifteen or twenty years inside whatever environment they had access to.

Most people in this position are not lacking ambition. They are correctly reading their environment. In a room where initiative is punished, ignored, or absorbed by someone with more standing, the rational response is to stop offering it. What reads as passivity is often a learned and accurate response to years of feedback.

The “high agency” people are not, mostly, people with more grit than everyone else. They are people who happened to be raised, schooled, employed, or befriended in environments where initiative paid off.

What Institutions Can Actually Do

If agency is partly environmental, then schools, employers, programs, and communities are not just places where it is observed. They are places where it is produced or stunted. A few things separate the rooms that produce it from the rooms that do not.

Give people decisions that matter. Most institutions default to compliance. But you cannot build initiative in someone whose every meaningful decision is made for them. Real agency requires real stakes, like a budget the person actually controls or a problem they own end to end.

Shorten the distance between idea and action. High-possibility environments compress the path from “what if we” to “let’s try it.” Low-possibility environments stretch that path through committees and approvals until most ideas die of exhaustion.

Make failure survivable. People need to see colleagues fail and recover before they will believe the same applies to them.

Put people next to other people who act. Possibility spreads socially. Agency is caught more than it is taught.

Agency Is Infrastructure

We talk about agency as if it were a personality test. It is closer to infrastructure, something a society chooses to build, fund, and distribute. When roads are missing in a region, we do not say the residents lack the personal virtue of mobility. We say the roads are bad.

We have spent the last several years debating how to identify high-agency individuals. We have spent almost no time asking how to build more rooms where agency becomes the obvious response, and how to get more people inside them.

In a world with more uncertainty and more tools than ever, that question matters more than almost anything else.

Below are the top things I’ve been reading and watching this month. Some of them connect to the argument above more directly than others.

What I’m Reading

Brian Eno’s Remedy for Burnout and Despair

A sharp reminder that creativity often comes from tension, not comfort. Best line: turning despair into a defense of joy.

Ten Ways of Thinking About Gradual Disempowerment

A real risk with AI is not replacement, but slow erosion of decision-making. You give away a few choices, then a few more, and eventually you forget how to choose. This piece maps that drift clearly.

What I’m Reading in Print

The Cancer Ward by Aleksandr Solzhenitsyn

A novel about illness on the surface, but really about decay in systems and people. Set in post-Stalin Russia. Uncomfortable in a useful way.

What I’m Watching

A Day in the Life of an Ensh*ttificator

Funny and uncomfortably accurate. Shows how products and platforms degrade over time, and how we slowly accept it.

What I’m Thinking About

The essay above is partly a reaction to something I kept hearing on the road this past month. I gave keynote speeches to graduating students at University of Prince Edward Island, Northeastern University, and University of Toronto Scarborough.

Across those conversations, one theme kept coming up. The job market feels unstable in a way that is hard to plan around. That is not just an economic issue. It is a generational one.

If early career paths feel more fragile, the long-term effects compound. On wealth. On confidence. On whether people believe the system works for them at all. We do not talk enough about that.

It is also part of what made me want to write the opening essay this month. If young people are entering environments that feel structurally less reliable than the ones their parents entered, then the question of what produces agency, and who gets access to the rooms where it forms, gets sharper rather than softer.

If you have fostered a high-possibility environment, whether a team, a program, a classroom, or a community, I would love to hear what worked, what surprised you, and what you wish you had known earlier.

Until next time,

Scott

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A good friend of mine was stuck in Dubai as the conflict in the Middle East escalated. Texting with him made it feel much closer, and much heavier.

I know for some people, this is not abstract at all. It’s family, it’s friends, it’s real loss.

Lately, one feeling keeps coming up in conversation: the world feels less steady than it used to.

This is not a geopolitics newsletter. What interests me is the practical question underneath all of this.

How do you build some stability in your own life when the world feels so unstable?

A few things that have been useful for me.

1. Reduce your exposure

Most people try to manage how they feel. Fewer people manage what they consume.

If you are checking the news constantly, the problem is not your mindset. It is your inputs. More information does not create clarity. It usually just creates noise.

Most people are overexposed and underprepared.

I have noticed that when I check the news too often, I do not become better informed. I just become less calm and less useful.

I have found it much more effective to limit when I engage with the news, and to be deliberate about when I step away. Treat information like caffeine. Useful in small doses. Unhelpful when it becomes constant.

2. Stay close to people

When things are stable, planning works well. When things are unstable, relationships matter more.

Most opportunities do not come from perfectly predicting what happens next. They come from being close to people, staying in conversation, and being top of mind when something shifts.

If you do nothing else this week, reach out to a few people you have not spoken to in a while. No agenda. Just reconnect.

3. Leave room to change

There is a strong pull to try to figure everything out and lock into the best possible path.

The problem is that highly optimized plans tend to be fragile. When conditions change, they break.

I have found it more useful to keep some slack. Leave room in your schedule. Stay open to changing direction. Keep a few options alive, even if it feels inefficient.

In a more uncertain world, flexibility tends to outperform precision.

Anyway, below are a few of the things I have been reading and thinking about this past month.

Online content I’m reading

The Smartest People I Know Are Obsessed With a Skill Many Were Told Is Useless
A strong argument against outsourcing your acquisition of knowledge. The more you rely on tools to do the thinking for you, the weaker your judgment becomes over time.

How to be “high agency” at work
Simple, practical advice on taking ownership. The people who stand out are rarely the most credentialed, they are the ones who step forward before being asked.

The Ozempicization of the Economy, Kyla Scanlon
One of the clearest explanations I have seen for why so many people are drawn to shortcuts and speculation. It is less about greed and more about people trying to regain a sense of control.

The real reason some people are instantly likable
Useful reminders on warmth. Small behaviors, like how you greet people or how present you are in conversation, matter more than most people expect.

Framework I keep coming back to

Goodhart’s Law:

“When a measure becomes a target, it stops being a good measure.”

You see this everywhere once you start looking for it. Hiring processes. School systems. Even how people approach productivity.

It is worth asking where you might be optimizing for the wrong thing.

Books I’m reading

The Status Game, Will Storr
A helpful lens on how status shapes behavior. Much more of what we do is driven by status than most people are comfortable admitting.

Seeing Like a State, James Scott
A critique of top down systems that ignore local context. It explains a lot about why well intentioned policies often fail.

Sweetland, Michael Crummey
A quiet, heavy novel about place, loss, and what happens when communities disappear.

Home Truths, Carolyn Whitzman
A sharp look at housing in Canada. Useful if you want to better understand why the system feels stuck.

Closing Thoughts

And if you have read or found something worth sharing, send it my way. I read everything.

If this was forwarded to you, you can subscribe below for monthly notes on work, uncertainty, and how to stay steady when the world is not.

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The world may not get steadier anytime soon. Your life still can.

Scott

Hey there,

I used to end vacations exhausted, with a full camera roll and a weird sense of failure. Not because the trip was bad, but because my brain kept replaying what I missed.

It took me a while to name what was happening. I was not failing at time management. I was treating days like a problem to solve, as if there was always a better version of it hiding one more decision away.

That is why the idea of finitude landed. Not as philosophy, but as relief.

Last year I read Oliver Burkeman’s Four Thousand Weeks. His reframe: your life is finite. Your time and attention are limited. Trying to do it all creates a constant hum of stress, even on good days.

The best time management habit is not cramming more into your day. It is accepting that you cannot do everything, then choosing on purpose.

After leaving Venture for Canada, I tried something different while travelling. On some days, I wandered with no plan beyond a long walk and one good meal. No itinerary gymnastics. No scorekeeping. It felt freeing.

A small practice I am trying: When I feel that familiar urge to maximize, I do this quick tradeoff exercise.

1. Write three things you are no longer trying to keep up with this season.

2. Write one thing you are choosing instead.

3. Book the first 30 minutes for that one thing on your calendar this week.

Links worth your time

How to prepare for the next decade
A clear set of questions to help you make smarter career choices over the next few years. Best for anyone feeling uncertain about what to prioritize.

The new rules of small talk
Practical scripts you can use immediately. Best for anyone who wants to feel less awkward and more present in everyday conversations.

The century of the maxxer
A sharp critique of obsessive self improvement culture, focused on the incentives that drive it. Best for anyone who feels stuck in constant self optimization.

Management as an AI superpower
AI will keep getting better at tasks. This is a useful reminder that the human edge is directing work well, setting priorities, making decisions, giving feedback, and creating clarity when things are messy.

My latest writing

We do not have a talent shortage, we have a hiring system problem
AI has made applying effortless, and now screening is breaking. If you are thinking about this too and want to compare notes, reply to this email.

How to deal with career anxiety when you have no clear plan
A set of next steps for moving when you feel stuck, plus a simple way to reduce spiraling when you do not know what comes next.

Books I am reading

The Leopard
A novel about living through a messy transition, when the old world is fading and the new one is not here yet.

Unlikely Insider
Jack Austin’s career is a great lens on Canadian public life and how Canada navigates a shifting global order. Thanks to a reader for suggesting this!

The Lobster Trap
How a local industry became a global business, and how it is changing again under new pressures.

A quote I am chewing on

“Didn’t jealousy create the plot of one’s life”
From The Loneliness of Sonia and Sunny

Advice I am considering

“The appetite grows by what it feeds on.”

I keep noticing how quickly more becomes the default setting. More plans. More work. More input. More everything. Even good things can fall into the trap of more, more, more.

A question I have started asking before I say yes.

Is this feeding the life I want, or is it just feeding the appetite?

Send me your favourites

Have a book, tool, or idea that is changing how you operate? Email me at scott@scottstirrett.com. I would love to feature it in a future edition.

Or, forward this to the person who turns rest into a to do list.

Until next time,
Scott

PS: If someone forwarded you this and you want future issues, hit the subscribe button below.

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Hey there,

When I think about what anchors me right now, I picture scenes like this, a public square, a fountain, people milling around, civic life happening in real time.

One night in Washington, DC, I watched a 20-year-old student candidate win an Advisory Neighbourhood Commission race by a handful of votes, after months of organizing across campuses and pleading with friends to drag their roommates to the polls.

That campaign was part of DC Students Speak, a student advocacy group I cofounded in university. We helped elect seven students to hyperlocal roles with real influence over neighbourhood decisions.

It left me with a simple belief. When the future feels shaky, the most reliable buffer is not a perfect plan, it is a strong local fabric. People who trust each other, institutions that work, and a shared sense that problems can be solved together.

That is why I am excited to share that I am joining the Shorefast Institute as a Senior Advisor, supporting government relations, policy development, and fundraising. This is an advisory role, so I will also be working on a few other projects this year, more soon.

Over the past year, I have gotten to know Zita Cobb and the Shorefast team, and I have genuinely enjoyed it. What they have built is remarkable.

I respect how seriously Shorefast recognizes the strengths every community already has, culture, identity, local knowledge, relationships, natural beauty, and pride. Their approach starts with those intangible assets, then builds an economy that fits the place, so prosperity strengthens what makes the community itself worth staying in.

If this was forwarded to you, use the subscribe button below to join over 2,000 subscribers. Each month I share ideas, tools, and books that help you thrive in an uncertain world.

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As things speed up, here’s what I’m paying attention to this month.

The best articles I read this month

If you only read one this month, read Amodei.

The Adolescence of Technology: Confronting and Overcoming the Risks of Powerful AI

Most AI commentary is either hype or doom. This is neither. It is a sober argument from Dario Amodei, CEO of Anthropic, on what could go wrong sooner than people expect, and what it would look like to respond like adults. Be forewarned - this piece is long but excellent.

Intelligence Is Getting What You Want Out of Life

A sharp gut check if you feel like you are doing well but not feeling good. The core idea is that you can be winning a game you do not care about, then wonder why the payoff feels empty.

Why Aren’t Smart People Happier?

Great framing, intelligence helps with well-defined problems, but most of life is not well defined. There is no agreed scoreboard, so being smart does not automatically make you happier or wiser.

Claude Code and What Comes Next

This captures why coding agents feel like a real shift, not a new toy. If you want to understand what AI that does work looks like, this is a clean entry point.

Sometimes The Reason You Can’t Find People You Resonate With is Because You Misread The Ones You Meet

A surprisingly useful lens on friendship through Aristotle’s three types, pleasure, utility, virtue. It will make you rethink who you are skipping over, and why.

The best books I read this month

The Loneliness of Sonia and Sunny, Kiran Desai

A quiet, piercing novel about what it feels like to move between worlds and never fully belong to any of them. It is also honest about how trauma travels with you, even when your life looks “successful” from the outside.

Flesh, David Szalay

A fast, unsettling read that keeps pressing the same question, how much of your life is choice, and how much is impulse dressed up as a story you tell yourself later. People call it a book about masculinity, and that is in there, but the deeper thread is appetite, shame, and self deception.

Politics on the Edge, Rory Stewart

Stewart is at his best on the practical side of governing, how incentives, bureaucracy, and delivery actually work. The book is a clear diagnosis of why many democracies struggle to do the basics well, and how that failure corrodes trust.

Concept I’m considering

The purpose of a system is what it does, not what it claims to do.

Stafford Beer’s point is simple. If a system reliably produces a certain outcome, that outcome is its real purpose, even if everyone involved has good intentions. If you want the output to change, you have to change the incentives, rules, or feedback loops that produce it.

A quotation I cannot shake

“Death is the moment when somebody comes and says: You know those three things that you’ve always thought of? They’re not true. You’re not permanent, you’re not the most important thing and you’re not separate. So, I think about it a lot, but I find it a joyful thing, because it’s just a reality check.” -George Saunders

One last thought

It feels like we are living through a genuine inflection point. Prime Minister Carney’s Davos speech hit a nerve because it named what many people are sensing, the ground is shifting.

Amodei’s essay took me close to two hours to read, and it genuinely rattled me. Since GenAI tools arrived only a few years ago, the pace has been staggering. It feels like we are entering a new era, and a lot hinges on whether our institutions, incentives, and norms can keep up.

All that is to say, the purpose of this newsletter, sharing ideas and tools that help you stay steady and make good decisions in uncertain times, feels more important than ever.

Thanks to everyone who replied to the last edition. It was the most read one to date, and I really appreciated the thoughtful notes.

Until next time,
Scott

Hey there,

For most of my life, I treated the New Year like a control exercise.

I set clear goals and detailed plans for who I thought I should be twelve months later. At the time, it felt disciplined. Looking back, it was mostly about certainty. If I could define the future clearly enough, maybe I could relax.

That rarely worked.

After graduating, while working at Goldman Sachs, I set ambitious goals around mastering corporate finance. Months later, I quit my job, moved back to Canada, and started Venture for Canada. Those goals became irrelevant overnight.

Life moves slowly for long stretches, then changes direction all at once.

Nearly twelve years after founding Venture for Canada, I am in a phase where uncertainty is not something to minimize. It is the terrain itself.

For the first time I can remember, I did not set traditional New Year’s goals. Instead, I am practicing something less tidy and more honest.

Staying open.

Letting go of rigid goals has changed what I notice. These are a few things that have been sticking with me.

Articles I’ve been reading

Questions to Ask Your Friends
Conversation feels thinner than it used to. This piece argues that the depth of our relationships is shaped less by what we share and more by what we ask. I found myself wishing I had asked some of these questions years ago.

What Makes Someone Charismatic
I have always been skeptical of charisma. It can feel performative. This essay reframed it for me. At its best, charisma is not charm. It is attention. The ability to make someone feel fully seen without trying to impress.

Dan Wang’s 2025 Annual Letter
AI, geopolitics, books, croissants. This was the single most thought provoking thing I read this month. Curiosity is the throughline.

Why Everyone Loves Japan
It feels like half of North America is visiting Japan right now. This essay helped me articulate why the place feels so distinct. It offers a different version of modern life. Transit that works. Tradition without stagnation. At times, traveling there felt like stepping into an alternate present.

Books I’ve been reading

What We Can Know by Ian McEwan
Set a century in the future, this novel is unlike any science fiction I have read. It is about many things at once. Climate change, revenge, infidelity, poetry, love, regret. McEwan is less interested in predicting the future than in examining memory, guilt, and how people make sense of their lives in hindsight. The book takes sharp turns without ever feeling plot driven, ambitious in scope but deeply intimate in execution.

Isola by Allegra Goodman
A historical novel based on the true story of a young woman marooned in the Gulf of St Lawrence. Quiet, restrained, and deeply humane. A story about endurance without romanticizing suffering.

Things Become Other Things by Craig Mod
Part memoir, part travel writing, part cultural observation. Written from Japan, this book moves slowly and deliberately through landscapes, walks, and moments most people rush past. Instead, he sharpens how you notice place, rhythm, and time.

Norwegian Wood by Haruki Murakami
One of Murakami’s most grounded novels. No surreal detours. Just a raw story about grief, desire, and responsibility. It reminded me of The Catcher in the Rye, but lonelier.

The Place of Tides by James Rebanks
What begins as a book about harvesting duck feathers becomes a meditation on place, inheritance, and what we lose when everything starts to look the same.

A quotation I’m sitting with

“Death exists, not as the opposite, but as a part of life.”

I first read this line in Norwegian Wood. For a long time, fear of death sat quietly underneath much of my anxiety, especially during the pandemic. Learning to see death as something that walks alongside us, rather than something stalking us from afar, has been grounding. It has made life feel sharper, not smaller.

Movies I’ve been watching

Knives Out: Wake Up Dead Man
Smart, playful, and unapologetically entertaining. This movie knows exactly what it is.

The Perfect Neighbor
Told almost entirely through police body camera footage. Difficult to watch. Necessary to watch. A devastating look at how systems fail people who need protection most.

The New Yorker at 100
Few magazines blend seriousness and wit the way The New Yorker does. This film captures why it still matters.

Closing thought

This newsletter is my attempt to make sense of uncertainty in public.

If you are entering this year without a clear plan, you may simply be paying attention. What is one thing you are trying less hard to control right now?

And if you have a book, article, or idea I should check out, I would love to hear.

Wishing you a steady start to 2026,

Scott

Hey There,

For the past few weeks I have been in Japan on a two month trip. Earlier in the month I was moving quickly with events for The Uncertainty Advantage across Ottawa, New Brunswick, and the UK. Stepping into quiet after that pace was jarring. It gave me something I have not had much of in close to twelve years at Venture for Canada. Long, uninterrupted time to read, write, and think.

A few days ago in Beppu, sitting in an onsen facing the ocean, I noticed how long it had been since I had given myself that kind of stillness.

Japan has a way of making you see your patterns clearly. The quiet slows you down, and the unfamiliar parts speed you up again. Very little English. Ticket machines that look like aircraft panels. Train stations that feel like puzzles. I spent fifteen minutes trapped in a loop of wrong exits in Okayama, certain I had walked the same hallway again and again.

That moment made something obvious. Adaptability starts with paying attention. When you finally stop running on urgency, you notice the habits that no longer fit. And once you see them, it becomes much easier to update them. The faster you release an outdated pattern, the faster the next step becomes obvious.

Online Content I’m Reading

The hunger to be everything
Trying to be infinite is the quickest route to misery. Pick lanes. Stick to them.

The reality of being a popstar
Charlie XCX continues to be one of the most honest voices online. Sharp, self-aware writing about pressure and identity.

Friction Was The Feature
Hiring is broken. A thousand AI-generated applications for one job makes screening meaningless. This piece argues that friction was used to filter for effort. Now that friction is gone, the system is buckling.

Ben Evans on AI trends
Straightforward pattern recognition on how AI is spreading across the economy.

Heiliger Dankgesang
Dean Ball explains why an AI model’s character matters as much as performance. He’s a big fan of Anthropic and the work they are doing to create aligned AI. Earlier this year I was invited to attend the Anthropic Economic Futures Symposium and was very impressed by their approach to AI.

Books I’m Reading

Breakneck by Dan Wang
Read it in a day. Wang argues that China is run by engineers and the United States is run by lawyers. Progress comes from mixing both instincts. Pair it with Abundance.

Kuni by Tsuyoshi Sekihara and Richard McCarthy
A compact guide to how small communities can rebuild themselves through shared responsibility and practical local systems. The authors show that renewal does not require scale or large institutions. It comes from people investing in a place together and creating structures that support participation and reciprocity.

Small Is Beautiful by E. F. Schumacher
A sharp argument for why economies work best when they stay rooted in human scale. Schumacher shows that real progress comes from systems that respect people, place, and limits.

Mother Mary Comes To Me by Arundhati Roy
One of the strongest memoirs I’ve read this year. Roy writes with clarity and precision. Her mother becomes a fully realized human on the page.

What I’m Watching

A House of Dynamite on Netflix
This film looks at how the United States responds to a real missile threat. After visiting Hiroshima and Nagasaki this month, the theme carried a different weight. It made the stakes feel immediate rather than historical. A reminder that nuclear risk is not a distant concern.

Everything Everywhere All at Once
Finally watched it on the flight here. The film is chaotic, but the underlying message is clean. You cannot live every possible life. If you try, you end up choosing nothing. Regret is built into being human. You have to decide anyway.

Japan Recos So Far

A few places that reinforced the value of slowing down.

• Naoshima for its art and quiet edges. Here’s the link to my Instagram with some pictures.

• Kurashiki for its canals and slower rhythm.

• The Hiroshima Atomic Bomb Museum for unfiltered history.

• Ichiran in Fukuoka for a simple reminder that even a bowl of ramen can reset your pace.

If you have your own Japan tips or favourite spots, I would love to hear them.

A Quote I’m Thinking About

“If human vices such as greed or envy are systemically cultivated, the inevitable result is nothing less than a collapse of intelligence. A man driven by greed or envy loses the power of seeing things in their roundness and wholeness, and his very successes become failures.”
-E. F. Schumacher, Small Is Beautiful

Let’s Connect

I am experimenting with the format of this newsletter. If you have thoughts on what you want more of or less of, reply and tell me. Input from readers shapes this.

A quick thank you. This newsletter started in January and now reaches over two thousand readers with an open rate around 60 percent. Your replies have been a highlight. Writing this each month forces me to pay attention to what actually moves my thinking, not just what fills my schedule.

If you are new here, welcome. I am glad you are part of this and hope these monthly notes give you something useful to think about.

Wishing you a holiday season with enough quiet to notice what actually matters.

If this edition gave you something useful, feel free to forward it. Curious minds compound.

Until next time,
Scott

Hey there,

For most of my twenties, I was relentlessly self-critical. No matter what I achieved, I convinced myself it wasn’t enough. That mindset led to exhaustion, anxiety, and burnout disguised as ambition.

I’ve realized that the more ambitious the environment, the less self-compassionate people often are, especially among those trying hardest to prove themselves.

One of the most powerful mindset shifts I’ve learned is simple: talk to yourself the way you would speak to a friend.

When something doesn’t go your way, skip the blame. Try curiosity instead. Ask what you would say to someone you care about, then say it to yourself.

That idea has changed not just how I handle mistakes, but how I live day to day. This photo was taken on a recent trip to Quebec City, where I went for a quiet walk alone one afternoon. It reminded me that sometimes the most self-compassionate thing you can do is something as simple as taking a solo walk and breathing.

Advice I’m Considering

Life is a series of bets, not guarantees. As decision scientist Annie Duke reminds us, luck plays a bigger role than we think. Sometimes a bad decision leads to a good outcome, and a good decision leads to a bad one. The goal is not to be right every time, but to make thoughtful bets, learn from the results, and stay in the game long enough for good decisions to compound.

Online Content I’m Reading

How To Learn Self-Compassion As An Adult (The Good Trade)
A thoughtful piece on unlearning self-criticism and building everyday kindness. It suggests noticing small wins, using gentler language with yourself, and protecting rest as an act of respect.
→ Read it on The Good Trade

Technological Optimism and the AI Future (Import AI)
I saw Anthropic Co-Founder Jack Clark speak earlier this year and found him thoughtful and nuanced, a rare mix of optimism and caution. His piece explores how optimism can guide responsible AI progress, reminding us that the future of AI depends less on what it can do and more on what we choose to do with it.
→ Read it on Import AI

A Personal Update

This is my last month working at Venture for Canada. After more than a decade leading the organization, stepping away feels both surreal and significant. On October 14, Steven Wang officially took over as VFC’s new CEO. A Harvard Law graduate and Rhodes Scholar, Steven brings exceptional intellect and vision, but what impresses me most is his humility and deeply held values.

VFC is in excellent hands, supported by a strong and dedicated team that continues to deliver meaningful impact across the country.

After 11 years, it felt like the right time to take on new challenges and reenergize myself. I’m proud of what we’ve achieved together. We raised over $80 million and supported more than 10,000 young Canadians through programs that build entrepreneurial mindsets and career resilience — far beyond what I imagined possible when I founded VFC 11.5 years ago.

This decision reflects the same self-compassion I’ve been learning to practice: knowing when to pause, reflect, and make space for what comes next.

Stay tuned for what’s ahead.

The Uncertainty Advantage

Over the past few months, I’ve been sharing ideas from my book, The Uncertainty Advantage, at events across North America. Recent highlights include a virtual talk through Georgetown University’s Pivot with Purpose, an initiative of the School of Foreign Service supported by The Rockefeller Foundation that helps international development professionals navigate career transitions after funding cuts.

I also recently spoke at McGill University, the University of Toronto, RBC, the Banff Forum, Lab2Market, Uken Games, and TieCon. Each event reminded me how deeply people are searching for ways to thrive amid uncertainty, and how self-compassion often sits at the center of that work.

I’m now booking a limited number of 2026 speaking engagements focused on themes from The Uncertainty Advantage: embracing uncertainty, developing adaptable leaders, and building cultures of self-compassion and resilience. If your organization or community would like to book me to speak or facilitate a workshop, reach out at scott@scottstirrett.com.

Book I’m Reading

1Q84 by Haruki Murakami
A surreal novel that blurs the line between reality and imagination. Murakami builds an alternate Tokyo where two lonely characters navigate parallel worlds that feel slightly off-kilter, like a dream you can’t quite wake from. It captures uncertainty not as chaos, but as mystery, and reminds me that meaning often lives in the spaces we can’t fully explain.

What I’m Watching

One Battle After Another
Paul Thomas Anderson’s latest is equal parts chaos and poetry. It follows flawed, deeply human characters fighting invisible battles, some internal and some against the world. It’s a heavy film at times, with moments of violence, but it’s worth it if you’re in the right headspace. Like much of Anderson’s work, it’s not about winning or losing, but about the quiet resilience of people who keep showing up.

Let’s Connect

Have a book, tool, or insight you swear by? Reach me at scott@scottstirrett.com. I’d love to feature it in a future edition.

If you enjoyed this, feel free to forward it to a friend. The more curious minds in this little corner of the internet, the better.

Until next time,
Scott

Hey there,

Since the pandemic, one change has made the biggest difference in my life: I’ve become intentional about spending time with friends and loved ones.

My favourite habit has been hosting more dinner parties. My husband, David, is quite the chef; he handles the cooking, and I’ve happily taken on the role of cleaner. It’s a simple ritual, but it’s become one of the most meaningful ways we invest in our relationships. There’s something grounding about a night filled with conversation, laughter, and a pile of dishes at the end.

The data shows why this matters. Between 2003 and 2022, American adults reduced their average hours of face-to-face socializing by about 30 percent. Homes are increasingly designed around screens, not connections.

And yet we already know what truly makes life fulfilling. Harvard’s 80-year happiness study found one consistent truth: the quality of our relationships is the strongest predictor of well-being.

In a world that feels more uncertain by the day, nurturing those connections is not optional. It is the foundation for resilience, joy, and a sense of purpose.

Let’s dive in.

Online Content I’m Reading

A few pieces that stood out this month, each exploring how we use technology, connect with others, and make sense of the world we’re building.

21 Facts About Throwing Good Parties
My favourite takeaway: “Prioritize your ease of being over any other consideration: parties are like babies, if you’re stressed while holding them, they’ll get stressed too.” Every decision flows from the host’s serenity. Mediocre pizza from a relaxed host beats perfect hors d’oeuvres from a frazzled one. A joyful reminder that connection thrives on calm energy.

The 25 Most Interesting Ideas I’ve Found in 2025 (So Far)
Derek Thompson never misses. Twenty-five sharp, visual insights spanning technology, culture, and economics, each one the kind of idea you’ll end up quoting at dinner.

Real AI Agents and Real Work
AI agents are not just demos anymore; they are starting to do real work. This piece breaks down what they can handle today and why the outcome depends less on the technology itself and more on our judgment. The same system that drafts a research paper in minutes can just as easily produce seventeen useless PowerPoint decks. The real edge is knowing what is worth doing.

The Dawn of the Post-Literate Society
Nearly half of U.S. teenagers barely read today, up from 15 percent in 1985. This essay argues that when a culture stops reading, it does not just lose knowledge; it loses curiosity and creativity. A sobering look at what is at stake if deep reading disappears.

Advice I’m Considering

Give first. The most impactful people are generous in helping others. Think about ways to help efficiently, whether that means introductions, short notes, or advice that takes you five minutes but means a lot to someone else. For more on this topic, I recommend Adam Grant’s Give and Take.

Tool I’m Loving

Gamma. I have never been a fan of making PowerPoints. After testing several AI tools, Gamma is by far the easiest to use while producing high-quality decks. A genuine time saver.

Book I’m Reading

Embracing Defeat by John Dower
I’ll be spending December travelling around Japan, so I’ve been reading more Japanese history. This Pulitzer-winning book vividly captures how Japan rebuilt after World War II, a story of reinvention that feels surprisingly relevant today.

The Uncertainty Advantage

On the theme of community, I was thrilled to host my in-person book launch in Toronto earlier this month. Writing a book seems solitary, but it is really a team effort: editors, beta readers, mentors, and friends (plus a few patient dinner guests who listened to early ideas).

I have also been busy speaking about the book, with recent events at Global Affairs Canada, QueerTech, and Ivey Business School. Next up: Oxford University, the London School of Economics, and the University of Toronto.

If you’d like me to speak with your organization or class, reply to this email. I would love to connect.

In The News

A few recent pieces from me that explore this month’s themes of community, authenticity, and navigating uncertainty:

Don’t Rely on the Safe Route (The Hoya)
I shared why playing it safe can sometimes be the riskiest move and how embracing uncertainty has shaped my own career choices.

Why Gay Men Struggle With Perfectionism, Pressure and Overachievement (Gay Men Going Deeper Podcast)
A personal conversation about identity, self-compassion, and learning to replace pressure with purpose.

The Uncertainty Advantage: Thriving in a Chaotic World (Moolala)
A thoughtful conversation about how to stay grounded and optimistic in times of change: Bruce Sellery has been a generous supporter of both me and the book.

How I Landed a Job at Goldman Sachs Right Out of College (Business Insider)
A reflection on how an unconventional twist to my résumé opened an unexpected door early in my career.

Let’s Connect

When I look back at the past few years, what stands out most is not career milestones but the moments of shared presence. Late-night conversations. Quiet walks. A crowded table.

Technology will keep evolving. Our schedules will stay busy. But community, the small and intentional act of showing up for one another, is what makes it all meaningful.

So maybe this month, reach out to someone you have been meaning to see. Host that dinner, even if the table is messy and the menu is improvised. Those imperfect moments often become the ones that matter most.

And if you have a book, tool, or idea you swear by, I’d love to hear from you. Just hit reply or email me at scott@scottstirrett.com. I often feature reader picks in future editions.

If you enjoyed this, consider forwarding it to a friend. The more curious minds in this little corner of the internet, the better.

Until next time,
Scott

Hey there,

One of the most fascinating parts of AI isn’t the outputs themselves, but what they reveal about how we learn. Often, the systems don’t explain the “why” behind their answers; they just work. That mirrors how much of life actually happens. We cook meals by taste, not by chemistry. We recognize a friend’s face instantly, without running through the biology of vision.

AI is showing us that progress doesn’t always depend on mapping every step in between. Sometimes it comes from useful patterns, even if they’re not fully explained.

That shift raises a bigger question: what if the future of discovery isn’t about drilling endlessly into the details, but opening new fields altogether? Could it bring a whole new scientific revolution that goes beyond the hard rules of physics?

With that in mind, here’s what caught my attention this month—pieces that sharpen how we adapt without needing the illusion of certainty.

Online Content I’m Reading

AI is radically changing entry-level jobs, but not eliminating them
Are entry-level jobs dead? Not quite. This piece argues that AI is reshaping, not erasing, early-career roles. The tasks are evolving, but the need for learning and apprenticeship remains.

35 thoughts about AGI (and 1 about GPT-5)
Steve Newman offers a thoughtful and surprisingly accessible reflection on what “artificial general intelligence” actually means, a buzzword too rarely defined.

When your job interviewer isn’t human
Prediction: AI will soon dominate the first stage of candidate screening. Humans will still make the final calls, but more often at the end of the process rather than the beginning.

Where are all the trillion-dollar biotechs?
Forget Big Tech—the next giants may be in biology. From programmable cells to lab-grown meat, biotech is emerging as a trillion-dollar industry hiding in plain sight.

Advice I’m Sitting With

Create a life mission statement. Mine is simple: “Help others achieve their full potential.” It is the thread running through my work at Venture for Canada, writing The Uncertainty Advantage, and conversations like this one. Without a true north, you are like a ship drifting wherever the wind blows. With one, adaptability becomes a strength rather than a spiral.

Book Update: The Uncertainty Advantage

The Canadian launch was an incredible start. The book debuted at #1 on Amazon.ca in multiple categories, and I’ve been so grateful for the notes from readers who discovered it through a post or a friend’s recommendation. Thank you for helping bring these ideas into the world.

Now comes a milestone I’ve been looking forward to: on September 16th, The Uncertainty Advantage launches in the U.S.

Here are three ways you can support:

• Read the book: Grab a copy here in the format or store that works best for you.

• Spread the word: Share it with a friend, colleague, or student who could use a little resilience in uncertain times. You can also leverage this media kit.

• Bring the ideas to your community: If you know a team, school, or company navigating uncertainty, reply to this email. I’d love to explore speaking with them. This fall I’ll also be giving talks across Canada, the U.S., and the U.K., including at Oxford, Georgetown, Ivey, UBC, and more than 20 other campuses and organizations.

• Watch the virtual book launch event: The panel featured book endorsers Amanda Lang (CTV News), Janet Bannister (Staircase Ventures), and Gorick Ng (The Unspoken Rules).

What I’m Watching

House of the Dragon
I went in skeptical since spin-offs often disappoint. But this Game of Thrones prequel has surprised me. In some ways, I prefer it to the original: strong characters, moral ambiguity, and plenty of fire.

A Quote I’m Pondering

“Most people overestimate what they can achieve in a year and underestimate what they can achieve in ten years.” — Bill Gates

A good reminder that adaptability is not just about short-term pivots, it is also about staying the course long enough to let compounding take effect.

Let’s Connect

What is something you have adapted to recently, a plan you had to change, a path you rethought, or a new opportunity you seized? I would love to feature a few reader stories in the next edition.

And as always, if you have come across a book, tool, or idea worth sharing, send it my way at scott@scottstirrett.com

If this newsletter sparked a thought, smile, or new resource for you, consider forwarding it to a friend. The more adaptable, curious minds in this little corner of the internet, the better.

PS: This has nothing to do with deep learning or uncertainty, but above is a recent picture of Luna. Every newsletter deserves at least one cat cameo.

Until next time,
Scott

Hey there,

When I was 22, I left a well-paid job at Goldman Sachs in New York City to start a nonprofit from scratch. It was the most uncertain thing I had ever done, but also the most energizing.

One day on my floor at Goldman, I even met NBA legend Dikembe Mutombo (see photo above). On paper, I had “made it”: working in a prestigious firm, rubbing shoulders with celebrities, earning more than I had ever imagined at that age. And yet, I took a risk and walked away.

Fast forward a decade. During COVID, I was diagnosed with OCD. This time, uncertainty felt very different. Instead of fueling me, it weighed me down. Some days even the smallest unknowns felt overwhelming.

The point is, our relationship with uncertainty ebbs and flows. Sometimes it is thrilling, other times it is exhausting. But here is what I have learned first-hand: uncertainty is a teachable skill.

And like any skill, you can get better at it.

That is the core of The Uncertainty Advantage, how to shift your mindset so uncertainty becomes a strength, not just something to endure. The book is now available in Canada, where it debuted as the #1 book in Career Advancement and Professional Development, and it will be released on September 16th in the U.S. If you are in Canada, I would be grateful if you picked up a copy this week. If you are in the U.S., pre-orders make a huge difference.

• Independent bookstores in Canada

• Amazon Canada

• Amazon U.S. (Pre-order)

• Indigo

The moments that scare us most often hold the seeds of our greatest strength.

Online Content I’m Reading

GPT-5: It Just Does Stuff
Ethan Mollick’s example: GPT-5 “thinks for 24 seconds” and then builds worlds, writes code, and plans businesses.

The Death of Partying in the U.S.A.—and Why It Matters
If humans are wired for connection, what happens in a society that is partying less and isolating more?

Advice I’m Considering

Your happiness is closely tied to the quality of your relationships. This summer has been full of reconnections with friends and family, and I am grateful for the reminder.

Books I’m Reading

White Teeth by Zadie Smith
The novel that launched her career, an intergenerational look at identity and colonial legacies.

Vera, or Faith by Gary Shteyngart
Shteyngart’s latest shows how a fraying society shapes the lives of children.

What I’m Watching

Sort Of
A gem of a show following a non-binary Pakistani Canadian navigating life in Toronto. A tender, funny exploration of queerness and identity.

A Quote I’m Pondering

“Do not be afraid of work that has no end.” — Avot de Rabbi Natan

Let’s Connect

What is a moment of uncertainty you have stepped into that ended up making you stronger? I would love to hear your story, just hit reply.

And if this resonated, feel free to forward it to a friend. The more curious minds we gather in this little corner of the internet, the better.

Finally, writing The Uncertainty Advantage was not a solo act. I am grateful to the mentors, friends, and early readers who shared wisdom and encouragement, and especially to my parents, my husband David, and the team at Dundurn for their support in bringing it to life.

Until next time,
Scott

Hey there,

In early 2021, I was trying to hold everything together while quietly falling apart.

The pandemic dragged on. My parents were divorcing. Venture for Canada was facing existential uncertainty. And every small unknown felt like a five-alarm fire in my mind.

Eventually, I was diagnosed with obsessive-compulsive disorder and began intensive therapy with an incredible specialist, and slowly, I got better.

But the biggest turning point wasn’t clinical. It was personal.

I started talking to myself the way I’d talk to a friend. Not with blame or panic—but with curiosity, patience, and kindness. That shift in tone changed everything. It didn’t make the pain disappear, but it transformed my relationship with it. And that’s what made healing possible.

Above is a photo of me from that time, smiling on the surface, with a tiny kitten named Luna on my shoulder. What it doesn’t show is everything beneath the smile: the 4 a.m. panic walks, the obsessive Google spirals, the weight of trying to hold it all together. Luna didn’t fix things, but her quiet presence reminded me to care for something outside of myself. And in doing that, I slowly remembered how to care for myself.

Last week, I shared a version of this story on LinkedIn. The response, dozens of thoughtful, brave replies and DMs, reminded me how many of us are quietly carrying heavy things. Vulnerability doesn’t repel people. It connects us.

Much of what we see online is a carefully curated highlight reel. But behind the filtered smiles, so many people are just doing their best to hold it together. That’s why I believe self-compassion isn’t just nice to have—it’s a life skill, especially in a world that feels more uncertain by the day.

It’s also a theme at the heart of The Uncertainty Advantage, which comes out August 19 in Canada and September 16 in the U.S. The book explores how to thrive in a world where nothing feels certain, and why being kind to yourself is one of the most powerful tools at our disposal

Here’s what’s been sparking ideas for me lately:

🔗 Online Content I’m Reading

When to Quit: A Framework for Life’s Toughest Decisions
“Never give up” sounds noble, until it keeps you stuck. Annie Duke (former poker pro turned decision scientist) makes a sharp case for quitting smart. If you’ve been wondering whether to let go of something that no longer fits, this one’s for you.

The Rise of the Agent Manager
AI agents are multiplying, and soon, we’ll need people who can manage and coordinate them. Think air traffic controllers for digital assistants. This piece gave me a glimpse of how “manager” might mean something very different in just a few years. Shoutout to my friend Aly Dhalla for the rec.

Notes to Myself – Seth Godin
Godin turns 65 and offers 65 small truths. It reads like a mosaic of wisdom. Favourites: “Attitudes are skills,” “Imposter syndrome means the work matters,” and “Pick your customers, pick your future.”

The Death of the Student Essay—and the Future of Cognition
This one stuck with me. It’s not about AI killing the essay. It’s about what happens when we stop teaching people how to think deeply, write clearly, and wrestle with ideas. It’s a cautionary tale: one that feels more urgent by the day.

The Unseen
What happens when people feel invisible? This piece explores our growing crisis of depersonalization, from standardized service jobs to algorithmic interactions. A sobering look at what it means to be truly seen in a system that often forgets the human.

💡 Advice I’m Sitting With
“The yes within the no.”
This summer’s been full—between Venture for Canada, launching the book, and showing up for the people I care about, I’ve had to say no more than usual. A friend once told me that every “no” is actually a “yes” to something else. That lens has helped me make space for what matters most.

📚 A Book I’m Reading

Dinner with King Tut by Sam Kean
Imagine ancient history written with the pace of a thriller and the messiness of MythBusters. Kean joins experimental archaeologists who do history—sailing ancient ships, recreating rituals, and occasionally setting things on fire. Funny, nerdy, and sneakily profound.

🎬 What I’m Watching

Sirens
This limited series delivers rich-people chaos, cult-y undertones, and sibling drama. All set in a remote coastal estate. Julianne Moore plays an unnervingly magnetic socialite, and the writing keeps you guessing. It made me reflect on who we see as “villains”—and why.

🎤 On the Road

A heartfelt thank you to my friend (and reader of this newsletter) Debi Ogunrinde, whose generous introduction led to an upcoming speaking event with the Rhodes Scholars at Oxford this November. I’m incredibly grateful.

This fall, I’ll also be speaking at a number of other events across Canada, including at the University of Waterloo, McMaster, York University, and with the Loran Scholars, as well as at nearly 15 additional communities and organizations.

If you're organizing a gathering, leading a team, or part of a group navigating uncertainty, I’d love to connect. I’m booking a handful of remaining talks this fall focused on themes from The Uncertainty Advantage, especially around resilience, self-compassion, and thriving through change.

Just reply or reach out to stirrettscott@gmail.com. Always happy to chat.

📝 My Writing

If the themes in this edition resonated, here are a few recent pieces where I dig deeper:

• How to Be Kinder to Yourself in an Age of Constant Chaos
  Reflections on inner dialogue, resilience, and the unexpected power of a hype document.

• How to Trump-Proof Your Career (Fast Company)
  Still timely: practical advice for building career resilience in times of political and economic volatility.

• Canada Should Lower the Voting Age to 16 (The Globe and Mail) - Paywalled
  Why young people deserve a stronger voice in shaping the future, and what we can learn from other democracies already doing it.

📨 Let’s Connect

Have a book, tool, or idea that shifted your thinking? I’d love to hear about it. Just reply or email me at stirrettscott@gmail.com. I often feature reader picks in future editions.

If this resonated, I’d be honoured if you shared it with a friend. The more curious, self-compassionate humans in this little corner of the internet, the better.

PS: How do you practice self-compassion when life gets chaotic? I’d love to hear.

Until next time,
Scott

Hey there,

Lately, I’ve been learning tennis. I’m not exactly Wimbledon material. I didn’t grow up playing much, and physical coordination has never been my strong suit. But surprisingly, I’m loving it.

What’s struck me most is how energizing it feels to be a beginner again. Most of my learning happens in mental spaces: reading, writing, and work. Tennis is different. It forces me to be present, let go of expectations, and embrace the discomfort of not knowing what I’m doing.

I keep returning to the beginner’s mindset—staying open and engaged even when you don’t feel in control. This mindset is especially important now, when the pace of change is accelerating.

Before we dive in, a quick thank you: this newsletter now reaches over 1,300 readers, and the last three editions have each had an open rate above 60 percent. I’ve loved reconnecting with many folks through these emails—your replies genuinely make my day. And, a special thanks to the 25 early readers who signed up to review advance copies of my book, The Uncertainty Advantage.

Here are a few things that have caught my attention lately, both on and off the court:

📖 What I’m Reading

Are You Stuck in Movie Logic?
Three simple but powerful tips for navigating tough conversations: zoom out to name the real issue, admit when you’re scared to bring it up, and don’t wait to be certain before speaking. Honest talk starts before you have perfect words.

Why I Don’t Think AGI Is Close
A refreshingly grounded take on why we’re not as close to artificial general intelligence as many think. Rational, rigorous, and a useful counterbalance to the hype.

SEO for AI: Generative Engine Optimization
AI is reshaping how people discover content. This piece explores how the shift from search to suggestion is changing what it means to be “findable” online.

Why the Age of AI Is the Age of Philosophy
A thoughtful deep dive into ethics, consciousness, and what it means to be human when machines can mimic thought. Ancient questions, newly relevant.

What “Working” Means in the Age of AI Apps
AI is accelerating startup growth, but it's also reshaping how we define work. This article examines new metrics for progress in an age of speed.

📚 Early Praise for The Uncertainty Advantage

“Success isn’t about making one perfect decision. It’s about continuous action and learning along the way. The Uncertainty Advantage is an essential guide for young professionals looking to build resilience, take smart risks, and create opportunities in an unpredictable world.”
— Sukhinder Singh Cassidy, CEO of Xero and author of Choose Possibility

Over the past few weeks, I’ve spoken about uncertainty and adaptability at events hosted by the University of Waterloo, McMaster, York, League of Innovators, The Loran Scholars Foundation, Sonova, Uken Games, and The Student Commission of Canada. If you'd like me to speak at your organization, just hit reply.

💡 Advice I’m Considering
Build your own personal advisory board.
Instead of relying on a single mentor, gather a handful of people you trust across different areas of life. Think of it as surrounding yourself with a sounding board for the big calls.

🛠️ Tool I’m Loving
Cassidy.ai
Curious about AI agents? Cassidy makes it easy to build and test them, even without coding skills. A fun way to get hands-on with what’s coming next.

📚 Book I’m Reading
Apple in China by Patrick McGee
One of the most fascinating business books I’ve read in a while. McGee explores how Apple and China shaped each other’s rise—an essential read if you're interested in global supply chains, geopolitics, or the future of tech.

🎬 What I’m Watching
Somebody Somewhere (HBO)
This understated gem follows a group of quirky, mostly queer characters in small-town Kansas. It’s funny, heartfelt, and a quiet masterclass in showing how community sustains us during hard times.

📝 What I’ve Been Writing

“The Real Threat of AI Isn’t Job Loss. It’s Meaning Loss.”
The deeper risk of AI isn’t just automation. It’s the erosion of purpose.

💬 Let’s Connect
What’s something you’ve tried recently that made you feel like a beginner again? And have you come across a great article, book, tool, or show lately? I’m always looking for new things to check out and share here. Just reply to this email or reach me at stirrettscott@gmail.com.

If this newsletter made you think, smile, or discover something new, consider forwarding it to a friend. The more curious minds we bring to this corner of the internet, the better.

Until next time,
Scott

Hey There,

Lately, I’ve been thinking a lot about a question Jeff Bezos once posed: What will you regret not doing when you’re 80? It’s a simple but clarifying lens, shaping a big decision in my life.

After 11 years, I’ve decided to step down as CEO of Venture for Canada this fall. Leading VFC has been the most meaningful experience of my life. But at my core, I’m a builder. And after more than a decade growing VFC, it feels like the right time to start building something else.

In the meantime, here’s what’s been catching my attention lately:

🔗 Reads That Shifted My Thinking

What to Do?
Paul Graham tackles a timeless question with a modern twist. He argues that the most meaningful lives combine helping others, caring for the world, and making good new things. It’s a short, thought-provoking read about why creation, not just critique, is one of the best ways to live fully.

How We Actually Use Gen AI
Forget the hype—this article gets into the nitty-gritty of how workers are really using Gen AI on the job. The big takeaway? Adoption is messy, uneven, and driven by real needs, not corporate mandates. A useful reminder that transformation happens from the ground up, one line of code or email draft at a time.

The AI Will See You Now
AI therapy is becoming a real thing. This piece is both personal and practical, exploring what it’s like to open up to a chatbot and where the future of mental health might be headed.

What Is an AI Agent?
If you’ve been hearing buzz about “AI agents” and wondering what’s hype and real, this A16Z interview is a thoughtful read or listen. It digs into what’s working and what’s still stuck in theory.

📘 Want to Read The Uncertainty Advantage Before It’s Out?

This summer, I’m sharing advance copies of my book The Uncertainty Advantage with a small group of early readers.

I’ve got 25 advance copies to share. If you'd like to be among the first to read The Uncertainty Advantage and leave a quick, honest Amazon review, just hit reply and let me know.

Here’s a recent endorsement I’m incredibly grateful for:

“Experimenting, gathering feedback, and being open to a pivot are foundational tools for building a startup in uncertain conditions. As the advice and practical frameworks in The Uncertainty Advantage show, they work just as well for finding the path forward in life.”
— Eric Ries, author of The Lean Startup

If you’ve enjoyed this newsletter, I think you’ll get a lot out of the book.

🛠️ A Tool That Earned Its Keep

Contra
If you’re hiring freelancers, skip Fiverr and UpWork. Contra has a better interface and higher-quality talent. I’ve used it recently and was genuinely impressed.

📚 Books That Hit Home

Perfection by Vincenzo Latronico
A slim but powerful novel about the search for meaning in a curated life. Feels like a literary time capsule of the 2010s. Thanks to a reader of the newsletter for the recommendation!

James Patterson by James Patterson
Say what you want about his prose, but Patterson is a master of branding and scale. This memoir, told in short vignettes, is both self-aware and full of insight into the business of storytelling.

📺 What I’m Watching

North of North (Netflix)
A visually stunning, quietly powerful series set in Canada’s Arctic. It doesn’t rush or over-explain. Instead, it trusts you to sit with silence, absorb the landscape, and witness the nuance of Inuit life on its own terms. This is one of the most respectful portrayals of the North I’ve seen: grounded, deliberate, and refreshingly free of clichés.

📨 Let’s Connect

Have a book, tool, or article you think I should check out? Just reply or email me at stirrettscott@gmail.com. I love hearing from readers.

And if you enjoyed this, feel free to forward it to a friend. The more curious minds in this little corner of the internet, the better.

Until next time,
Scott

Hey there,

Between OpenAI’s new image features and Google’s Gemini upgrades, the AI world has been sprinting. To keep up (and stay a little less overwhelmed), I rely on two excellent newsletters: Superhuman and The Rundown AI. Bonus: Superhuman was founded by Venture for Canada Fellow Alum Zain Khan, and nearly 1 million subscribers later, he’s crushing it.

One theme that keeps popping up lately? Uncertainty. Not just how to tolerate it, but how to turn it into an edge. That idea is at the heart of my upcoming book, The Uncertainty Advantage, and as a thank you for being here, you’re getting early access to the intro. You can read it here:

👉 Read the intro

Now, onto the rest, because this month’s been a ride. Let’s dive in.

📖 What I’m Reading

Sam Altman’s Productivity Playbook

This blog post from the OpenAI CEO breaks down how to actually get meaningful work done, and it’s both brutal and refreshing. Forget time hacks; think focus, energy, and doing the hard thing first. Whether you’re leading a team, building something new, or just trying to cut through the noise, it’s a reminder that productivity isn’t about doing more, it’s about doing what matters.

AI 2027 Forecasts
This analysis from top researchers explores where AI is headed, and it’s equal parts thrilling and alarming. Whether the future is utopia or something… less so, understanding the range of possibilities is key to staying prepared. Especially for anyone leading, building, or just trying to keep up.

Gen Z and the New Career Map

Why are younger professionals changing jobs so often? It’s not impatience—it’s a survival strategy. Between gig work, declining job security, and constant reorgs, Gen Z is adapting to the terrain, not breaking the rules. This article reframes what looks like instability as intentional navigation.

💡 Advice I’m Sitting With

“There is no possibility without uncertainty.”

Everything good—love, creative breakthroughs, meaningful work—requires stepping into the unknown. The more uncertain the moment, the more potential it holds. Uncertainty isn’t just the cost of change—it’s often the signal you’re on the right track.

🛠️ Tool I’m Loving

Wix
I’ve been playing around with Wix while building my personal site for the book launch, and I’m seriously impressed. It’s intuitive, sleek, and makes WordPress feel like a fax machine. If you're building anything, portfolio, landing page, small business, it’s worth checking out.

📚 Books I’m Reading

Abundance by Ezra Klein & Derek Thompson
This book reframes modern challenges as design problems. It explores how old rules (like zoning laws) create new bottlenecks for progress, especially in housing and clean energy. Big ideas, presented clearly.

Intermezzo by Sally Rooney
This might be my favourite Rooney novel yet. It’s a slow-burn, beautifully written story of two brothers navigating love, grief, and identity. Her talent for building emotional tension through subtle moments is on full display here.

Prediction Machines by Ajay Agrawal, Avi Goldfarb, and Joshua Gans
This book reframes AI as a drop in the cost of prediction, not a wholesale reinvention of intelligence. It’s a practical, clear guide to understanding what AI can (and can’t) do for businesses and society. Instead of breathless hype, it offers a grounded framework for thinking about how AI will reshape decision-making, risk, and value creation.

🎬 What I’m Watching

Ali Wong Netflix Specials
It’s been a while since I’ve laughed this hard. Ali Wong has this incredible ability to be outrageous, tender, and sharp all at once. Her takes on life in your 30s and 40s? Chef’s kiss.

The Brutalist (available for rent on Amazon Prime)
A quiet, haunting film about a Holocaust survivor turned architect, wrestling with trauma while building a new life. It’s meditative, heavy, and stunningly shot. If you’re in the mood for something that lingers long after the credits roll—this is it.

📢 Book News: The Uncertainty Advantage

Endorsements have started rolling in. Here’s one I’m especially grateful to share, from someone who helped spark my journey:

“The Uncertainty Advantage is an essential guide for anyone navigating today’s rapidly changing economy. Scott Stirrett brilliantly lays out how embracing uncertainty isn’t just necessary—it’s an advantage. A must-read for anyone looking to turn unpredictability into opportunity.”
— Andrew Yang, Co-Chair, Forward Party and former U.S. Presidential Candidate.

Eleven years ago, Andrew’s book Smart People Should Build Things helped inspire me to launch Venture for Canada. Full-circle moment.

✉️ Let’s Connect

Have a book, tool, or insight you swear by? Reply to this email. I’d love to feature it in a future edition.

Also, I’d genuinely love to hear how you are doing. This newsletter mostly goes out to folks I know, and one of the best parts of writing it is getting to reconnect. If you’re up to something exciting, going through a transition, or just want to catch up - drop me a note. And if there’s any way I can be helpful, please don’t hesitate to reach out.

If you enjoyed this, feel free to forward it to a friend. The more curious minds in this little corner of the internet, the better.

Until next time,
Scott

Hey there,

At the height of the pandemic, I found myself in the thick of uncertainty. Running a fast-growing organization, facing personal crossroads, and watching the world shift in ways no one could predict—it felt like trying to read a map with half the landmarks erased. The instinct was to search for control, for a clear answer. But over time, I realized something: your biggest advantage isn’t what you know—it’s how well you handle not knowing.

That’s why I wrote The Uncertainty Advantage (Dundurn Press, August 2025). It’s not about eliminating doubt or finding foolproof plans—it’s about learning to navigate the unknown with confidence. Inside, you’ll discover how to make better decisions in uncertain times, turn setbacks into opportunities, and develop the resilience to take bold career leaps.

If this resonates, I’d love for you to be among the first to read it. Pre-order your copy today.

🌐 Online Content I’m Reading

🔹 Which AI to Use Now: An Opinionated Guide (One Useful Thing)
Not all AI tools are created equal. This breakdown helped me rethink when to use Claude vs. ChatGPT vs. Gemini. If you're trying to make AI work for you, this is a must-read.

🔹 When I Lost My Intuition (Aeon)
This essay hit home—so much of leadership relies on gut instinct, but what happens when intuition fails? An anesthesiologist’s story about losing his ability to ‘read’ a room is a fascinating take on decision-making under uncertainty.

🔹 Intelsat as a Model for International AGI Governance (Forethought)
How do we govern Artificial General Intelligence (AGI) on a global scale? Will MacAskill and Rose Hadshar suggest looking to Intelsat, a 1960s multinational satellite initiative, as a blueprint. Their argument: a balanced, collaborative governance model—rather than unilateral control—could be key to managing AGI responsibly. A thought-provoking read on the future of AI policy.

🔹 The Joy of Clutter (Aeon)
Growing up, I bought into the minimalist movement. But this piece makes a compelling case for curated chaos—embracing the layers of life reflected in a space filled with meaningful objects. My favourite line:
"The best clutter is a byproduct of taste and time, accrued and overlaid as a space is lived in and used."

🛠️ Tool I’m Loving

🔹 TrueSize
As a geography nerd, this tool blows my mind. Most world maps distort country sizes—especially landmasses near the poles. TrueSize lets you see the real scale of countries by dragging them around on a map. Canada is huge—but maybe not as huge as you think.

📚 Books I’m Reading

🔹 The Brothers Karamazov – A philosophical deep dive into faith, doubt, and human nature. It’s what I call Type Two Fun—not always enjoyable in the moment, but deeply rewarding in hindsight.

💡 Advice I’m Considering

"Life is a marathon punctuated by sprints."

Yes, self-care matters. But sometimes, you need to go all in. Writing The Uncertainty Advantage was one of those sprints—intense, exhausting, but ultimately worth it. The key is knowing when to push and when to recover.

🎬 Content I’m Watching

🔹 Conclave (Prime Video) – Ever wondered how a Pope is chosen? This gripping drama dives into the high-stakes politics behind one of the world’s most significant decisions.

🔹 Nickel Boys (Prime Video) – One of the best book-to-film adaptations I’ve seen. Told largely from the protagonist’s perspective, it’s heartbreaking, immersive, and based on real events.

🔹 Nr. 24 (Netflix) – After visiting Norway last year, I was fascinated by this WWII story of Gunnar Sønsteby, Norway’s most decorated war hero. Stunning landscapes, gripping storytelling.

🧠 A Quote I’m Pondering

"The only function of economic forecasting is to make astrology look respectable."
— John Kenneth Galbraith

📢 What Readers Are Recommending

One of my favourite parts of writing this newsletter is hearing from you. Here are some standout recommendations from readers who responded to last month’s edition:

🔹 Great Mental Models – Shane Parrish (A framework for better thinking and decision-making.)
🔹 Outlive – Peter Attia (A deep dive into longevity and optimizing health.)
🔹 The Anxious Generation – Jonathan Haidt (Exploring the impact of social media on young people’s mental health.)
🔹 The Wide Wide Sea – Hampton Sides (A sweeping historical narrative about Captain Cook’s last voyage.)
🔹A Gentleman in Moscow – Amor Towles (A beautifully written novel about resilience, exile, and finding meaning in confinement.)

Let’s Connect!

Got feedback, ideas, or resources I should feature? Drop me a line: stirrettscott@gmail.com.

If you enjoyed this, share it with a friend—the more curious minds, the better the conversations.

Until next time,
Scott

Hey There,

A few weeks ago, I caught myself doom-scrolling about AI, politics, and the economy—again. It made me wonder: how do we stay grounded when uncertainty is the only certainty? Lately, I’ve been experimenting with ways to not just survive, but thrive in uncertainty, including launching a TikTok account to share quick, actionable career advice.

Let’s dive in—because in times of uncertainty, the best thing we can do is keep learning.

🛠️ Tool I’m Loving: Midjourney

Midjourney creates stunning AI-generated images, but crafting the perfect prompt? That’s an art. A hack I use: ask ChatGPT to write Midjourney prompts for you. Try this one for a cinematic, moody scene:

A cinematic, high-resolution image of a solitary lighthouse standing tall on a rugged cliffside during a dramatic storm. Towering waves crash violently against the jagged rocks, while flashes of lightning streak across the dark, stormy sky. The lighthouse’s powerful beacon cuts through the heavy rain, casting an eerie glow over the turbulent sea. The atmosphere is moody and intense, with rich, detailed textures, realistic lighting, and a dynamic sense of depth. Photorealistic style, dramatic contrast, and a 16:9 aspect ratio, ensuring a visually striking composition suitable for a newsletter banner.

Give it a try—AI helping AI. Check out the AI-generated image above—I used this exact prompt.

🌐 Online Content That’s Sticking With Me

Why Gen Z Will Never Leave Home (Maclean’s) – Soaring housing costs are forcing many twentysomethings to remain in their childhood bedrooms. This article paints a vivid picture of family life without empty nests, highlighting the financial and social implications of a generation unable to fly the coop because of structural challenges.

Gradual Disempowerment: How AI Could Erode Human Control – Not all AI risks involve robots taking over. A bigger concern? AI quietly eroding human decision-making in key systems, making us passive bystanders in our own world.

The Philosopher L.A. Paul Wants Us to Think About Ourselves (The New Yorker) – Ever had a life experience so big that you became a different person afterward? L.A. Paul calls these transformative experiences—decisions like becoming a parent or making a radical career move that reshape your identity in ways you can’t predict. Her work challenges traditional decision-making frameworks and forces us to rethink how we navigate change.

📚 Books I Enjoyed

Four Thousand Weeks: Time Management for Mortals: Burkeman challenges our obsession with productivity, arguing that life is too short to chase the illusion of getting everything done. His advice to embrace limitations and focus on what truly matters resonated deeply.

The Wager: David Grann’s The Wager is a true page-turner, plunging into the high-stakes drama of 18th-century naval exploration. While we face our own uncertainties today, their story is a powerful reminder of resilience and adaptability. A fascinating read about drama on the high seas.

The White Album: I stumbled upon this book somewhat randomly while browsing my shelves—a used copy I picked up years ago but never got around to reading. Joan Didion, one of the greatest essayists of the 20th century, captures the spirit of the 1960s with her signature mix of razor-sharp observation and detached coolness. In an era of upheaval, her reflections feel eerily relevant, making this collection as compelling today as when it was first published.

💡 Advice I’m Considering: Tame The Gremlin

A coach once introduced me to the concept of the “gremlin”—that inner voice that replays conversations and convinces you that you said something dumb. Sound familiar?

Next time that voice pipes up:

1. Label it – “Oh, that’s just the gremlin again.”

2. Laugh at it – The gremlin takes itself seriously; you shouldn’t.

Caring too much about what others think kills risk-taking and creativity. Recognize the gremlin, then ignore it.

🎬 What I’m Watching

100 Years of Solitude (Netflix) – This adaptation of Gabriel García Márquez’s classic novel is visually stunning and makes me want to book a flight to Colombia immediately. If you love magical realism, epic storytelling, and gorgeous cinematography, you’ll be hooked.

Flow (Apple TV+) – An animated film about a cat and its friends escaping a flood—with no dialogue. Proof that storytelling transcends language.

A Real Pain – A deeply moving film about two cousins on a journey through Poland that explores grief, family, and identity. I watched this on a flight and found myself unexpectedly in tears—haven’t been that emotional watching a movie in a long time. A poignant reminder of how storytelling can cut right to the core.

🧠 A Quote I’m Pondering

“Life shrinks or expands in proportion to one's courage.” – Anaïs Nin

Let’s Connect

Have a book, tool, or insight you swear by? Hit me up at stirrettscott@gmail.com—I’d love to feature it. And if you enjoyed this, forward it to a friend. More curious minds = better conversations.

Until next time,

Scott