Betting On Yourself
Being Weird In An Increasingly Weirder World
Being antifragile helped me get through the hardest days of my life. When you’re grieving and it feels like there’s nothing worth living for, it’s easy to get in your head. I was at one of my lowest points, a friend asked me, “what advice would you give yourself if you were your best friend?”
That question, jolted me out of my funk.
My advice my best friend would be to do something, anything. I believe in the idea that mood follows action. So that is the advice I would give. In the haze of grief I had forgotten that waiting on permission or inspiration to feel better wasn’t going to work. In spite of the uncertainty facing me, the way to get through that hell was to actively move through it (apologies to Churchill for botching his quote).
Living a High-Agency and Antifragile Life
There’s a rare breed of individual who, when faced with serious obstacles, doesn’t crumble. Instead, they lean in, ask better questions, and ( perhaps against the current trend of playing the victim ) get things done. These are high-agency people. Mash that high-agency mindset together with Nassim Taleb’s concept of antifragility — systems that actually benefit from disorder — you start to see a playbook emerge for living in an uncertain world.
Let’s walk through five traits of high-agency people and see how they overlap with Taleb’s antifragile mindset. If you’re looking for motivation, go read a fortune cookie. If you’re looking for a way to stop outsourcing your future to “market conditions” and committee meetings, read on.
Believe Problems Are Solvable , Even when Physics Says Otherwise
High-agency types wake up in the morning assuming the universe is glitchy but hackable. We’re not delusional, but we have a sense we can nudge and shape the universe in ways that will get us closer to our dreams. We don’t believe in waiting for permission, or the right timing, or a self-proclaimed guru in a Patagonia vest.
We believe that most problems can be solved if you remain curious and committed.
Taleb would probably grunt approvingly here. Systems that break under stress are fragile. But people who treat challenges like weights in a gym actually become stronger through exposure. High-agency folks don’t run from problems; they metabolize them.
Practice: Next time you’re stuck, instead of asking “Why is this happening to me?”, ask “What experiment can I run in the next 24 hours to push this forward?” And then do it. Taleb might call that skin in the game. At our Second Harvest retreats, we call that Tuesday.
Question Experts, Institutions, and the Guy With the Microphone
High-agency people are allergic to default thinking. If “everyone knows” something, that’s usually a neon sign pointing to a broken assumption. Peeling back consensus to see what’s rotting underneath is the sense that what everyone else is doing, might not mean it’s the right thing for you.
This also happens to be the beating heart of Taleb’s work: skepticism of large, centralized, overconfident systems that can’t withstand volatility. Fragile institutions fail loudly and catastrophically. Antifragile systems thrive in chaos. Antifragile looks like decentralized wisdom, iterative tinkering, and small bets . Bets you take on yourself.
Practice: When given a rule, policy, or opinion , especially if it comes from someone with a title or too many Twitter followers , ask: “Who benefits if I believe this?” Then ask: “What happens if I try the opposite?”
Note: this doesn’t mean ignore expertise. It means treat it like milk: check the expiration date and sniff before swallowing.
Use Death (Yes, Death) as Motivation
Morbid? Sure. Effective? Absolutely.
High-agency individuals don’t need five-year plans and Gantt charts to motivate them. They have a clear sense that life is short, fragile, and not a rehearsal. This awareness doesn’t depress them — it sharpens them. It lights a fire. It gives them a giant permission slip to act now, not after the next planning offsite.
Antifragile systems use volatility and uncertainty as inputs, not excuses. Death is the ultimate uncertainty, and high-agency folks use it not as a reason to fear, but as a reminder that playing it safe is often the most dangerous move of all.
Practice: Ask yourself what you would do differently this week if you knew you had just five more years to build, write, create, or lead. Then…start doing some of that. Even just a little.
Procrastination is a tax on your potential. Death is the auditor.
Build a Custom Operating System (Not Download Someone Else’s)
High-agency folks don’t look for blueprints. They look for raw materials. There is no “7-step system” they follow because they’ve realized no one else’s life map includes their terrain.
Optionality, or the idea that there is more than one way ahead, leads to creating a portfolio of actions that lets you take advantage of positive Black Swans (those rare, unpredictable, game-changing events). You don’t get optionality by copying what worked for someone else. You get it by creating your own surface area for luck to land.
Practice: Instead of asking “What’s the best way to X?”, ask “What’s a way that fits my weird skills, schedule, and tolerance for chaos?” Then test it. Adjust. Repeat.
You’re not trying to scale to get to an output. You’re thriving in the process too. There’s a monumental difference.
Seek Uniqueness Over Sameness
The high-agency mindset doesn’t aspire to fit in. It aspires to matter. These people don’t copy-paste their personality from a corporate culture deck or whatever’s trending on LinkedIn this week. They build moats with their uniqueness. And in doing so, they become not just antifragile — but indispensable.
As Alex Murrell says, “When every supermarket aisle looks like a sea of sameness, when every category abides by the same conventions, when every industry has converged on its own singular style, bold brands and courageous companies have the chance to chart a different course. To be different, distinctive and disruptive.”
Taleb reminds us that systems built on sameness collapse quickly. Resilience comes from diversity — of thought, approach, risk, and temperament. High-agency people are naturally divergent thinkers. They are less concerned with being agreeable and more interested in being useful. Ideally, both. But if they have to pick…
Practice: Ask: “Where am I being generic?” Then stop it. Be specific. Be strange. Be someone others can’t easily replace or ignore.
You don’t need everyone to like your approach. You just need the right people to need it.
Be the Change You Want to See in the World
High agency isn’t about hustling harder. It’s deciding to play a different game where you don’t just follow what everyone else is doing. Combine that mindset with Taleb’s principles, and you’ve got a worldview that doesn’t just survive uncertainty… it grows because of it.
So the next time you’re tempted to write another to-do list, maybe start with a don’t list:
- Don’t wait for permission.
- Don’t believe everything you’re told.
- Don’t try to be average on purpose.
- Don’t fear the unknown.
- Don’t forget you’re going to die.
Now go build something that lasts longer than a trend. Something that bends with pressure. Something that gets stronger when the world gets weird.
Because it will.
