Last week, I listened to Never Enough: From Barista to Billionaire by Andrew Wilkinson. I expected a standard business memoir. What I didn’t expect was something far more elusive: ambition.
Wilkinson, co-founder of Tiny—a Canadian holding company with more than 40 businesses—seemed to have it all: money, freedom, success. But beneath the surface, he was anxious, scattered, and burned out.
What struck me wasn’t the scale of his achievements, as impressive as they were, but how familiar his dissatisfaction felt. He was living the dream—wealth, autonomy, prestige—and still, it didn’t feel like enough.
But I know the feeling of working hard, hitting the milestone… and wondering, in the quiet after, why it didn’t feel better.
Normally, I focus on one big idea per issue. But Wilkinson’s story landed differently: a collection of hard-won truths, each one challenging assumptions we tend to carry about work, success, and what it’s all for.
So, instead of narrowing this issue to one big idea, I’m sharing the ten that stayed with me. The first half explores how ambition can subtly lead us astray. The second is about how we begin to find our way back.
Part 1: How Ambition Misleads Us
1. The Trap of Chronic Dissatisfaction
Wilkinson spent years building. More revenue. More businesses. More wins. But the feeling he was chasing—fulfillment, pride, peace—never arrived. Ambition without a clear goal becomes a recipe for perpetual restlessness.
2. Optimization Doesn’t Equal Peace
He tried to solve dissatisfaction by optimizing everything. Cleaner delegation. Fewer meetings. But the more efficient things became, the more disconnected he felt. Some problems don’t need better processes—they need better purpose.
3. Money Solves Money Problems—Not Meaning
Making money was the easy part. Wilkinson figured that out early. What he didn’t expect was how little it helped with everything else: anxiety, insecurity, identity. Money removed friction—but it didn’t resolve meaning.
4. Burnout Comes From Misaligned Effort
Wilkinson didn’t burn out from working too much. He burned out from working on the wrong things. Goals that looked impressive but felt hollow. Projects that earned praise but drained energy. Effort wasn’t the problem. Alignment was.
5. Mimetic Desire Is the Root of Many Bad Goals
Much of what he pursued wasn’t rooted in clarity. It was mimetic, borrowed from others without realizing it. Startups. Investments. It’s easy to confuse admiration with aspiration when you’re surrounded by others chasing the same things.
Part 2: How to Find Your Way Back
6. Anti-Goals Clarify What You Actually Want
Instead of asking “What do I want?”, Wilkinson flipped the question: “What do I never want again?” The answers came fast—urgent meetings, back-to-back calls, anxiety on Sundays. By defining what to avoid, he got clearer on what mattered.
7. Freedom Without Structure Feels Empty
Wilkinson thought stepping back from day-to-day work would feel liberating. However, without something to ground his time, the freedom felt disorienting. Autonomy, he learnt, only works when it’s pointed at something that matters.
8. Delegating Doesn’t End Anxiety
Even after hiring smart people to run his companies, Wilkinson couldn’t relax. He still checked in constantly. Still felt the weight. Delegation only helped once he let go internally, not just operationally.
9. Introspection Is a Skill, Not a Trait
He wasn’t naturally reflective. He had to learn how to pause. Reading, honest conversations, and long periods of discomfort—none of it came easily. But the more he practiced, the clearer things became. Slowness revealed what speed kept hidden.
10. Build a Life That Feels Good, Not Just Looks Impressive
The biggest shift wasn’t tactical. It was personal. Wilkinson stopped chasing what looked good from the outside and started paying attention to what actually felt good on the inside. Calm. Focus. Purpose. That became the goal.
Forward, But to Where?
Not everything in Never Enough will resonate. But one idea stayed with me:
Unchecked ambition will take you far, but it won’t ask where you want to go.
Wilkinson didn’t burn out because he wanted too much. He burned out because he never asked if the wanting still made sense.
Ambition isn’t the problem. However, left to its own devices, it tends to follow momentum, ego, and comparison.
If you don’t define what matters, ambition will decide for you. And its version won’t lead to meaning.
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