I once heard a story about a fisherman who lived in a small coastal village. Every morning, he would take his small boat out to sea, catch a few fish, return by noon, and spend the rest of his day playing with his children, taking siestas with his wife, and enjoying evening drinks with his friends.

One day, a businessman from the city noticed his routine and approached him. “Why don’t you stay out longer and catch more fish?” he asked. The fisherman replied, “Why would I do that?”

“Well, you could sell more fish, make more money, and buy a bigger boat,” the businessman explained. “Then you could catch even more fish, hire others, and eventually own a fleet of fishing boats.”

“And then what?” asked the fisherman.

“Then you could move to the city, run your fishing empire, and become very wealthy!”

The fisherman thought for a moment and asked, “How long would this take?”

“Perhaps 15-20 years,” replied the businessman.

“And then what?”

“Then you could retire, move to a small coastal village, wake up early to go fishing, play with your kids, take siestas with your wife, and enjoy evening drinks with friends!”

This story perfectly captures the central theme of Andrew Wilkinson’s book “Never Enough: From Barista to Billionaire.” It’s a refreshingly honest account of what happens when you achieve everything you thought you wanted, only to realize you’re still chasing more.

I first discovered Wilkinson through his company, Tiny. Operating from Victoria, British Columbia - far from the traditional power centers of New York and Silicon Valley - Tiny bills itself as the “Berkshire Hathaway of the internet.” Like Berkshire, they maintain a decentralized structure, giving their acquired companies significant autonomy. While it would be premature to draw financial comparisons with Berkshire, the philosophical similarities are striking. Perhaps, in Tiny, I had stumbled upon what investing in early Berkshire might have felt like.

But “Never Enough” isn’t just another business success story. It’s a deeply personal narrative about the psychological toll of constant achievement-seeking. Wilkinson’s journey from a coffee-shop barista to building a billion-dollar company is fascinating, not for the wealth he accumulated, but for the wisdom he gained about what truly matters in life.

What Did I Get Out of It?

Wilkinson and I are about the same age, but our paths couldn’t be more different. While he was building companies and taking risks, I was climbing the corporate ladder, choosing safety over uncertainty. You might wonder what someone like me - working a regular job - could learn from a serial entrepreneur’s story.

But that’s what makes “Never Enough” interesting. Yes, Wilkinson tells his story through the lens of business, but his lessons about money, success, and life apply to anyone. Whether you’re building companies or working in one, the way money changes you, the trade-offs you make with time, and the things that actually make you happy remain the same.

Here are five things I learned from his journey:

Money Doesn’t Fix Everything

I remember times when a McDonald’s burger felt like a luxury I couldn’t afford. Now, years later, with a stable job, I can take my family out to dinner without checking my bank balance first. Life has gotten easier, but something interesting happens - the goal posts keep moving.

Wilkinson captures this feeling perfectly when he writes:

“For my entire life, money had been a problem. Now, finally, I had ’enough’ of it. Real money. I wasn’t rich, but I wasn’t broke, either. For the first time ever, checking my bank account didn’t fill me with dread.”

But then something changed. He continues:

“And I quickly discovered that the human mind is naturally ungrateful, quickly habituating to what we already have, and constantly chasing after the next new thing. Psychologists refer to this as the hedonic treadmill. The idea that we have to keep running faster and faster, buying more and more, simply to maintain the same level of happiness.”

I see this in my own life. When I first started working, I thought a certain salary would solve everything. Then I got there, and suddenly that number didn’t feel like enough. As an accountant who loves investing, I keep tracking numbers, setting new targets. Maybe another investment property? A bigger portfolio? Expensive toys for Hamza and Anya which I couldn’t afford growing up?

Wilkinson’s experience shows this doesn’t change, even at much higher levels. He shares a telling conversation with a wealthy businessman:

“I asked him what it was like to be so rich and successful. To have all that money. To own those buildings. All that respect. ‘I’m drinking the same pint you are, aren’t I?’ he responded, looking a bit melancholy.”

This hits home. While I track my investments and plan for my family’s future, Wilkinson’s story reminds me that the number in my bank account won’t magically bring contentment. Date nights with Sana, playing with Hamza and Anya, or maintaining my workout routine - these things already give me what money promises but can’t deliver: happiness.

The lesson isn’t to stop being ambitious or to ignore financial planning. Instead, it’s about recognizing that while money can solve certain problems, it creates new ones and never delivers the complete satisfaction we imagine it will. As I obsess over my investment portfolio, I try to remember this. The goal isn’t to stop earning or growing wealth - it’s to stop expecting money to fix everything else in life.

Build Systems, Don’t Do Everything

Wilkinson’s biggest breakthrough came when he stopped trying to do everything himself. He writes:

“I had a revelation: previously, I had thought of my business as…me. It was all in my brain and it was my job to hold everything together with dental floss and duct tape. My ever-growing backpack full of stress bricks, crushing me into the trail as I trudged uphill. Every problem was mine. If I didn’t show up, nothing would happen.”

He discovered a better way:

“Now, it became clear that my business didn’t have to rely on me. I could craft a machine to do everything. A machine that, if engineered just so, with the right people and processes, would convert raw material into a fully formed product without me lifting a finger.”

His key insight applies beyond just business owners:

“This had led me to the epiphany that there is always somebody else who loves the job you hate. You might find accounting boring, for example, but I promise you there is somebody whose idea of a great night is eight hours of pivot tables in Excel.”

Working in corporate finance, I see this play out differently. While I can’t build my own company’s systems, I can create processes that make my work more efficient. Instead of being the person who does everything, I focus on building templates, documentation, and workflows that others can follow. This way, when I take time off to be with Sana and the kids, things don’t fall apart.

Wilkinson calls this “Lazy Leadership,” but I think of it as smart work. He explains:

“I adopted a mantra. I began to repeat it, over and over. I was ‘Teflon for tasks.’ Never again would I do something that could otherwise be done by someone else.”

This mindset helps me at work too. Instead of being the hero who solves every crisis, I try to build processes that prevent crises from happening. When Hamza has a football game or I have to take care of some personal work, I want systems in place that let me step away without everything falling apart.

It’s tempting to be the person everyone depends on. When your boss needs something urgent, being the go-to person feeds your ego and sense of importance. But this is dangerous thinking. No matter how crucial you feel, at the end of the day, it’s still a corporate job, and everyone is replaceable. The real value comes from building and documenting processes that empower your team to function without you.

It isn’t about avoiding work - it’s about working smarter. Whether you’re running a company or part of one, success comes from building processes bigger than yourself. This way, your value comes from your ability to improve the system and empower others, not just from being the person everyone needs to call when things go wrong.

Watch Who You Spend Time With

Wilkinson noticed something interesting about success - it changes not just what you want, but why you want it. He writes:

“I noticed that whatever the people around me cared about, I began caring about, too. Business awards. Exclusive conferences like TED and Davos. Events like Burning Man and Art Basel. That was what other successful entrepreneurs seemed to care about, and I found myself wanting to fit the mold.”

He explains this phenomenon:

“What caused this, I later realized upon reading Luke Burgis’s book Wanting, is something called mimetic desire. The idea that whatever those around you model as being valuable and important, you unconsciously find yourself caring about and wanting, too. Whether it’s as simple as a fashion choice, like a wristwatch, or as complex as a meaningless professional title that you could spend decades trying to achieve.”

The danger, as he points out, is subtle but real:

“What’s sad about this mimetic phenomenon is that it convinces people to sacrifice their own happiness to achieve whatever goal their peers have assigned value to, even when it’s not an authentic desire of theirs.”

I see this in my own life. We all have insecurities, and some people - even well-meaning ones - have a way of feeding them. They might casually mention their investment returns, their children’s achievements, or their latest promotion. Each comment, though perhaps innocent, can leave you feeling inadequate, pushing you to seek validation in ways that don’t align with your values.

When I’m around certain colleagues or friends, I find myself questioning my choices. Should I be more aggressive with my investments? Am I doing enough for Hamza and Anya’s education? Should I be climbing the corporate ladder faster? These thoughts often surface not because these things matter to me, but because they matter to the people around me.

Wilkinson’s experience shows how this can spiral:

“I could feel that they were no longer rooting for me. That I was now a competitor, rubbing their faces in it. The tallest blade of grass, which needed to be cut down to size. An envious look on their face as I told them about a recent win—something I soon learned to censor—or the almost imperceptible flash of a smile under a grave face when I shared a loss.”

I am not saying that we should avoid successful people or stop being ambitious. Instead, it’s about being mindful of whose values you’re adopting. Are you pursuing that promotion because it aligns with your goals for work-life balance, or because it’s what others expect? Are you chasing investment returns because they serve your family’s needs, or because you want to match someone else’s success story?

The people we spend time with shape our desires, often without us realizing it. The key is to surround yourself with those who celebrate your authentic choices rather than make you question them. Sometimes, the most successful person in the room isn’t the one with the biggest title or bank account, but the one who’s stayed true to their own definition of success.

Owning Things Own You

While I can’t relate to Wilkinson’s struggles with multiple homes and yachts, his insights about ownership apply at any scale. He writes about his experience with luxury:

“My life was seemingly spent tending to…my life. The kicker was that most of my homes were sitting empty 90 percent of the time. No one, not me or family or friends, was even enjoying these lavish abodes. I was going to all this effort to maintain these assets for no other reason than simply to have them.”

His conclusion is telling:

“It’s not that I regretted trying this stuff. Some of it was fun and gave me experiences that made for great stories, but I started to learn the lie that we’ve all been told is just that, a lie. A marketing scheme dreamed up by some executives in an advertising office on Madison Avenue.”

While I’m not managing multiple properties or yachts, I see this pattern in my own life. My eight-year-old car and simple wardrobe might suggest I’ve moved beyond material desires, but my credit card statements tell a different story. Each month, the bill grows - online courses I never complete, Amazon purchases that remain unopened, subscriptions I barely use.

Wilkinson’s experience with grand possessions and my struggles with smaller purchases share a common thread. He notes:

“To me, the ultimate luxury was having the ability to cancel all my meetings on a whim and hang out with my kids, just because I felt like it.”

This hits home. The things we own - whether big or small - demand our attention, money, and time. Every possession carries a hidden cost, not just in maintenance but in mental bandwidth. The unused course nags at your conscience, the unopened Amazon package reminds you of money poorly spent, and the growing credit card bill becomes another source of stress.

The lesson isn’t about living like a monk or never buying anything. It’s about being honest about what ownership really means. Whether it’s Wilkinson’s empty vacation homes or my collection of unfinished online courses, the truth remains: things end up owning us more than we own them.

Starting is Better Than Finishing

Wilkinson explains this lesson through a conversation with an aspiring entrepreneur:

“What does it feel like to have such a big business?” he’d asked, wide eyed. I was honest. “Okay, imagine that you love chopping wood in your backyard,” I said. “You do it for fun. To relax. To enter a flow state. Then, one day, your neighbor pops his head over the fence and asks you if you could chop him some wood, too. He offers you $20. Suddenly, the thing you love doing becomes a business. Before you know it, you’re chopping wood for all your neighbors. You buy a truck and start selling door-to-door. It’s just you and a bunch of buddies, side by side, chopping wood and working outside. The business grows. And grows. And grows. And a decade later you wake up. You’re in a little glass office, perched atop one of many sawmills. You look down at the hundreds of workers beneath you, operating the industrial equipment on the factory floor. Huge logs getting fed into machines that slice the wood. Totally automated. And there you are. Isolated in your little office, wearing a suit, the air-conditioning blowing a chill down your back. No axe. No fresh air. No friendly coworkers. Just you sitting in your office, doing some paperwork—alone.”

He found inspiration in a different approach:

“Watching Jiro Dreams of Sushi, a documentary about Jiro Ono, an eighty-five-year-old sushi master in Tokyo, I found myself wiping away tears. Instead of scaling his business like I had, he had focused his entire life on honing his craft. For over seventy-five years, since he was just ten years old, Ono had obsessively improved every aspect of his sushi… His restaurant was humble. Just ten seats in an unassuming corner of a Tokyo subway station. And yet, he had three Michelin stars—the culinary world’s highest honor.”

This resonates with my own experience, though at a different scale. When I write, I don’t have an end goal in mind. I’m not trying to build a following or become a famous writer. Instead, I write to understand things better, to make sense of what I read and experience. The joy comes from the process of discovery, from connecting dots I hadn’t seen before.

Wilkinson’s story and Jiro’s approach remind us that maybe we’ve got it backward. We often focus on the destination - the promotion, the bigger house, the successful business - when the real satisfaction lies in the journey itself. Whether you’re building companies like Wilkinson or writing essays like me, the beginning, when you’re learning and growing, might be the best part.

You should always remember why you started in the first place. For me, writing isn’t about reaching an endpoint; it’s about the continuous journey of learning and understanding. Perhaps that’s why there’s no end goal in sight - because the journey itself is the point.

Who is This Book For?

Charlie Munger once said: “All I want to know is where I’m going to die, so I’ll never go there.” He wasn’t talking about death - he was talking about learning from others’ mistakes. Munger believes that while we can learn from success, we learn more from failure, especially other people’s failures.

That’s how I think about “Never Enough.” It’s not just a book for entrepreneurs or people trying to build billion-dollar companies. It’s for anyone who has ever wondered if more money, more success, or more status would make them happier. In other words, it’s for most of us.

Wilkinson’s journey from a barista to a billionaire serves as a guide - not for how to get rich, but for what happens when wealth and status become the end goal rather than a byproduct of doing what you love. His story shows us the pitfalls of success before we fall into them ourselves. Whether you’re climbing the corporate ladder, building a business, or investing on the side, his insights about the hedonic treadmill, the burden of ownership, and the influence of peers apply universally.

The best way to learn is by doing, but the second-best way is by learning from others’ mistakes. Wilkinson’s honesty about his journey - the empty homes, the constant chase for more, the realization that true luxury is time with family - helps us examine our own motivations. Why do we want what we want? Are we chasing these things because they align with our values, or because others tell us we should?

This book won’t tell you how to get rich. Instead, it will help you think about what “enough” means for you. And perhaps that’s the more important question to answer.

Read this book if you:

• Find yourself always wanting more, even after achieving your goals
• Wonder if success will finally make you happy
• Want to learn about wealth and status without the painful lessons of acquiring them
• Need help examining why you want what you want

The value of “Never Enough” isn’t in teaching us how to build successful companies - it’s in helping us understand what success actually means, before we spend years chasing the wrong definition of it.