I have been journaling since the early days of the pandemic. A Moleskine — black, medium, the one I have always used. There is something about the physical act of writing that surfaces things the screen does not.
Last week I was reading back through old notebooks and I started to make a list. The milestones in my life that I had planned, worked toward, and achieved more or less as I intended. Then another list. The milestones that happened differently — that arrived through a conversation I did not plan, a door that opened from a direction I was not facing, a moment whose significance I did not understand until years later.
The second list was longer. Significantly longer. And some of the things on it were the most important things in my life.
I started thinking about luck.
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Start with the things you had no hand in at all. The country you were born in. The family you were born into. The era you arrived in — whether you came of age during a boom or a recession, during a war or a period of relative peace. Your name. Your religion, until you were old enough to question it. The language that shaped your first thoughts. None of this was chosen. All of it shaped everything that followed.
This is pure luck. Not the earned kind, not the prepared-for kind. The kind that simply happened to you before you had any capacity to participate in your own story.
Seneca wrote that luck is what happens when preparation meets opportunity. It is a satisfying line. It has been quoted approvingly for two thousand years. But Seneca was born into a wealthy Roman family of the equestrian class. His father was a famous rhetorician. He was educated in Rome, connected from birth to the people and institutions that shaped Roman intellectual life. When Seneca talks about preparation, the preparation he is describing was itself prepared for him by circumstances he did not choose. The observation is not wrong. But it is incomplete in a way that matters — it mistakes the output of luck for its absence.
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"Luck is what happens when preparation meets opportunity." — Seneca Seneca was born into a wealthy Roman family with connections to the imperial court. His preparation was itself partly luck. The line is true and incomplete at the same time. |
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In September 2001 I was in the United States, looking for work. I sent approximately two thousand CVs. Two thousand. The market after September 11 was not a market anyone would have chosen to enter. Everything had changed in the preceding weeks and the consequences were still unfolding. I found a job eventually — through persistence, through the right connections forming at the right moment, through a decision by someone I had never met before to give me a chance in a sector I was not certain I would stay in.
That job put me in telecommunications. Telecommunications defined the next twenty-five years of my career. The sector, the relationships, the expertise, the identity — all of it traced back to a single yes from a person whose name I still know, in a moment that could easily have gone differently. Was that luck? Was that preparation? Was that persistence? It was all three, intertwined in a way I cannot separate cleanly even now. Two thousand CVs and one yes and everything that followed.
Then there is my wife. I arrived in a country I had not planned to live in permanently. She was in the same building as me — different company, different floor, different life trajectory entirely. She is not from this country either. We were both there by a series of decisions that had nothing to do with each other. I saw her in the elevator one day and said hello in the local language. Bună. What is the probability of that specific moment? Of two people from different countries, different companies, different paths, being in the same elevator in the same building in a city neither of them had planned to stay in? The question is not rhetorical. The probability is genuinely very small. And yet.
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The startup world has produced some of the most honest thinking about luck in business precisely because the failure rate makes luck impossible to ignore. Most startups fail. Most of the ones that succeed do so for reasons that the founders themselves struggle to fully explain — the right timing, the right investor meeting at a conference the founder almost did not attend, the pivot that only happened because the first idea collapsed, the first customer who came through a friend of a friend who happened to mention the product at dinner.
But dig deeper into the background of the people who succeed and a pattern emerges that the hero narrative almost never mentions. Rich families. Connected parents. Ivy League schools where the right relationships form before the first company is started. Access to capital that most people simply do not have. The founder who dropped out of Harvard to start a company still got into Harvard first. The garage startup still had a garage — and parents who could absorb the financial risk of a child not earning. The success is real. The luck that made it possible is systematically hidden.
When you look at these people as icons and ask why that is not you — you are comparing yourself to an illusion. The full picture of how they got there is not in the TED talk or the biography or the Forbes profile. What is shown is the result. What is hidden is the starting position. That comparison was never fair.
The ones that succeed then write books about the principles that led to success. The ones that fail, with identical principles applied with identical effort, largely disappear. The survivor bias in business storytelling is almost total — we learn from the people who made it, who are the least representative sample for understanding what actually determines outcomes.
Annie Duke's book Thinking in Bets makes this point with precision. We judge decisions by their outcomes rather than by the quality of the decision-making process that produced them. A good decision that leads to a bad outcome looks like a bad decision in retrospect. A bad decision that leads to a good outcome looks like wisdom. The outcome tells you almost nothing reliable about whether the decision was right. And outcomes depend heavily on factors outside your control — which is to say, on luck.
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But here is the question that matters practically: if luck is so significant, what can you actually do about it?
The honest answer is that you cannot control luck. But you can increase the surface area of it. The more connections you make, the more experiments you run, the more doors you open without knowing what is behind them, the more opportunities luck has to find you. This is not the same as saying preparation creates luck — it is saying that exposure increases the probability of fortunate collision. Show up in more rooms. Say yes more often to things whose outcome you cannot predict. Be findable by the right accident.
But here is what the motivational culture will not tell you: life does not value your effort. It does not appreciate what you deserve. It is completely indifferent to whether you worked hard or showed up or gave everything you had. The decision to push further or to stop is yours alone — and both are legitimate choices. The culture that says always push, always hustle, never quit is part of why millions of people suffer from anxiety and depression. Because they are pushing toward something they never stopped to question.
The hardest question — and the one most people never seriously ask — is whether what you are chasing is actually yours. Is this what you want? Or is it someone else's goal, someone else's definition of success, someone else's value that you absorbed somewhere along the way and have been imitating ever since? That question is genuinely difficult to answer honestly. But it is the most important question the surface area of luck eventually forces you to face.
There are communities and researchers now specifically studying this — running small experiments to understand what behaviours increase the probability of fortunate outcomes. The findings consistently point toward openness, curiosity, and the willingness to follow an unexpected thread even when you cannot see where it leads. The analytical mind that wants conditions controlled before committing is, in this specific domain, a disadvantage. The person who says hello in the elevator without knowing why is doing something the optimiser cannot replicate.
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"What you seek is seeking you." — Rumi |
I think Rumi is pointing at something close to what I mean by intention. Not goal-setting, not planning, not the SMART framework. Intention is the orientation of your attention and energy toward something — the direction you are facing when luck arrives. The goal tells you exactly where to go. The intention tells you what kind of thing you are looking for, and then allows luck to determine the specific path. Goals are closed problems. Intentions are open ones. And the most important things in life tend to arrive through the open ones.
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One last thing worth saying.
When you look at someone who has more than you — more money, more success, more of whatever you are measuring — the natural human response is to look for the explanation in their choices, their qualities, their effort. Sometimes that explanation is right. Often it is incomplete. And sometimes the shortcut is simply not acknowledged. Some people take shortcuts and are celebrated as successful. The benchmark itself is broken.
We measure success by wealth and celebrity and visibility. But consider this: if you had one choice — keep a silent surgeon who saves lives every day or keep Ronaldo and Messi — which one would you choose? The answer tells you something about the gap between what we celebrate and what we actually need. The surgeon is luckier than Ronaldo in some ways and less lucky in others. Neither of them chose their starting position. Both of them are benchmarks for someone who is comparing themselves to the wrong thing.
This is not an argument for passivity. Effort matters. Preparation matters. Choices matter. But the benchmarking — the comparison of your outcome to someone else's as though the starting conditions were identical — is a game you cannot win because the starting conditions were never identical. Luck is not evenly distributed.
What is worth doing instead: find the area where you are luckier than most. There is always one. The country you were born in relative to most of the world. The health you have that others do not. The people who stayed. The elevator you happened to be in. The job you found after the two thousandth CV. Gratitude is not a spiritual practice. It is an accurate accounting of the luck that is already in your life that you have stopped seeing because you are focused on what is missing.
Some people realise this early. Some realise it late. Some never do. The realisation does not change the luck. But it changes what you do with it.
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This week's insight You cannot control luck. But you can increase the surface area of it — more rooms, more conversations, more willingness to follow an unexpected thread. Set intentions rather than only goals. And stop benchmarking your outcome against someone else's as though the starting conditions were the same. They were not. Find the area where you are already lucky. It exists. The gratitude that follows is not soft thinking. It is accurate accounting. |
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