Making Your Own Luck
How to do it and why
Luck is a funny thing. Most rational people deny its existence and laugh at people who buy lottery tickets. When I worked in Las Vegas my colleagues told me about “slot machine tournaments” and I smirked with superiority. Gambling is a tax on the stupid and nobody’s good at games of chance. Except for one thing - that’s not true.
Determinism is the idea that someone - God, fate, physics has set in motion a chain of events and their outcome - whom we marry and our jobs are just the outcome of a very long series of causes and effects. The opposite of determinism is Free Will. This model says we’re all driving our own car, making decisions that benefit or harm us.
Clearly neither is entirely true which is what makes luck interesting. When is our life the consequence of events and when do we get the credit? The answer is best found in luck which is perhaps one of the least well-understood gifts in life.
What you think about luck begins with examining one basic ingredient - randomness. Flip a coin and call it. 50/50, right? Actually, not quite. This is why David Blaine lives in a mansion, not on the streets. There are edges everywhere, tiny fluctuations in air temperature, one side of the coin a bit heavier and a table that’s not quite level. Randomness exists in mathematics but the world gives us imprecise instruments to to detect it. Sleight of hand and loaded dice are common.
The idea of true randomness is beautiful - when it happens it’s the closest thing we have to the sound of God’s voice.
To make sense of what in life was our choice and what was predetermined, I often think of faces. If life was a chatroom, fortune could only be attributed to our wits, skills and charm. But in this life we walk into friendships, romance or combat with the mug we were born with. Some poker players learn to mask it but the rest of us can be easily read.
This is me, aged 8. Even then, most classmates could tell I was curious and gentle. Some provoked me and learned of my sharp little fists. We hear lots about nature vs. nurture or about twins, separated at birth who have similar lives. It’s amazing to think how differently we might have turned out with someone else’s face. Put another way, you’re lucky to be who you are.
Back to luck. Consider your life. If I’d said no to meeting a “Boston real estate expert” in 1999, my children would either not exist or look rather different. Did I interpret that moment, meeting a petite woman in a cabled sweater, as the luckiest of my life? No - at the time I wondered why she knew nothing about real estate.
I’ve been blessed with a lucky life. I sometimes tell people about how I engineer luck. When I’m in New York, I work at the Peninsula Hotel. Hasn’t paid off yet but I did have a conversation with LL Cool J once. This idea of "putting yourself in the mix” is a kind of luck-hunting philosophy - not that different than competing to attend an elite school. Or flying first class to chat up your seat-mate. Unfortunately, the powerful can smell ambition from arrivistes like myself, and they don’t liked feeling hunted. Neither would I.
Yet we’ve constructed an entire society to lubricate luck - casinos that erupt with money, bars with bottle service and status-based zip codes and cars. But wealth and status are endpoints - luck’s an ingredient, a glint in the eye, irreverence and an edge. If randomness is elusive, luck is magic. Real magic.
You see it in sports, that swagger at the 3 point line as a player surrenders to fate and hoists up the game winner. It’s a letting go of ownership. It’s not “my” shot or “our” basket, just a dance and a throw. Just then, you can see it, the product of 1000 steps or one fortunate accident. A swish and the game.
Luck.


