How to Get Lucky

Succinctly:

  1. Be open.
  2. Make lotsa little bets. Collect free non-lottery tickets.
  3. Always take care of your downside.

Luck is an attitude, not a thing. Be open to experiences and opportunities.

We don’t pay truck to the role of luck in successful people’s lives. I get irked with business biographies as unbalanced personality cults where luck or psychopathology noticeably outruns talent.

Smart, productive, and ambitious are table stakes these days. Luck, and having help (and being raised white, male, and in the West to be clear about entitlement), often play an outsized role in many success stories we lionize as self-made.

So, how do you get lucky? How can you get more luck? How can you make it so opportunities gravitate to you? Some cultures, believe luck is an innate quality you’re born with, like hair colour or blood type, or something you can literally negotiate via hecatombs to unseen forces.

But, our ideas about luck are merely stories we tell ourselves to explain patterns that seem to benefit or work against us.

If you look deeply enough, feeling lucky is generally an attitude of openness to experiences — a pure, mental sleight of hand to take what is given and riff on it. That, and at least in my experience, open generosity: giving time, effort, and resources to things that haven’t actually benefitted me directly. For some reason, these always seem to come back to me in good karma and alternative contributions.

Luck is an Attitude

Openness to experience and opportunities are the precondition to luck. Everything else is really the stories we tell ourselves about outcomes. Don’t believe me? I don’t think I can provide a more illustrative example than an episode of noted mentalist Derren Brown’s The Experiments series on The Secret of Luck. Watch it. It may change your life (and certainly your perspective.).

(ping me if this link ever stops working)

What does this mean in practice? Leave yourself open to opportunities and actions around you. Interact more with the world.

Contact back that random ping. Ask what that recruiter on LinkedIn actually wanted. Go someplace different for a weekend getaway. Go to that new restaurant. Accept the party invite. Take up a new skill. Read that book your friend raved about instead of shutting them down. Ask. The. Hottie. Out.

The quanta of luck is individual action.

Sure, you can believe in your fickle gods and goddesses, make your sacrificial hecatombs, and consult your star charts, especially if they make you more secure about taking a chance, but if Derren Brown can convince an enture village to pat a random dog statue, what chance do you think you have to not rationalize what they tell you?

Smarter Luck

OK, so how do you get better at luck? How do you make yourself smarter about it? No one wants to depend on dumb luck either through getting it or in terms of it saving you. What can we do to just make ourselves more lucky?

Lotsa Little Bets

I’m not a big believer in big, all-or-nothing bets. There’s this unsavoury, macho thing in business sometimes where people are lionized who take unconscionable rolls of the dice and get dumb lucky. Be aware of it.

A smerter approach is to make lots of little bets with low downside and high upside potential. How do you find these?

Much like leaving yourself open to taking actions when opportunities present themselves (and even more, seeing them as opportunities, rather than say… setbacks), you should explicitily start to get comfortable with making lots of little bets.

First off, this starts to reduce the risk of making any reasonable bet, but the other thing is it teaches you longer term that not having a bet go your way is not fatal. Most people are loss averse, we tend to focus on what we may lose (pride, prestige, $10) rather than a bigger upside even when your downside is small. So, get comfy with making small bets.

So, think of it a little like investing. Lots of small bets diversify your risk of any one particular bet not going your way. Think about having a portfolio of little bets going all the time to promote your upside and the fact any one or two things not going your way is not going to make you miserable.

Collect Free Non-Lottery Tickets

Great advice for Naseem Talab in terms of trying to figure out how to live in such a way as to make yourself both open to capitalize on, and to insulante yourself from Black Swan type events, he suggests:

Collect as many free non-lottery tickets (those with open-ended payoffs) as you can, and, once they start paying off, do not discard them. Work hard, not in grunt work, but in chasing such opportunities and maximizing exposure to them.

So, the idea here is to seize any opportunity, or anything that looks like an opportunity. Though he feels that true opportunities are much rarer than I feel they are. His argument is that positive Black Swans have a necessary first step, which is actually being exposed to them. If you are never exposed to them before they become those events, you miss out.

So, his advice is to work hard in chasing those sorts of opportunities and maximizing exposure to them.

A lot of his advice revolves around creating new opportunities for chance encounters, like getting out there to salon-type events and even cocktail parties. You never know where you may be exposed to interesting and new information and opportunities. “… gain exposure to the envelope of serendipity.”

Protect your Downside

Feeling luckier doesn’t mean you’re infallible or invulnerable. Luck is a story you tell yourself. Don’t get swayed by your own press.

Your goal here is to just create a system where you are just more likely to get good outcomes.

So, always have a grasp of how big your downside is on any particular bet. And, the total amount of downside you are carrying across all bets you’re making. It’s a bit like making sure you can service your debt load when you’re buying things on credit. You want to make sure that a catastrophic cascade failure affecting many bets somehow is not an extinction level event.

If you’re like me, financial downsides are not as important to take note of as time commitments. I often find even small bets carry time commitments that can add up quickly. Much like limiting my work in progress and experiments I run, I try to at least note what small bets are taking up quantitatively in terms of time. Otherwise, interesting and shiny opportunities sometimes eclipse the time I should be spending on other things I’ve set as priorities (thing like, ahem… blogging.)

I keep a little log personally. It’s handy, keeps me honest about my thoughts when I made the bets and my assumptions, and kinda makes sure things never get out of hand.

Fin

I’m just really hoping everyone can take this to feel just that little bit luckier here in 2022 and as we roll into the Year of the Tiger 🐯. Especially after the last two years of COVID, feels like everyone deserves it. And who couldn’t use being a little bit luckier. Bonne chance!

Let me know what you think about the post on twitter @awws or via email hola@wakatara.com and if it actually made a difference for you. I’d love to hear feedback about your own thoughts, processes, or approaches and what may have worked for you or tweaks to the above. Reasoned opinions on why I might be wrong and what might be even better always welcome.