Collect as many lottery tickets as you can

How to make important life decisions

The most important decision-making principle that I know of is to collect as many lottery tickets as you can, then double down on the ones that start paying off. 

Many people have written about the importance of maximizing optionality and serendipity in life. The two most influential reads for me have been:

• Your life is driven by network effects, James Currier

• Antifragile, Nassim Taleb 

Principles are powerful because they can help simplify complex decisions with many variables. 

I’ve applied this particular one to decisions both large (“Should I move from Singapore to Silicon Valley?”), and small (“Should I go to this dinner party tonight even though it’s inconvenient?”). 

Pick lottery tickets with high convexity

Not all lottery tickets are equal. The best ones have capped downsides, and uncapped upsides. 

Nassim Taleb calls this “Convex Tinkering”, which he defines as making “low-cost mistakes, with known maximum losses, and large potential payoff (unbounded)”. 

A prerequisite is having enough context to form a probabilistic assessment of both the pain and gain. This usually comes with experience, or you can also shortcut it by getting benchmarks from people who’ve been there. 

One example: I had two job offers in the US in 2017, one from a risky crypto startup, the other from Google — safe, prestigious, and well-paid. 

I picked the former, which had higher convexity in the three areas I cared about: mentorship and learning, professional network, and financial outcome. The bet paid off on all fronts, but even if it hadn’t, its downside would have been very low. 

Conversely, the biggest mistakes of my life were mistakes of omission, not commission. In 2018, I passed on the chance to angel invest in a few protocols because I thought crypto angel investing was too risky relative to other asset classes. One of them turned out to be Solana. It was a dumb mistake — the downside was $10k per bet, and the upside millions.

Treat lucky breaks with urgency

“Many people do not realize that they are getting a lucky break in life when they get it. 

If a big publisher (or big art dealer or movie executive or a hotshot banker or a big thinker) suggests an appointment, cancel anything you have planned: you may never see such a window open up again. 

I am sometimes shocked at how little people realize that these opportunities do not grow on trees.” - Nassim Taleb 

It’s human nature to be lazy. The best way to counteract it is to behave with urgency when you spot a highly convex lottery ticket by assuming it’s rare.

It’s the way of the alligator: Charlie Munger calls it a mix of extreme patience and extreme decisiveness.

This means moving before you’re ready, or when you have imperfect information about the payoff function, because opportunities decay quickly. 

Ryan Graves’ net worth from Uber is now $1.6B.

I’ve seen entrepreneurs make or raise millions by answering an email, even though they felt they weren’t ready yet. I’ve seen friends hustle for a second date who ended up getting married to that person.

How to attract lottery tickets 

Some activities are lottery ticket magnets. Depending on what you’re into, this could be angel investing, writing, tweeting, having a podcast, or being a serial entrepreneur.

Don’t just collect tickets for the sake of collecting them. The direction in which you collect them is really important, and compounding leads to exponential outcomes. The trade-off between time spent exploring and exploiting is a personal decision based off your stage of life and career. 

Don’t forget to re-assess and double down on whatever tickets are starting to pay off. Truly great outcomes in anything — be it career, dating, or friendships — require dedication after the initial investment.

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