DGQ 18: If you lived your life 1000 times, what would be true in 999 of them?

luck, clover, serendipity

I first heard this question from Morgan Housel quoting a Navalism (for the uninitiated, that means has its source tracing back to the one and only Naval Ravikant). And it makes you think, that in the multiverse, where each version of you lives a different life and makes different choices, what would stay constant?

These are things that are not attributed to luck. And as Morgan mentioned, “those are the things you want to focus on in life.” When predicting the future, many try to predict what will change, but the best bets with long time horizons are on those that don’t change. Things that aren’t attributed to luck. Or chance. In this world we live in, you’d be quite surprised the number of small, accidental decisions we make that lead to life-changing events.

Like you being 10 minutes late to a party meant that you somehow just showed up at the same time as your future spouse. And it was because of that, that led you to have a two-hour long conversation with him/her. Otherwise, you’d have spent the entire party hanging with your college friends.

Or because you forgot to bring your umbrella on a day it rained, it made you run into a hotel for shelter, where you stumbled upon the investor who led your Series A round. Because he/she too forgot to bring an umbrella.

Of course, I could play hypotheticals forever. Although I find it’d be a fun exercise to really examine how much of your most life-changing moments were due to serendipity.

As someone who makes their living on attempting to predict the future, that means we have to go back to first principles. For instance, human nature. Reid Hoffman’s framework that all great consumer products tap into one of the seven deadly sins. Something that despite innovation is timeless. Anecdotally, I do find some of the greatest investors — LPs and GPs alike — to be avid students of history, philosophy or psychology.

In the same interview I alluded to above, Tim Ferriss mentions another line once written by Don Knuth when he was quitting the use of email:

“Email is a wonderful thing for people whose role in life is to be on top of things. But not for me; my role is to be on the bottom of things.”

In life, while catchy and interesting and the talk of the town for that brief moment, sometimes it’s better to get to the bottom of things than to stay on top of things. After all, you only have so many letters on your tombstone.

Photo by Yan Ming on Unsplash


The DGQ series is a series dedicated to my process of question discovery and execution. When curiosity is the why, DGQ is the how. It’s an inside scoop of what goes on in my noggin’. My hope is that it offers some illumination to you, my readers, so you can tackle the world and build relationships with my best tools at your disposal. It also happens to stand for damn good questions, or dumb and garbled questions. I’ll let you decide which it falls under.


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