the optionality approach to getting lucky: dead ends, treasure chests, and bottomless pits

The Optionality Approach to Getting Lucky

We’ve established that there is no such thing as cosmic justice: it rains on the just and the unjust alike. But over the course of a lifetime, we at least vaguely shuffle in the direction of getting what we deserve. The goal of this post is to get us from ‘vague shuffling’ to ‘slightly-more-purposeful ambling’.

If you want to get lucky, the usual advice is that you have to be prepared, and then wait for opportunities. This is not very helpful.

Instead of wandering aimlessly and hoping for the best, we can use a simple framework to figure out which opportunities are worth pursuing.

This is the filter I run over pretty much every decision these days. It’s called the optionality approach…

Futurama compound interest cover image

Futurama Taught Me Everything I Know About Compound Interest

Futurama is one of the greatest cartoons of all time. If you haven’t seen this gem of the early noughties, here’s the basic premise: Pizza delivery boy Fry accidentally falls into a cryogenic freezer at the turn of the new millennium, and wakes up 1000 years in the future.

In the sixth episode, ‘A Fishful of Dollars’, Fry re-discovers his old bank account, which contained the princely sum of 93 cents at the time he was frozen. Over the 1000 years he spent as a human popsicle, he is told the balance has compounded from less than a buck to the staggering sum of $4.3 billion. Hijinks and capers ensue…

Advanced Investing: The Barbell Strategy for Investing

Advanced Investing: The Barbell Strategy for Bastards

Marry an accountant, but have occasional flings with rock stars. Lift very heavy weights for a few repetitions, then do lots of low-impact cardio. Work a secure and boring job, while pursuing highly speculative ventures on the side.
The common thread running through all these ideas is called the ‘Barbell Strategy’, and it’s useful for all sorts of big decisions – from your career and work, to health and fitness, and of course, your investment portfolio…

The Barbell Strategy: How Not to Be a Starving Artist

The chances of making it big as an artist, writer, or entrepreneur are vanishingly small. However, there is one way to not only give yourself the best shot possible at succeeding, but avoid a bone-crunching existential crisis if things don’t go according to plan.

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