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…

how to make your own luck dartboard cover image

How to Make Your Own Luck

There’s no such thing as cosmic justice. Plenty of good people suffer in various horrible ways; plenty of bad people die rich and happy and surrounded by loved ones. This is not part of some grand plan. It doesn’t ‘mean’ anything. It’s just the arbitrary shuffling of atoms bouncing around a universe-sized billiards table.

There are three common ways of responding to this situation. Unfortunately, two of them are kind of messed up…

office hours cover hammock

Office Hours

When I quit my job to go traveling in 2016, I had a vague romantic notion of freelancing on the road. See ya later, corporate drones! No more sterile office cubicles for this guy! Instead, I’d tap away on my laptop while I sipped mimosas at the beach, or dash out genius missives from a hammock in the middle of the jungle.

As it turns out, hammocks are not ergonomically designed workspaces, direct sunlight on a laptop screen causes a hellish glare, and sand and electronics don’t play nicely together.

Constraints that liberate cover image

Constraints That Liberate

“Every morning I roll out of bed and ask myself, what should I do today?”

These were the very first words I wrote on Deep Dish, 2.5 years ago. I’m as surprised as anyone to find that I still have that same untrammelled freedom today. If I had to try and pin down the central theme of this blog, it’s exactly that: opening up your options. I’m not going to stop writing about that stuff any time soon.But I do want to introduce a new through-line.

Something I’ve learned the hard way during this extended sabbatical is that you can absolutely have too much of a good thing. Total unconstrained freedom is – well – kind of freaky, actually…

Goals Gone Wild

Every month, the blogging mafia convene: if you know what’s good for you, the first post of the year better have something to do with goals and resolutions, and at least one mention of the phrase ‘new year, new me’. I’m sorry! They’ll break my kneecaps if I don’t do what they say! My compromise is to write a post […]

Madness of crowds: Mona Lisa scrum at the Louvre

The Madness Of Crowds

I propose this general principle of travel:

If you skip the top-tier or ‘must-do’ attraction, you will usually have a way better time at a fraction of the price.

I’ve noticed this more times than I can count, but was too scared to say anything out loud in case I looked like an uncultured idiot. Privately, I think of most of these brand-name experiences as expensive box-checking exercises: been there, done that, bought the T-shirt. I wonder if we’re trapped in an Emperor’s New Clothes situation, where everyone is secretly underwhelmed, but no-one wants to defect from the agreed-upon narrative. Instead, we post up our happy snaps and loudly reassure each other how great it was…

How to Make Friends as a Solo Traveler

The first stage of being a solo traveler is fear. I flew into Bangkok in the middle of a thunderstorm. Sheet lightning and flickering neon signs threw the grimy streets into sharp relief as I took a cab through the pounding rain. The driver dropped me in the vicinity of my hostel, overcharged me for the fare, then pretended he didn’t have change for my fresh banknote. When I finally found my accommodation, soaked to the skin, I realised I was the only one staying there. There I was in a megacity of eight million people, and I’d never felt more alone…

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…