What is optionality? If you want a thorough answer, check out the big juicy book I spent the last couple of years writing.
In the meantime, I’ve written a post that links together everything I’ve written in one place, and gives a taste of what the book is about for new readers.
Here’s my definition of optionality, adapted from the introduction of the book, followed by 10 principles for navigating an uncertain world…
Blogging is an endurance sport. It takes a while to hit your stride, but as Deep Dish’s 4th birthday approaches, and with it, a million views and a thousand comments, I think I have a decent sense of whether it’s all been worth it. Is blogging really that rewarding? Did I waste my time on this thing? Should you start […]
I started this blog with a vague premise that there was something valuable about trying weird things, and taking a few steps off the beaten path. I didn’t have any actual justification for this at the time, so I borrowed an impressive-sounding quote from some famous sage or other: ‘All life is an experiment.’
Emerson’s non-conformity schtick was enough to get me started. But now I have a much better model for why this is important, and how to make experiments.
Over the last five years, I’ve done something like 100 lifestyle experiments great and small.
Generally these have ended well; occasionally not so well. When I say I have a ‘much better’ model of how to run experiments, that’s a relative term. I have at least managed to avoid doing really dumb shit, although this was initially as much by accident as by design.
Here’s my rough guide to self-experimentation:
The truly horrifying part of becoming an adult is the realisation that other adults don’t know what they’re doing. Remember the feeling of falling asleep in the back seat while your parents drove you home? You will never, ever experience that level of security again. Growing up is the constant disappointment in discovering that no-one is infallible: not your parents, not your teachers, not your personal heroes, certainly not your politicians.
It’s dangerous to rely on the judgement of ‘grown-ups’, or to wait until someone gives you permission to act. Sometimes you have to take the initiative, even if it means doing slightly goofy stuff…
Babies love putting things in their mouths: dirt, insects, bits of grass, their own poo. They have no sense of fear or self-preservation, and come up with endlessly creative ways to place themselves in mortal peril. Once they learn to talk, their constant experimentation with the world transcends the physical to the philosophical. They want to know everything. They are bottomless pits of curiosity, with very little in the way of attention span or self-discipline. Your typical two-year-old can only concentrate on a task for six minutes at a time. Young children are not self-aware enough to feel much in the way of shame, or embarrassment. Nothing is off-limits. In a word, very young people spend almost all of their time exploring.
The elderly are set in their ways. The only foreign objects they put in their mouths are dentures and hard caramels; occasionally followed by a fork to extricate said caramels from said dentures. They tend to have stable routines, rituals, hobbies, and social circles. They rarely try new things or experiment with new identities. They’ve lived long enough to know what they’re about, and they intend to wring out every ounce of enjoyment before the curtains come down. In a word, very old people spend almost all of their time exploiting.
The ‘explore-exploit’ constraint is one of the most useful ideas I’ve come across…
Our meatsack bodies slavishly plod along at the precise rate of one second per second. But our minds are unbounded by the constraints of time or space, free to wander the past at will, and poke into the distant corners of the future.
The ability to create vast, hyper-detailed simulations of the past and future is the closest thing we have to a superpower, because it lets us do the following…
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…
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…
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.
“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…
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 […]
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…
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…
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…