what does optionality means? 10 rules for optionality in an uncertain world

10 Principles of Optionality For an Uncertain World

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…

Announcing the optionality book: how you can get involved

Announcing Optionality, the Book: How You Can Get Involved

As many of you know, I’ve been working on a book project for the last few years. Now I can finally announce it officially: Optionality: How to Survive and Thrive in a Volatile World is a thing that exists in the world!

This is a synthesis of everything we’ve been thinking about here on the blog, and much more. I’m really proud of it, and excited to make it accessible to as many people as possible.

Briefly, the book lays out a strategy for not only becoming resilient to future shocks, but positioning yourself to profit from an unpredictable world: investing, insurance, social support networks, health and fitness, and skills, all viewed through the lens of making confident decisions under uncertainty.

It takes a village to write a book. I’ve tested some of the ideas here on the blog, and have benefited enormously from having readers give feedback on the structure, title, design, and early drafts.

It also takes a village to launch one. As a first-time author, I’m asking you, dear readers, for help in marketing the book and spreading it to communities and groups that would benefit from it…

personal security audit cover image

Getting Hacked and Getting Hard

CLEARANCE SALE! VANS SHOES CHEAP! I was as surprised as anyone to hear that I’d pivoted from blogging to hawking knock-off footwear on Facebook. After pulling down the scam posts and changing my password, I checked my activity log. At least three interlopers had somehow managed to access my account, one of them several years ago. Creepy, but unimaginative: they didn’t lock me out, or steal my identity, or use my password to access other sites. As far as I know, my nudes are still between me and Zuckerberg.

Then there was the second incident: I changed my Google password, immediately forgot it, and couldn’t get back in. I filled in the account recovery forms over and over, and sat there silently panicking as each robotic form rejection destroyed a tiny piece of my soul. There was no way to get in touch with a human being. With one moment of carelessness, I was sure I’d lost all my work, and years of treasured memories.

On both occasions I got lucky: it could have been much, much worse. Screwing up for a third time was probably tempting fate, so I decided it was time to actually sit down and sort out my online security…

All life is an experiment cover: Einstein beakers illusio

The Self-Experimentation Guide

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:

premature exploitation: popping the bubbles a little too soon

The Embarrassing Problem of Premature Exploitation

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…

the art and science of mental time-travel: cover image

Time Travel for Pleasure and Profit

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…

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…