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…
One of the immutable laws of the Internet is that it’s impossible to write a LinkedIn morning routine parody so ridiculous that it couldn’t be mistaken for the real thing.
This genre of hustle-porn sucks, but not because the hustlers are wrong. I’m annoyed because they’re right—at least, in theory—but they spray so much fluorescent orange Cheez over everything that any sensible person is immediately repulsed. If we dismiss the ‘morning routine’ trope as the performative humblebragging of grifters and Silicon Valley narcissists, we’re throwing the baby out with the (essential oil-infused) bathwater…
This is a GTD guide I wrote for the Roam Research team. I’ve since developed a much smoother workflow, so I’ll update this guide soon. In the meantime, this should give you a decent intro to both GTD and Roam.
The central idea of GDT is to capture and close ‘open loops’—to get stray thoughts, to-dos, and concerns out of your head, and pin them to the page for future processing.
This frees up mental bandwidth so you’re not feeling guilty or overwhelmed, and means you don’t have to rely on the memory of your leaky meat-computer. As David Allen says: “Your mind is for having ideas, not holding them.”
There are dozens of approaches to implementing GTD, each tailored to a different set of tools and preferences. Here’s how you can set up a simple GTD-style system in Roam…
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:
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…
It’s always jarring and mildly insulting to hear that extremely famous and successful people are unhappy with their position in life. You ingrate! How dare you be miserable! Stop appropriating my culture!
The reason I feel betrayed by superstars like Tim Ferriss who talk openly about struggling with feelings of inadequacy is not so much actual class resentment, but the assault upon my own convictions that once I achieve [$NEXTBIGTHING] I will be content with my own position in life…
Probably you’ve read articles about how Obama wears the same suit every day, or Mark Zuckerberg has seventeen identical grey t-shirts in his wardrobe. The idea is to deliberately eliminate inconsequential daily choices and free up mental bandwidth for more important decisions; like ordering extrajudicial killings or strip-mining billions of people’s private information to sell to advertisers.
I say this lifehack is is much more useful and wide-reaching than streamlining your wardrobe: you can automate the important things, too.
If you wear the same outfit over and over, nothing bad happens. Maybe you don’t get invited to Fashion Week. But what if you eat the same food every day?
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 […]
Napoleon Hill was a pretty shitty human being, but you have to give him props for being perhaps the the greatest conman in history. It’s not just the sheer brazenness of the con, but that he got away with it scot-free, and continues to be revered long after his death. Think and Grow Rich, published in 1937, is still a bestseller today. It has 4.5 stars on Amazon.
None of the glowing reviewers seem to be aware that rather than soaking up the principles of the greats, curated and distilled over 20 years, they’re reading fiction cut from whole cloth by a conman whose only expertise lay in parting fools from their money.
As incredible as this is, it’s not the topic of this post. Ideas must be judged on their merits, and Think and Grow Rich is the perfect jumping-off point for exploring the positive thinking phenomenon.
Hill didn’t come up with the ‘Law of Attraction’ himself, but he perfected the archetypal self-help format: if you trace back the explosion in gurus waxing lyrical about the the power of belief, Think and Grow Rich is ground zero. Every purveyor of inspiration porn for the last 80 years—Tony Robbins, Oprah, Deepak Chopra, The Secret—has a direct lineage to this book.
It all starts with this idea: If you believe in yourself, the universe will provide. Conquer your thoughts, and you conquer the world…
Elon Musk is the real-life Ironman, and exactly the sort of superhero we need – because he puts the lie to the tired old cliche; ‘jack of all trades, master of none’. In this post, I want to make the case that cultivating broad interests and skills not only dovetails perfectly with the frugal life, but acts as a sort of force multiplier – a booster rocket that can propel you towards your money goals at blistering speed…
Imagine your dad giving you a stern talking-to about the facts of life, except your dad is Canadian, has an IQ of ~150, and is voiced by Kermit the Frog. That’s Jordan Peterson, the University of Toronto psychology professor whose lectures I’ve been binge-watching recently. When I heard he used a research-backed ‘self authoring’ program with his students to great success, I had to give it a try. Here’s the verdict…
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.
