An Interview with Alain de Botton

Alain de Botton thinks you’re a hellish proposition.

It’s nothing personal, mind. Basic sanity is simply beyond our reach. Everyone has an appalling amount wrong with them. The only people we can think of as profoundly admirable are those we don’t yet know very well.

I’m eager to establish my muttonhead bona fides as soon as possible, so I botch six separate attempts to secure the Skype connection to London. De Botton waits patiently, gently offering suggestions as if to a rather dim child.

That ought to do the trick. Now we have a clear line, from one hellish human to another…

Better to Reign in Hell Than Serve in Heaven

‘Better to rule in hell than serve in heaven’ is the fervently-held belief of many freelancers, entrepreneurs and digital nomads I’ve met over the last few years. They’ve all walked away from overbearing bosses, steady paychecks, and nine-to-five office hours to build their own dominions.

There are no rules in hell! You can set your own hours and fire annoying clients and be your own boss and blow off work to go drinking at 11 in the morning. But liberty always comes at a price…

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…

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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…

eating the same food every day

Same Salad, Different Day

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?

stockmarket charts: how safe are index funds, anyway?

Beware of Geeks Bearing Formulas

The history of finance is a history of brains dashed on the pavement. The fact that many people tend to be ‘irrationally’ wary of the markets starts to take on a new significance: the suspicious folk-wisdom has often been correct, while the ‘experts’ have consistently been dangerously wrong.

Hence Warren Buffett’s warning: beware of geeks bearing formulas…

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.

A Fistful of Dong: The Cost of Living in Da Nang, Vietnam

This is the first time I’ve felt a little guilty about writing one of these posts. The beach town of Da Nang is an underappreciated gem. It’s the smallest of the big five cities in Vietnam, and much less well-known than Hanoi or Saigon.

But it’s been vaunted as an up-and-coming hub for digital nomads in recent years, so the cat’s out of the bag already. If it starts getting overrun with bitcoin enthusiasts and wellness coaches, I swear it’s not my fault…

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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…

Digital Minimalism review - cover image gazing into the abyss

Digital Minimalism Review: Gazing Into the Abyss

Maybe you hear a mischievous little voice in your head that whispers ‘jump!’ every time you walk across a bridge, or lean over a balcony. In a similar way, I have recurring fantasies of shutting down my social media profiles, deleting this website, and generally trying to erase my presence from the Internet.

And so, I need to read a book called Digital Minimalism like a depressed person needs a lecture on antinatalism. Of course, I read it anyway…

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Tips For Reading 100+ Books a Year

There’s a stomach-sinking moment of realization that comes in every reader’s life: you’ll run out of years long before you run out of books. Like the monstrous hydra, every title struck off your reading list spawns three more to take its place. The unread piles glowering at you from the bedside table only grow larger. So many secrets, so little […]

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 […]

Living on $10,000 a year: Deep Dish 2018 spending report

Living on $10,000 a Year: Attempt #2

Last year, my goal was to live the good life on less than US$10,000. I ended up going about six hundred bucks over my target, but was pretty happy with the attempt. This year, I didn’t have any particular goal in mind. Since I’d already built a spreadsheet and got in the habit of tracking my expenses, I kept up […]