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…

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…

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 […]

Fuck-You Money Part II

If you ever need a refresher on the importance of fuck-you frugality, go peel off a $100 bill, and subject yourself to the silent, brooding judgment of Benjamin Franklin.

The side-eye is so doleful it traverses time and space. It’s almost as if Franklin knows his face is about to be a) rolled into a tube and stuck up some degenerate’s nostril, or b) used to purchase another superfluous piece of junk that will, in short order, be discarded upon a mountain of previously purchased superfluous junk.

Franklin’s not mad; he’s just disappointed. He wants us to be better…

Somebody wants you to do something, fuck you. Boss pisses you off, fuck you! Own your house. Have a couple bucks in the bank. Don't drink. That's all I have to say to anybody on any social level. Did your grandfather take risks? I guarantee he did it from a position of fuck you. A wise man's life is based around fuck you.

The Joy of Fuck-You Money

Humphrey Bogart used to keep a $100 bill in his dresser drawer at all times—a decent chunk of change in the 1920s. He referred to it as his ‘fuck-you money’, because it meant he’d never be forced to take a crappy part. According to Bogie, the only good reason for making money was “so you can tell any son-of-a-bitch in the world to go to hell”.

Unlike Bogart, I am not a tough guy. One time I cried in front of my boss. She gave me the rest of the day off. In fact, all my bosses have been great. I’m struggling to think of a single person I’d like to say ‘fuck you’ to.

But there are plenty of people who I’d like to politely say ‘no thanks’ to. And I say it all the time! It’s great. If I think back on the last few years, fuck-you money has changed my life.

Tabah lot, Bali on the cheap cover image

Bali on a Budget: Living on Less Than $800 a Month

Bali offers a delightfully low cost of living and high quality of life. This being my fourth trip in as many years, I figure I’ve got enough spending data to do a decent breakdown of my expenses.

I’ve tracked every last rupiah during my time here, and crunched the numbers on my spending. What follows is a full cost-of-living breakdown including all the nitty-gritty stuff (like insurance and bank fees) which most reports seem to forget or ignore.

Futurama compound interest cover image

Futurama Taught Me Everything I Know About Compound Interest

Futurama is one of the greatest cartoons of all time. If you haven’t seen this gem of the early noughties, here’s the basic premise: Pizza delivery boy Fry accidentally falls into a cryogenic freezer at the turn of the new millennium, and wakes up 1000 years in the future.

In the sixth episode, ‘A Fishful of Dollars’, Fry re-discovers his old bank account, which contained the princely sum of 93 cents at the time he was frozen. Over the 1000 years he spent as a human popsicle, he is told the balance has compounded from less than a buck to the staggering sum of $4.3 billion. Hijinks and capers ensue…

Why Im buying the iPhone X, and you should too

Why I’m Buying the iPhone X (And You Should Too)

I’m on the verge of tears by the time the Apple keynote livestream starts, because I’m sure the WiFi will lag. But it runs smoothly, and relief washes over me in an awesome wave.

Tim Cook takes the stage. “Apple has always believed that technology infused with humanity can improve people’s lives and change the world,” he says.

It’s a powerful statement, delivered with a grandeur that approaches the sublime. The universal message crosses all boundaries and instills one with the hope that it’s not too late for us to better ourselves.

The iPhone X is the star of the show. Oh, my God! Look at that subtle golden finish. The tasteful slenderness. It’s made from an aerospace-grade 7000 series custom aluminum alloy. The glass has a seven-layer colour process, to make sure it’s a beautiful precise hue. I’m sweating…

Specialisation is for insects - Elon Musk's Roadster cruises through space

Specialization is For Insects

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…

Living On Less Than $10,000 a Year

At the start of 2017, one of my goals was to try and maintain a flâneur lifestyle while living off less than US$10,000 (or NZ$15,000).
I’ve logged every rickshaw ride, every water refill, every bowl of noodles. Nothing escaped the merciless conditional formatting of my spreadsheet, which blazed a furious red whenever I overshot my daily or monthly spending targets. Now, with an entire year’s worth of spending data in front of me, it’s crunch time. Here’s how I did…

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…

A Sense of Perspective: The Time I Received Five Marriage Proposals in One Day

The Time I Received Five Marriage Proposals in One Afternoon

That fateful afternoon in the slums of Jakarta is seared into my memory forever. No ego-boost here – just people desperate to escape from grinding poverty. Travel is a uniquely powerful way of broadening your perspective, but talk is cheap. No amount of sanctimonious think-pieces and gratitude journaling will put food in hungry bellies. The good news is, we have an amazing opportunity to actually do something…