Hello! My name is Richard Meadows. I’m a journalist, itinerant bum, and finance columnist. I started Deep Dish in 2016 because I wanted a place to document my personal experiments and, metaphorically speaking, let it all hang out.

For a structured overview of the blog and a selection of the best posts, check out the Start Here page. For a distillation of my ideas and life philosophy, check out my book, Optionality.

If you want to know a bit more about me, here’s my attempt to thread all my ideas and mistakes into one semi-coherent narrative. It’s kind of self-indulgent, but hey. You asked for it!

Accumulation Phase

My first job as a business reporter tossed me headfirst into an ocean of money. Not literally, unfortunately: journalism is not exactly lucrative. But someone did put me in charge of the Budget Buster column, which meant I got to explore a new financial topic every week (now six years and counting!).

After interviewing the unofficial leader of the early retirement movement, Mr Money Mustache, I started making a raft of lifestyle changes. Eventually I was saving half of my income, and built a spreadsheet to measure and track my progress. In three-and-a-bit years, I went from being penniless to building a net worth of $100,000.

With the savings pouring in, I needed somewhere to put my cash. I started learning about the basics of investing, lost $10,000 in the worst investment ever, then got straightened out by a billionaire hedge fund manager.

While compound interest was working its magic, I was lucky enough to start building momentum in various other domains, including health, reading ability, and notetaking. I later learned these were local instances of a freaky and all-pervasive force of nature called the Matthew Effect.

I also published my best-ever piece of gonzo journalism: eating 222 large pizzas in a row to try and make a point about dumb nutritional advice.

And just like that, the ‘Deep Dish’ was born!

Exploration Phase

Stashing six figures of fuck-you money was the trigger to quit my job, get rid of all my worldly possessions, and buy a one-way ticket overseas.

I wanted to see the world, free up some time to tackle the various projects swirling around my head, and relax a little from the strictures of the business world…

before and after
before and after

Living out of a 22L daypack forced me to scrutinise every new possession that came into my life (I unironically think Marie Kondo is a genius).

Besides walloping me over the head with my own good fortune, travel generated a constant stream of ambiguity, and got me thinking about the importance of community.

After meeting a nomadic tribe of entrepreneurs and freelancers, I accidentally started living the real-life four hour work-week. My favourite haunts included Chiang MaiDa NangBali, and Medellín, which helped keep my expenses as low as $10,000 a year (breakdowns for 20172018, 2019).

I used this time to cut back on TV and social media, and started flexing my writing muscles. My first blog post went viral, and my ugly mug ended up splashed across international media sites. That was trippy.

I also started doing copywriting for the likes of American Express, some technical writing—including the white paper for Roam Research—and freelancing for outlets like VICE and Sunday magazine.

Crisis of Faith

I used my sabbatical to read a shitload of books and meet smart people, which had the effect of rubbing my face in a puddle of my own ignorance. After venturing down the rabbithole of behavioural economics, voodoo psychology, and signaling theory, I became pathologically self-conscious about everything.

At the same time, I was finding out that extreme personal freedom was kind of freaky. All the constraints I’d boldly removed had left me untethered. I decided offices and routines might actually be good for getting shit done, being self-employed is a mixed blessing, unbridled hedonism is kind of dystopian, and work is not necessarily something to escape from.

I lost my enthusiasm for the whole ‘early retirement’ thing, and became less judgmental about the trade-offs people make around money. My beloved minimalism and frugality turned out to be tribal identity movements—or in the worst case, masochistic pissing matches. They were useful constraints, but they weren’t quite what I was looking for.

The Optionality Epiphany

I’d long been interested in the concept of ‘optionality’, which I first came across in the writing of Nassim Taleb. I started wondering if it might contain the grand unifying theory of flourishing and risk management, and… I haven’t been able to stop thinking about it since.

After years of work, revisions, and missed deadlines, I finally finished my book on the subject, the highly imaginatively titled ‘Optionality‘. This ended up being the best piece of work I’ve ever done.

Optionality is agnostic to the truly bewildering range of human values and preferences. It offers insurance against an increasingly unpredictable world: tail risk events like the COVID-19 pandemic, the tunnel vision of rigid goals, the importance of developing broad skills, preparing for a market crash, and justified suspicion of geeks bearing formulas.

With the optionality approach to getting lucky, I hunted for asymmetric returns, used a barbell strategy to balance speculative projects, and rejigged my portfolio to get some exposure to potential moonshots.

I also loaded up on other cheap options with massive upside: reading books and blogs written by weirdos, meeting lots of people, putting my own ideas out into the world, replying to thousands of emails from readers, freely giving praise and gratitude, and investing social capital (or cold hard cash) in friends and strangers whose talents had not yet been widely recognised.

This strategy has worked out very nicely so far: mostly in avoiding shooting myself in the foot, but also in systematically collecting opportunities for major upside. Some of these options have started paying out, and the future looks promising.

The Exploitation Phase

exploitation phase

As I approach the ancient age of 30, I’m twiddling the dial a little away from ‘exploring’ and towards ‘exploiting’.

I firmly believe that most people don’t do anywhere near enough exploring. And I’m still optimising my life to maximise opportunities for serendipity to strike.

But as I learn more about myself, and collect high-quality options, I’m taking my foot off the gas.

That means slowing down the travel, and spending at least six months or a year in any given country. It means selling out to Big Stuff: owning more beautiful, high-quality things, loosening the purse-strings on other spending, and lugging around an entire checked suitcase’s worth of possessions.

It means fewer quake books, and less of a fixation on trying to hoover up All The Knowledge.

And in some areas of life, it means stopping the optimisation process altogether. I had a good talk about status anxiety with Alain de Botton, and set some concrete ‘Good Enough’ metrics to force myself to stop and smell the flowers.

In the realm of health and fitness, I’m pretty much done. I’ve decided that calisthenics is the king of all exercises, feel good about my plant-based diet, will happily eat the same meals almost every day, and am generally a creature of habit.

I’m no longer looking for novelty in daily life, either. Something I never expected is that my greatest source of satisfaction comes from long, sustained periods of work, with occasional breaks for travel or hedonistic stuff. I love productivity porn now. WTF?

Right Now


  • As of 2020, I’ve dropped almost all my other projects to finish the Optionality book


Health and Fitness

  • Experimenting with a couple of nootropics (modafinil, melatonin)
  • Practicing periodic extended fasting for 5-7 days


  • Learning a second language
  • Experimenting with knowledge management techniques (variations on Zettelkasten, SRS, and the latest from the Roam Research cult)


  • Developing an interest in aesthetics after years of thinking it was dumb
  • Starting out with the principles of design; looking forward to learning more

What Else?

My God. You’re insatiable!

– Rich

The end