What I’m up to now, what I was up to before, what I was up to before that, etc

Go to the Start page for an overview of the blog and a selection of posts.

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

Now | Accumulation | Exploration | Crisis | Optionality | Exploitation

Right now

(last updated in 2024)

My daughter just turned one. Trying to savour every moment of my time with her. I’m shifting my identity to ‘house husband’, it’s weird but I’m into it. Building furniture, doing some home improvements. Check out my sweet built-ins.

I spend a few hours a week writing options premium for income. My first couple years of trading were shit but things are going well now. I am cautiously optimistic.

On the creative front, hyped to return to blogging after a long break. Learning how to edit audio for book club with the fellas, loving have a lower-friction creative outlet. Feels like less is at stake now I have no audience. Want to try my hand at short fiction but don’t have time right now.

On the health front: getting married in January, so doing a little bulking cycle for vanity reasons. Keep getting waylaid by daycare sicknesses but it’s getting better. Playing club tennis, starting to improve again after newborn-related plateau. This is maybe the best year of my life so far.

Accumulation phase

After interviewing early retirement guru Mr Money Mustache, I started saving as hard as possible. I faithfully measured and tracked my progress, and took my net worth from zero to $100k in a few years.

Having learned the basics of investing, I almost immediately lost $10,000, got straightened out by a billionaire hedge fund manager, and remain an efficient markets true believer to this day (…mostly).

With compound interest doing its thing, I started trying to build momentum in other domains, e.g. health, reading ability, note-taking.

I also published a piece of gonzo journalism that haunts me to this day: eating 222 large pizzas in a row. The ‘Deep Dish’ was born.

Exploration phase

The end

Once I had some fuck-you money I quit my job, got rid of all my worldly possessions, and bought a one-way ticket overseas. 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).

Travel walloped me over the head with my own good fortune, 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 did some writing projects. My first blog post went viral, and my ugly mug ended up splashed across international media sites. That was trippy.

I also started dabbling with copywriting and technical writing, for e.g. the white paper for Roam Research, and freelancing for e.g. VICE and Sunday magazine.

Crisis of faith

Reading a shitload of books and meeting smart people made me realise how dumb I was. After tumbling down the rabbitholes of voodoo psychology and signaling theory, I became pathologically self-conscious.

At the same time, I found 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, and unbridled hedonism is kind of dystopian.

I fell out of love with the whole ‘early retirement’ thing, and realised that while minimalism and frugality were useful constraints, they weren’t quite what I was looking for.

Optionality era

Having learned the concept of ‘optionality’ from Nassim Taleb, I couldn’t stop thinking about how it might contain the grand unifying theory of human flourishing.

After years of revisions and missed deadlines, I finally finished my book on the subject, the imaginatively-titled ‘Optionality’.

Optionality is important because 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, balanced speculative projects with a barbell strategy, and rejigged my portfolio to get 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.

Exploitation era

exploitation phase

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

I think most people don’t do anywhere near enough exploring. And I’m still running experiments that create 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. It means selling out to Big Stuff: owning more beautiful, high-quality things, and loosening the purse-strings on other spending. 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. For e.g. in the realm of health and fitness, 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. After talking about status anxiety with Alain de Botton, I set some concrete metrics to force myself to stop at the point of ‘good enough’.