Hi. I’m Richard. I started this blog to document my experiments, and help others who are interested in taking a few steps off the beaten path.
If you want to read more about me, head on over to the ‘About’ page. For a distillation of my work to date, check out my book Optionality.
Most people follow along through my email newsletter. I try to write high-quality posts, which means you’ll only hear from me once or twice a month (three times if I’m on fire).
When you sign up, I’ll also give you some free tools and resources, including the custom net worth tracking spreadsheet I used to hit my savings goal.
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Where to Start?
The underlying theme of the Deep Dish is generating high-quality options through simple living and exploration. Here’s a taste of the most-used tags:
Feel free to jump into the archives and work your way through all of the posts in order. If you prefer a hand-picked selection, here are my most popular and/or useful pieces in each topic area:
- How to Save $100,000 by Age 25 – My viral ‘coming out’ essay on the benefits of simple living, which set the stage for everything that followed
- The Joy of Fuck-You Money – How to improve your life with a relatively small sum of money, rather than eat shit sandwiches for years while grinding toward ‘early retirement’
- Net Worth Tracking – Cutting through the smoke and mirrors of financial success, and measuring the only number that matters (includes spreadsheet)
- Constraints That Liberate – Imposing deliberate constraints to generate high-quality options in life
- The Optionality Approach to Getting Lucky – A primer on asymmetric options: hunting for Treasure Chests (capped downside + open-ended upside) while avoiding the Bottomless Pits of Doom (open-ended downside + capped upside)
- The Embarrassing Problem of Premature Exploitation – The forces that conspire to force us into settling for low-quality choices, instead of continuing to explore and build optionality
- Time Travel for Pleasure and Profit – The difficulty of predicting our own future preferences, and why optionality becomes more valuable as the world gets increasingly weird
- The Barbell Strategy for Buying Quality Stuff – After hitting peak pathological penny-pinching, I lay out a model for deciding what’s worth splashing out on
- The Year of Becoming a Fancy Bitch – On relaxing the pursestrings slightly
- An Animated Investing Guide for Beginners – Exactly what it says on the tin
- The Efficient Markets Hypothesis is Not Dead – Why you almost certainly can’t beat the market, and coming around to the serenity of passive index investing
- Beware of Geeks Bearing Formulas – Nitpicking the hidden assumptions of the FIRE movement, and modelling how well they hold up in edge cases
- The Barbell Strategy for Bastards – How I bastardised Nassim Taleb’s investing advice and rejigged my portfolio to get exposure to asymmetric returns
- Getting Rid of All Your Stuff Feels Like Taking a Big, Dreamy Dump – On the satisfaction of ditching all my worldly possessions to go live out of a backpack
- Throw Away Your Television – A sanctimonious rant about passive leisure, addiction, and opportunity costs
- The Life-Changing Magic of Tidying Up is Utterly Deranged, and I Love It – The method behind Marie Kondo’s apparent madness, and why ‘does it spark joy?’ is the best life heuristic I’ve ever come across
- Digital Minimalism Review: Gazing Into the Abyss – The case against solitude, shopping for a new identity, and making more deliberate trade-offs
Health and Fitness
- The Pizza Diet: Eating 222 Large Pizzas In a Row – The problem with restrictive diets and the concept of ‘clean’ and ‘dirty’ foods
- Same Salad, Different Day – Increased mental bandwidth, health benefits, and guilt-free enjoyment of taking an 80/20 approach to eating
- Fat People Are Heroes – Exposing the dirty little secret of muscular people by applying the Matthew effect of cumulative advantage to obesity and fitness
- Losing 20kg and Readjusting to Life as a Skinny Guy – A personal essay on quitting weightlifting, body image, and rapid weight loss
Goals and Vaulting Ambitions
- Goals Gone Wild – Why most goals are kind of stupid, and should be used as sparingly as possible
- Is The Law of Attraction Real? – Predictive processing, voodoo psychology, and the perils of fetishizing positive thinking
- Getting to ‘Good Enough’ – Reining in Type A impulses, stopping to smell the flowers, and slouching towards mediocrity
- How Not to Be a Starving Artist – Using a barbell strategy to balance speculative projects with a conventional stable career
- Specialization is For Insects – Making the case for accumulating broad skills across many different domains
- Better to Reign in Hell Than Serve in Heaven – Charting a middle path between unconstrained personal freedom and wage slavery
- Living The 4 Hour Work Week – Dissecting the monster Tim Ferriss created 10 years ago (the good bits, and the slightly manky bits)
- The 100 Books Challenge – Very earnest personal essay on my relationship with reading over the years, and laying out a challenge to myself
- How to Read 100+ Books a Year – On finally completing the challenge, the tricks and techniques I learned, and why I won’t be repeating it
- Quake Books That Shake Your Foundations and Rattle Your Brain – A chronology of ‘view quakes’ over time, and the importance of creative destruction to prevent calcification
- Hiking the Himalayas in Flip-Flops – Fun but kind of dumb adventure in which I learn the difference between the Remembering Self and the Experiencing Self
- The Madness Of Crowds – On signalling and social contagion, the Mona Lisa as aesthetic herpes, and why it pays to go where the tourists aren’t
- The Benefits of Travel – Being forced to deal with a constant stream of ambiguity, solve problems on the fly, and bend with the winds of fortune
- Ultralight Travel Packing List: 10 Countries, One 7kg Bag – The challenges and rewards of compressing an entire life into one little bag
- Meditations on Momentum – Unmasking the force of nature that creates ‘compound interest’ in every domain of life, and its terrifying implications
- The Brave New World of Wireheading – Why pure hedonism is dystopian, and the difficulty of resisting primitive forms of wireheading
I love hearing from like-minded people, and I try to reply to every email (it sometimes takes me a little while to clear my inbox, so give me a few days’ grace).
If there’s anything I can help you with, feel free to get in touch using the Contact form. I’m pretty inactive on social media but you can also hit me up on Instagram (mostly travel pics and calisthenics stuff), Twitter (occasional hot takes), or come be my friend on Goodreads (book reviews and recommendations).
Hope you enjoy exploring the site.