Optionality: How to Survive and Thrive in a Volatile World
Richard Meadows, 2020
The best predictor for good writing is the writer, and I really appreciate it when I come across sincere works that only that specific person can produce. Like many others, I came across Richard's work through the How to Save $100,000 by Age 25 article on his blog the Deep Dish. At the time it felt like someone dumped an ice bucket on me yelling... What are you doing, spending all your money on worthless crap! Since then I've followed his journey to accrue what he calls in the book the "currencies of life": knowledge, financial, social and health capital - all in the pursuit of a strange little thing called optionality: the right, but not the obligation to take action.
The book draws on many timeless lessons from the likes of Naval Ravikant, Taylor Pearson, Venkatesh Rao, Kevin Simler, Cal Newport, and Tyler Cowen. Although I follow these people's work directly and was already familiar with most of the concepts introduced in the book, it was still interesting to learn about how Richard incorporated these lessons into his life and how they got him to where he is today. It never felt like I was reading an encyclopedia of mental models for creating optionality (though you could treat it that way if you want), instead it was colored with the anecdotes that only someone who has walked the walk can share, all with that unique Deep Dish comedic twist.
Key themes that spoke out to me: leverage, asymmetries, and just how applicable the barbell strategy can be for various aspects of life. The trick is to prune everything that doesn't matter to truly elevate the ones that do. The "ones that do" in this case being the things that have a capped downside but unbounded upside. One example being how you spend your money. Applying the barbell here means: splashing out on a small set of items, and be frugal with everything else. The splash-out category includes your "tools of the trade" - a laptop that whose downside is capped at $2000 and upside is unbounded when you use it to write code, design products, or publish your writing. The economical category are things like T-shirts to lounge around in. It seems simple to do, but many people are still wasting their hard earned cash with things in the middle of the barbell like a regular T-shirt that has been marked up several times in price when a logo was slapped on it.
Concrete examples and actionable tips like these run throughout the book, I won't include anymore because I'd recommend you pick it up and see what resonates most for yourself. It's split into 6 mini-books to answer different questions of optionality: why, how, what, what if, when, and what next. Respectively, these cover: reasons you should bother with optionality, the art of decision making, where to look for asymmetries to accrue your currencies of life, risks, timing, and meaning-making. I loved that the book was structured this way because makes the content modular but still allow the concepts to build upon each other.
This is the sort of book that you wish you could gift to your younger self. It contains bookshelves-worth of how you can increase the surface area for "luck" to happen. I imagine that for an 18 year-old, stuck wondering about her place in the world, this book contains enough of what Robin Hanson calls "*viewquakes"—insights which dramatically change your world view—to start looking to possibilities outside the constraints of the superficial values and zero-sum games that many are stuck playing today. No matter how old you are, this book would likely contain some viewquakes for you. In recent years I've come to believe that happiness is not the light at the end of the tunnel, it can be found in every step you take through the tunnel itself. The trick is to know where to look. Humanity has a lot more options today than at any other time in history. So if you've been feeling stuck, the best time to start looking was yesterday, but the second-best time is now.