Essays

It's a small world, but I'd hate to have to paint it.”  —Steven Wright How confident are you about your ability to judge your own expertise? Do you think you generally know what you are good at and what you are bad at? Most people suffer from overconfidence bias. They tend to think that they know more than they really do. But surely you, in your infinite wisdom, are not one of these … [Read more...]

Horace Mann, often credited as the father of the modern education system, began opening The Common School in the 1830s. The purpose of the Common School was to teach students how to follow directions effectively so they would be prepared for factory work. A few years after the first Common School opened, Mann couldn’t find enough “normal” teachers to help make the students “common.” So, Mann … [Read more...]

“Whenever you feel that some situation or some person is ruining your life, it is actually you who are ruining your life…Feeling like a victim is a perfectly disastrous way to go through life. If you just take the attitude that however bad it is in any way, it’s always your fault and you just fix it as best you can — the so-called “iron prescription” — I think that really works.” — Charlie … [Read more...]

Developing a basic understanding (and a sense of intuition) around how complex systems and complexity science work may be the most important things I’ve learned and it's deeply impact my thinking. What is Complexity (Science)? Before we talk about complexity science, it's important to understand how the term complex is used. A complex environment is one where cause and effect are impossible … [Read more...]

When I learned to read, I was focused on trying to consciously remember what each chapter was about after I finished it. Like most most people, most of the reading I did growing up was for school. The reason you read something for school is because there is a test. You test well by being able to hold a factual account of what happened in the book in your conscious memory. Over the … [Read more...]

TL;DR The OODA loop was a tool developed by military strategist John Boyd to explain how individuals and organizations can win in uncertain and chaotic environments. It is an Acronym that explains the four steps of decisions making: Observe, Orient, Decide Act. This article will give you the understanding you need to turn ambiguity into advantage and risk into results in your career, … [Read more...]

I love Derek Siver’s question: “What are you optimizing your life for?” For the last few years, my answer has been “interesting.” I always felt sort of dumb for saying that, but then I read a paper called Driven By Compression Progress. The paper looks at humans as information processing machines that are compressing information to make themselves more efficient. Compression is the ability to … [Read more...]

TL;DR Making a core values list takes 15 minutes and will help you make better decisions. Note: If you’d like to skip straight to the full list of personal values, click here. Have you ever been faced with a difficult decision and not known which direction to take? Have you ever spent days or weeks or months going back and forth on a decision? You start with “Yes I will do it,” then “no I … [Read more...]

Margin, in a strict business sense, is the difference between how much you can sell a product for and how much it costs to produce. In a more general interpretation, margin refers to the edge of something, the amount which something falls short of or surpasses another item. You can build margin into your day by leaving a gap between your scheduled meeting and tasks so that you have room to … [Read more...]

Early in his life, Benjamin Franklin, one of the primary framers of the American Constitution, outlined his best morning routine: “...I rise early almost every morning, and sit in my chamber without any clothes whatever, half an hour or an hour, according to the season, either reading or writing.” In Franklin’s Autobiography, he elaborated he would “rise, wash, and address Powerful … [Read more...]

  What do the world’s foremost tank commanders, chess grandmasters, and SaaS entrepreneurs have in common? What are the shared attributes of people who have achieved mastery across different domains? How to become an expert in your field? Likely you’ve heard the cliched advice: work hard, work smart, be passionate, etc. Here’s one you probably haven’t heard that’s actually more … [Read more...]

  If you’re trying to reach your potential, when should you double down on your strengths and when should you mitigate weaknesses? One view as it relates to whether you should optimize for stronger strengths or shoring up weaknesses is that “if you work on your weaknesses you'll end up with a lot of mediocre weaknesses.” This is terrible policy. You can do fine in life if you are … [Read more...]

There are at least two overarching mental models for looking at the world: One could be called the bell curve and the other, the 80/20 curve. When I was marketing my book, The End of Jobs, I spent a week sending personal emails (in Gmail, one by one, not in bulk) to two hundred people who I thought could potentially be in the top 1% of my readers, the people most excited about the book. In … [Read more...]

On a snowy day in late 1927, a young corporate executive looked down past his toes, past the trusses of the bridge he was standing atop, and stared into the choppy waters of Lake Michigan. Earlier that year, his first daughter had died and he had lost his job as president of a building company. For years, he had been plagued by a fear of failure and now it had all come true. He had no job, no … [Read more...]

  “New metaphors are capable of creating new understandings and, therefore, new realities.” -Lakoff, George; Johnson, Mark. Metaphors We Live By How many times have you heard some platitude that translates to “improve your mindset?” I get why people give this advice. I can point to certain mindset shifts that have had a profound impact on my quality of life and would like … [Read more...]

  There is a difference between correct/incorrect and right/wrong decisions, and over the long run it’s much more important to be correct than right.   I discovered this framework in What I Learned Losing a Million Dollars by Jim Paul and Brendan Moynihan. The correct/incorrect distinction is based on the Expected Value (EV) of the decision. Right/wrong is based on … [Read more...]

“Jeez, man, that motorbike almost ran you over!” I gave a perfunctory wave to the British backpacker, acting as if crossing a busy street in downtown Saigon without looking was normal behavior and strolled on. The Vietnamese office worker turned his head back at me and glowered before rolling his right wrist back and accelerating away on his red and black Yamaha Nuovo. The white cord of my … [Read more...]

I was sitting outside a wine bar with some friends a few weeks ago and we were going around the circle answering the question - "what are you most excited about right now?" "Online publishing!" I blurted out. Peter Thiel poses the question in his new book Zero to One- "What important truth do very few people agree with you on?" While I think the secret about online and self-publishing is out, I … [Read more...]

"You can have virtually anything you want, but you can’t have everything you want." - Ray Dalio "Our experience tends to confirm a long-held notion that being prepared, on a few occasions in a lifetime, to act promptly at scale, in doing some simple and logical thing, will often dramatically improve the financial results of that lifetime. A few major opportunities, clearly recognizable as … [Read more...]

  Something that I get asked a lot is how I read so many books. People often want to know how to read more often. Last year I read 60 books and am on pace for about the same this year. I'm not going to win any contests but it’s a pretty good pace for me. I’m a subscriber to the voracious input, focused output theory of productivity. A book a week gives me more than enough to chew on … [Read more...]

Are your friends or colleagues bothering you that you must read Antifragile? Did you just finish and aren't quite sure if you wrapped your head around it? As part of my work at Mutiny Funds, a deep area of interest for me is how to make systems more antifragile, starting with investors portfolios and going from there. To that end, these are the notes that I put together for myself after … [Read more...]