Check out my bestselling book on habits, Superhuman by Habit. .
On a recent podcast I was on, I was asked why I took so many risks. I stuttered for a second before answering the question because I was trying to think of an example of a big risk I took. I couldn't think of any, so I had to answer the question in a different way.
At the same time, I understand why people have the perception that I take a lot of risks. I think the difference is in how we perceive risks, and I'd argue that my method of doing so is more accurate.
When I calculate risk, I look at the statistics and before blindly applying them, I ask how relevant they are to me as an individual.
In some cases, they're fairly universal. My risk of dying in an airplane crash is the same, per mile, as anyone else's. The financial risk I accept by investing in a particular stock is the same as well.
But some statistics can be very accurate for a population yet way off for an individual. When I began riding a motorcycle I looked carefully at what actually caused motorcycle accidents. Alcohol was a factor in 50% of crashes, and since I don't drink I can eliminate that. I eat a healthier-than-average diet, so my risk of many diseases is decreased. I'm on my computer all the time so my risk for carpal tunnel is much higher than for most.
There are also cases where a good outcome and a bad outcome are different for different people. In many cases missing a flight would be okay for me because I could stay longer somewhere and have enough experience that I could probably get the airline to give me another flight for free. And if they don't, I have enough miles that I can bail myself out. But for an executive on his way to an important meeting, missing a flight could be disastrous.
You have to consider your individual chances of different outcomes, and then assess how good or bad those outcomes are.
When I decided to drop out of school, my outcomes were very different than most. Getting a normal job was a worst-case scenario for me. I remember thinking I'd rather just be homeless in Hawaii than have a cube job. Some people really love their normal jobs, so we would be opposites there. I like figuring out my own way to earn money and having a lot of autonomy, so having to hustle and figure out how to earn an income for myself was a major plus.
I also learn really well on my own or with a one-on-one coach, and poorly in a lecture situation. I enjoy learning and always seek it out on my own, but school was taking up a lot of the time I would have spent on learning. Other people learn best in classes and take advantage of professors' office hours and study groups. Neither way is better, they're just different.
So for me school was causing me to learn less and was costing me money while bringing me towards a normal job. I felt like staying in school was risky because it was having an immediate negative effect on me and was moving me towards a path that I considered to be a worst-case scenario.
On the other hand, I felt confident I could start a business on my own and really looked forward to doing so. So to me there was no risk in dropping out of school, other than having to disappoint people who worked hard so that I could be there.
Another interesting example is money. A while after I got to the point of "unlimited runway", I had bought just about everything I wanted that was within reach of that order of magnitude of income. I had a good laptop, a good watch, a good motorcycle, a good car, a good house, some good art, and a few good articles of clothing. The income left over allowed me to buy flights and inexpensive healthy food.
The things I could buy in the "next level up" aren't interesting to me. I don't want to eat fancy food, go to expensive nightclubs, fly first class, go on expensive vacations, buy designer clothes, or live in a fancier house. I would enjoy many of these things, I'm sure, but none of them matter to me enough to spend money on them.
However, levels above that are very interesting to me. I'd love to buy really good art, buy an airplane, fly groups of friends and family members around, start a foundation, and hire a private chef.
For that reason, it's actually riskier for me to try to earn small consistent returns than it is for me to try to go big. So I invest my money in more speculative things like cryptocurrencies and a hedge fund. The same is true of how I spend my time. I limit the number of coaching clients I take on so that I can have a lot of time to work on things like CruiseSheet which could someday be sold for a lot of money. Getting a job would be extremely risky as it would guarantee me an income that wouldn't make my life functionally better, but would decrease my chances of creating a valuable company.
Dating is another example. It feels risky to make yourself vulnerable and commit in a relationship, but if you want to find a long-term partner, it's much riskier to hedge your bets, as you're unlikely to find yourself in a relationship that's strong enough to last.
By the way, all of these examples are presented without judgment. School is unequivocally less risky for many, probably most, people. So is investing money conservatively. If you are deeply affected by rejection and don't want a long term relationship, you're better off keeping your cards close to your vest. I chose these examples because the first two put me opposite most, and the last because it's more universal.
One of the main points I hammer through this blog is the importance of making your own thoughtful decisions. I think one of the best parts of this world is our individuality, because I believe that when we're all off doing our own things, that creates a lot of good for everyone. Making your own decisions is the process of using data to guide your choices, but it's also the process of examining the data to make sure it applies to you.
What outcomes are good for you? Which are bad? Are there individual factors about you that make certain outcomes more or less likely? One of few things that's universally risky is not taking the time to direct your own life, as that's a path towards regret and missing one's potential.
Photo is Mount Fuji from a plane I was on today. Cool surprise to see it out the window as I wrote this post.
This feels like a slightly ironic title, as today I spent sixteen hours showing my cousin and her boyfriend around one of my favorite cities in the world, Budapest. No work, except for writing this post before I go to sleep.
On the other hand, the only reason I can take a full day off and not wish that I was working is because I'm in the habit of getting massive amounts of work done in short periods of time.
We all get work done. It's easy to find time to send an email, do a couple errands, and make some progress on a project. But how do you do the big things like write a book, start a new site, or find and purchase a property?
You're going to be disappointed when I tell you the answer because it's obvious and it's not a hack.
Due to CruiseSheet growing and my new coaching project, my income has gone up quite a bit compared to previous years. This has been a strange transition for me, as I'm used to being the guy who doesn't really make much money, but does clever things to maximize it. Now I have a more normal income.
So far I haven't really changed, but I suspect that if things keep going well I will be less relatable to people who don't make too much money when I talk about money. For that reason, I'd like to freeze this moment in time and explain how I think about and use money. I suspect that my habits will mostly stay the same, but you never really know.
People think about net worth and income, and while those numbers are useful, they're just a small part of the picture. Focusing on them will cause you to make mistakes.
The two factors I always think about are runway and quality of life. If those numbers are high, then nothing else matters. They are a complete picture.
I have a technique that I use to deal with a lot of situations that I call setting strong defaults. It started with dating as a means to eliminate the ridiculous and common "but where do YOU want to eat?" loop where each person keeps asking the other person where they want to eat, and tons of time an energy is wasted on a decision no one really cares about. Now I use it for many things, from dating to work.
There's a balance in relationships where women typically want a man to lead in decisions, but also want to be heard and to have the option of having input. Very often men don't realize this and they keep asking their girlfriend what they want to do, only to have the question flipped back to them. They think that they're being nice, but actually they're imposing the responsibility of having to choose on their girlfriend.
To solve this problem, I decided that I would always suggest something with the assumption it would be what we chose, but would always agree to counter-suggestions. So I'd say something like, "Hey, how about if we have dinner at Chipotle?"
If she says that she wants to go to a different restaurant, then I'd just accept and we'd go there, since I don't really care where we eat and my primary motives are to not spend a lot of time deciding where to eat, and to make it easy for her to not have to decide where to eat.
I'm about halfway through a transatlantic cruise, which means I'm also halfway through writing a new book. This time I'm writing a follow-up to Life Nomadic, since so much has changed about traveling and being a nomad since I wrote my first book. Also, the tech section in that book is embarrassingly out of date, so it's time for a refresh.
This time I'm focusing on what it takes to be a nomad in a sustainable way. I'm talking about maximizing points and miles, finding flight deals, beating jet lag, packing, gear, government programs like APEC and Nexus, how to make money, how to learn languages, cruising, and flight tricks. I'm also going to get into depth on what I think is the future of nomadism, which is buying properties with your friends.
I'm keeping this post super short because I have a ton more I have to write for the book today, but I wanted to ask for early feedback. What do you want to hear more about? What would make the book super valuable to you? My primary goal is to enable people to fit as much travel into their lives and budgets as they want.
When you travel most of the time and do it with only a small backpack, eventually all of your travel gear becomes very high quality. You buy something nice, love using it, and it retains its utility for a long time. If you buy something low quality, it breaks or frustrates you, and you end up replacing it with something high quality, which lasts.
Not everything I traveled with was of the highest quality at first, but through that process it became so. I noticed that my mindset changed as my belongings became higher quality, and that convinced me to extend that standard across the rest of my life. At this point nearly everything I use at home or while traveling is the best available.
First, a word about quality, as I often see people who have things they think are high quality, but are not. At least by my definition. Quality is derived from purity of design and from best materials.
When something is designed, I want for it to be designed to complete its function as perfectly as possible, requiring the least from me, and only then to take into account aesthetics. For example, my watch is decent looking, but not as good as other watches. However, the operation of it is a dream come true. Breitling clearly understood that a frequent traveler (they designed it for pilots) would want to be able to know the time anywhere around the world at a glance, but would also need a way to switch between time zones effortlessly. And maybe he'd need to time things.
Most people don't live a life that's in alignment with what they want to do. That's not a criticism of any of those people; for our entire history as a species we have had to spend most of our time doing things we don't want to do in order to survive.
All of us are going to have to do things which we don't want to do. Next week I have to file my taxes. Two days ago I had to wake up at four in the morning. The problem isn't that we sometimes have to do things we don't want to do, it's that we choose life paths that lead towards goals we don't actually want.
This creates a doubly bad situation, because progress towards any goal is filled with things you don't want to do. There's some strategy around minimizing that and finding enjoyment in mundane tasks, but let's not pretend that having people do things which they don't want to do is something to strive for. Then once you reach a goal you didn't actually want, you don't feel as satisfied as you expected you would, the lack of satisfaction creates disappointment, and you have to start on something new again.
I'm fortunate to have a life where I basically love everything I do. I love programming, I love working through problems with people in coaching, I love doing real estate deals with my friends, and I love writing. In my leisure time I do things which really satisfy me, like drink tea with friends, do escape rooms, go to operas and ballets and symphonies, work on little side projects, build things, etc.
Today I woke up to the alarm I set on my phone. My bedroom curtains opened automatically, triggered by the alarm. I walked into the bathroom to brush my teeth. On my mirror, which has a 40" LCD hidden behind it, I saw my agenda and noticed that one of my coaching clients had booked a session for Monday.
I made myself some tea, packed my bag, and headed out to the airport. As I left, my door and security door locked themselves, my water heater turned off (valve and power), the thermostat adjusted its setpoints, and the lights turned off. I hit one button and my vacuum left its dock and started vacuuming.
In that half hour, a lot of things happened automatically.
I haven't tracked it, but I'm guessing that having my curtains open automatically makes me get out of bed faster. It's much easier to pop out of bed when the sun is streaming in than when room darkening curtains are drawn. Let's say that saves me five minutes.
When I first bought my place in Vegas, I did it only because it was an incredible deal. As a frequent visitor to Vegas I assumed that I'd stay there once in a while, and AirBnb it out to recoup my costs. Or if it turned out that I really came to dislike Vegas after spending more time there, I could sell the condo with a small percentage loss that would amount to very little.
Fast forward two years and now I live here, as much as I live anywhere. I haven't analyzed my time, but I'd guess that I spend about half my year here, usually in one or two week chunks.
What strikes me most about Vegas is that it's certainly a place that more people should live. It's not for everyone, of course, but cultural assumptions about it are certainly keeping people out who should be in.
Here are some of the things I love about Vegas:
It's easy to analyze when things go poorly, but that it doesn't come as naturally when things are going well. When things are good it's very easy to just brush it away by assuming that the success was somehow due to you. I know I've thought that many times, especially when I was younger.
As I've thought about some recent successes, I've thought about the value of putting myself out there, making myself vulnerable to failure, with the aim of increasing my exposure to good things happening.
There are a lot of things that you can do to increase the chance of good things happening to you.
If you're dating, you're going to have the best chance at meeting someone good if you're on every dating site, always messaging people, and strike up conversations in real life with strangers you find attractive. You're going to face a lot of rejection that way, but that's the (relatively low) cost you pay to drastically increase your chances at meeting someone good.