The normal financial path that's prescribed by our society is to get out of school, get a job, and then start making money and keep making as much money as you can until you retire. That works for some people, but it also leaves a lot of people unsatisfied and feeling trapped within the rat race. I've followed a different path, some parts deliberately and others by accident, and I think it could serve as a reasonable guide for anyone who doesn't want to have a job for life.
First Phase: Some Independent Income
The first phase is just to start making any independent income. The two best times to do this are when you are in school, and thus have few responsibilities but plenty of free time, or when you have a job that you're trying to escape.
Don't try to hit it out of the park, just try to make some money. If you can do it in a way that is perpetual, that's a lot better than something that takes up your time, but either one is good.
I have a surprising number of single friends who are in their 30s. I don't think that this is a problem by any means, but I know that a lot of them don't actually want to be single. I'm married and think that being married is pretty cool, but I could also see a great path being single or just dating, so this post is only for people who are single and don't want to be.
The biggest realization that single people in their 30s need to make is that what they have been doing is not working. Dating is hard, finding the right person is hard, but... you've been working at it for at least 15 years and many other people have been successful in that time. At this point, the problem is your approach, not the outside world.
I would (and did) make dating a top priority. Not in title, but in practice. I would be swiping Tinder and every other app every day, and if that wasn't getting me enough matches I'd be dusting off the boots and making myself approach people in person. It doesn't really make any sense to leave something as important as your life partner up to chance. You wouldn't do that with any other major area of your life.
You can argue that most people meet their significant others by chance, but that's because most people just wait years and hope something happens, not because that's the most effective method for finding love.
I don't usually write about current events because I don't necessarily think that yet another semi-informed opinion floating around is of much value. This time the event is easily actionable on a personal level, though, and I'm personally doing what I can to make the best of the situation, so I figured I'd share.
Before I get started, I want to recognize that some people are suffering and dying, many more are scared, and just about everyone is going to be affected financially. In the short term this is going to be very bad for a lot of people and at least somewhat bad for all of us.
Like most people I have older family members I'm concerned about, and as you can imagine my business was hit to an extreme level. My income is actually negative this month because all I've been doing for the past 30 days is canceling cruises. I don't invest a ton in the stock market, but my retirement accounts took a hit, too. I mention this to put my next few points in context.
Despite all this, I think that over the long term coronavirus may end up being one of the most positive events for humans in recent history. I understand that that sounds crazy or hyperbolic, but I don't think it is.
A couple weeks ago I wrote a post about what I think single people in their thirties should do. A few people emailed my about it, and one reader named Jack asked some really good questions. Rather than reply to him directly, I asked if I could reply to his email as a blog post. Here are his questions, as a single thirty-something-year-old, and my answers.
I actually think most people are not selective enough, or are not selective on the correct criteria. For you to really succeed in a healthy relationship, you should be able to be happy single too. Someone should add to your life, not "complete" it. Someone who is in that position will naturally be selective. I remember distinctly thinking that I'd rather be in a great relationship than single, but would rather be single than be in a merely good relationship.
We all have our own criteria, but there are also some universal ones that I think everyone should consider. Among the most important would be a commitment to growth, and good communication skills. It's great to find the most perfect person ever, but what's more important is the quality of the relationship you will build together, and these sorts of traits will lead to a much higher quality relationship.
In some ways I'm professional advice giver these days. I talk to people monthly and help them make big decisions that will impact their lives greatly. I also do events where 7-10 people join me somewhere and we try to plot the course of their next few big moves. Giving advice is an enormous responsibility, especially when you know it's likely people will follow through on it, so it's something I take very seriously and to which I have given a tremendous amount of thought.
That wasn't always the case, though. When I became a professional gambler in the early 2000s, I tried to convince all of my friends to do it. I was enthusiastic and proactive, but nobody listened to me, even as they saw me do well. The same thing happened when I learned about pickup a few years later.
Those two events were a huge lesson to me. I'd heard that people won't take advice unless they ask for it, but I had cracked two major problems that all of my friends had, and I was absolutely flabbergasted that none of them took my advice.
Now I give no advice unless someone asks, or if I have the type of relationship where there's an assumed openness to advice. I'd say that that group of people is 10-15 in size maximum.
A lot of people in my life seem to be at the end of a phase of great focus. They worked on a startup and sold or otherwise exited it, they built a business that's now running without them, or they left a job and are taking time off before the next thing. It's interesting to see how they deal with the loss of that focus.
I remember being a kid, and my whole life was exploration. One of my favorite things to do was to tromp around through the woods and look for worms, weird bugs, or cool rocks. Sometimes I could smash a rock and inside would be some crystals, like a geode. I had no aim in life, but I didn't need an aim to drive myself. I just went. There were always new woods and new rocks.
This sort of exploration didn't ever seem urgent, but it always seemed important. When we first moved to Austin my siblings and I went out into the woods with purpose every day. Sometimes we would find something new, sometimes we would just go over what we had already found.
That's how I felt when I first found computers, too. There was so much to learn and do, and none of it had much of a point. I'd spend hours trying to get a game to work or to make a program that didn't really do much except show some cool ASCII art and ask me questions.
Feedback I get often is that I do a lot of crazy things that are really fun, but that they aren't practical for normal people. I understand where this comes from. I marvel almost every day at how very good my life is, and how if I didn't already have it, it would seem unattainable. Besides the things that actually matter, like having a great family, wife, and friend group, I get to live in several places across the world, drive a cool car, and generally do whatever I want.
If you're rich, these things would all be very easy to do. But if, like me, you're not rich, you have to rely on finding sweet spots. This has essentially always been the case for me because I've always been frugal and have always had tastes that exceeded my means by normal standards.
A sweet spot is a situation or combination of situations that gives you something that seems like a luxury at a value that most people wouldn't believe.
I bought a two bedroom condo less than fifteen minutes from the strip for under $50,000. I bought an island with a close group of friends for under $10,000 each. I bought my dream car, a Bentley, for $22k.
Common knowledge says that buying a boat is a pretty dumb financial thing to do, and yet I find myself on the precipice of buying one. I'm in a familiar holding pattern where I haven't actually made any committment to doing something, but I also realize I've done enough research to know I'm probably going to do it. Normally I research, do the thing, and then write about it, but this time I thought I'd talk about it before I did it.
About a year ago I realized that you could ski in Las Vegas. I hadn't thought to look before, for obvious reasons. Skiing was a ton of fun, especially with my wife and friends, and it actually increased how much I like Vegas by a couple percentage points.
That realization made me think about what other things Las Vegas might offer that I've never even thought about, especially outdoors things. People who live in Las Vegas often say that the nature is their favorite aspect, which was totally counterintuitive to me at first. I spend all of my working time indoors, so it makes sense to look for outdoor activities for recreation.
The big obvious attraction is Lake Mead. You always hear people talk about it and you see it from above on certain flights. It looks amazing and unlike any other lake I've ever seen. I searched and the marina is under an hour away from my house.
In 2018 I wrote 52 blog posts on a cruise and scheduled them for the following year. They actually ended up lasting more than a month longer because of other posts I wrote in real time throughout the year. I originally did this because I wanted to find a way to eliminate the weekly pressure of having to come up with a topic and write, but I've continued it for a second year because, in addition, I think it produces better quality posts.
Last year when I did this I didn't have any posts I was burning to write. When I revealed what I had been doing, a couple people gave me the feedback that the posts felt a little bit forced and not written out of excitement. I could see their perspective and I think that it was the result of having to come up with so many ideas in such a short time.
This year was the opposite. I had so many posts that I was dying to write all year, so I put them in a text file. When time came to write them I was bursting at the seams to go. I hope that the enthusiasm has come through this year.
I really liked that I could go over my entire year and see what topics I hadn't covered enough and which ones I'd written too much about. I haven't looked through previous years to verify, but it feels like these years, especially this one, have been pretty well balanced.
I have almost no interest in politics, but I am interested in our country and society, so I inevitably get dragged into various political topics. If there's one thing I'm certain of in that area, it's that most people's interaction with politics is both harmful to themselves and counterproductive for society. At the risk of making many readers furious, I'd like to share my thoughts on politics.
First, though, watch my favorite video discussing politics that I've ever seen. It's the interview between Ben Shapiro (very conservative) and Andrew Yang (very liberal). Whether or not you agree with any of either of their positions is not relevant. Look at how they communicate. Both are clearly very intelligent, very respectful, and were looking for areas where they agreed. When they came across areas in which they disagreed, they tried to tease apart the underpinnings of why they disagreed. Sometimes they found common ground, other times they didn't.
I would love to see more conversation in this style. Just how refreshing it was made me realize how starved of intelligent debate our society is. I also found myself agreeing with both of them in ways I didn't expect I would.
Most people agree that division is one of our biggest problems in society. But how many of us can admit that both Trump and Obama did some positive things as well as some negative things? That's such an obvious and basic true statement, but almost everyone will bristle at it. If you cannot concede that a candidate you didn't vote for has done some positive things, and that someone you did vote for has done something negative, you are part of the problem.