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.

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.

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.

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.

As I always say, I really do believe that I have the best group of friends that a guy could ask for. I use friends as a shorthand, but I really mean it to include everyone who surrounds me, including my wife and my family. The people in my life are truly incredible, and a day doesn't go by where I don't think about how lucky I am to have them in my life.

Across a lot of dimensions they're very different, but most or all of them have a few core things in common. I first realized this many years ago when I was so busy with Sett that I no longer had time to just hang out with everyone all the time. I thought about all the people I was friends with and wanted to become better friends with and distilled down what they had in common.

By far the top quality that is shared with everyone is that they are all very genuine and authentic. That can mean a few different things, but I mean it to say that none of them try to put on a front and pretend that they're someone they're not. They know who they are and they accept it.

This feels normal to me now, because I spend very little time with strangers, but on the rare occasion I spend time with someone who isn't as authentic it is plainly obvious immediately and I notice how much effort it takes for me to accomodate the difference. Someone who puts on a front is generally doing it to mask a big insecurity, and that insecurity needs to be walked around in conversation.

Living in an RV was one of the best things I could have possibly done for the eight or so years I did it. It allowed me freedom, both physical and financial, made it easy for me to travel, forced me to become minimalist, and taught me a lot. If I were still living in an RV today, that would probably be a mistake.

When I moved to LA for a year to learn how to date, I was out in clubs nearly every night. I dressed crazy and had few obligations that weren't social. I grew tremendously as a person during that time, but I couldn't be more glad that I'm not doing it anymore.

In 2008 I had a backpack worth of stuff and I left the US for nine months on a backpacking trip around the world. I don't know any other way I could have gained the perspective and learned as much as I did, but my possessions can't fit in a bag anymore and I'm in the US almost every month.

Those are three examples, but I could go on for days about all of the things that I did, especially things that defined who I was, that I no longer do. I don't regret any of them, but I am simultaneously glad that I am no longer doing them.

As I wrote (last week), it's very easy to criticize problems, and it's easy to categorize things as good or bad without any nuance. I think that it's a lot more productive to recognize the good in everything and everyone, and so in that spirit I'd like to challenge myself to share some positive things about things I don't like.

Fast Food

I never eat fast food myself, but I am impressed with how efficiently our system can bring people nutrition. It may not be ideal nutrition, but I think it's great that people who are struggling can get a quick and tasty meal for not much money.

Apple Products

Last week I posted about buying our fifth group property, an apartment in Tokyo. I got more emails and messages about this post than any in recent history, and people asked a lot of good questions, so rather than address them individually I will answer them all in a blog post. It's also worth mentioning that I go into more detail on the topic in my last book, Forever Nomad.

How is this actually better?

Experience

A few people asked questions about how this is actually better than just renting an AirBnB. I think that this is a really good question and is the hardest one to answer. I've tried a few times and I think I've done a bad job at actually getting the idea across, so I'll try in a little more detail here.

For the past three years I've been actively searching for an apartment in Tokyo for my friends and I to buy. It was by far the most difficult city in which to find a suitable apartment, and even up until I got the notification a few minutes ago, I wasn't entirely sure that it would happen.

One of the biggest challenges in Tokyo is that you must buy a vacant apartment. An apartment that is occupied may take years to vacate, as apparently renters are entitled to renew their leases with no price increase. If you want them to leave or even to increase their rent, they must agree to it.

Location in Tokyo is not as simple as finding the center of the city and trying to get as close as possible. The ideal situation is to get an apartment that is a short walking distance away from a station that hosts lines that provide good coverage.

Last, most apartments in our price range (around $100k US) were not only small but only really had one room. I felt strongly that we would want to have two rooms so that two groups or individuals could each have a little privacy.