When I talk about buying properties with friends (we've bought an island, a flat in Budapest, an apartment in Tokyo, and an apartment in Hawaii), some people get it immediately. Others don't get the point, quickly do the math and realize that they'd save money and hassle if they just stuck with Airbnbs. It's hard to rebut that argument, because most of the benefits are hard to explain unless you've experienced them. But as I sit here in Honolulu Airport on my way back from a trip to Hilo, I think I can use this trip as an example to illustrate why it's worth buying properties with your friends.

First, the decision to do a trip at all was much easier. The three of us that went on the trip all own the property together, so it makes Hilo an obvious place to visit. There are also no logisticts to worry about. We can come or go on any days we want, don't have to check in or meet someone to get keys, and have our minivan parked out front. Imagine if we wanted to go to Maui. We'd need to rent cars, choose an airbnb, and all go on the same days because no one wants to pay for an Airbnb by themselves if others leave early.

And, of course, the marginal cost was totally insignificant. We had to buy plane tickets (or use miles, more realistically), but we had no lodging or car rental costs. Because of this we can go on trips whenever we want, so we tend to travel together much more often. Before owning a place in Hawaii I visited once every few years. Now I go once every few months, almost always with at least one of the other owners.

Once we arrived in the apartment, everything was just as we left it. I changed into my linen Hawaiian shirt and board shorts, both of which sit in a plastic bin under one of the beds. I took out my set of sheets and made up one of the beds. Unlike an unfamiliar apartment or AirBnb, I feel like I'm home.

When I was a kid and something needed to be repaired or built, my father did it. He plumbed things, ran new lights and wires, built new walls, and even built new additions to our houses. Because everything you see as a child seems normal, this all seemed normal to me. It was just one of the jobs that dads had, along with teaching you to ride a bike and driving you to the museum every weekend.

It didn't occur to me that everyone didn't do things like this until one of my roommates hired a handyman to hang a single picture frame. My father was a carpenter and handyman, so like when you copy a copy in a xerox machine, I was a worse handyman. Now that we have a new old house and there are almost unlimited projects ahead of me, I think a lot about how lucky I am to have a father who taught me this stuff.

As I see others approach similar projects, I realize that although there is a skill gap, there are also some gaps in perception. Understanding a few things about construction and doing projects can make you feel much more comfortable and willing to try by yourself.

1. Almost anything can be fixed easily and cheaply, so you don't have to worry too much about messing things up. I recently wanted to see what was in the crawl space above the ceiling and there were no hatches, so I just cut a hole in the wall of a closet and peeked through. Once I saw that there was enough room for me to crawl around up there I expanded the hole to be just barely big enough for me to squeeze through. I don't mind doing this because I know that the small hole would be trivially easy to repair, and even a big one isn't all that hard.

I like writing about things that I used to be terrible at but am now good at, because I can be sure that those things could be learned by anyone. In the past I was unable to stick to anything. I went through various phases of convincing myself it didn't matter and accepting that I would probably never be able to stick to anything because it wasn't "who I am".

In particular I had a very tough time sticking with projects. I would start one project, get bored or frustrated or distracted, and switch to a different one. I was only able to change my behavior when I had a few key realizations:

1. If you always switch projects, you will never finish a project, and thus never receive the rewards of that project. This is incredibly obvious, but never comes to mind when we're thinking about giving up on a project. This doesn't mean that it's always best to stick with every project, but it does mean that you have to have some ability to finish a project.

2. When I want to quit a project, it's usually because I've experienced most of the downsides and none of the upsides. If I'm halfway through a programming project I've done a lot of work, have probably experienced a bunch of frustration, still have some outstanding issues to deal with, and haven't made a single customer happy or received a single penny. It's important to recognize that this is exactly the wrong position from which you should make a decision.

My very first "business" was buying and selling used Palm Pilots and Apple Newtons. I would negotiate back and forth over the smallest increments of money, both on the buying and selling side. When I first started, my inventory was one Apple Newton, so it was important that I get the best price possible.

After making a little bit of money buying and selling these things I had some savings and could start buying things for myself. As you might imagine, I used the same principles in buying those things and still tried to save the most amount of money possible.

I started all this in high school and college, and a lot of my peers were frugal, though often in different ways. I noticed that most frugal people care about absolute price rather than value, whereas I only ever cared about value.

As I grew up, though, I noticed that most of my peers stopped being frugal entirely. Frugality was a response to not having enough money, not to wanting money to buy them more utility. Once they had enough money to buy things, the frugality switch turned off.

I know many people are cursing 2020 and are glad that it's over, but the older I get the more I realize that any time is good time, and that what we do with what we're given is more important than what we are given. So I'll just come out and say it: 2020 was an amazing year, and while it was obviously significantly worse in many ways, it was still overall the best year of my life.

Last year I wrote that it felt like such a dense year, with almost every day being packed and accounted for. This year was mostly the opposite, with long stretches of empty time with not only nothing to do, but very little I could do.

While I wouldn't want every year to be this way, it was really refreshing to have such a big change and to take on the challenge of adapting to it.

As usual, here are the highlights of my year:

There are several different difficulty levels on which you can live your life. They are ascendingly difficult, though the difficulty is really mostly in switching to that method of living. Once you get to the next level it actually becomes far easier. An analog would be financial investing-- it's hard to save a lot of money when you don't have much, but doing so makes it easier for you to live later and also makes it easier for you to save more and invest better.

Most people will use a combined version of several of these levels, so you may not find that you are entirely described by just one.

The easiest level is to do the wrong thing. For example, if you eat garbage food, do drugs, and play video games all day, you never really have to challenge yourself. Most people are resourceful enough that they will figure out a way to survive in this situation, but they will probably not find that their lives become better over time.

The decision making process here is a simple and likely unconscious, "what would give me the least immediate pain?". Ironically the avoidance of immediate pain usually generates (with interest) future pain. Avoid the pain of being healthy now and you are likely to be plagued by disease for decades.

I wasn't planning on writing about this because I don't think it's all that interesting, but so many people have been surprised and asked why we moved that I guess it warrants a post!

Five years ago I bought an apartment in Vegas. It cost $50k, was in a great location, and had two bedrooms. I didn't know what I was going to do with it, but it was just such a great deal that I figured it was impossible that I wouldn't find some good use for it, whether it was renting it out or using it as a crash pad (at the time I visited Vegas every month).

During the renovation I spent more time in Vegas than I ever had, and lived more like a local than a poker-playing tourist. Through that process I discovered that Vegas is the best place to live in the US (unless you need a local job or good public schools), and ended up moving into the apartment full time. Eventually I even sold my RV.

My apartment here was great. I assumed I'd keep it forever, so I went crazy with renovations, doing things like putting heated black marble floors into the bathroom and building a tea room. Once my wife and I decided to move in together, though, it became clear that it wasn't going to be enough space. Luckily the apartment next to us went up for sale, so we bought that one too.

I live in two "bad" neighborhoods. One is my apartment in Vegas, and the other is our shared apartment in Hawaii. The way I'd define both areas is that they're among the cheapest housing in their respective cities, and they're bad enough that when an Uber driver understands where you are going, they feel comfortable saying things like, "Oh wow, that's a really bad place". A guy in Vegas whose job is working with homeless people said encouragingly, "Don't worry... you'll make it out of there some day."

In both cases, my primary motivation was the location, and in both cases the apartments are a handful of blocks away from some of the nicest areas in the city. I've also found that "bad area" usually means "non white people who aren't rich live here" a lot more than it means that the place has problems. I'm sure that there are places I could live in other cities that would be actually dangerous or materially bad.

In both cases, there are a few neighbors that are disruptive. They're loud at night or they argue loudly or they crank their car stereos as they leave for their jobs in the morning. I tend to get along with them okay and have never had any sort of confrontation. Our old downstairs neighbor in Hawaii seemed to probably be on meth and argued pretty loudly with her boyfriend. She also grew a really nice garden that we could see from our window and was really nice to us, so it was more of a disregard or lack of awareness around social norms. Or maybe it's just drugs and alcohol.

There is probably also a slightly higher chance of being the victim of theft, though probably not any other crime. I think the actual chance of being a victim of these things is far lower than the perceived risk, though. The areas seem sketchy, but they tend to not be big targets since it's assumed that if you live there you're poor. The worst thing that happened was a few blocks away (in a much worse looking area) in Vegas an abandoned house became full of drug addict squatters and some subset of them launched a crime spree on our neighborhood. Our house was broken into, as were six others. According to the neighbors who had been there for decades, no one had been broken into there before. That isn't entirely true, though, because someone reached under my gate once and stole my shoes.

This year's gear post isn't all that different from last year's (can you guess why?) but there are enough new cool things that I think it's worth doing one. Hopefully travel becomes a little more normal in 2021 and I have the opportunity to test out some more gear.

Wool and Prince Button Down

I've talked about this button down for who knows how many years now, and I still love it just as much. I still haven't replaced the shirt that I bought two years ago, though a lack of travel this year definitely contributed to not needing to replace it.

Usually in my annual gratitude post I write about people in my life. My family and friends are an easy source of unending gratitude. This year, though, I want to write about something a little bit different.

This year I'm grateful for my country, the United States. This has somehow become a slightly polarizing sentiment and sometimes interpreted as being partisan, and it's become en vogue to bash our country and focus only on its faults. And, yes, our country has its faults, both at the highest levels in government down to all of us as individuals. But we can be grateful for something even if it isn't perfect.

I'm grateful that we live in a country where a good life is possible for most of the population. Opportunity may not be distributed as evenly as we could aspire to, but we have a country where people can visualize a life they'd like to live, whether urban or rural, frenetic or peaceful, tropical or in the desert, and can work towards getting that life. I like that we have so many states that are so different, and that we can window shop between them and choose the one best for us.

Congress has an abysmal approval rating, and our president's rating isn't too impressive either. And yet, government functions enough to keep us safe and stable. Often as Americans we take this for granted, but if you look at what entire populations in many people in other countries have to deal with, we have it quite good. I'm grateful for the system that we have which has held up remarkably well to the challenges of our current times, and to all the people who work in government, often in unseen positions, who are the gears that keep our society moving.