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One of the greatest luxuries in life is to not have to worry. This isn't possible for all people at all times, but there are things all of us can do to be more carefree, especially those of us who have only "first world problems".
Be very deliberate about taking on obligations. The obvious example is debt, which I talk about all the time. Most people make debt decisions based on their current situation, and not an evaluation of all reasonable outcomes over the term of the loan. Rather than worrying about the debt before they assume it, they are forced to worry about it over the term of the loan. And of course if something happens, it's even harder to be carefree.
Obligations extend beyond finances, though. Everything you purchase, especially large purchases, comes with some obligation. For example, with all of the properties I've bought with my friends, I'm essentially always on call to deal with them. More than once I've gotten an email from our Hungarian accountant saying, "You really need to come here by the end of the month to sign a document." Those obligations are worth it to me, and I can remain carefree and deal with them only because I've been judicious about taking on other obligations.
Don't totally avoid obligations, just make sure that the benefit accrued from them justifies the obligation.
It's always worth working as hard as you can for things to turn out well, but it's not worth worrying about if they don't. If you have the habit of making the best of setbacks, you'll often find that some of the best things that happen to you stem from the worst. Even COVID, which massively disrupted my life, my business, and my wife's career, has been overall positive and I would prefer to be where I am today than where I would be if it didn't happen. Aim for best case scenarios, but don't assume that worst case scenarios are all that bad.
These days when bad things happen to me I just think, "It will be interesting to see how this turns out", and usually the result is good. I sometimes take it as a challenge, refusing to let something bad remain bad, and instead thinking, "What would it take for me to be glad that this happened?"
Even if we minimize obligations and recognize that things will go wrong but may end up good anyway, we all have things on our minds that we worry about or wonder about. However, we all also have a ton of things that are going great in our lives and things that have happened that are positive. Focusing on these positive things doesn't eliminate worry, but it helps put it in context.
Focusing on positives and gratitude can change a mindset of constant worry to one of, "Wow, my life is so great and so many good things are happening that even if a few things coming up don't go my way, my life is still going to be great." As a carefree person, that's generally what I'm thinking.
It seems that sometimes people worry because it's part of their identity and it makes them feel safe. If they are constantly worrying, nothing will slip by them! Of course, the real effect is that they create problems that don't exist.
It feels great to be carefree and it feels great to be around carefree people. Keep your obligations small, accept that not everything will go your way, realize that "bad" events often lead to the biggest wins, appreciate all the things that have gone will, and let go of your worrying identity.
Picture is a crazy skull art thing at Area 15 in Las Vegas
I was one of the very lucky ones, though it took me a long time to understand just how lucky I was. I grew up with loving parents, siblings with whom I never fought, very involved grandparents, and a bunch of cousins who I count as close friends today. I made friends with incredible people as early as kindergarten (one of whom is still one of my closest friends), and continued to have really excellent people as friends for the rest of my life. I thought that this was totally normal and nearly universal for a very long time.
Like anyone I've had big challenges in my life, but none of those challenges came from any sort of childhood trauma. If anything, my childhood helped me get through them.
As time has passed, I've met more and more people with childhood issues that continue to affect their daily lives. This was very surprising to me at first, but when I thought about how I continue to benefit from a good childhood, it made sense that issues from childhood would continue to plague people.
Through coaching, as you might imagine, I've seen a lot more of this sort of thing and have gotten to explore it in depth.
Since my last blog post I traveled internationally for the first time in almost seven months. That period of time represents the longest time I've stayed in one country since 2008, I think. It was a weird experience for a number of reasons and made me reflect a lot on travel and being stationary.
In some ways I've been surprised at how much I've liked not traveling. Or, rather, I think that my lifestyle of nearly constant travel caused me to forget about the benefits of staying still. Staying in Vegas I've enjoyed seeing the seasons change, connecting a little bit more with local people, having a rock-solid routine, and doing projects that require longer sustained periods of time.
That said, I have of course been dying to travel.
The first thing that surprised me was what a big deal it felt like to travel. Before COVID I would go all over the place with very little planning, but planning a 3 day trip to Mexico felt like a big deal. It gave me a little glimpse of how most people think of trips as "big deals".
We all want good things to happen in our lives. Sometimes these good things stem from obvious wins that can be picked up easily, like accepting a new job offer or going on a second date when a first date went well. In thinking about which events in my life were most positively impactful, however, I noticed that many of them were not obvious wins. They were maybes, which I turned into wins.
For example, take buying an island with my friends. This is definitely not an obvious win. It could have lead to fights with my friends, it could have turned into a big money pit, or apathy could have left it undeveloped and relatively useless. However, my friends and I worked hard to turn that maybe into a big win. We've had zero fights, have kept costs low, and have built it out to the point of being a great destination for ourselves and our friends and families.
Relationships, particularly marriages, are another one. I got married on the one year anniversary of meeting my wife. People congratulate each other on marriage as if it's an obvious win, but I'd categorize it as a maybe. I've seen people for whom marriage has been a huge negative as well as those for whom it's been a huge win. The marriage isn't a win, but what you do with it can be a big win.
Is dropping out of school or quitting your job a win? Like the other examples, it all depends on you.
We make hundreds or thousands of subconscious decisions each day, but just because they're subconscious doesn't mean that we have no influence on them. Quite the opposite, they are actually dictated by our principles and the lenses through which we view the world. By changing those things we can automatically and effortlessly make better decisions.
One of the most important lenses through which we make decisions is our time scale. We make decisions to effect positive change in our lives, but WHEN that positive change takes place can vary a lot.
For example, a drug addict makes decisions on a very short time scale, maybe just a minute or an hour or so. Addicts know that the substances or behaviours they use are bad in the long term, but that's not a time scale that they are concerned with. If you want to optimize for the next few minutes of your life, choosing to use heroin makes a lot of sense.
On the other hand, some people optimize for infinity. I dated a girl once who was totally unwilling to spend money on anything (she actually spent tons of time entering sweepstakes so that she could win everything she needed), but had saved up tons of money. Even when the money would have a huge benefit to her life, she would not spend it.
A friend asked me if I had any rules for investing, not necessarily in stocks but in other things, and I said that I didn't have hard and fast rules, but thought about it more in terms of principles. What are those principles, she asked? Well... I didn't quite have an answer ready.
I've thought more about it and decided to put it all in one place publicly.
First, I divide investments into "risk" and "no risk" categories. You could argue that everything has some risk, but I consider the no-risk investments to be things where, in my estimation, there is less than a 2% chance of loss. This is arbitrary and subjective, but for my investments there's a pretty clear cut line.
Investments that fall into this category would be CDs, fixed rate return stuff like BlockFi USDC coins, and investing in a friend's real estate development where he pays me a fixed return.
My friend Michiru was very excited about a new thing that some of her Japanese friends had brought to San Francisco. It was called a "puzzle break room" and her description of it made absolutely no sense to me. She kept insisting that I would love it and that I absolutely had to go, but I only reluctantly agreed to go when she wrangled a free ticket for me.
She was right. The hour where I tried and failed to solve the puzzles went by in a flash and I was left wishing there was another one that I could do immediately.
Fast forward five or so years and I've probably done at least one hundred puzzle games. I've done over fifty in Budapest alone. When I'm with my other escape game friends we set fastest time records a good 20% of the time or so.
Escape games are absolutely one of my top few favorite forms of entertainment, and the problem I now have is that it's hard to find good ones that I haven't done in the cities that I visit. You would think that after doing so many I would have seen everything, but the truth is that almost every game I do has some element that I haven't seen before, often many of them.
A friend and I were discussing food. I told him that I didn't care about food, and he laughed and said that I cared more about food than anyone he knew. I am so obsessed with ingredients and quality and wouldn't eat at a lot of restaurants.
I thought about it and realized that he was right. I do really care a lot about food. I try to learn about what goes into it and how it's made and I have very strong opinions on both of those things for a wide set of foods. I probably wouldn't voluntarily eat 95% of the items outside of the meat and produce aisles of the grocery store.
And yet... I still feel like someone who doesn't care about food. When I'm by myself in the US (and even most of the time when I'm not) I eat the same exact thing every day. A small bowl of nuts at 4pm, Chipotle at 6pm. I love those foods, but if they went away I'd just substitute them with something else and carry on. In my mind, someone who really cared about food wouldn't do that.
A month or two after I began quarantining for Coronavirus, someone commented that the virus must have really impacted me. No, I said, it didn't have any big effect on me. Then I thought about it more and realized that it destroyed my main business, my wife's career, and my entire lifestyle of traveling all the time.
For the past few days I've had a spring in my step. Why? Because I'm writing some tax-loss-harvesting and rebalancing software, of course.
Yesterday, as I was coding, I realized how monotonous the code I was writing was, but how much I was enjoying writing it. It was a strange combination. I don't always love coding, and the monotony does get to me at times.
I thought about why that was, and I realized it was because I had become fascinated with portfolio optimization. I was really curious about how it worked, how different strategies would affect results, and what would happen to my hypothetical portfolio once I made the changes.
On a smaller scale, I had become fascinated with how to program the algorithm. Do I sell over-proportioned positions first? Do I tax loss harvest first? If I don't have enough cash left to buy a share of the most under-proportioned stock do I hold the cash or buy the second most?
Partially because of my previous two posts about managing your finances like a billionaire and because of the obvious impact of of coronavirus on CruiseSheet, I've gotten a lot of emails recently around money and finance. I realized that there's one missing piece that I may not have talked about much before, but which may be valuable to readers.
We all have infinite ways to spend and invest our money, and since it's a finite resource, it's important to make sure that it's managed in a way that will bring maximum benefit (whether to us personally, our families, the world around us, etc).
I think most people do a pretty bad job of this. They have no idea why they're saving money (and thus usually don't save much), and they spend money like everyone else spends money, gaining only accidental overlaps with what would benefit them most.
The way I manage and spend my money is based on two fundamental principles (which could change over time as my preferences change, and are not the same as they were 5 years ago)