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Your Past
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.
The most common thing I see is parents, usually fathers, setting expectations for a child based on their own lives (and often their own shortcomings). If the father was a lawyer, then any level of achievement that doesn't look very much like his path in life is a complete failure.
A perfect example of this was a guy who made a million dollars in a year through his business, proudly told his father, and his father said, "Ok fine, but when are you going to get a real job?". This dynamic is really surprisingly common. I see it all the time.
If you're in a situation where your past works against you, the first thing you have to do is to recognize that you are not your past. You may be acting like you are, and you are certainly affected by it, but you aren't bound to it. There are plenty of examples of people who have broken free of their pasts, and if they can do it, so can you.
Especially in the case of parent issues, it's important to understand that your parents can mean well, love you, have the best intentions, and still totally screw it up. You can judge them and their influence on you separately. For example, imagine a new parent who is terrified of the responsibility of a kid, is underslept, and is trying his best. As the kid gets older he wants security for him so he tries to drill in the importance of a good job, maybe because that's what his parents did. As his child grows up and veers away from the narrow path to success that the parent is familiar with, he keeps trying to nudge his child in the right way, fearful that he won't have a good life if he doesn't follow the path that he knows.
In this example it's easy to see how a parent could be trying to do the best with what he's got, and how it could also make the child feel like he's not enough if he makes his own choices. Understand that following your own path isn't a judgment on your parents, it's just a judgment on some of their advice.
A principle that I believe is a universal truth is that you will never be happy and satisfied living up to someone else's standards. You may share some standards with your parents, siblings, and peer group, but probably not all of them. Think about what you truly believe, what you truly want, and judge yourself according to those standards. If someone judges you against their own standards, just realize that that's their problem. It's not fair to set standards for other people and to hold them to them.
Sometimes your past self will set standards for you. This happens often if you've created an identity around something you did, and you now feel like you have to live up to it. You have the right to reinvent yourself and your goals and standards any time you want.
Where would you be if you weren't hampered by your past or your upbringing? Where would you be if you had the love and support that you wished you had? As you think about that, realize that there is nothing physical stopping you from getting there. It's all mental. Mental barriers are real, but they are also malleable and can fade away.
Think about what you want for yourself and think about how to get there. Identify goals that aren't really yours, but are products of your past. Surround yourself with people who support you and hold you to your own standards, not theirs. Take the positive parts of your past and let go of the negative parts.
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Photo is another drone shot of San Miguel de Allende.
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My First International Trip in 7 Months
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".
Turn Maybes into Wins
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.
Your Time Scale
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.
Investment Principles
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.
Why I Love Escape Games (Even in VR)
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 Basic Formula for Contentedness
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.
Being Fascinated
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?
Choosing How to Invest Time and Money
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)
Managing Your Money Like a Billionaire: Part 2
This is a continuation of last week's post. Read it first or this won't make much sense. One clarification from last week that several people pointed out is that my definition of Beta was too simple and a better definition is that Beta is the reward you get for taking risk. The end result is the same, though: diversify your risks to receive a somewhat steady reward while having the risks counteract each other as much as possible.
I also realized that I probably should have waited for this post before inviting comments, because several people pointed out why you wouldn't want to lever up in the current climate, which I address here.
Preserving Money
I was starting to understand the blueprint for managing finances. You want the most balanced portfolio possible, so that you can that add leverage to maximize the return for any given risk tolerance. As I delved into these portfolios and saw their historic performance, the graphs looked a lot more palatable than the index fund graphs that had previously turned me off.