Every year I struggle to write my gratitude post a little bit, not because I can't think of anything I'm grateful for, but because there are so many things that it's hard to focus. This year, just for fun, I'm going to try to highlight some smaller things in my life that I'm grateful for.

But first, I can't write this post without acknowledging and thanking all of the people in my life. I have the most incredible friends and family and they all contribute a tremendous amount to my life. Everyone has the ability to make great friends, but not everyone has the chance to meet as many great people as I've met and befriended, and I think it's pretty rare to have a meaningful and positive relationship with every single member of one's family as I do. I may not be a 1%er financially, but I think I must be in terms of people in my life, I must be.

So first, to my friends and family who read this: thank you so much for being in my life.

Each day I think many times about how grateful I am for various things, both big and small. I do this because I have a lot to be grateful for, but also because I know that the active process of being grateful will make me more happy and satisfied with my life. Being grateful is a skill that you can build, and building it enables you to get all of the benefit of everything in your life, which makes it a very high-leverage skill.

When I asked for blog topics before writing this annual batch, I got a lot of great suggestions with almost no overlap at all. The one exception? Everyone wanted to know what I think about marriage.

I think that this comes from my history as a pickup artist, and a perceived incompatibility with the two. This is sort of funny to me because I think that getting into a great marriage with a great person is a very obvious end goal to pickup. Or maybe the confusion just comes from the fact that I live a pretty weird life. In which case: fair enough.

I'm still very happily married. On our anniversary I realized that I was even happier to be married than I was on our wedding day. Maybe that's because you don't really understand if or how your life will be changed once you get married, but once you settle in and proactively make it a good marriage, you get to feel the benefits.

Marriage, or even relationships, seem to be a much bigger chore and more difficult to most people than they feel to me. We've had exactly one argument ever that I can remember (though it did resurface again a few months later before being totally resolved). Once in a while one of us raises some concern or issue and we have a "difficult conversation", but I can't think of any where both of us didn't leave feeling better and glad we had the conversation.

Almost twenty years ago I was a professional gambler and I ended up getting a little bit sloppy with my procedures, which resulted in casinos catching me and confiscating all of my money. I only paid taxes when I removed money from casinos, so I kept most of it in them, which meant that my net worth dropped by over 90% in one day.

Should I regret my actions which caused that?

I remember the day. I remember waking up, where I was sitting when I looked at my computer and realized what had happened, and even where I went for dinner, who was there, and what I ate. I also remember not being upset by it, and in some ways feeling relieved. I had had enough gambling and was ready to move on anyway.

I'd certainly take the money back if someone offered it to me, but maybe my life would be different now in a way that I wouldn't want. I'm 100% happy with my life now, so I can't really say that I regret it, because maybe that small change would have a ripple effect and make my life worse today.

I saw an interesting debate on Twitter recently between two guys who were debating whather it was better to focus on one's strengths and leverage them for results, or whether it was better to shore up weaknesses and become more well rounded.

The conversation caught my attention because it really is a common situation people find themselves in, and most people tend to focus exclusively on one side or the other. But just like the idiom "Work smart, not hard", you might ask yourself why not just do both?

The way I see it, your primary output should come from your strengths. I coach people because I have a lot of experience with understanding people and giving advice, and I'm now very good at it. I would never have done it 10-15 years ago when it wasn't an absolute strength.

At the same time, it's important to realize that your greatest strengths are actually the combination of several strengths, just as a dish you eat is good because of the combination of ingredients more than any one ingredient individually. So the way that you create a valuable and defensible strength is by building up weaknesses until you have a combination of strengths.

A few years ago I started writing a monthly report to a few friends sharing my progress on CruiseSheet. My primary motivations for doing so were that these friends were interested and asking about it anyway, and I felt that they might hold me accountable or offer me some good advice along the way.

Those benefits came, but the biggest benefit was unexpected. Writing a monthly report forced me to take an accurate look at my month, assess my progress, and think about where I wanted to go from there. Sometimes a month felt pretty lackluster but I'd look back and see that I'd done a lot more than I remembered. Other times it went the other way and I realized that I hadn't done much at all.

I enjoyed writing the monthly report so much that I started writing a general life one for a much smaller group of friends. I have categories like finance, coaching, friends, family, and miscellaneous. Just as my CruiseSheet specific one made me reflect on what I was doing within the business, this one helped me keep track of my life.

The biggest thing I've learned from my general monthly email is how much actually happens in a month. Sometimes the month seems to have flown by, but as I am forced to take a few minutes to reflect on it and look through my schedule, I realize that actually quite a lot has happened.

Four years or so ago I bought a small condo in Las Vegas. I did it almost entirely because it seemed like a great deal and because I visited Vegas sometimes, and not at all because I intended on moving to Las Vegas. Since then, things have escalated.

I now live in Las Vegas full time with my wife. She bought the condo next to mine and we combined them to make a bigger condo. In addition to our two condos, friends and friends of friends have bought ten others in our neighborhood. We have a waiting list and continue to try to buy nearly every condo that comes up for sale.

My one complaint with Las Vegas was that it didn't have as many of the types of people I like to hang out with as other cities, so I figured I would try to change that by importing them.

We are beginning to approach a critical mass where there are usually other people in town besides us, which has made it even more fun to be there.

Sometimes new tasks can be daunting. I was in Hawaii trying to fix our minivan, and even though the steps involved in replacing spark plugs and wires looked quite easy, I wasn't particularly confident that the van would start when I turned the key.

I've noticed that a lot of people, including people who are incredibly competent within their own domains, are terrified of doing something new. Sometimes they're so paralyzed that they're not even willing to try it.

I may have been that way before too, but something I always remind myself is, "Dumber people than me have done this before."

That's not an insult to anyone else or a mechanism to inflate my own ego. It doesn't mean that I'm smarter than everyone who has ever attempted whatever it is that I'm up against. All it means is that at some point in history, someone with less ability than me has probably succeeded in doing whatever it is I want to do.

One of the main reasons my friends and I have bought home bases around the world rather than just relying on AirBnBs is that it makes it easier to develop good routines in each one. I've found that having a good routine in a place and going back to it over and over again is a great way to stay productive while traveling and to get to know each place in more depth.

I thought that I'd share my routines in each one to illustrate how I stay productive and why I like each place so much.

Vegas

Vegas is definitely my main home base and I spend more time there than any other home base. For that reason, my routine there is tho most important one to me and it's the most strict and developed.

When I asked for blog posts at my last Budapest event, one person asked how I spend my time on airplanes. At first I didn't think I had all that much to say about it, but as I thought about it I realized that airplane time is actually quite critical, especially when you travel a lot and have a lot of airplane time.

My overriding top priority on airplanes is to manage my sleep schedule. If I max out productivity on an airplane but then have jet lag for several days later on, that use of time on the plane was actually a major mistake. So even if I don't get anything done on a long flight other than adjust my sleep schedule, I'm happy.

If you've read my anti-jetlag strategy, you know that the crux of it is to compress all discomfort into the travel day so that I can seamlessly transition between two different time zones. What that means, more often than not, is that I'm exhausted when I get on the plane and my only job is to stay up for a few hours before I go to sleep.

For that reason, I usually watch TV shows or listen to fun podcasts. I tend to hoard shows that I like and save them for flights. That lets me keep more of my productive time when I'm not on airplanes, and then when I'm tired and on a flight, I can use those shows to burn through flight hours.