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.

The common view of luxury, consisting of fancy hotels, expensive clothing, and jewelry is an odd one to me. Those things are luxurious in that they are certainly not necessities, but it often doesn't seem like they are doing the person indulging in them much good. On the other hand, with a little bit of creativity one can find luxuries that actually matter. They may not be necessary, but they bring a lot of joy or benefit.

My favorite luxury is having a private gym inside our apartment. We put rubber down in one of the empty bedrooms, I bought a commercial grade weight-stack workout machine, a compact squat rack, a barbell and weights, adjustable dumbbells, a bench, and a big TV and sound system. I spent less than $2000 on the equipment and we sacrificed a room, but now I can work out any time I want in any clothes (no shoes!) while watching a random cooking show on Netflix at high volume.

Having my own gym reduces the hassle of working out by about 50-70%. No changing, commuting, waiting for machines, driving back, etc. I just walk downstairs, do my thing, take a shower, and get back to work. I didn't have my own gym for most of my life and I was just fine, but boy do I appreciate having it now.

I bought an LTE card for my laptop and I pay an extra $25 a month for service to it. Some months I don't use it, most months I rarely do. But when wifi isn't working somewhere or I forgot to get the wifi password from a friend, having that LTE card is the ultimate luxury. I could just tether off my phone of course, but then I have to make sure tethering is on and I have enough batteries and all that. Again, a luxury.

I was a little bit nervous the night before I held my first Superhuman event in Las Vegas. People had paid a fair amount of money and had traveled long distances for an event, but I hadn't planned anything. It was very important to me that everyone have an amazing time at the event. Still, I restrained myself from trying to plan out what I would say.

The few times I'd go to a conference or workshop that was carefully scripted, I was disappointed. If you already know what you're going to say and don't intend on having an interactive experience with the audience, you may as well just put it up on video.

This is how I do almost everything, and have been doing it for years. I don't think that it is the right strategy for everyone and I am very aware that it has weaknesses, but it works great for me and I wouldn't do it any other way.

My basic premise is this: I want to develop my skills and mind to the point that I can execute at a high level at a moment's notice, even if I'm doing something that I don't normally do. I focus on root skills that are broadly applicable rather than specific one-time-use skills or plans.

One very common thing I work on with coaching clients is social skills. Through that work I've seen a lot of common patterns and have come to use a three layer model to think about and discuss how people are interacting with the people around them. If all three layers are in good shape, you will have a great social life. If even one is missing or lacking, so will be your social life.

The first layer is who you are at your core. This is important for many reasons, but in this context it's important because any relationship with any depth will eventually expose your true self, so it better be something good or you will be doomed to surface level friendships and will find yourself spending most time with acquaintances.

I saw this problem a lot in the pickup community. Many people would fix the outer layers so they would get dates and have girls around them, but they were totally unable to have relationships because they hadn't worked on themselves enough.

The traits you should have at your core could be up for debate, but I think most people would agree that integrity, compassion, and a good moral compass would be included here. If you don't have these traits, you'd be well served to figure out how to cultivate them, though the path to that goal may be a long one.