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In the year before I met the woman who is now my wife, I was dating with purpose. I didn't necessarily aim to find a wife, but I was pretty intentional about what I was doing. And since I ended up finding an amazing woman and marrying her, I figured I'd share what I learned from it to help men and women looking for something similar.
The biggest mistake I made by far was traveling so much. I wouldn't do it any differently, but huge gaps between the first few dates torpedoed a lot of relationships that may have otherwise worked. In fact, if it weren't for my friend Todd pushing me to fly to visit, I probably wouldn't be married. ("You never like a girl this much. You are an idiot if you don't see her before your next trip")
Despite your best efforts, a lot of it will come down to random chance. My wife told me that she only swiped right on me because I mentioned cruises in my profile and she figured we'd have something to talk about since she liked cruising too. There was another girl I was dating earlier with whom it may have worked out if her ex-boyfriend didn't show up in her life between our first few dates. You just never know.
That said, the key is just maximizing surface area. Figure out what it is you want and spend as much time as possible with potential partners. That also means spending as little time as possible with those who don't fit. One thing I think I did really well was stop seeing girls once incompatibilities surfaced, even if it was going really well.
It's important to be who you are on the first date. I see a lot of friends run into trouble when they put on a little bit of a show on the first few dates. I never do that, because I want accurate advertising. So I show up in my only outfit for every date, go drink tea, and try to tell them early about anything that might disqualify me. If you do this, you start a relationship with trust and don't run into trouble later.
Especially in large cities, I see people paralyzed by choice, always trying to find someone better. But if you keep switching checkout lanes in the grocery store, you never make it out. My strategy was always to look for people who match my criteria, and when I find one I focus on her and act as if she's going to be the one. Not in a creepy needy way, but basically not allowing myself to sabotage the relationship in search of a mythical "perfect" person.
I was really fortunate to find someone who had a very similar approach. We never talked about marriage or anything like that early on, but both had the philosophy that if we are dating we will put our best effort forward to make it a great relationship.
If I were to boil my philosophy down, I'd say it's to get out there and meet as many people as possible, but to know what you're looking for and filter hard for it. Once you find it, give it your best shot, because finding someone you're really compatible with is hard!
Photo is from a show called Fuerza Bruta that I saw in Vegas. A good portion of it takes place with the cast members on a clear plastic stage a few inches above your head. Really cool!
I used to be neutral, or maybe slightly negative on museums. There was something pleasant about being in them, but I didn't really know what I was supposed to do there, and always felt like I was doing it wrong.
And it turned out I was doing them wrong. I was introduced to a guy who is now one of my close friends, Nick Gray, who hosted guided tours of the Met. I actually delayed meeting him for a while, because a tour of the museum sounded very boring to me.
When I did, though, I saw the museum through a different lens. It didn't matter what I was supposed to do at a museum. It was a public resource that I could use in any way I wanted. Nick's Museum Hack tours were irreverent and fun, and focused on the less famous pieces of art in the museum, but gave a lot more context on them.
Now I have my own way to enjoy museums, which is heavily influenced from what I've learned through Nick (I thought it was exactly the same, but now I find that when we go to museums we do it differently).
To be honest, I don't read a ton anymore. I had a couple years where I read 50-100 books per year and that had the effect of exposing me to just about every book anyone had ever recommended to me and burning me out a little bit. I still read a bit, but not like before.
Of the hundreds of books I've ever read, a few stand out as being so excellent that they're in a league of their own. I recommend them all the time to friends and to coaching clients, and have probably recommended all three somewhere in this blog before, too.
1. Difficult Conversations
There are very few books that I can say really changed me and how I interact with the world, but this one very obviously did. Nearly every person I've recommended it to has told me that they loved it and it had a big effect on them as well. I know of several relationships that it saved directly.
A friend of mine was telling me about how she struggled with regret, specifically around cryptocurrency. Why hadn't she sold at the top? Why hadn't she bought more when it was lower? The questions nagged at her and she would beat herself up about it.
Like her, I didn't sell at the top or buy more at the bottom. It doesn't bother me at all, though. What's the difference?
I think that she and I have different definition of what a mistake is. In any given day there are thousands of publicly traded equities, assets, and commodities. Nearly each one has gone up or down in the past 24 hours, so by her definition, all of us have made thousands of mistakes because we would have been better off buying or shorting them all.
If you are going to count those as mistakes, though, you must count everything else as a triumph. Each breath that kept you alive, each car you passed that you did not accidentally step in front of, each glass of water you drank.
Two years ago CruiseSheet didn't have individual informational pages for each cruise. Cruises are large purchases, though, so I thought that it would be much better if I could have a lot of written information, graphs, and pictures. With around 12,000 cruises on offer at any time, the selection changing every day, writing them individually would be impossible. What would it take to automatically generate an actually useful page for every single cruise? It would be a garguantuan task.
While much of our days is filled with small tasks, emails, course corrections, and tweaks, these sorts of activities merely keep us on track or trend us towards progress. To move forward in big steps, we must give ourselves huge tasks and power through them. How do you do that, feel good about it, and still produce top quality?
There would be no way to incrementally get this feature built. It would require a massive multi-disciplinary overhaul involving weeks of work and a lot of learning. And quality mattered a lot. If the pages were too similar, Google would ding me and people wouldn't want to read them. Each page needed to share a ton of useful information and present it in an inviting way.
When I first approach a task like this, I revel in the possibility of the outcome. I imagined looking at a full sales page for each cruise and how much better that experience would be. I got excited.
Two weeks ago, ten people came to Las Vegas to participate in my event, Superhuman 2. When I did the first one a year earlier I was nervous about how everyone would get along and how I would fill the time in a useful way. This year, even with a much longer format, my only real concern was whether or not the attendees would be as awesome as they were the previous year.
In particular, the first year's group was so open and supportive of each other, that I wasn't sure how possible it was to replicate that. I do everything I can to create that sort of environment, but really most of it is out of my hands. I suspect that even one person could mess up the environment if they really wanted to.
Also, this year three of the attendees were women. Last year it was all male, and I was a little bit worried that having women there might cause men to be more hesitant to be vulnerable.
As you could probably guess, all of those concerns were totally moot. Our group this year was absolutely fantastic. What was most interesting to me was that although no individual from this year reminded me at all of any one individual from last year, the groups felt very similar to me.
In 2017 I built a small cabin in the woods of Nova Scotia. I did almost none of the building, but did do most of the design of the cabin and am now doing the follow-up work on it.
Building a cabin is shockingly cheap. It's one of those situations where you get about 80% of the benefits of a house for only 10% of the money. Sure there's no running water and the fit and finish is a bit rustic, but that's part of the charm. At the end of the day you can have a waterproof structure that's very comfortable and useful, and can pay less than $10,000 to build it.
First you have to find some land. My friends and I bought an island together several years ago, so that part was checked off for me. There is cheap land all over the place, made many times cheaper if you can get friends to split it. For a simple cabin you don't need electricity or water, so you can buy land that's not very useful to other people.
I also have at least one friend who built a cabin on his friend's land. No one who buys many acres actually needs so much space, and they might be happy to have you have a little cabin there as well.
Sometimes I wonder if I'm annoying because I talk so much about good sleep, but even when I talk to readers about it, it seems like almost no one actually prioritizes and gets good sleep. This is amazing to me, as it's actually a pretty pleasant and easy way to get a huge boost in your life.
Rather than extoll the many virtues of getting proper sleep this time, I figured I'd share how to actually do it.
By far the most important thing is to go to sleep and wake up at roughly the same time every day with no alarm clock. If you're already doing that, you're probably in good shape.
Under these circumstances, you will naturally sleep somewhere between 7-9 hours. For me it's almost exactly 8 on average, though any given night varies between 6-10.
Maintaining a healthy relationship while traveling can be hard, but it doesn't have to be. Like anything, there are pros and cons, and by mitigating the cons and focusing on the pros, you can even make it a good thing. As someone who travels for the majority of the year, I have a lot of experience.
I'm married. My wife and I live together and travel together when we can, but we are separate for a big portion of the year, mostly due to my voluntary travel.
There are some parts of this that I really like. To some degree absence does make the heart grow fonder. After I've been gone for a month, no matter how much we communicate, we are really excited to see each other. During the periods of time that we have limited time together, our time together feels more special. I'm not sure if she feels the same way, but being apart also gives me perspective and makes me appreciate her even more.
Those advantages come with some very obvious disadvantages, though. By default, traveling a lot is probably not beneficial for a relationship. Fortunately, there are ways to mitigate those downsides.
I love planning trips for my friends. I think that it's a great way to do a service to my friends, to spend time with them, and to foster new connections between them. I believe that if all of my friends are good friends with each other, that makes my friend circle very strong.
The biggest trips I've planned for friends are two one-week train trips around Japan where I planned an entire secret itinerary. I've also planned lots of cruises where I organize the port stops as we go. Countless friends and groups of family have come through Budapest and I've taken them around.
People always thank me for organizing these trips, but it's totally unnecessary. I benefit just as much as they do, and it's a lot easier than people expect.
The hardest part is just picking some dates and making the trip happen. The best way to do this is choose a few "anchor" people and work with their schedules to find good dates. You book your flights and then start inviting other people. You will never get everyone to go at once, but if you have a few people locked in early, you know that you'll at least have a good small trip and it will build momentum.