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It begins with a basic acceptance that we will never really understand what's going on around us. We'll be wrong all the time, and oblivious even more frequently. It may feel as though we understand ourselves and our world around us, but the number of times we are wrong or surprised illustrates how little we actually know with certainty.
What do we do with this uncertainty?
We consider the facts that we accumulate, even though our perceptions on which those facts are based are often incorrect, and we fill in the gaps with assumptions that make sense. Then we turn those assumptions to fact with a magic wave of a mental wand.
This idea is uncomfortable for all of us, maybe even repulsive. It's hard to swallow the idea that the world is so big and complex that no one really understands with certainty much of what's going on.
But it's not much a stretch to see some good in this as well. While we'd never be disappointed or look stupid if we were always right, we'd also lose our capacity for delight and surprise. And I know it's easy to point at any number of problems in our society, but humanity does pretty well for itself despite mostly fumbling around in the dark.
Amid all of this uncertainty, we must act decisively all the time. You pick up enough signals from someone you like, so you ask them out. A situation seems dangerous, so you avoid it. Your boss hasn't been so warm to you recently, so you worry that your job is in jeopardy.
In my experience everyone has a thermostat in their brain. Some are set all the way to cool and interpret everything negatively. If someone does something nice for them, they must pity them. And they don't want their pity, so it actually makes them resent the person. Others are all the way hot, where everything seems good. That's me.
I was talking with a friend recently about how I'm always positive. He says that I don't write enough about it because I don't understand how unusual it is.
We talked about an incident in high school. I was in color guard, where I put on tights and jazz shoes, picked up a flag, and danced to Jewel's "Foolish Games" in front of big crowds at competitions. I was the first male to ever sign up.
At the senior skit, which I didn't attend because I was at a color guard competition, I was a character. They had me fencing another student in a series of duels. The guy playing me was wearing a skin-colored leotard.
When I heard about this and saw it on video, I was flattered. I'm not above poking fun at myself, especially when I break the mold and dance around twirling a flag. It is funny. The kids who put on the show were the jocks and popular kids. I wasn't ever close friends with any of them, but I'd chat with them as much as an introverted nerd could, and always got along well.
So I took it as friendly ribbing. My friend was certain that they were making fun of me in a bullying sort of way. We both see the other's point logically, but neither can really relate on an emotional level.
It's impossible to know who's right. Probably neither of us are. Maybe some of those kids really didn't like me and put the bit in to spite me. Maybe some admired that I had done something controversial like that and thought it was fun to joke about. Maybe some didn't even know who I was and just liked the idea of one of their friends dressing in a flesh-colored leotard.
The interpretation of it does matter, though. Because I have a very strong bias towards seeing things in a positive light, that incident makes me proud. It reminds me that I was brave enough to go against the grain and that people noticed it. But if I was the kind of person who saw it in the worst light, maybe I'd still be affected by it today.
Whether they loved me, hated me, or felt someway in-between, believing the positive would have ended up working out best for me. That's true of most situations like this.
I was talking with someone the other day about a date she'd been on. She really liked the guy and he seemed to really like her, but there were some potentially negative signs from him. She and I both agreed that 80-90% of the signs were positive, and the rest were unclear or negative.
She was concerned that the negative signs meant that the positive ones were just the result of politeness and that he may not be interested. I interpreted the negative signs as minor signals of nervousness or hesitation.
But think about their next date. Which set of assumptions will make it go better on average?
I'm not encouraging you to ignore reality. If a guy has a gun aimed towards you in an alley, it's not going to serve you to think that maybe he's just a gun enthusiast who wants to show you the cool barrel on his gun. If your friends sit you down to have an intervention, you should probably take their counsel and make changes.
But when there's indecision or gray area, you're generally better off just assuming the best and acting on it. You will be wrong sometimes, and sometimes that error will cost you and you would have been better off being pessimistic, but not usually.
People worry about being oblivious, but they rarely worry about sabotaging themselves. No one has accurate enough perception to be totally neutral. We all color our experiences positively or negatively and act based on those perceptions.
If you have a positive bias, you may be seen as naïve or oblivious when you're wrong. I can't think of examples where this has happened to me, but I'm sure it happens. Being cynical seems cooler for some bizarre reason.
But your life will go better if you take the risk of seeming oblivious and give yourself the benefit of the doubt. Harmful incidents will roll right off your back, you give yourself some space ahead to grow into, and you never sabotage yourself with pessimism.
How do you do that? Keep a journal, mental or written, where you write the positive version of any event you interpreted negatively. The point is just to train your brain to start using those pathways. And you can look back and see examples when you were right.
I'd rather be wrong once in a while while expecting the best than wrong once in a while expecting the worst. Things just work out better that way.
Photo is last night in Shibuya. Feels great to be back!
For a long time I was very proud of the fact that no girl I had attempted to kiss had given me the cheek. I thought that this meant that I was a precision sniper of dating, finely attuned to the subtleties of the male-female dynamic. I knew when girls wanted that first kiss to happen and had been right every time.
I mentioned this to someone and they said something like, "Well, you're probably playing it way too safe then. You've avoided rejection, but you've probably not kissed a bunch of girls who wanted you to kiss them."
The wind was taken out of my sails immediately. I had been looking at it all wrong this whole time. Something I took as a sign of success was actually a sign of a different sort of failure.
If you never fail, you are leaving success on the table. It's comforting to imagine that you are perfect, but perhaps more likely that you aren't pushing far enough past your comfort zone.
Thanksgiving is probably my favorite holiday. Although it started with religion, it's become a secular holiday that's pretty pure. Everyone who celebrates it does so with people they're close to, and they think about what they're thankful for. There's a bit of gluttony mixed in, but even that includes a lot of healthy food.
Today will be the first time I celebrate Thanksgiving with friends instead of family. I'm grateful to have the option, and it makes me think of how lucky I am to have such great friends and family. I love my friends as though they're family, and I consider my family members to be some of my closest friends as well.
The emotion I feel the most throughout my day is gratitude. I'm always thinking about the various people in my life and how lucky I am to have them there. I think about the people who were in my life but aren't anymore, and I'm grateful for how they affected me. I think about how lucky I am to have a roof over my head, Chipotle and sardines in my belly, and the ability to constantly travel around the world. I think about how glad I am that this world exists and that I get to be here. That one fluke alone is enough to flood my brain with gratitude.
And, of course, I'm grateful to have you and people like you reading my blog and my books. I was having dinner with my friend Ramit the other night and we were talking about blogging. I told him that I may not have as many readers as some other blogs, but that I thought my readers were the best group of readers out there. I'd take that trade any day. Whenever I meet you guys I'm totally humbled to have such smart and interesting people care about what I write.
I get called weird a lot. Not usually in a bad way, usually as a term of endearment. Looking at it objectively, I see the argument — I'm definitely a strange person who does unusual things.
The thing is, I don't feel weird. My day to day life feels pretty normal, and the decisions that I make also feel very standard. Take in input, process it, make the best decision possible, move on.
The disconnect, I think, is because of how I make those decisions. When I think about why I often end up doing very different things than most people, it boils down to one key distinction: I completely disregard decisions that others have made in similar scenarios.
Here's why. While everyone obviously has a ton in common with each other, we also have enough differences that decisions can't be made in a one-size-fits-all manner. You and I could be in the exact same scenario, but because we value different things and have different abilities, the correct decision for each of us could be opposite.
As you may have noticed, I've been very early on some big cultural trends. I was into pickup way before it was mainstream, was one of the first "digital nomads", was living in an RV before the tiny house craze, and was playing poker profitably before it went big, etc.
This isn't because I'm clairvoyant or because I invented any of these things, it's just because I'm very comfortable with risk and am willing to try new things and see what happens.
I thought that it would be fun to talk about some things that I think will happen in the future. Maybe I'll be right and maybe we'll laugh at how far off I am, but maybe some will resonate with you and you'll get into them earlier than you would have otherwise.
1. Shared Assets
To break with my normal style of post, I thought this week I'd share some of my favorite software that helps me get work done on a daily basis. Because I use Linux it won't all be applicable to you, but maybe some of the ideas will be, and a lot of the software is cross-platform.
Ubuntu + Gnome
I love the Ubuntu operating system. In particular I like how everything just works super easily (including typically tricky things like printers), and that it's infinitely customizable. I spend a lot of time on my computer, so small customizations have a big effect on long term productivity.
Gnome is a "window manager" for linux. I switched on a whim and I LOVE it compared to Ubuntu's default window manager. I think it's way better than OSX, Windows, and Unity (Ubuntu's default).
For the past few years I've been in a state of near-constant motion. I was in Budapest for five weeks straight last month, and that was by far the longest I'd been in one place in years. This lifestyle now feels totally normal to me, so I thought it might be interesting to share what it feels like to live such a life, both good and bad.
Maybe the best part of moving around constantly is that I have a "presence" in different cities around the world. I have friend groups in Vegas, San Francisco, New York, Tokyo, and Budapest. In any of these places I can land and immediately feel at home, navigating by memory, calling up friends, going to favorite restaurants, etc.
Because I go to all of these places with relative frequency, I'm generally never gone for too long. So although I don't get to see all of my friends every week like I'd like to, I generally see them every 1-3 months (longer for Tokyo).
If you call these five places my homes, you could say that I have a five "half homes" rather than one full home. In other words, it feels like the sum of these partial residences is greater than one residence, in terms of connection with friends, getting to know a city, etc.
I'm going to start writing a little wrap-up about the island every year, partly because I want to chronicle it for my own reading later, but also because there's been a lot of general interest in the island.
If you're late to the party, nine friends and I bought an inexpensive island off the coast of Halifax in 2013. It was untouched forest when we bought it, but we have now built trails as well as structures, the only significant one being a 30' diameter yurt.
This year we got two trips in. The first was a massive trip with twelve different people coming and going, averaging eight to ten at any given time. Five of the owners came on that trip as well as seven guests.
Having so many people here at once was a feat in and of itself. I think the maximum we'd had before was four. But this is the first year that the yurt was up, as we finished it at the tail end of the preceding summer, so we had plenty of space for everyone.
Two days ago I closed on a property in Budapest (right where districts V, VI, and VII meet, if you know the area). It's not just my property, though. I share it with eight of my best friends. It's the latest piece of the puzzle in my recent quest to have home bases around the world in my favorite places.
We bought an island off the coast of Halifax, now a flat in downtown Budapest (best European city in my opinion), and are buying up a neighborhood in Las Vegas, with each of us owning our own apartments.
Tonight I'll sleep in our Budapest place. Tomorrow I'll fly to Halifax and stay on the island for a week. Then I'll fly back to Vegas. It is a really cool feeling to fly around the globe and always be home.
Now that I've done this a few times I'm going to share specifics on how it works and how we organize everything so that you can do the same. And before you dismiss the idea thinking it's too expensive or complicated, think about this: my share of the island, share of the Budapest place, and entire place in Vegas cost me around a fourth of the median sales price for a house in the USA. So while this sounds extravagant (and feels like it), it's actually very inexpensive compared to how most people you know live.
I've been working a lot on marketing recently, as you've hopefully noticed if you subscribe to CruiseSheet's (awesome) newsletter. A basic part of marketing is thinking about the funnel. At the top of the funnel you have people who go to the web site, and at the tiny end of the funnel you have people who actually book a cruise.
Ideally you'd want that funnel to be tube shaped so that every person who visited would also book a cruise, but that's not possible. So while you try to stretch the opening at the bottom of the funnel by increasing conversions, you also try to get more people into the top of the funnel, since some of them will make it all the way down to the bottom.
Over the years I have had some really amazing ideas for blog posts. Hopefully you've read a few of those posts, but the majority of them never got written. That's because I have the exact same thought process every time: