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A few months ago I had a troubling thought: maybe I've forgotten how to be productive.
I am not a naturally productive person. I skated by in school, putting homework off until the last minute, if I did it at all. After I left school I was reasonably productive with my gambling thing, but it was never days full of long hours of work, more like and hour or two most days.
After gambling I started a bunch of other projects. It was always hard to get myself to work on them, and other than the first day or two when I was filled with that "new project energy", I'd procrastinate a lot.
Then, a few years ago, I decided to get serious about work and I slowly ramped up until I was working 12-14 hours per day on Sett. That might sound horrible, but I actually loved it. I learned to love work and it was a huge relief to discover that I was capable of working hard for a prolonged period of time. There was at least a year or two where I consistently worked at a rate I was happy with.
I'm always thinking about minimalism. A lot of why I think about it is because I have both very minimalistic tendencies as well as some on the opposite side of the spectrum. That sits well with me, because I consider it cause for alarm when one subscribes entirely to the dogma of any group. It's a sign of not thinking for oneself.
So I think a lot about that balance. Am I becoming too minimalist? Am I swinging too far in the other direction? What's right for me?
A common thread for me is to think about what will make my life the simplest. That doesn't mean that I'll have the fewest possessions or fewest relationships or fewest responsibilities, it just means that I'll remove barriers from my life. I try to think a lot about what I want my life to look like, what will enable me to do the most, and how to minimize friction on that path.
For example, I only wear one outfit. This simplifies my life drastically as I never have to choose what to wear, laundry is always quick and easy and can be done in a sink if necessary, etc. With the exception of trying out new gear (which is both my hobby and business), I must think about clothing less than almost anyone.
It's been an interesting month so far. Two relevant things happened: first, I got some critical feedback that I needed to hear but sort of stung, and second, CruiseSheet has been doing extremely well.
For the longest time I've run my businesses as I thought they should be run. I'd hear people out and take advice on small things, but even when lots of smart people I love and respect said that I should do something big differently, I wouldn't. I'd listen and feel like I was considering it, but really I knew I wouldn't take the advice.
And then later I'd think to myself about how I had my own way and how great it was and how some day people will see that my way was right!
But that day never really came.
I think a lot about what an outsider would assume about me if they were to get a deep view of me. What would they think my priorities are? Would they think that I will succeed? Would they think I'm a good friend? When the answers to these hypothetical questions is out of line with what I want, I adjust. It's a little hack to get perspective.
Today I found myself asking when that hypothetical observer would assume I was optimizing my life for. Hmmmm...
I think that almost everyone optimizes for the very short term. One day. One week. A month. Maybe a year. Who is really doing things for five years from now? Any of us? The lady across the aisle from me on this plane is drinking a Pepsi Max, eating chocolate, and playing a game on her iPad. When is she optimizing for?
We were all alive in 2011, and back then it wasn't all that easy to imagine 2016. Abstractly we could, but who among us could really feel what it would be like to be alive now?
I was encouraged to watch the TV series True Crime, which I was told was excellent. I watched the first couple episodes and found all sorts of things I didn't like about it, which made it easy for me to stop watching the show and write it off.
This happens to me for most TV shows, but it's not an accident. I've cultivated a strong inclination to dislike TV. Usually an optimist, I encourage myself to be very negative when it comes to "low-value" media. I love walking out of movies so much that I'm always looking for a reason to bolt within the first half-hour.
A few days ago I reached a place of disgust with myself. I thought-- "What are you doing? Is this all the effort you're willing to pour into your goals? Are you trying to be mediocre? It's time for a big change!"
That may sound like negative self-talk, but I've developed on purpose an inclination to have those sorts of moments. I see them as fire breaks. If I'm not performing at my best, or near my best, I want to have some level of exasperation towards myself.
Ask anyone what their top priority is, and I bet you get at least three. And if you were to observe their actions, maybe you'd notice that the top priority they're acting on has nothing to do with any of the three they listed.
We all want a lot, and that's because it's easy to want a lot. I want happiness, fulfillment, lots of money, great friends, a great relationship, and just about everything else out there.
It's easy to want a lot. What does it take for me to add something to my wish list? Nothing. I just added a jetpack, and it took me two seconds and felt great. A jetpack! How cool would that be?
But in the same way that great design is defined by negative space, our true wants, those that we will work towards, are defined by those things that we give up.
I say this not to complain or even to suggest that it should be otherwise, but it occurs to me regularly that I live in a world that was not only not designed for me, but may have been designed for the opposite of me.
I'm in Queenstown, New Zealand right now with a couple friends. We went downtown to eat dinner and then searched around for something else to do. Queenstown has a cute compact downtown area full of pedestrian streets lit by shop signs. We passed by store after store and couldn't find one we wanted to go into.
Finally we settled on Starbucks where we drank drinks we didn't really want. There we searched online for something to do, came up empty, and went home.
This happens to me all the time. It doesn't bother me, because I expect it and because I understand that I'm the one who is off. I've made strange decisions that have left me incompatible with the world by default.
Being funny is an interesting phenomenon. Why are people funny? Why does it matter? Sure it makes you feel good when someone is joking around with you, but so do back rubs and compliments. Why do we like it when people are funny?
One theory is that humor is an indicator of intelligence, and we like intelligent people because we can learn from them and rely on them. And unlike other examples of intelligence, humor is really hard to fake.
For example, I could memorize a lot of facts about marsupial animals. If I were to rattle those facts off at you, you might think that I'm pretty smart. But at the same time you'd know that maybe I just memorized them. Memorization is easy, so we don't necessarily think people who know some facts are intelligent.
But humor requires taking unrelated concepts, relating them, and putting them into a familiar context. That's really hard to do, especially in real time. If someone recited a bunch of copied jokes you wouldn't think he's intelligent, but if he made some funny off-the-cuff comments you would.
Two years or so into working on Sett, an experienced entrepreneur friend of mine brought up the topic of taking investment. He thought that we should raise money and was interested in being the first person to invest.
So we talked seriously about it. One of the questions he asked was whether I wanted to build a lifestyle business or a "real" business. I felt a tinge of offense to the question and answered that I definitely didn't want a lifestyle business.
And yet... I never did anything that someone building a "real" business would do.
A year and a half ago I declared that it was time for WifeQuest, where I'd get serious about dating and find someone to spend the rest of my life with. That's something I want and everything else in my life was going well, so it seemed like the right time for it.
Want to totally change your life in just one day with one little tip? Too bad, because that's not how it works.
Once in a while a small thing does totally change our lives. Someone happens to say something to us at just the right time and it impacts us forever. Other times we gradually make a change but we point to one moment as the moment it "happened".
It's great that these things do happen sometimes and there's nothing wrong with trying to spark them, but at the same time it's important to recognize that most lasting powerful change comes from slow and persistent work on hard things.
I'm naturally not a very hard worker. So I tried different quick fixes to become a harder worker, but I'd always regress back to procrastinating and not working very hard.