Well it seems I broke my streak of publishing these on my birthday. Oh well, better to still get it out late than not get it out at all. 

This is the fifth post in this series. If you’re curious you can read my previous posts on 25, 26, 27, and 28. 

Every year I say “okay this is the year I’ll take it easier” and it never seems to happen. Since my last birthday: Cosette and I had a baby, I learned programming, became a sorta crypto influencer, helped launch a video game, started consulting crypto projects on their tokenomics, and launched an SEO and DeFi course.

So once again it was a crazy year and I’m amazed by how different life is now than it was last year. But surely this year will be different… 

Anyway, here are some assorted thoughts and lessons I took from this year. Most of these are inspired from themes in the Medley over the last year, which has now transitioned from a link roundup to more of a weekly essay. I like the new format much better. 

Escaping Local Maxima

There’s a computer science challenge where you have to figure out how to design a program to find the optimal solution, when there are many locally optimal but not globally optimal solutions it could get distracted by. 

The analogy Chris Dixon uses is climbing a hill. If you just tell the program to go up, it will climb to the top of the highest hill it’s already on, but then it will be stuck there. If there’s another higher peak, it won’t seek it out. 

To get around this you have to introduce some randomness into the system. It needs to make occasionally suboptimal short term decisions in order to reach the best long-term solution. 

Each of us is climbing our own mountain, and it’s tempting to always focus on going up because going down or asking if we picked the right mountain is scary. We don’t want to give up the hike and have to start again. 

But like the computer program, if we climb to the top of the first mountain we pick, there’s a near-zero chance we’ve picked the best mountain. Sometimes we have to look around and say “you know, that mountain might be better.” 

Writing is the only work I do completely for itself. Everything else is at least partially motivated by money, since it turns out money is kinda useful and the more of it you can make faster the less you have to make later. At least in theory. So while I was pretty set on writing for the meaningful work mountain, I knew there was still some searching to do for the best money mountain. 

The search worked. Last year was more lucrative than I could have expected to achieve from content marketing or course making without selling out. And I had fun doing it! Depending on the goal, sometimes the best way to achieve it is to abandon the current path and find another. If my goal is to reach a comfortable enough degree of financial independence to focus on writing full time, without having to write “what will make money,” crypto work is a much better mountain. 

And while it is scary to walk back down the mountain to try again, you at least should have some good hiking muscles. You never know how the skills you built on one mountain will help you on the next one.

Zoom Out

One mentality I’ve often railed against is the long-term career plan encouraged in college. You need to study hard to get good grades to get that first job so you can get promoted over the next 20 years and become a partner and then all your problems will be solved and you’ll be eternally happy. Something like that.

I’m more a fan of the driving in the fog analogy. You have a rough idea of where you are and where you want to go towards, but you can only see a little bit ahead of you, and you have to keep making progress based on that. And the less committed you are to a certain outcome, the freer you are to take the roads that make the most sense for you. 

For the last 7 years since I graduated, I’ve rarely thought about work and progress on a longer than 1-2 year timescale. With Growth Machine the focus was always on hitting the next revenue milestone or fixing the next problem. With this blog I’ve never really had any goals, it just keeps growing. With starting down this crypto road last year my only goal was to figure out some way to make money within a year so I didn’t have to live entirely off savings and passive income. 

Now I’m trying to think a little more about the long term with work and money. 

The money one is important because in crypto land, everything moves so fast and there is always a chance you could find that one opportunity that launches you into the land of fabulous riches that you feel like you need to make a lot of money very quickly. 

Even outside of crypto though, there’s always that sense that you could be making more money faster. That whatever pace you’re at isn’t good enough. 

Having a kid has made me zoom out a little and look at money on a 25 year timescale. If I’m 29 now, and my last kid might turn 18 in 25 or so years, then I just need to make enough to give them the life I want them to have between now and then, and to give Cosette and I the life we want after.

That’s a long time! I don’t need to hit any insane income numbers, or major wealth events, or crazy compound growth rates to have a pretty good outcome. And it’s not like I’d retire and chill on the beach even if I did. So letting myself stop obsessing over trying to grow our wealth as fast as possible, and thinking instead about what kinds of habits will work out well over 25 years has been a great way to reframe things. 

On the work side, one thing I want to lean more towards is finding a work focus and style that I could conceivably stick with for the next 30+ years. It’s obviously writing. That’s the thing I happily work on even when there’s no financial return, and when there is a financial return, it’s the most emotionally rewarding. I make less from my Substack than most other projects, but the emotional satisfaction is much higher. 

Income is not the only metric. The source of income matters quite a bit for your psychological satisfaction. And I feel the best when I’m getting paid for my writing compared to anything else. 

So I’m trying to do a little better job of zooming out. Not being overly fixated on the present, and doing a better job being in the now instead of future.

Ease Is Not Always Optimal

I’ve written extensively about note taking and productivity in the past, and one of the common themes in note taking especially is the ease of capture. 

Taking notes on what you’re reading is essential for synthesizing the knowledge. I’ve published so many book notes more for myself than anyone else. It helps me compress what I get out of each book. 

Over the years I’ve used Evernote, then Roam, and now I’m using a mix of Roam and physical note cards. I still pull all my notes into Roam to make them easy to publish, but for my real note taking and knowledge organizing I’ve started using physical note cards. 

Why physical? If you’ve spent a little time on computers you probably know that more information is not always better. When you plug a query into Google and get 10,000,000 results, most of those are not particularly helpful. Quality is more important than quantity in an age of such abundance. And most people who use a note taking tool and who save their book highlights know you almost never go back and review those highlights. 

So by creating a physical zettlekasten for my favorite notes, I’ve added a final filtering step to make sure that whatever goes in the box is a high quality idea I’m confident I want to remind myself of in the future. By having to write it out by hand, I’m forcing myself to be much more selective than when I can simply copy and paste 

Think about how much more meaningful it is to get an ecard vs a physical card. The ecard is much lower effort, it takes time and energy to pick out a physical card and give it to someone. Effort is what gives the card and your notes more value. 

Our knowledge management too should be effortful and deliberate, or else we will fill our libraries with trivia, and then what was the point of doing the organizing in the first place. There’s also a certain permanence to it. Sure my notes and library could burn down in a fire, but it could also be something my kids leaf through in 30 years. That’s fun to think about.

Ebb & Flow

This concept was discussed in “Working in Seasons” and “Reading Season.” It doesn’t make sense to try to work at a consistent pace all year. As the year and our energy levels change, our work level and focus should adjust along with it. 

You might have periods of intense focus with very high output, and then extended periods of rest and recuperation. Most of my very productive work tends to get done in a total of one to two months of the year. Theoretically, if I could isolate those time periods, I could work a lot less and relax a lot more. 

But we have to be careful about that naive interpretation of this cycle. Having periods of very high output does not mean the other periods are wasted. Those rest periods are what lay the groundwork for the bursts of productivity. If we force ourselves to have extremely high output every week, it’s more likely that we’ll just burn ourselves out or drain all our creativity. 

There’s a good analogy from Mastering the Market Cycle about pendulums:

“But whenever the pendulum is near either extreme, it is inevitable that it will move back toward the midpoint sooner or later. In fact, it is the movement toward an extreme itself that supplies the energy for the swing back.”

It’s easy to look at one side of the pendulum and go “that’s the good side, I want the arm to always be on that side.” But the only way it gets to that side is by swinging there. When the pendulum is swinging back and forth it ends up on that side effortlessly. Gravity works with you. If you try to permanently keep it on that side, you’re constantly in a battle against gravity. I’d rather have the forces of nature on my side than against me. 

Enjoying rest also requires having something to rest from. If we try to live a life of perpetual ease, we’ll get restless or succumb to ennui. We need those periods of intense focus and meaningful work so we have something to pour our potential energy into as it builds up at the opposite peak. 

Cycles, tides, seasons, the natural world is full of these ebbs & flows. We want to fix everything to convenient time tables and calendars but at the end of the day we’re animals too. We should embrace these shifts in energy rather than struggle against them. 

It Won’t Ever Be Enough

I remember being a senior in college and writing “$2,000 a month” on my whiteboard. 

I figured if I could just get to that level of passive income, my basic lifestyle costs would be covered and I wouldn’t need to take any job I didn’t want to take. 

I eventually passed that goal and was able to live the passive income life for a little bit (discussed here), but it got old fast (more here). Then I set new goals for a new level of lifestyle I wanted to be able to support. 

I hit that goal, and the next one, and it turns out that hitting your lifestyle, passive income, net worth, and other financial goals don’t bring all that much satisfaction. You can always think of a next threshold to aim for, and always end up moving the goal post as soon as you hit it. 

My interest now is actually in removing financial complexity. More than a certain amount of money, I don’t want to have to think about money. And if you’re constantly trying to grow your net worth, passive income, whatever, then you’re not really living a rich life. If you’re still thinking about money all the time, then you need to work on that fixation more than you need to work on hitting whatever goals you’ve set. 

So I’m trying to think more about building a lifestyle that satisfies my wants for certain things (high quality food, for example) without requiring me to constantly think about money, or growing my revenue streams. If my family can be comfortable in the lifestyle we want in perpetuity while I get to continue exploring my interests, and don’t feel compelled to do whatever will have the highest financial ROI, then that’s winning in my eyes. 

Moving the goalpost to the next arbitrary number isn’t going to bring much satisfaction, so thinking more about building an extremely sustainable lifestyle is a better goal. Harder to quantify, for sure, but a goal is more of a direction than a destination. It doesn’t need to have a clear completion criteria. 

Rituals & Hosting

One of the best investments you can make is in your community. It’s tough to make friends and be constantly social in the world of remote work, Netflix, and social media, but everyone wants to spend time IRL with people who share their values. 

Hosting is a great way to facilitate this. Bringing together groups for dinners, breakfasts, coffee, adventures, parties, whatever, is something everyone enjoys and appreciates but are often hesitant to initiate themselves. It’s really worth making the effort to initiate these get-togethers. 

Constantly planning things gets exhausting though, which is why rituals are so helpful. Having pre-set times and places for different events gives everyone an easy way to see each other, without having to rely on one point person to constantly bring everyone together. 

A successful ritual is one where:

• People can rely on it every time period (e.g. weekly) 
• It’s casual enough for people to show up regularly, but not feel obligated to attend
• It could continue without the initial point person perpetuating it

It could be anything: group coffee, a workout class, a running group, a swimming group. Creating regular social activities with people you want to spend more time with is the best way to see them more often. 

Part of it relates to what I talked about in Default Now. Instead of filling your week with work and then hoping to squeeze social time in around it, fill your week with regular social activities (rituals) and fill the work in around it. 

Everyone else wants more of these activities too, they’re just waiting for someone to initiate them. It may as well be you. 

Have a great year!