The Long, Slow, Stupid, Fun Way | #153

September 11th, 2021: It’s been three years since I first moved to Taiwan. I moved there in 2018 without any plans and not knowing what was going to happen. I’ve gotten married, committed to writing, started an online business that’s supporting my life, and still don’t quite know what comes next.

We are back in Taipei this week after spending some time in Southern Taiwan which is incredible. I’m sad I haven’t spent much time there before this week.

Greetings to the 20+ new subscribers this week! If you’d like to join them:


#1 The Long, Slow, Stupid & Fun Way

Last week I set a goal of 5,000 subscribers by the end of September. It felt weird to put something like that out there. Yet one friend pushed me further, “why not 10k?” When people who know me well push me, I take their input seriously. Yet upon reflection, I sensed that thinking about 10k gave me the answer I needed.

I’m not writing here to get subscribers, I’m writing it because I genuinely enjoy it and so do at least 20-30 people who keep telling me so. I’m writing to those people. I’m writing to the 75 people who bought my book. Not future potential subscribers.

While more subscribers may enable me to directly monetize my writing or make more money in the short run and ensure I can keep doing this indefinitely, the money will not actually change my approach to life over the next couple of years.

I was explaining this to someone during a curiosity conversation and a phrase came out of my mouth, the “long, slow, dumb, fun game.” Here’s how I’d describe it.

  • Long: Focus on the meta-game of finding the work I want to keep doing indefinitely. Don’t get distracted by shiny objects.

  • Slow: Do things slowly. Start small and level up over time.

  • Stupid: Lean against obvious ways to make more money when you sense it’s not the thing that will matter over the long run.

  • Fun: Am I still having fun? Keep going. If not, quit, optimize, or scale back.

Of course, this isn’t an original idea. Somewhere deep in my brain was a memory of Frank Chimero’s talk titled “The Long, Hard, Stupid Way” which dropped online almost ten years ago. In it he describes his approach:

And what’s really interesting is when you look at doing things the long, hard, stupid way, it’s sort of a spectrum (raises hands apart): there’s the way that I do it that’s very painful and difficult, but ultimately the way I feel compelled to make things; and then there’s optimum efficiency over here. I think what’s interesting is to sort of look at that gap and to analyze it. I think that, from the perspective of someone who makes things—and I bet that a lot of people out there are also folks who make things in some capacity—when you work the long, hard, stupid way, it looks a lot like toiling and worrying and starting over and scratching good ideas to look for better ones

The LSSF way is a slight remix of this idea and in a similar way rebels against efficiency or optimization.

The LSSF way optimizes for the individual rather than best practice. I think a lot of the world is shifting in this way too. For many people work was something you did five days a week in an office, most of the year. Now people are realizing that model might be more negotiable than we imagined and people are trying to figure out what kind of model might work for them.

Consulting was a fast and smart game. It was taking business problems and running them through a human-driven search function to land on the best practices, analyses, or mental models that increased profit. It’s one of the best games ever invented and has led to incredible prosperity. However, if you aren’t wired to play it on the highest level of difficulty, it often induces low-grade anxiety that people struggle to shake.

Solopreneurship can also be played on fast and smart mode but it’s hard to sustain for long stretches of time. I can do it for a month but then I need a break. I’ve seen a handful of people play in this mode non-stop but they are the exception, not the rule.

The fast and smart game starts with a goal and works backward. Because these are competitive games, there tends to be one way of playing that wins out.

The long, slow, stupid, and fun way rejects the dominant mode of play optimizing around extrinsic goals and in doing so opens one up to having to develop alternatives. Such a person is rarely a cutting-edge early adopter but is not a laggard either. They are willing to experiment with working on different things, in different ways, and using new kinds of tools as soon as the friction to getting started is reasonable. The whole goal becomes learning from doing and figuring out what it tells you about what to do next.

Sascha Chapin recently wrote a post titled “Thing You’re Allowed To Do.” He offers a list of things such as “Board the plane at the last minute rather than standing in line for 30 minutes.” Obvious, I know. But so few people ever seek to stand out from the common way of doing things that we tend to forget there are infinite ways to play the game of life and work.

Here is the thing I think more people should realize they are allowed to do: work on whatever you want to even when you’re in a full-time job.

When I was at BCG I volunteered to work with the internal training team. I did this by walking to the desk of the training manager and telling her I would prioritize her work above my own. This was stupid. I wasn’t going to get any sort of rewards for volunteering time that would take away from my day job, but it was what I wanted to work on. My follow-through earned her trust and she had me join several training weeks around the world. During those trips, I got to spend time with a guy who made his living around this work. He was fully alive and became another role model of how I might want to live in the future.

Six years later, I’m running an online training academy and negotiating with three companies to design training programs. Long, slow, and stupid though. I could be making $350k at BCG.

The key part of the LSSF is the “F” and I think this is the part Chimero missed. For decades, we’ve been attached to a default path story about how one should live that was paired with the idea that it probably wasn’t going to be fun. You gotta work, right? I designed my life around the idea that work kind of sucked but that you can just make your life outside of work great.

Luckily, I’ve discovered the fact that you can not only like your work, but you can also find it thrilling. Yes, thrilling. That’s the word I used when I was talking to a fellow solopreneur this week. It felt silly to say but his virtual fist bump told me I was on to something. The joy of finding something you know you want to keep doing is a lasting kind of fun that rarely gets talked about.

The LSSF way might even be more ambitious over the long term. It’s one thing to make a ton of money, it’s another to declare that you are going to try to do something for 25 years and see if it works out. When you look back in history, you find that people like Keats, Van Goh, and Thoreau died before anyone really cared about their work. Like I said, might be more ambitious. Most of the time, stupid and crazy.

Thoreau even said, “The life which men praise and regard as successful is but one kind. Why should we exaggerate any one kind at the expense of the others?”

He was the OG off-the-default-path blogger.

The thing about his line is that there are plenty of ways to be regarded as successful in today’s world. The range of options is likely well beyond what he could have imagined. What would have shocked him, however, is that there are now billions of people and many of them fail to imagine different ways of doing the things they do.

We’re living in a time in which the common knowledge about possible life paths is shifting. For 75+ years the story of the default path had an overpowering hold on our imaginations and over time, we started to approach that game in a single way.

Fast and smart.

The long, slow, stupid & fun approach is just one answer but I hope to discover others. All I know is that we’ll need better modes to play if we ever hope to make the default path fun again

So no subscriber goals. I’m just going to keep writing.


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