The unhappy optimizer
I originally conceived of this post as a “what I learned” post with lots of takeaways for others, but I’m really sick of reading advice, frameworks, and takeaways from others. I’ve been getting much more value out of reading people’s stories and deciding the takeaways for myself.
In that spirit, this is a story about how a obsessive focus on optimization led me astray.
For as long as I can remember, I’ve been intensely curious with a focus on optimization and personal growth. These are useful skills for a software engineer, and they have served me well at many jobs.
I don’t exactly know the origin of my curiosity. I remember always feeling different in school. I didn’t wear the right clothes, say the right things, or know anything about pop culture and music. My glasses were big, my hairstyle outdated. I was shy, and I was made fun of, even at a small private Christian school, then more often at a public high school.
I wanted to reduce the distance I felt between myself and others. There wasn’t anyone in particular I wanted to be like, I just wanted to be more compatible with, and less different than, other people. And so began my obsession with personal growth.
Over time, the motivations evolved. Once I felt compatible enough with others, I became very curious about the rest of the world. I moved abroad and met people with very different backgrounds and interests. Then, once I had shored up the gaps in my knowledge of the world, I turned my focus toward preventing repeating mistakes that my nuclear and extended family had made. Things like saving enough money, living below my means, improving communication within a relationship, learning how to express my feelings, building quality friendships… the list goes on, but you get the idea.
Related to this obsession with personal growth, I also came to believe that I can’t disappoint anyone, ever, for any reason. Hence, I need to seek out answers to every question, learn something about every topic. I must excel in every environment I’m thrown into. Every class, every job, every chore. I must avoid every failure that I can learn how to prevent.
My curiosity of love of optimization was well-suited to my work building software, and a desire for personal growth made me very amenable to seeking and acting on feedback. That gave me a lot of confidence that my approach to life was working. I kept getting cooler job opportunities and promotions, and most people seemed to really like working with me.
I got good at preventing bad things from happening, both at work and in my personal life. That doesn’t mean I avoided trying new things - to the contrary, because I was obsessed with growth, I tried new roles at work, new relationships, new cities. And I didn’t mind when I failed or when something bad would happen, because I would ensure that I don’t repeat that failure.
I’ll illustrate with a few examples from work.
- At one of my first jobs, I attributed the success of our team to our manager because, when she left the team, we lost our air cover everything started to go wrong. This led me to eventually take a managerial position so that I could learn what it takes to build and maintain a great team.
- I noticed that Design departments tended to struggle at observability software companies, so when an opportunity came up to fix a small design team, I took it.
- I got frustrated with company culture at several companies I worked at. At one company, they only gave positive feedback, and rarely if ever constructive feedback. At another company, they kept underperformers around too long, which dragged their respective teams down. So I decided I must join a company much earlier, or even start my own company, so that I have more control over the culture and management standards so that this doesn’t happen.
I kept a running list of every problem I encountered at every company I worked at so that, when I start my own company, I can review the list and ensure I’m not repeating any mistakes. Even writing this now, a part of me still admires that I do things like this. I am meticulous, observant, and thorough, and these attributes have and will continue to serve me well.
However, during the course of working on one of my own product ideas earlier this year, I started to realize how scattered and unfulfilled I was feeling. I remember listening to a podcast where two people who were talking about a long-running study were talking about what they have learned and how much they have enjoyed running the study. I was struck by their enthusiasm for the work they were doing, and how I was not able to talk about what I was working on with the same level of enthusiasm. I had a nice, rationalized reason for what I was doing, but I didn’t actually want to be doing it. I realized then that I had lost the thread and was missing something with my approach to my career. So I stopped working on that idea and spent more time snowshoeing in the Columbia River Gorge and journaling (even more than usual). That’s when I came up with the term “unhappy optimizer” to describe myself. Several months later, the term still feels exactly right.
I don’t know if the concept of the “unhappy optimizer” is generalizable. Certainly I know others in their 30s who are also unhappily optimizing their lives and careers, even if their origin stories are different than mine. What the stories have in common is that the person realizes that something they have been doing that has worked for them for a while is no longer working.
I certainly don’t have any generalizable advice figured out yet. For myself, I’ve been getting reacquainted with what I loved about software in the first place: human-computer interaction. I love working with complex workflows, lots of data, rich interaction. That led me to get back into working with mapping tech again to build an outdoor route-planning app. And it’s been fun! I’m hopeful that focusing less on preventing failure and more on my interests will lead me to a better place.
There’s plenty of advice out there about the importance of following your interests, so it’s not really a novel conclusion if this indeed ends up being the solution. For me, it was easy to think that I was actually interested in solving and optimizing all these other problems that I encountered in life.
Maybe there are different types of interests. For me, working on a difficult human-computer interaction software problem is really deeply satisfying, as is writing these blog posts, or planning the details of an off-trail backpacking trip. While I appreciate a high-functioning engineering team and recognize that a manager plays a big role in that, managing a team of engineers is nerve-wracking for me and doesn’t really lean into my strengths. I like the feeling of having built or fixed a team, but the process of doing it is super painful for me, and it takes me away from thinking about the product and the customers, which I enjoy much more.
I love when something is done well, but I don’t always want to be the person that does the work to get to that outcome. Maybe this whole journey has been about learning my own interests well-enough to be able to distinguish the deep interests that I should wholeheartedly pursue from the ones I need to be ok with letting others pursue. Maybe I just generally need to be ok with with sub-optimal outcomes in areas outside of my deep interests.
The same thing that happened at work was happening in my life. I had taken every life lesson to heart: live below my means so that I have plenty of savings to weather unexpected events, learn how to communicate better with my wife, ensure I’m spending enough time each week with friends so I don’t let friendships fizzle out. At some point, I had checked every box, mitigated every downside. And then, instead of feeling accomplished, I felt more lost than ever. By focusing on optimizing all these various aspects of my life, I forgot to live, and to ask what I even wanted from life in the first place.
Sometimes life feels like I’m just learning oft-repeated truisms (e.g. “life is for living”) the hard way. This is why I like the stories behind what people have learned about life. The conclusion is less interesting than how the person got to that conclusion.
If you got this far, thanks for reading! I’m intentionally not publishing these posts as a newsletter, but a few folks have read them and emailed me about them with thoughts and feedback, and that’s felt really great, so thank you!