Dreaming of Jobs

Would Your Dream Job Make You Happy?

Nov 2, 2017 Matthew Lyon

Recently I left The Best Job I’ve Ever Had. As with leaving any good job, it was a bittersweet, hard decision. And I almost passed it up chasing a dream.

A few years ago, between jobs and my first child on the way, I decided not to pursue what seemed like my dream job. I described what I wanted to be doing as: designing and building tools to help people make data-driven decisions so they can make the world a better place. Bret Victor had recently published the hugely inspiring What Can A Technologist Do About Climate Change?. Both the sections Tools for Scientists and Engineers and Media for Understanding Situations spoke to the arc of my career. This seeming dream job was with a household name I respect, building a next-generation data-driven interface to help people make ethical decisions.

Yes, please! This spoke to what I felt was my life’s work, to what gets me excited about working in tech. But. It would have required relocating to an expensive hotbed of technical talent, or travelling there every other week.

I gave relocation serious thought. Perhaps without the impending newborn. Perhaps if we didn’t already own a home that allows my partner to pursue her gardening and landscaping passions. Perhaps if we weren’t happy with our city. I talked to some colleagues who live or have lived where this company was, and every single one advised against relocation. I thought about commuting every other week, and the idea was laid to rest almost immediately. It simply didn’t align with what I wanted for my family, or with the kind of partner or father I wanted to be. In the context of my life, it wasn’t my dream job at all.

By contrast, The Best Job I’ve Ever Had didn’t seem as exciting. I took solace in the environment’s pace, and in working with people I’ve known for a while and repsect. But the project proved more interesting than I thought it was on first glance. I got something in front of users much quicker than I could have at the seeming dream job. I had a high degree of autonomy. I worked on a problem personally intruiging to me. It challenged my technical and communication skills, and my understanding of how people interact with technology. I worked thirty-two hour weeks, on my own schedule, from home. The development and product teams understood how to work well remotely, how to talk about progress and knew rest is work. I was more effective at my work in this environment than I had been before.

Friends asked Are you hiring? and I had to respond The parent company has a corporate hiring freeze right now. Which cuts to the heart of it: I did choose to leave this job for another. It used to be that when a colleague pitched a new opportunity to me, I’d say, I’m happy where I am, but thanks. Then a few key people left. The environment started changing subtly. I still liked my job, but figured I wouldn’t in a year. So I started listening to my colleagues’ pitches. Some of those were compelling, and turned into interviews and offers. After an emergency all-hands on-site, I figured I should move on sooner rather than later, and accepted one of the offers.

This time around, an opportunity that came early in my search seemed like another dream job: an R&D position at a large company, working on a cross-disciplinary team doing data analysis tools for A/VR environments. Unlike a lot of places, my art degree and experience outside web programming with things like 3D modeling and DSP were seen as assets. But. I’m not a fan of this company or its CEO. The fast-paced environment sounded prone to crunch-time. The job would require a commute an hour each way across the metro area. We’d need a second car. The particulars of the dream didn’t align with my values, and I decided not to pursue it.

Ideally, I wanted to continue working from home. But the realities of my toddler screaming for me because he hears me yelling at my computer have set in, and after talking with my partner about it, we decided having a commute downtown, manageable by bicycle or bus, wouldn’t be so bad. I knew I wasn’t going to find another thirty-two hour week situation. So I reiterated to myself a philosophy that’s served well: Don’t look for what you think will make you happy; you can’t know. Rule out what you know contributes to unhappiness and be open to what remains.

As with The Best Job I’ve Ever Had, the job I chose this time around also didn’t seem as exciting on first glance. I’d be out of my comfort zone in a large non-profit with a very corporate office environment. As I mulled it over, I realized it had a lot of things I wanted in a job: working on a small, startup-like team in the early stages of product development, a compelling project that could materially improve people’s lives, continuing to work in my language of choice, excercizing my strengths as a generalist, opportunities to learn and to mentor, among people who respect the company and its leadership and genuinely enjoy working there.

I gave notice at The Best Job I’ve Ever Had, and it turns out my sense of it’s time to leave was right: a few days later, I would have been laid off anyway as part of a company-wide staff reduction.

Is the new job my dream job? I can’t know. I had to ask myself: what is your dream job? only to realize as a new father with a mortgage that I’m not in a position to pursue it right now. I can’t even know if I would be happy with what I think is my dream job. I’m fine with that. I’ve been at the new job for a week, and I’m more excited about the project than I was before I started.

Dreaming of Jobs Matthew Lyon 2023 — license: CC BY-NC-SA 4