Reframing My Relationship With Work

I’ve been on a career break for just over eight months. After enjoying my first obligation-free summer since childhood, I’m now starting to think about what sorts of work I want to do next.

One of the big motivators for my break is that I had had an unhealthy relationship with work. As far back as college, when something negative or personally difficult came up, rather than dealing with the issue at its core, I tried to power through it with work. On the surface, that approach seemed to be good for me: I graduated from college a little ahead of schedule, and I’m proud to have worked on challenging projects at several different companies. As good as this work was for shareholder value, though, it wasn’t always good for my mental health, and until recently, I had rarely considered that a concern.

It’s very likely that 2025 will be a year where I’ll have produced nothing of commercial value; that’s fine with me. Not working at a company means that I’ve been working on myself instead. The time I invest pays dividends in different ways than salary, bonus, or shares of stock. I’ve challenged myself to exercise more intensely this year than I had in the past, resulting in better fitness, and keeping my weight under control at a time when I’m not riding my bike to an office every day. Instead of refining my programming language skills, I’ve been honing my interpersonal skills, learning to be a better and more supportive companion to people around me personally, not just those who are going to write an annual review for me. Whether it’s physical exercise, language skills, social skills, or my chess game, regular practice and helpful feedback make me better. When I’m ready to take another job, I will have a better sense of boundaries between my work life and my personal life.

I had two moments last month, in the same week, that reminded me of how removed I am from the working world. First, I donated money to a public radio station, and they very nicely invited me to take a tour of their office to express their gratitude. As I told my guide, the brief tour was the most amount of time I’d spent in an office building this year. I felt very confused and out of place, like I didn’t even belong in an office environment after less than a year away from it. Secondly, I took a call from a corporate recruiter for the first time in years. The job seems interesting, although again, I found myself very unfamiliar with this type of call. It’s similar to a situation I’ve found myself in on some of my travels this year, where I have to jostle some stale spoken language I’d studied out of the attic of my brain, so that I can understand what’s being said to me in a foreign country.

Also recently, I reopened Katrina McGhee’s book Taking a Career Break for Dummies, which I read last year, to review the section towards the back about ending a break. McGhee took 20 months off work before coming back into the workforce as a self-employed career break coach. She advises people to take one-sixth of their break time to date as a time to focus on re-entering the workforce; for example, if someone’s been away for a year, the re-entry process might take two months. A big part of that process is introspection, identifying things that are of great importance to the person on a break. Most of my introspection is going to remain private, but for a future job in software — and I don’t foresee myself changing to a new career in the near-term — I came up with these priorities, in no particular order:

• A company that makes products I feel good about
• A working culture built on respect and teamwork
• Infrequent expectations to be available during nights and weekends. (I’ve even experienced this at Amazon!)
• Either an in-city office or a remote working arrangement
• A chance to learn new, interesting, skills and develop existing ones

I have some more travel coming up, but as I write this, there’s nothing on my calendar for 2026: no trips, no work, no classes, nothing big that creates an obligation. I’m having a great time working on myself and rebuilding what has broken down over the past 22 years. Nothing forces me back to the workforce, but I’m curious about my options.