On mid-career and thinking about your path forward

It’s hard to think about the long-term in short-term-focused environments, and these days a large part of the tech industry feels like it thinks only in the short term. Founders try to get products out the door before they run out of runway, VCs chase their next unicorns, executives focus on quarterly growth to the exclusion of long-term impact — in this world, it’s easy for individuals to feel like they have to keep up the same pace, always running from one thing to the next while trying to avoid burnout.

Much of the way modern organizations are run seems to exacerbate this short-term focus. Companies will offer huge signing bonuses to bring people on board, and then provide little in the way of regular raises or even cost of living increases. A lack of clear promotion processes, career frameworks, and meaningful guidance or growth opportunities does little to aid in long-term retention. When it feels like the only way to keep making progress at work is to change jobs every couple years, of course it’s going to be hard to think long-term.

One important thing you can do is to start thinking for yourself about what sort of shape you want your career to have. With so many different things that the IC track after “senior” can look like, if you don’t do any sort of planning you might find yourself going along whatever your current company has laid out. That path might not be a bad one, but you’ll want to make sure you find yourself there on purpose, not by accident.

When you’re ready to start thinking deliberately about what you want the overall arc of your career to look like, here are some questions to ask yourself:

Do you want to be a specialist or a generalist? Do you feel drawn towards an organizational focus or a technical one? Some amount of technical generalization is necessary to be a well-rounded senior engineer, but once you get to that point a lot of options can open up for you. When you know what sort of focus you want to have, it can be easier to start finding teams or organizations that align with those goals.
If that’s a hard question to answer, try starting smaller. What sorts of projects have you found most fulfilling? Are there types of work you’d like to do more of? For example, I’ve learned that I quite enjoy working on internal tools that do things like reduce friction around deployment processes, so when I think about new opportunities, I can ask specifically about those types of projects.
On the other hand, are there types of work that you’d prefer to get away from? Being a senior engineer doesn’t mean that you never have to do anything tedious or boring ever again (you’re still part of a team, and that will mean things like paying down technical debt or being on call). But if you’ve learned that there are some types of work that you can’t stand, that can be useful information to have as well. If you know you hate doing that last 10% of performance tuning, if your manager asks if you’d like to be on the new performance team that’s being formed, knowing that you won’t actually find that fulfilling can keep you from taking unpleasant career detours.
Are you happy with your current focus or do you want to try something new? For some people, the mid-career can be a good opportunity to change direction a bit now that you have a feel for how engineering work gets done. Organizations that allow people to try on new roles (such as the month-long rotations that I’ve seen at places like Etsy) can be great for people looking to explore their options.
Do you want to do public-facing community work? Things like speaking at conferences, blogging, doing coding livestreams, or offering office hours can be beneficial for both you and your communities. These efforts can also be draining (especially if you’re an introvert) and often mean commitments outside of your standard work, so it’s worth considering if they make sense for you. For example, I’ve deliberately taken a step back from doing as much public speaking as I used to while I’m dealing with my own burnout. This type of work isn’t for everyone, and that’s ok — you can still be an effective team member without having a big public presence.
What do you want to move towards? For a while, my job changes were driven by leaving toxic environments, trying to get away from jobs that perpetuated title and pay inequalities or otherwise dysfunctional workplaces. While those changes helped get me out of bad situations, they left me feeling adrift in terms of career direction. In an ideal world, things like fair compensation and a respectful work environment would be givens, so even if you have to do some moves away from things, looking for a positive motivational goal can help maintain a sense of direction and a reminder of why you’re putting in the work.
What values are important to you, both at an individual and an organizational level? If you care a lot about giving back to people around you, you might look for a role that specifically rewards things like mentorship or other community-focused work. If you care about how your work gets used in the world, you might consider working at a B-Corp. A misalignment of values can be a big contributing factor to burnout, so clarifying what is important to you can help you know what to look out for.

Questions like these can be super valuable when you start thinking about what your next role might be or what sort of organization you might want to join next. But they are big questions, and it takes time and energy to give them the consideration they deserve. There’s no magic wand that can summon a respite from the world, and most of us don’t have the ability to take a bunch of time off while we figure out what to do next. In the meantime, however, you might consider some of these as ways to try and carve out a bit of time and space for yourself to think strategically about your career:

Keep notes for yourself. You can start with a brag document to make sure your work gets recognized, but you can also keep records of more meta-work things. It can be useful to note things like conflicts you’ve had, challenging managerial relationships, or projects that felt more or less fulfilling. This can help you recognize patterns in your work environments, which can make it easier to make decisions even when you’re struggling.
Think about joining an older/more stable company in your mid-career. While they aren’t the right fit for everyone, organizations that have been around for a while and are used to thinking long-term are more likely to have things like well-thought-out career ladders, coaching and mentorship programs, or other established ways to help people grow their careers.
To that end, you can start asking about career growth, promotion processes, and retention when you’re interviewing. If you’re looking to get promoted to principal engineer, for example, ask how many people in the team/department are at that level and how many have been promoted from within versus hired into it. Asking about demographics can provide valuable insights as well. Being the first of anything can be challenging. If a company doesn’t have a great track record of supporting and retaining mid-career employees, especially for URMs who aren’t always given the benefit of the doubt or opportunities to “fail up”, you might be in for an uphill battle.
Optimize for relearning. Tech moves fast and that rate of change seems to keep getting faster. It may not make sense to try to keep one static set of skills in your brain forever — you don’t want to realize during a job search that your skills have gotten rusty. Instead, figure out how to become a smart learner. If you can pick up new skills quickly and apply foundational principles to new ideas, that ability to keep learning can help you stay relevant and flexible in your work.
Look for other ways to build stability into your career. One nice thing about my move to Germany is getting a permanent work contract and 5+ weeks of vacation per year — it’s a lot easier to have room to think when I actually have enough stability to take time off and disconnect. While “move to Europe” isn’t the answer for everyone, you can look into more local solutions, such as coordinating with your coworkers to try to achieve more flexibile working condiditions, connecting with peers across the industry, and building up a fuck-off fund.

While I try not to be too cynical, it’s important to remember that companies look out for their own best interests, not yours. Even the best teams or organizations don’t last forever, so it’s important that you are able to think strategically about where you want your career to go and what actions you can take to help get there. Gone are the years when you could expect that one or two organizations would provide stability over the course of your working lifetime. Instead it’s going to be up to you to figure out what a long-term career path means for you. Hopefully some of these questions and strategies will be helpful for you if progress has stopped feeling so linear and you’re trying to figure out where to go next. If you’ve found your own useful ideas, please share them with people around you, so we can help each other learn together how to build and maintain sustainable careers.