On mid-career challenges

When I started my career nearly fifteen-mumble-something years ago, I was working at a big corporation full of lifers. Many of the people I knew there had only worked at one or two companies over the courses of their careers. I started out with an expectation that I would do the same thing, that I would build a career at an organization where I would gain skill points and level up until I became an engineering fellow or distinguished architect or whatever fancy job title was at the top of the ladder there.

For most people in the tech industry, careers these days look nothing like that. Whether it be due to less job security in general, or the fact that oftentimes the only way to get a meaningful raise or promotion is to switch companies, people are ending up with more unpredictable career paths than in previous generations. Progress looks a lot less linear. This is especially true in startup environments, which often put less energy and resources into the growth and development of employees. While larger corporations often have clear career ladders and internal programs in place to help provide career guidance and training, startups (especially the sorts that say things like “we only hire senior engineers”) often aren’t able to provide the same sort of help and resources.

The past few years have felt like a big struggle for me in terms of career progress, and in true “oh god this must be my fault somehow” fashion, I’ve spent a long time looking inward and looking for ways to blame myself. I thought that I must have peaked before I hit 30, that it was all going to be downhill from here and that somehow this was because I’d done something wrong.

However, more realistically what I’m running into is a normal series of mid-career challenges in an industry where careers are no longer a linear progression at one or two companies. I’m not yet in my late career, where I would like to imagine that I’ll for sure have things all figured out (future-Ryn is looking back on this and laughing right now) and be senior enough to always be taken seriously. But I’m also no longer in my early career, where my goal was straight-forward — basically “become a senior engineer” — and everything I did was working in support of that.

I’m in a position right now where I have to figure out what comes next for me and how to navigate the challenges of getting there. I made it to senior engineer, I wrote a book, I spoke at a bunch of conferences, switched from ops to dev back to ops again — so now what? For some people, mid-career looks like figuring out what your next set of career goals might be, what you might want your next 10 years of work to look like. For others, it might mean changing careers — you might be in a position where you’re quite senior in terms of core skills such as communication, team dynamics, and project planning, but you came into tech from another field so your coding skills still have leveling up to do.

Setting goals is just one of the challenges that comes with entering your mid-career. Other challenges can revolve around everyone’s favorite skill, Dealing With Other People. Interactions with your manager become different as you start to need different things out of that relationship. Working with your peers changes too, as there are new expectations around what kind of role you will take in a team and how your behavior can impact the people around you. The nature of the work you’ll be doing will likely change as well.

Like so many things in the industry and in the world, these challenges are harder when you’re a member of an under-represented group. Being under-leveled, under-promoted, under-paid, and having to constantly prove yourself over and over slows down career progress. Having more caregiving responsibilities outside of work can mean making yourself less available for on-call or other things that might get you promoted. A non-traditional path into tech can keep people questioning if you should be here. I can’t speak to all the different challenges that people might face — I know that things like my skin color and traditional CS background have made some things easier for me — but I do want to acknowledge ways that these mid-career challenges can be exacerbated if you don’t fit the mold of “what an engineer is supposed to look like”.

Over the next few blog posts, I’m going to dive deeper into some of these challenges. I’ll cover things such as working with managers, being an effective team member as a mid-career engineer, dealing with the changing nature of your work, and finding ways to think about your career goals and growth. I don’t have all of the answers yet (even Super Cool Thought Leaders From The Internet TM don’t have all their shit together, I promise!) but I hope that I can at least offer some reassurance that it’s not just you, as well as some useful insights into what these challenges look like.