The terminal level rulebook.

At work, the Staff Engineer cohort has a monthly meeting. The agenda varies but most recently we talked about a common theme: how do you find career progression after reaching your organization’s terminal level?

Reaching the terminal level has a lot in common with graduating from your last educational environment (graduate school, high school, or whatever). Before you graduate, you have clear grades, graduation requirements, exams, and someone else is responsible for teaching you how it works. After you graduate, there’s no framework at all. The good news is that the previous system was an artifice. Your real goal was to learn as opposed to getting grades that represent learning. The bad news is that you have to learn to measure progress without the comfort of an artificial gauge.

As I get deeper into my career, I’ve tried to frame progress through my own career goals rather than a career ladder. I’ve also become skeptical of the artificial competition that career ladders deliberately create, but removing training wheels doesn’t inherently teach you how to ride a bike, so here are my rules for succeeding at the terminal levels:

1. There are still rules, they’re just poorly documented. After reaching the terminal level, the key thing to remember is that the road’s still there, it’s just unlabeled. If you convince yourself that there are no rules, you’ll end up misaligned and frustrated. It’s surprisingly common to see folks at terminal level get lost pursuing technically interesting work or “fun” technologies. These folks tend to exit well-managed organizations. You’ve gotta learn and follow the new, implied rules to stay aligned with authority.
2. Relationships outweigh rules. Rules are reinforced so often as you climb the career ladder that it’s easy to forget that someone created those rules, and those creators are now your peers. Rules just don’t work as well at the top of the career ladder because the population is so small. It can feel fair to apply the same rule to two hundred employees you consider from afar, but parents know the impossibility of fairly treating two individuals when you know them both very well. If you aren’t investing into your relationships with senior stakeholders, you’re ignoring these rules of the terminal levels.
3. There are many available projects but they are either urgent or ambiguous. Sometimes you’ll hear the meme that there are only a small number of company critical projects available, but my experience is that there is always a surplus of critical projects. It’s just that they’re difficult projects in one of two ways. Either they’re urgent with a fixed schedule driven by an external deadline or the project is missing someone capable of processing its surrounding ambiguity. The first category is probably familiar, so a quick example of the second: data locality. Data locality laws keep changing and your company’s international expansion plan will keep changing. It’s impossible to make forward progress on that sort of project without making simplifying assumptions despite knowing that some of them will be wrong. Most folks struggle to engage with problems where every aspect is unanchored and these projects remain unassigned (you could change the launch schedule, you could change your data architecture, you could change launch countries, you could introduce a regional vendor, you could…).
4. If you get stuck, move. When folks talk about the opportunities of working at a large company, they always mention that you can change your role every year or two to keep engaged. You can move around even at smaller companies, but there are often enough disadvantages that folks decide to stay put. At the terminal level, you’re released from most of the downsides to moving teams (reset progress on your next promotion, etc), and you bring with you sufficient organizational authority to accelerate whatever you switch towards. There’s always new things to learn in a different environment, even if it’s within the same company.

Hopefully these rules are enough to spark some internal dialog about how you want to spend your time and attention now that you’ve graduated to the terminal level. If the road is feeling too long or too wide open, then work with peers, friends or your manager to bring some structure to it. Structure is really helpful, but remember that now the structure is purely your tool rather than the organization’s.

If it isn’t serving you, it’s up to you to change it.