The tenure at my previous company spanned over a decade - 10 years and 5 months. I don’t have the data to prove it but anecdotally this is an outlier within my peer circle. I used to make this annoying joke of telling folks that I was “way past my expiration date” and in some regards this was only half a joke.

There’s always a variety of reasons why someone ends up staying somewhere a standard deviation or two above from the mean - for me it was a combination of complacency (both good and bad), parts of fear, but also other stuff outside of careers (starting a family, a little thing called the pandemic, etc.)

But looking back I think there are some interesting benefits for staying this long - of course there are also severe drawbacks that shouldn’t be ignored either. I think a lot of these observations can only be made in retrospect - having a goal of staying some number of years would be an odd objective to have at any organization.

I think the chief benefit is being able to view the long-term, several-steps-away consequences of decisions - especially at a macro-level like those at department or organizational level. These decisions are a mixture of technical ones but also people/process ones. What I mean by several-steps-away are the sort of cascading effects of those decisions that you see over longer time horizons, not the immediate using-this-framework-increased-our-performance ones.

Note that these consequences aren’t necessarily new singular rules-of-thumb either - the longer time horizon naturally gives you more stuff to evaluate, but more importantly it gives you more context in terms of that evaluation. And that context for evaluation helps build a more precise mental model of why something was contextually good or bad which in turn creates a more thorough judgment of that decision.

Over time, these mental models of what works and doesn’t can be very helpful in identifying your own management style and identifying what resonates with you. For things that you feel worked well, the additional context can help you identify the things that helped make it work well - things that you may need to sniff out and look for as possible prerequisites when trying to apply it a second time.

Other benefits of long tenures is the build up and development (ie influence) of institutional knowledge. This goes beyond magic constants or why an API behaves the way it does. I’m referring to the high-level business machinery of how/why decisions are made. This knowledge and the relationships one builds with counterparts on other teams is critical in helping you identify the right thing to build, understanding with greater clarity their motivations, and ultimately sniffing out the right boundaries of components.

That being said, staying a long time does have its own drawbacks - complacency and inertia being a big one. Those two things naturally build up overtime without any input so it’s very easy for time to slip by without you noticing. Moreover, without a periodic, healthy dose of self-reflection that inertia can take on flavors of stubbornness that inadvertently create debt. This especially holds true for decisions that are/were good at one point but don’t get re-evaluated in light of some larger changes (this was my mistake).

Working at the same place often implies working with the same set of folks as well. This can create some unintended effects too, especially around echo chambering. Exposure to different ideas, thought-processes, and values are important because it helps you both explore and gut-check a solution space. Obviously, relationships take time to build so forcing new people into situations frequently doesn’t do anything either. (One cheap-ish and common way to break out of this are conferences).

When I wrote this, I found myself having a tough time - dwelling on past mistakes and pondering unlived lives and what-ifs. It’s still hard not to fantasize about it, but I’m also cognizant that I learned a tremendous amount and came away with a stronger perpsective on things I never thought I would care about.