How does long tenure relate to learning?

Lately there’s been some discussion exploring the relationship between job tenure and learning in your career. Dan Luu summarizes one argument for long tenure as, “I feel like, if you care about learning, long tenures are highly underrated. In online discourse, a lot of people recommend job hopping frequently specifically to learn a lot and avoid stagnation, but I think that’s generally the opposite of correct.”

This is a tricky topic to discuss, because it’s easy to take any perspective as a personal criticism of your life choices. I get that! At one point in my career, I worried that my job tenures were too short for the opportunities I wanted. Conversely, in the days immediately following my stroke, I didn’t spend a moment worrying about tenure; I worried that I’d made the wrong short-term financial tradeoffs to protect my family if I was left unable to gainfully continue in my profession.

My broad thoughts on this topic are summarized in a forty-year career, but a few particular comments:

1. I agree: there are real lessons that are best learned through long tenure. In particular, repeated iterations of solving the same set of problems is deeply instructive as you balance against competitive and market forces
2. Every career decision is deeply context specific. If you try to apply generalities to your own experience, you’ll often worry about stuff that’s specifically not relevant to you. For example, I left my first tech job at Yahoo! after two years. However, Yahoo! Search had been largely sold to Microsoft and the product my team built was indefinitely paused before eventually being sunset. There was no alternative where I stayed on that team: that team didn’t exist much beyond my departure
3. As you look at advice folks have related to tenure (and really, any topic), look at what they have accomplished and ask yourself whether it relates to what you hope to accomplish. Folks are playing many different games in their careers, and you shouldn’t take advice from folks playing meaningfully different games than you (e.g. someone trying to lead the largest possible team—a horrible goal by the way—will act very differently than someone focused on advancing the wider industry’s approach to observability)
4. Sometimes tenure is much more about optics than reality. You might work at Google for eight years but significantly shift your team and focus every eighteen months. On a resume you could frame this as one eight-year stint, five 18-month stints, two four-year stints, or whatever. A resume’s long tenure won’t correlate directly to learning the lessons of long tenure
5. Depending on how you learn and how you build out your network, there are many ways to learn. I’ve worked with many folks who can only learn effectively from their own experiences, but I’ve also worked with many who’ve done a great job of learning from their network’s experiences. Depending on your approach to learning, you can certainly get access to the lessons of tenure from others without experiencing the tenure yourself directly
6. Tenure also teaches some bad lessons, which you’ve probably experienced when working with someone coming fresh out of their ten year stint at a FAANG company. This is because tenure can easily correspond with calcification

As my closing advice: all advice is wrong, think about your own situation for yourself.