So job tenures do seem to be shorter than ever, from the SDR level all the way to CRO and CMO. Layoffs are part of it, for sure — but so is voluntary attrition.

It’s super frustrating to many founders. In our quiet discussions, it’s often one of the first things that comes up. “We pay top of market, we have a great culture, we have years of runway, and great logos and problems to solve. Why do folks leave?”

I’m actually going to suggest actually — more folks should leave, faster. Yes, faster.

The world has changed since WFH started. It’s changed I think in more ways than we realized. Our relationships to work are just different.

So as part of a learning experience, I’ve asked dozens of executives who left roles … What Happened?

The stories are all different, but I finally saw one theme — everyone stayed too long. They stayed too long, and didn’t believe anymore. They stayed too long, and started to blame others. They stayed too long, and it just … hardened them. Even to what on paper was a great job.

And the problem with that hardening is … it stays with you. It’s hard to shake. It’s hard to let the frustration from staying too long go. At work. In personal relationships. With a bad vendor. Anywhere.

So this may sound like strange advice, but I do think it will be helpful:

  • Yes, if you have a good boss, a good job, and are appreciated and paid fairly — stay. Default to stay.  Even if the role isn’t perfect.  Probably, your next role won’t be as good. Every job has some grunt work and some negatives. Even CEO. Especially CEO.
  • But … but … if it’s just not you anymore. If you just don’t want to sell that product anymore, no matter how good the comp. If you don’t really care if one more feature gap is closed. If you don’t want to go visit that customer in person, that you know you should. If you just don’t want to show up, for whatever reason. For no reason, even.

Then calmly, quietly, and with respect, move on.  Folks today do seem to be staying in roles just … too long these days.  I don’t know why for sure.  Maybe it’s TikTok.  Maybe it’s too much change.  But things are different.

A related deep dive we did a little ways back:

And a related post here:

To Grow Your Career, You Gotta Stay Somewhere 2 Years At Least

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