Tip
Bob Baxley talks about his stint at Pinterest: “I bounced off the culture. My friend said ‘I thought of it as you bounced off the culture.’” He continues: “These careers are really hard. People think of it like climbing a pyramid. I think of it more like going out on a branch on a tree and the branch gets more flimsy. People falling off jobs is the common use case. We have a bias towards survivors.”
Turns out senior career transitions work exactly like this.
You’re evaluating the Chief Product Officer role. Big title, great comp, impressive company. But something feels off about the culture. The leadership team dynamic, how decisions get made, the intensity level—it doesn’t quite fit. You tell yourself you’ll adapt, you’ve done harder things. Two years later, you’re out. Not fired, just… didn’t work out.
Younger managers think this means they failed. You know better. You’ve watched enough senior careers to know the higher you climb, the more common these mismatches become. Your former peer who left Meta after 18 months, the VP who “mutually decided to part ways” with the fintech, the Chief Strategy Officer whose tenure at the enterprise company was quietly short—these aren’t failures. They’re the common case.
We have a bias toward survivors. We see the LinkedIn profiles of people who made it work and assume that’s the pattern. You’ve been in the room long enough to see what doesn’t show up on LinkedIn: the dozens of talented people who climbed high, found a bad fit, and moved on.
That pattern recognition—knowing that senior career setbacks are normal, not exceptional—comes from watching enough complete arcs. You know the branch gets more flimsy as you climb. You know cultural mismatch at senior levels is about fit, not capability. That perspective only develops from seeing both the survivors and the many who didn’t survive particular roles.
Context
Bob Baxley spent 35 years in design leadership at Apple, Yahoo, Pinterest, ThoughtSpot. His point about “bouncing off culture” at Pinterest came from recognizing the mismatch too late—Pinterest valued consensus differently than Apple valued directness.
For experienced leaders evaluating new roles, this isn’t about avoiding risk—it’s about recognizing that senior-level cultural mismatches are common and navigating them is part of the game. You’ve watched enough colleagues exit senior roles to know it doesn’t define their careers.