I once interviewed a very impressive candidate for a product manager/owner role. This guy stood out from all the other candidates, he had a slick binder full of all his accomplishments and could talk about then at great length. I would have loved ro work with this guy. But, it became clear to me he’d never experienced failure, and so I asked about some of his professional set backs, and it was even clearer that he’d only ever worked on projects that were able to get a lot of support from management at companies with the resources to all but guarantee success. I ended up having to tell management he’d be a poor fit as a result. The position was one that was almost guaranteed failure at a company shrinking over 10% a year, that was unable to stop the old habits that were no longer working. We needed someone who could fail on an almost daily basis, yet still manage to salvage something from the position. I think we got lucky and found someone who did this, she was able to consistently interact with upper management, and understood that 1% improvements compounded to make a great product. Sadly, she eventually got beat down enough arguing with management to leave, but her presense was invaluable in creating the culture my team currently enjoys.

And sadly, she will not make the mistake of taking similar project on again. Because it was not rewarded altrough people under her and after her appreciate it, she likely had no benefit from it.

She got more confidence and experience. That makes her a better leader in her next job. She moved on and chances are that she got a better job because she could convince somebody that she can succeed in a difficult environment.

Quoting parent: "Sadly, she eventually got beat down enough arguing with management to leave"

That is not more confidence. And likely, she does not want "difficult environment" job either - could have stayed for that. What you learn in such environment is to spot red flags sooner.

Such positions are not rewarded, she did not enjoyed that, she will likely seek different position next.

I probably would have hired the guy anyhow. If you have a great candidate, I think it would be difficult not to hire them just because they are going to face some challenges they have not in the past because that's all of us. No challenge is the same.

It depends on how you define risk. I find it crazy risky to tailor your resume in a way that results in people who are not "#2s" end up being your boss. In my experience, the only thing worse than a bad employee is a bad boss. I recommend letting hiring managers see the good, bad, and ugly of your experience. Let someone who can see through it all to recognize your value be your boss. And let everyone else walk away.

I wonder what some good examples of people that have gone on to have a strong second or third act after failing.

Probably 40% of fortune 1000 c level executives. You can reach a point where you continually fail upward. Some companies are willing to accept someone who failed at a company twice their size if they think the executive can get them to double their current size before they reach their point of failure.

I respectfully disagree and would say c-level people of major companies are the most risk averse of almost all people. They run from failure like it's a stain. They want to always look good in the eyes of 'the big boss' and often have very little interaction with them and so are keen to always impress.

In business politics, perception is the only thing that matters, so it's really hard to spin failure as success.

Also, their first reaction to failure will be to find someone to take the blame.