Chris Allen, CEO of RedFive, on Knowing When (and If) to Step Down

What does it mean to leave on a high note — and how do you know when that moment has arrived?

In a recent Wisdom From Wizards conversation, I sat down with Chris Allen, CEO at RedFive, to explore the CEO’s version of the classic dilemma:
Would you rather step down at your peak — or stay on as long as possible?

At first glance, it’s a question about timing. But Chris brought a sharper lens: What if the “peak” you think you’ve reached… isn’t actually the peak at all?

“That’s the tricky part, right? You don’t know. What you might think is your peak may not even be a peak. It could ratchet up again.”

Chris’s answer challenges the traditional hero’s arc — where the founder exits with a mic drop at their “moment of greatness.” Instead, he reframes leadership as a journey where milestones are only visible in hindsight. His pragmatic advice? Stick with it, not out of stubbornness, but out of the humility to recognize that momentum may still be building, even when it’s not obvious.

This moment captures what Wisdom From Wizards is all about: unfiltered insights from leaders who’ve wrestled with the real tradeoffs of scale.

Whether you’re nearing what feels like a high point, or wondering how much longer you want to stay in the role, Chris’s wisdom is a valuable reminder that clarity doesn’t always come in real time.

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