When to retire is one of the toughest decisions for any executive to make. For a CEO at the top of the pyramid, the decision is rife with complexities. Not only must the CEO relinquish day-to-day control, he or she must cope with the possibility of not having completed the strategic objectives developed at the outset of their tenure.

Executive Summary

When to retire is one of the toughest decisions for any executive to make. Hanging in there too long can tarnish the CEO's legacy, while leaving too early may founder the ship. Carrier Management reached out to four retired insurance company CEOs. Although their stories are different, they share similar values about life and work.

Like the song goes, “Should I stay or should I go?”

Hanging in there too long can tarnish the CEO’s legacy, while leaving too early may founder the ship. For a graceful exit, a capable successor needs to be in the wings, but this is not always the case. And captivating post-retirement activities must be considered, as it is psychologically damaging to jump off a fast-speeding train onto, well, the couch.

It’s also not easy to give up power. This may explain why many CEOs are getting older. From 2006 to 2018, the number of Fortune 500 CEOs age 65 to 69 more than doubled from 20 to 44, according to research by Korn Ferry provided to Carrier Management. The average age of a Fortune 500 CEO has gone up from 55.4 in 2007 to 57.4 in 2017, according to Spenser Stuart research. (2017 Spenser Stuart U.S. Board Index)

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