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Why an Athlete’s Retirement Made Me Rethink My Exit After Building a $2.7B Company

May 19, 2026
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Opinions expressed by Entrepreneur contributors are their very own.

Barry Sanders walked away from the NFL 1,457 yards wanting the all-time dashing file. He had rushed for 1,491 yards the season earlier than and sure had one other 4 or 5 seasons left in him. He retired anyway.

To anybody who confuses longevity with achievement, the choice seemed irrational. Sanders had already collected each validation price accumulating and chasing the file would have value him one thing he valued extra: his well being, his humility and the way in which he could be remembered.

For executives occupied with when to step down, tips on how to strategy CEO succession planning or tips on how to construct an enduring govt legacy, Sanders presents one of many clearest case research in trendy enterprise considering. What he did at 31 is what many CEOs refuse to do at 60.

Understanding when to step away

A CEO ought to step down when the function now not calls for their full capability — and that normally occurs earlier than the scoreboard displays it. Sanders knew he was nonetheless one of the best operating again in soccer when he retired. That was the purpose. He left at his peak as a result of staying longer would have traded one of the best for essentially the most.

There are normally three indicators that inform an sincere govt the season is ending:

The annual marketing strategy begins feeling straightforward to construct, which ought to by no means occur in a wholesome working setting.Management conferences and city halls start repeating the identical concepts as a result of the chief has run out of recent views.Board conferences turn into overly snug and predictable, which often is the clearest warning signal of all.

My final firm grew from $500 million to $2.7 billion over four-plus years. Income elevated nineteenfold and we bought at a twelve-times a number of, touchdown within the 99th percentile of our PE agency’s historic returns. That was one of the best season any CEO may moderately ask for — and persevering with previous it might have been the commerce Sanders refused to make.

Succession planning vs. strolling away and not using a plan

CEO succession planning is the deliberate preparation of the subsequent chief with sufficient runway for the transition to really feel secure reasonably than disruptive. The distinction between strategic succession and quitting comes right down to construction: a timeline, a successor and a management bench developed earlier than it’s urgently wanted.

Sanders’ retirement appeared sudden publicly, however internally, he had been getting ready for it for years. I’ve approached management transitions the identical method. I’ve by no means merely give up a task. I’ve at all times operated towards a timeline and ready the subsequent chief upfront, permitting delegation to speed up close to the top as an alternative of collapse below strain. Personal fairness environments reinforce this mindset by design. The clock begins the day the CEO indicators on.

Quitting is totally different. It’s the absence of succession structure. It’s the CEO who stays too lengthy, leaves and not using a plan or exits so abruptly that the group spends the subsequent eighteen months absorbing the shock. The excellence will not be emotional. It’s structural and visual the day the transition is introduced.

Constructing a legacy that lasts

Govt legacy is formed by defending the reference level.

The ultimate chapter usually turns into the lasting picture of a profession, which is why the final working function issues a lot. Sanders’ closing season — 1,491 yards and a tenth consecutive Professional Bowl — turned the picture folks keep in mind. Nobody remembers him limping by means of decline. The entice that retains many CEOs within the seat too lengthy not often presents itself as bare ambition. Extra usually, it reveals itself by means of id.

At a cocktail party, executives are sometimes requested a easy query: “What do you do?” For a lot of leaders, the title turns into the reply they’ve skilled themselves to offer. Dropping the function can start to really feel like shedding themselves. Even my very own youngsters most popular the model the place their father was the CEO of an organization.

Separating id from title is what makes stepping away manageable as an alternative of emotionally destabilizing. Sanders’ id was being one of the best operating again alive, not merely being an energetic one. Mine has at all times been constructing fearless leaders, not holding the CEO title itself. The monetary facet of stepping away is math. Math not often creates inside battle. Ego does.

What a CEO-to-chairman transition truly seems to be like

Transitioning from CEO to chairman solely works when the brand new function genuinely advantages from the previous govt’s expertise. It fails when the place exists primarily to protect proximity to energy. The distinction turns into apparent rapidly.

One mistake I made was remaining on a board after stepping down as CEO. With out meaning to, I influenced discussions in ways in which difficult the incoming CEO’s technique. Institutional reminiscence doesn’t disappear the day a title adjustments. We corrected it, and I’ve not remained on the board of an organization I beforehand ran since.

No new CEO actually desires the previous CEO hovering close by. The leaders who insist they’re snug with it are sometimes those who most want the separation. I’ve additionally watched mentors settle for smaller CEO or chairman roles into their seventies, solely to see the scope of these roles step by step shrink round them. A fantastic operator main a diminished mandate ultimately seems diminished themselves.

Sanders by no means accepted a diminished function, which is one purpose the picture of him at his peak survived intact. The higher various is commonly stepping away from a single working seat and dealing throughout a number of firms in advisory or funding capacities. That preserves the stature constructed through the closing working function reasonably than slowly decreasing it.

Recognizing your Barry Sanders second

Recognizing the Sanders second requires an sincere evaluation throughout three areas:

The capability check: Does the function nonetheless demand your full capability? If the annual plan writes itself and the board now not pushes again, the reply might already be no.

The succession check: Is the subsequent chief recognized, developed and prepared? If the transition requires greater than six months of runway, the method seemingly began too late.

The id check: Is the title your exercise or your id? If shedding the title seems like shedding your self, the attachment itself turns into the danger.

The executives who can reply these questions truthfully have a tendency to depart with their legacy intact. Those who can’t usually turn into cautionary examples quietly referenced by successors behind closed doorways.

Plan the exit with the identical rigor used to plan the ascent, and the legacy normally takes care of itself.

Barry Sanders walked away from the NFL 1,457 yards wanting the all-time dashing file. He had rushed for 1,491 yards the season earlier than and sure had one other 4 or 5 seasons left in him. He retired anyway.

To anybody who confuses longevity with achievement, the choice seemed irrational. Sanders had already collected each validation price accumulating and chasing the file would have value him one thing he valued extra: his well being, his humility and the way in which he could be remembered.

For executives occupied with when to step down, tips on how to strategy CEO succession planning or tips on how to construct an enduring govt legacy, Sanders presents one of many clearest case research in trendy enterprise considering. What he did at 31 is what many CEOs refuse to do at 60.



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