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

Barry Sanders walked away from the NFL 1,457 yards short of the all-time rushing record. He had rushed for 1,491 yards the season before and likely had another four or five seasons left in him. He retired anyway.

To anyone who confuses longevity with achievement, the decision looked irrational. Sanders had already collected every validation worth collecting and chasing the record would have cost him something he valued more: his health, his humility and the way he would be remembered.

For executives thinking about when to step down, how to approach CEO succession planning or how to build a lasting executive legacy, Sanders offers one of the clearest case studies in modern business thinking. What he did at 31 is what many CEOs refuse to do at 60.

Knowing when to step away

A CEO should step down when the role no longer demands their full capacity — and that usually happens before the scoreboard reflects it. Sanders knew he was still the best running back in football when he retired. That was the point. He left at his peak because staying longer would have traded the best for the most.

There are usually three signals that tell an honest executive the season is ending:

• The annual business plan starts feeling easy to build, which should never happen in a healthy operating environment.
• Leadership meetings and town halls begin repeating the same ideas because the leader has run out of new perspectives.
• Board meetings become overly comfortable and predictable, which may be the clearest warning sign of all.

My last company grew from $500 million to $2.7 billion over four-plus years. Profits increased nineteenfold and we sold at a twelve-times multiple, landing in the 99th percentile of our PE firm’s historical returns. That was the best season any CEO could reasonably ask for — and continuing past it would have been the trade Sanders refused to make.

Succession planning vs. walking away without a plan

CEO succession planning is the deliberate preparation of the next leader with enough runway for the transition to feel stable rather than disruptive. The difference between strategic succession and quitting comes down to structure: a timeline, a successor and a leadership bench developed before it is urgently needed.

Sanders’ retirement appeared sudden publicly, but internally, he had been preparing for it for years. I’ve approached leadership transitions the same way. I’ve never simply quit a role. I’ve always operated against a timeline and prepared the next leader in advance, allowing delegation to accelerate near the end instead of collapse under pressure. Private equity environments reinforce this mindset by design. The clock starts the day the CEO signs on.

Quitting is different. It’s the absence of succession architecture. It’s the CEO who stays too long, leaves without a plan or exits so abruptly that the organization spends the next eighteen months absorbing the shock. The distinction is not emotional. It’s structural and visible the day the transition is announced.

Building a legacy that lasts

Executive legacy is shaped by protecting the reference point.

The final chapter often becomes the lasting image of a career, which is why the last operating role matters so much. Sanders’ final season — 1,491 yards and a tenth consecutive Pro Bowl — became the image people remember. No one remembers him limping through decline. The trap that keeps many CEOs in the seat too long rarely presents itself as naked ambition. More often, it reveals itself through identity.

At a dinner party, executives are often asked a simple question: “What do you do?” For many leaders, the title becomes the answer they’ve trained themselves to give. Losing the role can begin to feel like losing themselves. Even my own children preferred the version where their father was the CEO of a company.

Separating identity from title is what makes stepping away manageable instead of emotionally destabilizing. Sanders’ identity was being the best running back alive, not simply being an active one. Mine has always been building fearless leaders, not holding the CEO title itself. The financial side of stepping away is math. Math rarely creates internal conflict. Ego does.

What a CEO-to-chairman transition actually looks like

Transitioning from CEO to chairman only works when the new role genuinely benefits from the former executive’s experience. It fails when the position exists mainly to preserve proximity to power. The difference becomes obvious quickly.

One mistake I made was remaining on a board after stepping down as CEO. Without intending to, I influenced discussions in ways that complicated the incoming CEO’s strategy. Institutional memory does not disappear the day a title changes. We corrected it, and I have not remained on the board of a company I previously ran since.

No new CEO truly wants the former CEO hovering nearby. The leaders who insist they are comfortable with it are often the ones who most need the separation. I’ve also watched mentors accept smaller CEO or chairman roles into their seventies, only to see the scope of those roles gradually shrink around them. A great operator leading a diminished mandate eventually appears diminished themselves.

Sanders never accepted a diminished role, which is one reason the image of him at his peak survived intact. The better alternative is often stepping away from a single operating seat and working across multiple companies in advisory or investment capacities. That preserves the stature built during the final operating role rather than slowly reducing it.

Recognizing your Barry Sanders moment

Recognizing the Sanders moment requires an honest assessment across three areas:

The capacity test: Does the role still demand your full capacity? If the annual plan writes itself and the board no longer pushes back, the answer may already be no.

The succession test: Is the next leader identified, developed and ready? If the transition requires more than six months of runway, the process likely started too late.

The identity test: Is the title your activity or your identity? If losing the title feels like losing yourself, the attachment itself becomes the risk.

The executives who can answer these questions honestly tend to leave with their legacy intact. The ones who cannot often become cautionary examples quietly referenced by successors behind closed doors.

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

Barry Sanders walked away from the NFL 1,457 yards short of the all-time rushing record. He had rushed for 1,491 yards the season before and likely had another four or five seasons left in him. He retired anyway.

To anyone who confuses longevity with achievement, the decision looked irrational. Sanders had already collected every validation worth collecting and chasing the record would have cost him something he valued more: his health, his humility and the way he would be remembered.

For executives thinking about when to step down, how to approach CEO succession planning or how to build a lasting executive legacy, Sanders offers one of the clearest case studies in modern business thinking. What he did at 31 is what many CEOs refuse to do at 60.