What CEOs Must Learn About Letting Go: ‘It’s Like Cutting Off An Arm’

As CEO of Guardian Life—a $90 billion mutual insurer—Deanna Mulligan had engineered a textbook succession that began when she first took the job. Over a 10-year period, she developed a deep leadership bench and hit critical KPIs for growth and performance. And she helped the board select and transition to a great successor.

And yet, on her last day—the supposed celebration of a career high point—the feeling blindsided her: “It was like cutting off an arm.”

For CEOs, this is the part nobody warns you about. You may swear you’ll never look back—but walking away from your life’s biggest stage can feel like amputating part of your identity. Even when the transition is carefully orchestrated, it’s rarely comfortable. It’s often existential. After a decade of preparation, leaving still forced a chilling question: Is this the last time I’ll matter this much?

1. The exit always feels bigger than you expect. Mulligan wasn’t caught off guard by the business mechanics of succession. She had groomed her replacements years ahead of time. “It’s what world-class companies do—we develop great talent,” she said. And yet, she confessed, “The greatest impact I’ve ever had might be over.”

2. Your predecessor may be more fragile than you think. This emotional turbulence is often hidden from view. Successors tend to assume that the outgoing CEO—especially one as accomplished as Mulligan—must feel confident, even relieved. But that’s rarely the whole story. “Many feel the weight of an impending end to the greatest, most important part of their career and maybe their life,” we wrote in CEO Ready: How to Earn & Keep the Job (Harvard Business Review, November 2025). Mulligan’s reflections reveal the hidden humanity behind the title. As a CEO candidate, the CEO you admire may be feeling quiet panic behind the polished handoff. “Don’t overestimate their comfort,” she cautions. Don’t mistake power for peace.

3. Reinvention requires release. Mulligan’s next chapter didn’t begin until she let go of what others expected from her. Retirement, it turned out, wasn’t restful. Not that she was idle: She wrote books, served on major high impact brand name boards for public companies and nonprofits—all great causes. It just wasn’t the life she wanted to live at this point in her career. “Acquaintances would unintentionally shame me into representing all women,” she admitted—pressed to join more boards, give back more and remain in the spotlight. Everyone had a “should” for her. But when she released the weight of expectation, something enthralling emerged: the opportunity to lead a disruptive insure-tech startup. “It was never a goal,” she said. “But it’s now a new kind of thrill.”

4. Everyone has a vision for you. Now that we’ve seen the cost and necessity of letting go, it’s worth revisiting how leaders get there in the first place. Mulligan’s transition began with a torrent of external expectations. “Everyone has a vision for you,” she said, “but unfortunately it’s not exactly yours.” Friends, colleagues and even family projected their values onto her career path—well-meaning, but not aligned with her own.

5. You can’t discover what’s next until you’ve released what was. This is one of Mulligan’s greatest leadership insights for the rest of us in any transition: As a high achiever, it’s not about finding something meaningful but the overabundance of high impact roles. “You’re drowning in an ocean of great and significant opportunities,” Marshall Goldsmith often recounts. The real threat to your impact isn’t scarcity—it’s surplus. Reinvention isn’t an act of momentum—it’s an act of subtraction. The ultra talented executive doesn’t suffer from lack of choice, but from the inability to say no to the good in favor of the great. When she stopped doing everything for everyone else, she created space to reconnect with what she wanted in this next chapter.

6. Don’t should on yourself. And that’s the final takeaway. The CEO role—and whatever follows it—must be pursued on your terms. Not because it checks a box. Not because others think you owe it to them or to the world. But because it’s the life you choose to lead—again and again. Even the most accomplished leaders must come to terms with the emotional weight of letting go. But if you give yourself permission to pause, to listen inwardly and to release what no longer fits—you just might uncover the next chapter of your future that’s not only thrilling, but deeply impactful at just the right moment in your already amazing life.