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If you’ve been a top executive for any length of time, you know that the role you’ve spent years mastering has become much more than a job—it’s a defining piece of your identity. So what happens when you step away from the corporate helm? “That identity question looms very large,” says Marc Freedman, faculty director of the Yale Experienced Leaders Initiative (ELI), as well as co-CEO and founder of CoGenerate. “You’re having to start from scratch, and it can feel like a very solitary journey.”
The good news? You’re far from alone on that road. According to a CoGenerate survey, 4.5 million Americans had already shifted into second acts, with an additional 21 million giving the goal high priority. With life expectancies longer than ever, Freedman says, we’re witnessing the emergence of a new life stage, one that does not have a well-defined script. “We’re no longer stuck with the three-part lockstep life course—school, work, leisure—that dominated our parents and grandparents experience,” he says. “That said, getting from one stage to the next requires a period of time to make a significant transition. We’re in the fitful process of actually constructing a new stage of life that doesn’t yet have a name.”
Freedman offers the following recommendations to ease the stress of that journey.
You’ve been known for your accomplishments and decision-making skills, but who are you without the title? That question isn’t just philosophical—it’s practical. “Take time to reflect on how your values and motivations have evolved,” says Freedman. What matters most to you now? Is it contribution, legacy, personal fulfillment, family? When you’ve explored those priorities, you can begin to hone in on a path that will best reflect them.
Not having immediate answers will challenge some leaders who are used to having them, but Freedman notes that an experimental approach is critical to finding your next chapter. “There’s an idealized notion about reinventing yourself—you go from being a CEO to opening up a vineyard or a bed and breakfast and the clouds part, the birds sing and everybody is happy,” he says. “But in reality, most people get from leaving that role to finding their next passion through trying on different things. That can take time, and can involve some things not working out as hoped.” Rather than viewing the latter as a setback, see it as a necessary step in a process that might involve sampling different roles, volunteering or taking short-term placements. The key is to explore opportunities that align with your evolving interests and skills. Remember—this phase is less about a perfect transition and more about exploring what fits best.
One common misconception is that stepping away from a CEO role requires a complete reinvention. Freedman’s experience shows that many successful second acts are less about changing careers and more about reintegrating existing skills into new contexts. One executive, who led a food distribution business for decades, realized while volunteering at a local food bank in Northern California that food banks were distributing processed and canned foods, while growers he knew from his previous role were throwing out perfectly good produce because they were blemished in some way. “So he created the farm-to-family program, which distributes 120 million pounds of food a year from growers to food banks. That was a new iteration of the skills that he had already accumulated,” says Freedman. “It’s not about changing who you are. It’s about taking what you know and redirecting it toward new purposes.”
“The transition from what’s last to what’s next is all too often a do-it-yourself project, which can be confusing and beset by questions of identity,” says Freedman. “That’s why the peer network is so important during this period.” A structured program, such as Yale’s ELI, which blends reflection with experimentation, connects participants with peers who are on similar journeys. It can help one another find clarity and purpose. For those still finishing up their professional act careers but contemplating what’s to come, ELI offers a blend of on campus and online learning. “That way you don’t have to relocate to a different part of the country to participate, but still get the benefit of the peer network.”
Planning for your next act isn’t about finding a clear-cut path; it’s about exploring possibilities, staying curious and understanding that fulfillment may come from unexpected places. Embrace the journey with the same passion and purpose that guided your earlier career, says Freedman. Whether you’re retiring, pivoting toward new ventures or planning a meaningful second act, approach the shift with intentionality and flexibility, allowing you to thrive not just as a leader, but as a pioneer of your next extraordinary chapter.
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