Part 2 of 2
In my last blog, When is Enough Enough? I explored how executives often stay in their roles too long—whether in business, nonprofit leadership, or other commitments—because they never define what “enough” actually means. Too many leaders push forward without a clear stopping point, leading to burnout, diminished passion, and missed opportunities to transition on their own terms.
But how do you know when it is truly time to step away? How do you recognize that you have reached enough before it is too late?
The Four Questions
One of the executives I coach, a highly respected attorney, shared a great exercise with me. She was talking with a wise and “seasoned” mentor who told her about four questions he asked himself when he decided it was time to retire.
These questions serve as a powerful litmus test for any leader wrestling with what is next.
1. Do I have enough?
Enough financial security? Enough personal fulfillment? Enough professional success? The answer does not have to be, “I have everything I have ever wanted,” but rather, “I have enough to walk away without regret.”
2. Have I had enough?
Work may have been fulfilling for decades, but if the passion is gone, the stress outweighs the reward, or the grind is no longer worth it, that is a sign that it’s time to move on. Some executives push through fatigue and frustration, thinking it will pass. But if the feeling lingers, it is time to take it seriously. (As I hear so many people say today, “Is the juice worth the squeeze?”)
3. Do I have something else?
Retirement is not just about leaving something—it is about going toward something else. A new passion, a hobby, volunteer work, consulting, travel—something that gives your next chapter purpose. The happiest retirees are not just walking away; they are stepping into something new. And in most cases, this is a combination of a new passion, hobby, volunteer work, travel, etc.
4. Do I have someone to do something else with?
Who will you spend time with? A spouse, family, friends, or colleagues in a new venture? Community and connection are crucial. Many executives delay retirement because work is their primary source of relationships. This is important: If you do not have people to share the next phase with, retirement can feel isolating instead of liberating.
When Other Executives Knew It Was Time
One CEO told me that he realized it was time when he no longer cared about the big decisions. He used to wrestle over strategies and numbers late into the night, but in the last year, he found himself disengaged, deferring to others, and feeling relief instead of excitement after big wins. That was his sign.
Another leader, the CEO of a family business, realized he had overstayed when his younger leadership team started privately discussing new directions—ones he was not fully aligned with. He recognized that his resistance to change was not good for the company, and instead of becoming a roadblock, he chose to step aside.
A nonprofit leader I know found that every board meeting felt like a chore. The vision that once energized her now felt exhausting. The mission had not changed—she had. When she asked herself these four questions, she realized she had enough, she had had enough, and she needed to make space for new leadership.
Tying It All Together
In When is Enough Enough? I explored the difficulty of letting go—how executives often stay past their prime because they do not recognize what “enough” actually looks like. This follow-up post provides a practical tool to help recognize that: four simple, but powerful questions to help you decide when it is time to move on.
If you are wrestling with retirement—or any major transition—take a moment and ask yourself these four questions. If the answers point toward stepping away, do not ignore them! Recognizing that enough is enough is not about quitting; it is about knowing when to shift into the next meaningful chapter of life.
Because when you have had enough, you owe it to yourself—and to those around you—to embrace that.
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