Part 1 of 2
(This is a two-part series on knowing when you have had enough—whether in business, leadership, or life. In part two, I’ll share a powerful four-question exercise to help you determine when it is time to step away.)
How do you know when you have had enough?
It is a question that applies to so many areas of life—work, leadership, wealth, commitments, even relationships. Yet, in a society driven by achievement, accumulation, and ambition, we often push beyond enough without ever defining what it actually means.
For many executives, the pursuit of success is endless. The goalposts keep moving. How much wealth is enough? The common answer is, “Just a little bit more.” But more money, more stuff, more influence—none of it necessarily leads to more fulfillment. Instead, it often leads to exhaustion.
When an Executive Has Had Enough
I recently spoke with a CEO who had built a highly successful company over decades. By all measures, he had accomplished what he set out to do—financial security, professional respect, and a legacy of strong leadership. But he was tired. He admitted that he had been thinking about retirement for years but never pulled the trigger. “I just kept telling myself: ‘One more year, one more acquisition, one more big milestone.’”
The truth of it? He had hit enough years ago. But he ignored it. He kept pushing until work became a grind, his energy for the business dwindled, and his passion faded. When he finally stepped away, he regretted not doing it sooner.
When a Leader Holds On Too Long
I have seen this same sort of thing in nonprofit leadership, too. A well-meaning, dedicated leader takes on the role of volunteer president of an organization. At first, they are energized by the mission, making a real impact. But instead of stepping aside at the right time, they hang on too long. They fear no one else will do the job as well as they do it. They worry about leaving things unfinished.
By the time they finally say, “I have had enough,” they are burned out—and so is everyone around them. The nonprofit has suffered, its vision diluted, its momentum slowed. What started as a labor of love became a burden they resented.
Knowing When Enough is Enough
So how do you know when you’ve had enough? Here are a few questions to consider:
1. Does your role energize or drain you? If you find yourself dreading what once excited you, it may be time to move on.
2. Are you adding value or just maintaining status quo? If you are no longer challenging yourself or driving progress, you might be holding on out of habit, not impact.
3. Are you staying for the right reasons? Fear, guilt, or a need for control are not good reasons to stay. Neither is not knowing what you will do next.
4. Is your presence hindering fresh leadership? Sometimes the best thing a leader can do is step aside so someone new can bring fresh ideas and renewed energy.
5. Do you feel relieved at the thought of leaving? If the idea of stepping away brings peace instead of panic, that is a clear sign.
The Courage to Embrace “Enough”
Knowing when to step away—whether from a career, a leadership role, or a commitment—is an act of wisdom, not weakness. It takes courage to recognize that you have done your part and that not only is it okay to let go, it’s also the right thing to do.
There is freedom in enough. The freedom to leave before burnout sets in. The freedom to transition on your own terms. The freedom to make room for what is next.
Maybe it is time to ask yourself, “Have I had enough?”
(Stay tuned for part 2, where I introduce four powerful questions to help you determine when it’s time to step away.)
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