For years, I’ve observed athletes, politicians, corporate executives, and colleagues maneuver through their careers advancing, transitioning, or retiring. I’ve admired those who seemed to know when to make a change, and I’ve often felt frustrated by those who didn’t.

There are those who ride the wave until it crests. They stay in a job, continuing in a role that fits, delivering a great impact and return on their unique investment of creative talent. Then, with the same finesse with which they rode that wave, they ride smoothly to the next opportunity. No matter where they are, their presence and leadership imbues their organizations with energy, enthusiasm, and inspiration — during their tenure and after.

Then there are those who never seem to “know when.” They advance and develop, making great contributions to their enterprise and the people it serves. Some receive numerous accolades for their achievements. Five years pass, then 10, 20, and even beyond, and they stay put. It seems that only a rare few can continue at the top of their game for extended periods, approaching their work with as much fresh energy, passion, and creativity as ever before. Staying in one spot for too long may be comfortable. Yet, in my experience, it also leaves us stale, feeling burned out, and empty.

It was 2008, and I was in my 5th year as president & CEO of the United Arts Council of Greater Greensboro and my 12th with the organization overall. I was uncharacteristically restless. When I first noticed it, I had no idea what it was or what was causing it. I tried ignoring the sensation, passing it off as a nagging ache and drowning it with my work priorities and busy schedule. But it was persistent, like a kid sister continuously tapping on my shoulder.

So I decided to stop fighting it and instead tuned in to it. I would lie awake at night, or go for a run, and ask, “What is it? Is it something to do with my family? My spouse? Work?” And on it went in my day-to-day activities and thoughts over several months. I’d query, wait, and try to listen.


I wish I could tell you that I had a clear and direct sense of “knowing when” (and knowing what), but it was more a steady growing awareness. Small shifts and events — meeting new people, unexpected outcomes, seeing barriers spring up in one place while opportunities grew in another — were actually pointing me toward a new course.

Accompanying this emotional journey was a more tangible recognition that I had accomplished the major goals I had hoped to achieve for the United Arts Council: debt elimination, significant revenue growth, re-focusing of organizational priorities, creating a new business model, and shoring up board and staff leadership.

Eventually, these 2 paths intersected, and it became quite clear. I knew what. I knew when. And when was now. The right course for me was to complete my tenure at the Arts Council, take some time off, and allow myself the space to renew my energy and shape what would come next.

Through this experience of questioning and the self-imposed sabbatical that followed, I came to believe that knowing “when” is about having the courage to tune in to your inner voice, trust it, and follow it. To make a courageous transition, consider these 5 tips:

  • Pay attention to the signs. When you sense burnout, boredom, or restlessness within yourself, move toward it, not away from it. Question it, listen, explore.
  • Move beyond the fear. What prevents most of us from taking the leap is fear — doubt in one’s own “personal capital” and self-worth.
  • Consult with mentors, advisors, or a coach. An outside-in perspective offers an invaluable process of reflection, goal-setting, and charting a course.
  • Trust in yourself. If you don’t, no one else will. Inventory your greatest attributes and skills, and consider these your key leverage points.
  • Take action. Otherwise you will never know “what could have been.” Of course, making a significant change can seem overwhelming. Take the big picture and break it down into smaller pieces. Outline actions to take for each that will advance you closer to your ultimate goal.


Jeanie P. Duncan

My courageous transition was an opportunity to unplug, pause, and live slow. And while it mystified many why I was leaving “at the top of my game,” I gained clarity around my unique assets, particular passions, and the importance of flexibility, autonomy, and overall quality of life. Ultimately, it sparked my internal entrepreneur, and I launched a new business earlier this year focused on helping individuals and organizations develop, navigate change, and realize their greatest capacity.

Jeanie P. Duncan lives in Greensboro, NC, and is the founder of Raven Consulting Group.

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