Preparation can give you the courage you need to make a bold move.
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Making a bold move to advance your career doesn’t start with feeling ready, and it rarely arrives on schedule. My own career change—definitely a bold move—came about in the most serendipitous way. I was working in academia at the time and had been tasked with selecting an executive search firm to help find our next dean. We reviewed five different firms, conducted Zoom interviews with three of them, and ultimately invited one firm to visit our campus for final presentations.
When the chosen search firm arrived on campus, I approached their managing director to introduce myself. Just five minutes into our conversation, he looked me in the eye and said, “I’m going to hire you!”—before catching himself and adding, “when you’re finished with higher education.”
That declaration created a fork in the road, spurring me to seriously consider leaving academia—a massive career change, especially given that I had tenure. At first, I wondered if I was ready. Then I realized that “being ready” was a myth. I didn’t need to be ready. I just needed the courage to make a move.
Fear-Based versus Wisdom-Based Hesitation: What a Career Change Taught Me
When I left academia, I was walking away from tenure, a six-figure salary, and decades of achievement. I didn’t necessarily feel “ready,” but I felt prepared. I spoke to multiple people who could give me their perspectives on the transition. I also updated my CV, got new professional headshots, met with my financial advisor to discuss what-if scenarios and financial cushion planning, lined up references, and bought a new business suit. And I put a date on it—a deadline by which I wanted to achieve this goal—and stuck to it.
Since I made my career change, I have coached many executives on their own bold moves—and I’ve found that it’s essential to distinguish between fear-based and wisdom-based hesitation. Fear-based hesitation sounds like, “What if I fail?” It’s grounded in fear. Wisdom-based hesitation sounds like, “I need to save more money before I can afford this transition.” It’s grounded in practical reality, emphasizing a need for preparedness. Don’t let fear masquerade as wisdom and become your excuse for staying stuck.
What Preparation Looks Like Practically, Physically, and Emotionally
Preparedness has many facets. Start by thinking through what your specific move requires and then write it down. Research. Talk to people who have made similar moves—then build the checklist that makes it real. What do you need, practically speaking? New skills? Connections? Educational credentials? Write it all down, figure out how you’re going to get it, and then put a date on it.
Just as important is your physical and emotional readiness. If you’re already hanging on by a thread, exhausted and on the brink of burnout, the added burdens that come with a bold move may be too much right now. The oxygen mask principle applies—you need fuel for what’s ahead. Delay doesn’t equate to failure.
Finally, consider your emotional preparedness. Bold moves can be lonely, especially if you’re moving to a new place or advancing to a higher level of leadership. It’s important to have a mindset of growth and solitude as opposed to thinking of it as lonely.
When Preparation Meets Courage
Taking the time to prepare for a bold move—whether it’s a career change or something else—isn’t about talking yourself out of bold action. It’s about ensuring you’re making calculated, thoughtful moves that set you up for long-term success. Sometimes the boldest thing you can do is take the time to prepare properly. The key is to take the first step.

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