6 Questions to Ask Yourself When You’re Considering a Professional Transition

For six years, I worked at what many in southeastern Minnesota affectionately call the happiest place on earth: the Woodson Kindergarten Center. And honestly, it earned that title.

Those years were filled with early mornings and open doors, long conversations with families as they navigated their child’s first school experience, and countless moments of learning alongside educators who understood that working with young children requires patience, presence, and care. I grew deeply in that space—not just as a school leader, but as a listener, communicator, and servant to a community.

It was meaningful work, and it was a lot of fun. And then, I knew it was time to move on. There wasn’t a crisis. There wasn’t a conflict. There was simply a quiet knowing that the season was changing. As Brené Brown reminds us, “Staying vulnerable is a risk we have to take if we want to experience connection.” I came to realize that I was asking myself: How do you know when it’s time to leave—even when nothing is “wrong”?

Questions Leaders Can Ask When the Fit Begins to Shift

Leadership transitions are often framed as responses to crisis: burnout, conflict, or failure. But some of the most important transitions don’t come from breakdowns. They come from quiet shifts in alignment.

Nothing was broken. The culture was strong. The relationships were deep. Yet over time, I noticed that decisions required more effort. The joy now felt thinner. The work I had loved began to feel heavier—not dramatically, but consistently. There wasn’t a single moment where I realized I needed to change course, but rather it was a growing awareness that I needed to try new things.

For educators sensing this shift, the challenge is asking the right questions before making a move. When we slow down, pause, and clarify before we act, we give ourselves permission to make decisions guided by purpose instead of pressure.

Whether you’re considering stepping into a more complex role, moving laterally into a new setting, or beginning to imagine retirement, these questions can help clarify what’s actually changing.

1. Am I growing—or primarily maintaining? Maintenance work matters, but if most of your energy goes toward preserving systems rather than developing new skills or perspectives, it may be a sign that the role has taught you what it can.

2. Where does my energy return—and where does it drain? This isn’t about avoiding hard work. The work that educators engage in will always be demanding. The key question is whether the effort feels purposeful or depleting. Important to note: Pay attention to patterns, not isolated weeks. We can have a bad day, a bad week, or a month of full moons, but be careful not to awfulize isolated seasons. 

3. Are my strengths being stretched—or simply taken for granted? Teachers are often promoted because they’re dependable. Over time, that dependability can turn into overuse. Ask whether your role invites you to develop new capacities or repeatedly draw from the same ones.

4. What version of myself does this role require? If the role increasingly requires you to operate in ways that conflict with your values or leadership identity, alignment may be shifting.

5. If nothing changed for the next three years, how would that feel? This question often brings clarity faster than spreadsheets or pros-and-cons lists. Notice your body’s response—not just your reasoning.

6. Am I staying out of commitment—or out of fear? Commitment is rooted in purpose. Fear often sounds like responsibility, loyalty, or timing. Distinguishing between the two matters.

Listening Before Leaping

Instead of rushing to interpret that feeling as dissatisfaction or fatigue, I slowed down. I paid attention to what still energized me and what no longer did. I listened to trusted colleagues who gently reflected back what they were noticing. I asked myself whether I was still growing—or simply maintaining.

One of the hardest lessons in leadership is learning how to distinguish between discomfort that stretches us and release that signals readiness for something new. Discomfort feels tense. It demands endurance. Release feels steadier. It brings clarity rather than urgency.

I wasn’t leaving because the work was hard. I was leaving because I had given what I was meant to give—and staying would mean holding space that someone else was ready to grow into.

Then, unexpectedly, an opportunity emerged to become a middle school principal. What followed wasn’t a rush of certainty, but a sense of coherence. I would return to the school where I had once served as assistant principal, this time as principal. Even better, the kindergartners I had served at Woodson Kindergarten Center were now seventh and eighth graders!

Leaving Well Is Part of Leadership

We don’t talk enough about how to leave well. Leaving well means honoring the people and systems that shaped you. It means recognizing that leadership isn’t just about staying—it’s about responding to what the work and the moment require.

Leaving was hard. I had to say goodbye to relationships and routines that had become part of me and success that had defined how I led.

But for me, stepping into a new role wasn’t an ending. I realized I was operating from strengths I had already mastered rather than developing new ones. I was plateauing. And the opportunity to bring change to a new environment called forth skills I hadn’t tapped into in years: risk-taking, systems redesign, and rebuilding trust from the ground up.

Since the move from kindergarten to middle school, I’ve had another, and yet another, and I am sure there’s another down the road. Each change and transition has helped me recalibrate, refocus, and prepare for another challenge, drawing on what I learned from my previous positions.