PART 2: Moving from Thinking About Change to Actually Doing It

🌿 THE NEXT CHAPTER JOURNEY A 3-part series for accomplished women redefining what success looks like next

Many accomplished leaders I know aren't afraid of change.

They're afraid of making the wrong change.

That uncertainty can keep you circling the same questions for months, even years:

"What if I step away and regret it?" "What if I lose what I've built?" "What if the next chapter isn't as meaningful as the last?"

Here's what I've learned from my own transition and from working with hundreds of leaders navigating theirs: No major transition begins with certainty. It begins with courage.

THE MESSY MIDDLE OF REINVENTION

The hardest part of any transition isn't the decision itself. It's the in-between.

The hardest part of any transition isn't the decision itself. It's the in-between.

That space after you've said no to what was, but before you've said yes to what's next.

Your old identity starts to dissolve, and the new one hasn't fully formed yet. It can feel disorienting, even for the most successful leaders.

When I left the company I'd founded at age 26, after eighteen years, I thought I'd have a clear plan within months. Instead, I had questions. I needed time (and space) to unlearn before I could reimagine.

The first month felt like detox. My whole way of operating had been structured around a certain set of responsibilities that entirely went away. I avoided anyone who wanted to discuss my career choices. I spoke mostly to family.

Looking back, I see that discomfort wasn't a bug in the process. It was the process.

WHAT COURAGE ACTUALLY LOOKS LIKE

Here's what I've come to understand: Courage isn't about never feeling afraid. It's about choosing movement, even in the absence of certainty.

And movement doesn't have to mean dramatic leaps. Sometimes the bravest thing you can do is design one small experiment.

LEARNING TO FAIL LIKE AN ENTREPRENEUR

I teach entrepreneurship at Georgetown, and one of the first things I tell my students is this: Entrepreneurial courage means feeling the fear of being wrong and experimenting anyway.

Entrepreneurs don't wait for certainty before they act. They test their assumptions through small, cheap experiments that give them real data about whether an idea makes sense before they commit everything.

The same principle applies to career transitions.

Instead of making major pivots based on assumptions (quitting to go back to school, taking a new job in a different field), you can test your hypotheses through smaller experiments that reduce both risk and anxiety.

Let me show you what this looks like in practice.

Chloe came to one of our Next Chapter Accelerator walking retreats after an impressive but exhausting career journey. Twenty years as a tenured university professor. Three roles as an executive director in the nonprofit sector. Decades of proven leadership.

And yet, she found herself ready for another reinvention.

Lee Ann had recognized a common thread through everything she'd done: advancing women's empowerment by dismantling barriers to their wellbeing. This through line felt significant. But she still lacked the clarity, knowledge, and confidence to pursue an entrepreneurial idea that had been quietly percolating in her mind for years.

During our walking retreat, something shifted.

"We explored the value of experimenting with low-risk opportunities," Chloe told me later. "This approach, combined with the physical journey, cleared my head and created space for fresh ideas. It made a big undertaking feel more doable."

Instead of attempting to launch a full business right away, Lee Ann applied lean startup principles to her career transition. She designed small experiments to test her assumptions about coaching and women's leadership.

Her first experiment: Enrolling in a low-cost online program for aspiring leadership coaches. A minimal investment that would help her validate whether she enjoyed the work and had a natural aptitude for it.

Her second experiment: Accepting an invitation to speak at a women's leadership conference. This allowed her to test her coaching framework with a real audience and gather immediate feedback.

Each small experiment taught her something valuable. Each one built her confidence to take the next step.

Just like a startup testing product-market fit, Lee Ann was testing career-passion fit through real-world validation rather than endless planning.

These systematic experiments led to the creation of the kind of program she'd always dreamed of, where she now equips women with the tools, strategies, and mindsets they need to overcome challenges and step fully into their power.

That's what courage looks like in practice: Not fearlessness. Strategic experimentation.

THREE COURAGE CATALYSTS

If you're standing on the edge of change, these three catalysts can help you move forward:

1. Clarity: You don't need the full map

Just the next mile marker.

Ask yourself: "What do I know for sure right now?"

Not "What's my five-year plan?" but "What's the smallest thing I could test this month?"

Lee Ann didn't know she'd create Badass University when she enrolled in that first coaching program. She just knew she was curious about whether coaching felt right. That was enough to take one step.

2. Commitment: Pick one small action that signals you're serious

Movement creates momentum.

This could be:

• Blocking a full day for reflection (not squeezing it between meetings)

• Hiring a coach or joining a program

• Signing up for something that stretches you

• Having the conversation you've been avoiding

• Testing one assumption through a small experiment

The action matters less than the signal you're sending yourself: I'm taking this seriously.

3. Conviction: Start before you're ready

The gap between "I'm thinking about it" and "I'm doing it" isn't knowledge. It's action.

You don't need more information. You need one small move that signals to yourself: I'm serious about this.

Lee Ann didn't wait until she had a business plan for Badass University. She enrolled in a coaching course while still working full-time. That single action changed everything.

What's the smallest thing you could do this week that would move you from thinking to doing?

The space between thinking about change and actually doing it isn't a gap you leap across in one dramatic moment.

It's a bridge you build through small experiments, honest conversations, and the willingness to feel uncomfortable while you figure things out.

You don't need to have it all figured out before you start. You just need to take the next step.

🌿AN INVITATION

If this reflection resonates, you might appreciate the Next Chapter Accelerator. It's not another leadership program. It's a space where accomplished professionals (men and women) get clarity through a structured process that brings clarity, courage and community.