The Flight from Boston: A Career Crossroads

A few weeks ago, I was on a flight from Boston to Austin. Just as the doors were closing, a woman a few seats away ended a call with a comment that stayed with me long after we landed:

"I don’t know what’s next for me, but I feel like I should have figured it out by now."

She didn’t sound lost. She sounded frustrated. As if she knew she had more to offer, but the path forward wasn’t clear.

I’ve heard variations of this from so many women- smart, accomplished leaders who have spent years excelling in their careers, only to reach a point where they know they’re ready for something more but aren’t sure what that looks like or how to get there.

Not stuck. But standing at a crossroads and wanting clarity on the right next move.

The Invisible Challenges of Career Growth

If you’re feeling this way, you’re not alone. As we progress in our careers, it becomes more challenging to see what’s next. You’re busy delivering results, leading teams, solving problems- and suddenly, years have passed.

The challenge isn’t just about finding the next role. The challenge is about making a move that aligns with your strengths, values, and aspirations in a way that feels intentional.

Here’s why it’s so difficult:

You know you need a change, but you don’t know how to articulate it yet. Maybe it’s a quiet restlessness or a sense that you’re no longer learning or growing. You might not have the words for what you want, but you know what you don’t want.

Talking about it won’t instantly make it clear. We wish one conversation could unlock the answer. But career clarity doesn’t come from a single moment of insight. Career clarity comes from exploration, reflection, and taking small, intentional steps forward.

The right conversations can change everything. The first step isn’t having a perfect plan - it’s getting out of your own head. The women who move forward fastest don’t do it alone. They find someone who can help them see what they can’t see for themselves. Someone who listens, challenges their thinking, and helps them shape a vision worth pursuing.

You Don’t Have to Have It All Figured Out to Take Action

The biggest mistake I see? Waiting until you have the perfect answer before making a move.

We tell ourselves we’ll figure it out when things settle down, when we feel more confident, when the timing is better. But momentum doesn’t come from waiting- it comes from small, courageous steps.

That woman on the plane? I don’t know what she’ll do next. But I hope she finds a conversation that helps her get there.

And if you’re reading this thinking, This is me, let’s have that conversation... because the clarity you’re looking for starts with the right conversation.