Leaping Into the Unknown: Sharing My Story with the Next Generation of Women Leaders | Girls Who Start Keynote by Caitlin Boshnack

This week, I had the privilege of speaking at my local high school for the Girls Who Start club, a student-led organization that empowers young women to explore entrepreneurship, leadership, and innovation. Standing in a room full of ambitious, thoughtful young women reminded me why one of my biggest values is sharing what I’ve learned—whether that’s empowering the next generation of leaders or swapping best practices with another female advisor. Every time I tell my story, I hope it gives another woman permission to trust her own.

Why I Shared My Story

My keynote was called Leap Into the Unknown: Discovering Who You’re Meant to Be. It wasn’t a polished highlight reel of wins and successes. Instead, it was about all the things that went wrong in my career—and how each misstep taught me a little more about myself, my values, and the kind of opportunities I wanted to create next.

We often hear stories of overnight success or carefully mapped-out career paths. But my journey has been anything but linear. I’ve gone from psychology to higher education, to wedding planning, to finance. Each leap felt scary and uncertain. And yet, every single one shaped me into the advisor, business owner, and woman I am today.

The Lessons I Shared

I structured the talk around six big lessons that came out of my journey:

• Rejection is Redirection. A “no” isn’t failure—it’s a nudge toward where you’re truly meant to go.
• Careers Aren’t Straight Lines. Each role teaches you something about what fills your cup and what drains it.
• Say Yes to the Jump. Even if the outcome is messy, saying yes opens doors you couldn’t imagine.
• Leap Even When You’re Afraid. Fear is often a signal that you’re standing on the edge of something big.
• Get in the Room. Sometimes the first step is just convincing yourself—and others—that you belong where opportunities happen.
• Resilience in the Fall. Even when things collapse, you can rebuild, stronger and wiser.

I also handed out “Carpe Diem” cards—tiny slips of encouragement like fortune cookies for courage. I asked the girls to keep theirs tucked in a notebook or phone case, ready to be pulled out when fear shows up. Because we don’t need to wait until we feel ready; we just need a small nudge to leap.

Why It Matters

Normalizing fear is one of the most powerful ways we can empower others. Every leap I’ve taken—from being rejected from my dream school to starting my own firm—came with plenty of self-doubt. But on the other side of those leaps, I always discovered something new about who I was becoming.

That’s why I keep saying yes to opportunities like this. Sharing our stories as women matters. Whether it’s with a young woman just starting out or with a peer navigating her own professional crossroads, every conversation helps us all feel less alone—and a little more courageous.

My Send-Off

I closed the keynote with a reminder: Don’t wait to feel ready. Let fear be your sign you’re on the edge of something important. Take the leap anyway.

Because every leap, no matter how messy, is shaping who you’re meant to be.