When I’m reviewing chess games, I love finding the move. That one moment that changed everything. For us chess players, it’s the moment where the story shifts and one decision reshapes the entire board. The English major in me always sees it as the turning point, the climax, the who, what, where, and why of transformation.

In my own life, I’ve had plenty of those moments. Starting Queens Gambit when I was fourteen. Choosing to stay in Pittsburgh and attend the University of Pittsburgh. Joining my first nonprofit board when I was still a teenager. Every one of those moments pushed me to create something new instead of waiting for permission. But one of my favorite “moves that mattered” didn’t happen on a chessboard. Actually, it happened a few years after college. I recently shared this with the Ellis School graduating seniors, and I want to share it here with you.

I had just graduated from Pitt. I had multiple organizations under my belt, national partnerships, and more board service than most people twice my age. But I stalled. I was doing what I thought I was supposed to do.

I started applying for jobs (jobs that didn’t excite me) and to graduate schools that didn’t really align with what I wanted. I convinced myself that this was the next step. That this was what would look good. What would make people proud?

And honestly? The world saw something I didn’t.

The hiring managers weren’t rejecting my skills. They were rejecting the idea that I needed their approval. They saw what I couldn’t yet admit: I wasn’t meant to fit into a job description. I had been building my own lane all along.

One Saturday morning, sitting across from my mentor and friend, I vented about how frustrated I was - the rejections, the confusion, the feeling of being stuck.

She looked at me, shook her head, and said, “Ashley, what the beep are you doing?”

I laughed. But then I paused. Because she was right.

Why was I trying to be someone else when I had already created something entirely my own? Why was I trying to blend in when I’d spent my whole life standing out? That moment - that conversation - was the turning point.

I leaned in. I stopped applying to jobs that didn’t fit and started building the path that did. That was my move that mattered.

I launched Queenside Ventures, a consulting firm that now works with top athletes, brands, and leaders in sports, media, and beyond. I help people slow down, think strategically, and make moves that truly align with who they are - not what the world expects them to be.

And of course, I have to bring it back to chess…

In the position below, it’s tempting to keep checking the king (white’s turn to move). To stay focused on what’s right in front of you. That was me (applying to jobs, trying to prove myself, hoping that something would click).

We think that the closer we are to something (in this case, the king; in my case, finding a job that aligned with others’ expectations of what I should do), the better. My chess students do this all the time! “Ms. Ashley, can the king be next to another king?”

We keep chasing proximity instead of purpose.

But if I had zoomed out and really looked at the full board, I would’ve seen the truth.

Yes, checking is great. But what about other advantages?

Qb4+, then grab that knight on d6. The king is protecting the queen, supporting that caption.

That’s the move. It’s not flashy. It’s not obvious. But it’s the move that changes everything.

Sometimes, the best decision isn’t about being closer to the king, it’s about seeing the bigger picture. When you finally zoom out, you realize you already had the winning position all along.