Why I’m Sharing This
When I left a role of more than eight years to step into something new, the anxiety was real—but so was the relief, and the space to reflect. During that time, I rediscovered an old story about a risk I took early in my career—a risk that didn’t go as planned but taught me more than I expected.
If you’ve ever hesitated to take a chance or face the fear of rejection, maybe this story will resonate.
The Hostess at the Restaurant: A Risk I Kept Putting Off
Early in my HR career, there was a hostess at a restaurant I often visited for work lunches. She caught my eye with her smile and kindness, but I never asked her out—partly because I was unsure, partly because I’d never done that before.
Years later, fate brought her back into my life in the most unexpected way. Suddenly, the risk felt more real—and more urgent.
The Moment I Finally Said Hello
With encouragement (and a bit of teasing from coworkers), I finally made the move. I introduced myself, and to my surprise, she agreed to meet for dinner.
Walking into the restaurant to ask someone out was nerve-wracking. But sometimes the hardest part is just showing up.
When She Didn’t Show—But I Did
The night of our date, she didn’t come. A manager left a note explaining she couldn’t make it and said she’d call, but she never did.
It could’ve been crushing. Instead, I felt peace. I had taken the risk, and that in itself was a victory. I learned that sometimes the outcome isn’t the point—it’s the courage to try.
The Confidence You Earn by Trying
This story isn’t about her. It’s about what happened inside me.
Taking that risk gave me the confidence to face bigger challenges later. I learned rejection isn’t failure—it’s part of growth.
Showing up is winning.
The Same Risk Shows Up at Work
That hesitation shows up at every level of an organization. The employee who won’t ask for the stretch assignment. The manager who won’t push back on a plan they know has a flaw. The high performer who won’t apply for the next role because they don’t feel 100% ready yet.
A “no” is loud and immediate. The cost of never asking is quiet—and it compounds: the promotion that went to someone who simply asked, the good idea nobody ever heard.
For leaders, the job is twofold: take the risks worth taking yourself, and make it safe for your people to raise their hands. When someone asks and hears “not yet,” how you respond decides whether they ever ask again.
What I Hope You Take from This
- Courage beats comfort. Waiting for the “right moment” can keep you stuck. Sometimes you have to leap.
- Rejection is not the end. A “no” doesn’t define your worth.
- Showing up is success. Taking the chance builds resilience and self-respect.
- Growth happens in discomfort. The tough moments teach us the most.
- Keep learning and moving forward. Every risk is a chance to grow.
Final Thought: Take the Leap
Whether it’s a career change, a personal goal, or asking someone out—taking a risk is scary. But the lessons you gain and the strength you build are priceless.
It’s part of the reason behind the name Shoreline. A shoreline is where what’s known meets what lies ahead—and every real risk starts right there, at the edge.
So, take the leap. You might not get the answer you want—but you’ll get something more important: the power to keep trying.
