The Two Most Terrifying Things I've Done—And What They Taught Me

When I was in grad school, my cohort friends convinced me that if I jumped out of a plane, it would help me overcome my anxiety about flying. I willingly—if not stupidly—agreed and found myself in a tiny plane over a bunch of fields in Missouri, dangling out of a prop Cessna about 3,000 feet above the ground, thinking to myself: What in the hell are you doing?

Now, I didn't have your typical "white-knuckle the armrest" flying anxiety. Unfortunately—and I don't mean to bring the tone down—I lost my childhood best friend when we were 16 in a small plane crash. She was flying with her father. After that, any type of travel involving flying made my hands sweat, my stomach turn, and my anxiety hit about 110. So why in the world

I thought jumping out of a plane would help this situation is beyond me.

Clearly, grad school logic isn't always sound.

But here's the thing: I did it, and I actually really enjoyed it. There was that split second after I let go of the plane and my body started hurtling toward the earth that I thought, "This is the stupidest thing I've ever done." But then my parachute opened, and I was slowly drifting toward the ground with a lot of time to think.

It was so incredibly peaceful. For a moment, I felt like my best friend was there with me. I don't think I'd ever felt such peace until that moment. I don't know if it was because I'd truly overcome my fear, or maybe because I realized I could do hard things and survive them.

What I do know is that to this day, after flying all over the world on multiple-hour trips, I still find peace when I'm up in the air. That leap made a difference.

Fast Forward to Fifty (and Seasoned)

Here I am, all these years later, and I still have fears and anxieties. I've always had a paralyzing fear of failure, especially when it comes to work. I put impossibly high standards on myself and always felt that stability was the holy grail. But now that I'm fifty and seasoned, I'm ready to put myself out there again and face my fears.

I finally did it. I quit my full-time job.

Yep, you heard me right. In the middle of an unstable economy with unemployment continuing to grow, I decided now was a perfect time to do it. Insert laugh track here. But all kidding aside, I thought: if I don't do it now, I'll never do it.

I have to say, I'm incredibly fortunate that my employer has been nothing but supportive of this decision. Having that encouragement makes stepping into the unknown feel less scary and more like the right choice.

So here I am, facing my fear again and moving forward to do the things I'm passionate about—nurturing those dreams I've kept on the back burner and trusting that success and financial stability will follow. Believe me, there's fear in this. But there's also a peace that has come over me. In fact, I don't think I've felt this peaceful since I was floating down from that plane all those years ago.

I have to thank Mel Robbins (who I'm pretty sure is becoming my personal therapist at this point) for inspiring me to see the possibilities and keep driving toward them. Seriously, check out her podcast if you haven't yet.

What's Next

Fifty & Seasoned is just one of my endeavors. I'm starting my own consulting firm. I've begun writing the book I've always wanted to write. And I see a lot more possibilities in my future—all worth facing a little bit of fear for.

Wish me luck, but honestly? I feel pretty confident I don't need it.

Sometimes the scariest leap is exactly what we need to find our wings again.