Why Doesn’t It Feel Like Flying?

I went sky diving a few weeks ago in Key West. To all of you who said I would love it, it would change my life, it’ll feel like flying, and I’ll want to jump a million times: you are wrong. I will never be jumping out of airplanes again. Did the thing. Will not be doing it again.

Why, you ask? Well first and foremost, I get very motion sick on airplanes and I’m scared of heights. I take a lot of drugs to fly commercial and it was as the plane that barely fit 3 humans in it was taking off that I realized I had not taken any drugs to prevent nausea. I held my hands in prayer the entire time as we rose in elevation above the clouds and the sea green ocean waters. I’m sure my skydiving buddy thought I was having some intimate and sentimental moment. It wasn’t that at all. I was praying I wouldn’t puke on him.

I was fine until they slid open the thin, metal door and I felt the cold air hit me. As I placed both my feet on the silver ledge outside the door in preparation to jump, I remembered what the safety instructor said on the ground: they will take care of any lack of motivation you feel. 

My instructor did just that. As my mind started to second guess this experience, I felt the push of his weight behind me and the sensation of falling. Fast. This is the part insane people like, and I enjoyed it for the first 20 seconds. It was like looking into an aquarium from the sky. The blue green waters. The sunshine. Wee, I’m flying! 

Then my brain caught up: “Holy shit, I’m falling.” My mind went right into panic mode with a litany of questions and one on repeat: why in the actual fuck did you do this?  I won’t share all the profanities from panic mode, but I will say this: I did not puke and that is all that mattered to me in that moment. 

Hitting the one month anniversary of moving into the van over the last week has felt a little like that last 20 seconds of free fall. 

Those of you who have ever taken a leap know. You’ve walked away from marriages, friendships, and workplaces that weren’t good for you. For some of us, that meant starting a company. You’ve stayed strong. Stuck it out. At first, your mind is so overtaken by the changes and details, but now it’s questioning why the hell we thought this was a good idea. Why I’m not more heavily under the influence of something to make this easier (joke, kinda). 

Why it doesn’t feel like flying.

It reminds me of starting Three Ears Media – the all night nightmares that start over every time I fall asleep, the random worries, the constant questioning. I thought taking the leap into my business would catapult me toward loving work and that’s just not what happened. Instead, it broke open every doubt I had in my talents. It shined a light on every imbalanced relationship in my life. It forced me to face my demons. 

It surely did not feel like flying. 

Truth is, no leap does – and van life is no exception. It takes time for newness and different challenges to feel good. We have to settle in, acknowledge what we don’t know. But you can’t skip the jump. Not the ones we have to take, no matter how hard. 

I started Three Ears 4 years ago next month and I can’t tell you when it went from paralyzing fear to flying, but I know I’m exactly where I’m supposed to be now. I’m sure you have a short list of things just like that in your life – massive change that manifested into a life you only dreamed about.  

However, in the meantime, I know I’m not alone when I say I beat myself up for not knowing, not figuring out, not doing something right every step of the way.  Sooner, Kat. Faster. Figure it out. My only option is to give myself a lot of grace for feeling so fucked up and trust that I’m here for a reason. That all of this is just the beginning before something beautiful – just like all the other massive leaps I’ve taken in my life. 

I also have to give myself a pep talk now and then. So today, I’ll give you (and myself) the same pep talk I did all those years ago. I still do it every morning and every time I wake up in the middle of the night wondering if I’m doing the right thing. I thought at least one of you may need it, too. 

You’re exactly where you need to be. You have exactly what you need to be successful. You know everything you’re supposed to know already. 


As a trans person, this mantra means even more. It’s a constant unlearning of the binary identity I was indoctrinated on my entire life and coming to an understanding of who I am without the guidelines of society. That makes existing in said society not so straightforward. That’s why I wrote this week’s blog post about ways you can improve the candidate experience for people like me. You can read that here

In the meantime, I hope you’re giving yourself whatever pep talks and love you need to get through the leaps. 

But damnit, you better leap.


Weekly Letters

Kat Kibben View All →

Kat Kibben [they/them] is a keynote speaker, writing expert, and LGBTQIA+ advocate who teaches hiring teams how to write inclusive job postings that will get the right person to apply faster.

Before founding Three Ears Media, Katrina was a CMO, Technical Copywriter, and Managing Editor for leading companies like Monster, Care.com, and Randstad Worldwide. With 15+ years of recruitment marketing and training experience, Katrina knows how to turn talented recruiting teams into talented writers who write for people, not about work.

Today, Katrina is frequently featured as an HR and recruiting expert in publications like The New York Times, Chicago Tribune, and Forbes. They’ve been named to numerous lists, including LinkedIn’s Top Voices in Job Search & Careers. When not speaking, writing, or training, you’ll find Katrina traveling the country in their van or spending some much needed downtime with the dogs that inspired the name Three Ears Media.