The Beginning of the End of My Flourishing Career

Alright, alright. I’ll start posting the columns here. But seriously, you bitches better start subscribing to Blue Skies. Or you know, be four months behind on this column. Up to you.

Originally printed in the January/February 2011 issue of Blue Skies Magazine

I have an A-License in corn landings, thank you.

You know, there are a shit ton of reasons people should (and do) jump out of planes. If you’re reading this, you probably already do, so I’ll spare you a corny list as to why you should.

My reason? Well my first jump was in 2005, I was a broke college kid and I landed that jump, went apeshit as a reaction to the adrenaline, and swore to myself I’d be an instructor someday.

But I forgot about it. Life got in the way.

At the time I rediscovered skydiving, I was head-down, balls-to-the-wall in my career at one of the largest global PR firms. Stationed in Chicago, by day, I was contributing to social media programs for big brands, and by night… well, nothing. My career, or the start of it at least, was my life.

Same old story, right? Someone from Corporate America discovers skydiving, it changes their life, becomes their life, and we all live happily ever after.

Let’s rewind for a second. So I, the up-and-coming, soon-to-be-PR-Agency-Queen-of-the-Universe, land a killer speaking gig at the South by Southwest (SXSW) Interactive conference in Austin, Texas. If any of you know anything about marketing, digital media, social media, etc, you know that speaking at SXSW is a huge fucking deal. I’m roaming around the convention center, all high on how awesome this opportunity is, when I run into one of my friends who happens to be a skydiver. You see, skydiving wasn’t even on my radar between July 2005 (my first tandem) and March 2010. But in all of his skydiver glory, he’s all, “hey, wanna go jump out of a plane tomorrow?”

PD New Beginning

Done and done.

So I play the “know it all tandem student” with the other people that are going that hadn’t jumped before. I confirmed that you don’t feel that drop that you do on a roller coaster, that your landing isn’t as hard as they make it seem on TV, and when they ask what it’s like, I say something clever about how it’s better than sex. So sue me. On a side note, those “I’ve done a tandem once so I’m a skydiver” kind of people bug the shit out of me now. Full circle, baby.

So we go, we jump, I land and I’m not nearly as floored as I was the first time. You know, the whole screaming, dropping f-bombs, swearing that it’s heaven on earth, none of that. I’m calm. I’m relaxed. My head is clear. I watch my video from that jump now and the camera flyer is all “OOOOOH MYYYYY GOOOOOD HOW WAS IT?” and I was like “it was great.” Dead-panned. Totally chill.

I solemnly swore to myself that I would get licensed that summer when I got back to the city. I wanted to do exactly what my friend did, get licensed, get gear, and skydive all over the country while I’m traveling for work.

So I return to the almighty city of Chicago, start researching my face off, and ultimately decide that I want to do my AFF at Chicagoland Skydiving Center. Couple reasons: their website is legit, which, is a little more difficult to find in skydiving. They also have all of the prices listed there and even when I saw all of that and then called manifest, they were super friendly on the phone.

Memorial Day weekend was my last weekend as a non-skydiver. I went out to CSC with a buddy of mine who had done five tandems (more on him later), did a tandem, signed up for ground school for the following Friday night.

I thought the tandem in March changed my life? June 11th, 2010, the night I completed ground school, was the beginning of a chapter I didn’t even plan on writing.

…to be continued



  • Loved your story and can’t wait to hear the rest. I am a recent graduate of the AFP program at Skydive Chicago, I graduated last August and got my A earlier this year. I love this sport. Blue Skies! Great article.

  • Thanks, Jerry! You should come up to CSC and make some jumps with us! Fuckin’ Pilot will be flying the plane and I’ll be updating Facebook about it. ;)

  • Sounds Great Sydney! Please add me on FB, there aren’t many Jerry Gruber’s listed, I am standing with my girlfriend after a jump for my profile pic, so I’m easy to find. Take care Sydney!

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