Sky Diving San Diego


I really, honestly don't consider myself to be brave. Or fearless. Or crazy. Or stupid. Or reckless or impulsive or an adrenaline junkie or blah blah blah.... any of the other adjectives people have suggested ever since I told them I was going sky diving.

In fact, it's quite the opposite. And it strikes me as funny that most of the decisions I've made that people have called "brave" are actually very much based in fear. Deep, opposite-of-crippling fear that I won't be alive or healthy or in a financial or lifestyle position to try all the amazing things that life has to offer.

I've always had an intense fear of regretting something I didn't do and I decided very, very early on that I would make that the guiding principle of my life. So I am constantly checking in with myself to ask, "What will I regret not doing?" and then making sure, whether it scares me or seems crazy to my friends or is, in fact, a little reckless... that I go do that thing. As soon as possible.

Sky diving just happened to be one of those things.

But it wasn't always something that I knew I needed to do. I've toyed with the idea on and off for the last ten years and had more or less decided that I was okay not having that be a part of my life. When I started writing my 30 Before 30 list earlier this year, though, I revisited the idea. And I decided then that yes, most definitely, I absolutely needed to go skydiving.

It was just the right time. Only it wasn't.

Pulling up to Skydive San Diego

Initially when my friend Shanna and I decided that we wanted to go, we decided to do it between our birthdays... sometime in April or May. But I had Coachella and then Shanna broke her foot and we pushed it back to the end of summer. Only by then, I had sort of lost my nerve. We would talk about it from time to time and I would get excited only to go home... and dwell on it... and get really... really nervous.

Nervous, by the way, is an understatement. Every time I thought about jumping out of a plane, I felt like throwing up.

So I dismissed and avoided the topic as much as possible. Until this past November, when Skydive San Diego posted a Groupon for tandem dives. Because nothing shouts safety like a good discount!

The difference in our approach that morning. This is (one of the many reasons) why I love Shanna. 

But seriously... between the Groupon discount and a Groupon sale that was going on at the time, the pass for a 10,000 foot morning dive would only be around $100... almost 50% off. That seemed too good to turn down, so Shanna and I took the (initial, albeit safer) plunge and bought our passes. Then we just had to pick a day.

We decided on the Monday after Christmas, a day we both already had off of work. As the day drew closer I got more and more nervous, but not enough to back out.

In fact, I knew deep down that I would be incredibly happy to have done it once it was over, but leading up to it? I was questioning my choice constantly. And for some reason I kept hearing the Darth Vadar theme song in my head whenever I thought about it, which just felt really pop culturally relevant.

The night before, lying in bed googling skydiving death statistics on my iPad, I was pretty sure that I was going to die or break my legs landing or worse: that Shanna was going to die all in the name of my need to jump out of a plane. It was almost enough to make me reconsider.

But nevertheless, the morning of I dutifully got dressed in my thermals, pulled on my Teekis with feathers on them (for good luck), and put a bright, hot pink sweatshirt (so it would be easier for the search party to find my lifeless body in a ditch). Then I drove to Shanna's house.

And as we said goodbye to Shanna's kids, her youngest screamed: "Have fun DYING!"

We were officially ready to jump out of a plane.

While you sign your life away on the waiver iPads, this old video of a decrepit lawyer explains that you can't sue if you die. 

The tandem dive briefing and harnessing area. 

The ride to Jamul was a little giddy, mostly surreal. We passed a sign alerting us that Skydive San Diego was three miles away and then suddenly we were there, at a few squat buildings off the side of the road. We walked into the office, e-signed all of our death and dismemberment rights away, and watched a short crackly video featuring a man who looked like the Crypt Keeper as he told us that we should reconsider. Well, maybe he didn't say it quite like that, but that's what it sounded like.

Once our electronic waivers were all signed, we walked up to the counter to sign in and pay for our deluxe video packages. These run about another $140 bucks, but for me, it was worth it. After all, I was only going to do this once. Right? I think.

Over the course of the next 30 minutes or so, we locked up our stuff in the car (there are no lockers), used the porto-potties, watched two planefuls of divers land safely, got harnessed in, and completed tandem training. Tandem training, by the way, is a brief explanation of how to do a modified camel pose when you leave the plane. It took 30 seconds. That's it. That's the training.

Now, we were actually officially ready to jump out of a plane.

I have no memory of this moment.

The ride up in our small propeller plane was short, maybe two or three minutes. It was about halfway in the air that my mind started to get foggy and I started to get very calm, but very confused. What was happening? Why were the divers putting on helmets? Why am I walking towards an open door at the back of a plane that is 10,000 feet off the ground?

And then suddenly... I was free falling through the air, just like in the Tom Petty song.

That speck in the bottom center is Shanna! 

I held on tightly to the straps until we righted ourselves and then my instructor told me to spread out my arms and have a look around.

In the words of Mindy Lahiri: Woah.

Probably the worst part of the whole day was having such an overwhelming experience happening too fast for me to hold onto it and let it soak in. The world was rushing by, it was hard to breathe because of the wind, my face skin was flapping in the breeze, I wanted to blink but didn't want to shut my eyes and I was trying to achieve the correct leg placement without kicking my instructor in the nuts. On top of that, I had my cameraman zipping around us in the sky and I wanted to smile and not look terrified in my pictures. What I'm saying is: it was really hard to stay as present as I wanted to be in those few precious seconds of freefall.

Still with all of that going on in my brain, I have split seconds stored away forever of what it feels like to fly. And it is wonderful.

I look so, so stoned in this one, though I assure you I was not. Just high on life, brah.

High-fiving my photographer/videographer mid-air while thinking, "Get away from me bro, you're too close, we're all going to crash into each other, get knocked unconscious and die!" He was cool about it.

Really having fun now!

Right after this last picture, we pulled our chute and flew high and away from my cameraman. And after the initial shock and "oh shit!" pain of a harness yanking me back up into the sky, everything sort of stopped. No more rushing wind, no more cold air squeezing past my goggles into my eyeballs, just a nice, long float down to earth, strapped to a male stranger in a baby bjorn for adults.

As we floated back down, my instructor Shane pointed out key landmarks in San Diego, all the way to the Mexican border. All I could keep saying was, "wow" over and over again to myself, under my breath, even though at that speed we could both hear everything the other person was saying. We drifted through a cloud and little cylindrical pink rainbows hung in the mist. I was flying.


For as much as the experience of flying is impressive, our beautiful city was what really took my breath away. It was another one of those "This is where I live" moments that hits me like a ton of bricks every time it happens.

Knees up! 

So relieved we were both alive!

The landing was not as scary as it would have been if I hadn't seen a half dozen skydivers land before we took off. I kept my knees up and high as we closed in on the grass and when Shane shouted "Stand up, stand up!", I dropped my feet and immediately felt shooting pains up through my ankles and shins.

But that? That was it. It went away after a second and then I just had to make sure I kept standing because, honestly, my legs were jelly.

Shanna landed a few seconds later, I hugged Shane and my cameraman and thanked them for a perfect first (and likely only) skydiving experience and then went to hug Shanna in celebration of not dying.

We were done! An hour and a half after we pulled into the parking lot, we were already on our way home. Our pictures arrived in our email before we even pulled back into Shanna's driveway. Then we spent the rest of the day trying to process what happened while drinking copious amounts of celebratory alcohol. Because we could.

And also, because we were skydivers.

The Official SanBriego Skydiving Video Drinking Game: Take a shot every time I wave at the camera. 

One last note: I will always share when I am compensated for or comped experiences, but this was not one of them. So no one is paying me to say what I am about to say: Skydive San Diego is the best. If you're ever considering skydiving, I whole-heartedly recommend them! Have fun flying!

Skydive San Diego
13531 Otay Lakes Rd
Jamul, CA 91935
Phone: (619) 216-8416