I Went Skydiving. My Parachute Didn't Open Correctly. But I Swear There's a Fundraising Point to it.

In 1996—my freshman year of college—I went skydiving for reasons that totally escape me now.

Technically speaking, I went “static line” jumping. This is when you don’t so much “dive” out of a plane, as you just sort of dangle under the wing while working up the courage to let go. After a few seconds of free-fall, a chord connected to you pulls the chute and then you fall elegantly to Earth.

This sorta looks what I did in 1996

Except my chute didn’t open correctly after it deployed. Which was terrifying.

I recently told this story to my new Marketing friend, K, over dinner. She put her hand on her chest, turned her head away from me, and said that just hearing the story made her anxious. Which is precisely the reaction I was looking for. So now we’re super-duper best friends.

I actually had a fundraising reason for telling the story, but I’m pretty sure the panic attack I inspired overshadowed the point of the story. Thus, this post.

Gear up! Let’s jump out of this Substack plane together and see who hits the ground first.

My parachute “malfunction” probably wouldn’t even register as such for a real skydiver. The fingers that bring you Fundraising for Breakfast will now demonstrate what my malfunction looked like:

The photo on the left is how the lines of a parachute are supposed to deploy. All lines connected to the parachute should be separate from each other to fully inflate the chute. The photo on the right is how my parachute actually opened: instead of lines extending out, some of them got tangled and crossed over when the chute deployed.

*Left hand over heart, right hand over my head, brown eyes toward Heaven*: What I’m about to share is 100% accurate to the best of my recollection. So help me Substack.

My training consisted of a ½ day “course” followed by the jump after lunch. The instruction was conducted by a couple of dudes who explained the physics of skydiving by way of war stories about their own jumps. (One of the them once nearly wound up in a lake and it was clearly his favorite story. His advice: “Try to steer your chute away from the lake.”)

Here’s a morning’s worth of skydiving training condensed into three bullet points:

• “The parachute does most of the work.” (I swear I’m not making this up.)

• “Pull the right toggle to go right. Pull the left toggle to go left. When you’re ready to land, pull down on both at the same time to slow down. That way you don’t break your ankles.”

• You’re given an earpiece and assigned a “spotter” on the ground who is an instructor with a pair of binoculars and a walkie-talkie connected to your earpiece. I don’t remember what my guy looked like, but for the sake of argument, let’s agree that he wore a turtleneck, hoop earrings, a square jaw, and a punchable face like this:

Fast forward to the afternoon.

I dingle-berry out of a plane at 3,500 feet, I let go because a stranger told me to, my parachute deploys, but I don’t fall gently to earth. I sort of spin and herky-jerky fall. A voice in my ear says something to the effect of: “Your lines are crossed! Don’t freak out!! Kick your left leg to the right…Harder…You need to kick harder than that. Again. There. You’re good. Enjoy the ride.”

In short, the guy with the binoculars got me to untangle the lines by using the momentum of my shifting weight to free the lines from one another.

I made it safely to earth, didn’t tell my parents for years, and have never done it again.

The parachute not opening is the thing that made my new friend uncomfortable, but the guy on the ground who helped me untangle the chute never really gets the screen time he deserves when I tell the story.

Fundraising isn’t like jumping out of a plane with a busted parachute. If it feels like that, you’re not doing it right. But I have my days and so do you and we both feel like we’re in freefall. And on those days, it’s best to remember that you’ve likely got more people with binoculars looking out for you who can bring you to a soft landing. Here’s what some of my favorite fundraising people have walkie-talkied into my ears in the past couple weeks:

• Susan or Renee in Marketing (I can’t remember who): “I like that sentence, but I don’t think it says what you think it does, Dan.”

• Jeff: “Let me help you get in touch with that that donor. I’ve known him for years.”

• Amritha: “Stop doing that. Let me do it.”

• Jules in Rochester: “You need DAF language? I got you! Here’s 5 things I’ve used…”

• New fundraising friend Sara in Montana: “Let’s talk about how people interview for fundraising jobs!”

So, I dedicate this post to the guy on the ground 30 years ago who talked me through a harrowing skydiving experience. I also dedicate it to my fundraising friends who help me kick free of my own tangled dilemmas on a regular basis.

And to K. Who likely didn’t make it to the end of this post without breathing into a paper bag but I hope we have dinner again soon. I’ve done lots of stupid stuff that’ll make you anxious in the retelling.

And to you. Thank you for attending my TedTalk about fundraising, static line skydiving gone amiss, and the voices I hear in my head when I try to do both things without crashing to Earth.