Emotional BASE jumping is the Ultimate Life Hack

My wife has a dream. She calls it her “lotto dream” — the big, extravagant lifestyle choice she would make if she could have anything in the world. Many of us do. Maybe you do, as well. Yours might be a chalet in Tuscany or a trip around the world or a wardrobe of couture.

Hers is a 90’s-era Toyota Tacoma pickup.

The other day, on a dog walk, we passed one sitting in a driveway, covered in dirt and cobwebs, and she swooned.

I said, “Babe, we have two cars. Just trade yours in and get one. It’s not like you’re lusting after a cherry Corvette. It definitely will cost less than your paid off Nissan.”

She was shocked. She literally put her hand over her heart and stared at me. (Side note omg she’s the best.) It hadn’t occurred to her that she could just... do that thing. Stop pining and buy the $10k used car! LIVE YOUR DREAM!

On the way home she was stunned and ecstatic. She waxed rhapsodic about how she will turn heads when she drives that old truck down the street. (I don’t know how you could look away from that level of pure joy, to be honest.)

Here’s a harder version of the same thing.

I have a friend who described her job as “a prison cell with the door open.” This friend is a relentless achiever. You know that tech company? She’s worked for it. She’s done marketing work that has made those companies millions. She looks at her career with a structured pragmatism — collecting resume builders, working for different size companies to get a breadth of experience, from startups to FAANG giants. She recently told me that the juggernaut for which she currently works has a culture that feels stiff and uninspiring. Her boss is “likable” but requires a lot of managing up. She figures she’ll spend another year or two there before it becomes unbearable. In the meantime, she’s cooking up ideas. She’s dreaming of side hustles.

I said to her, “You know how to make money.” Because she does.

Recently she pitched an idea to me to help me grow my business, in exchange for a percentage, which I immediately said yes to.

She said, “I’m not sure I do.”

Lady, you literally just got me to write you a check from a single text message. I must disagree.

The idea that you can’t make money? That’s what keeps you sitting in your prison cell, despite the fact that the door is hanging open.

But I don’t think it’s really about the ability to make money.

Starting something new requires you to jump off a cliff.

Working for yourself requires you to jump on a regular basis. When I started Whipsmart, my PR firm, I learned quickly how to do it.

Each time I reached out to a contact, took an intake call, wrote a proposal — I had to work through the emotional run-up. The reason we don’t jump off cliffs is because we have a reasonable expectation that we would die. Most of us stay safely on the ground, a truly reasonable decision. But there are a few thousand people each year who gear up and try BASE jumping — flinging themselves off of high places for fun. They push past whatever fear grips them because they believe the rewards will be worth the risk1.

Building my business took a lot of conversations, a lot of networking, a lot of proposals. Each time I pitched our services, each time I reached out to someone new, I built up the skill of the emotional base jump. Turns out, the work that I and my team did was valuable to a lot of companies. We have done incredible work over the years, and billed millions of dollars. Those base jumps were absolutely worth it.

It’s not that you don’t know how to make money. It’s that some part of you believes that the risks are so high that you’re safer sitting in that cell.

My wife can buy the truck. She always could. The story she told herself — that a Tacoma was a lotto dream, not a real one — was the only thing in the way.

We tell ourselves that our dreams are impractical, impossible, unattainable, not doable. In that way, we make sure they are.

What’s the $10k used car version of the thing you’ve been pining after? Go look at the price tag today.