Skiing Off Cliffs
It’s not the leap that kills you. It’s the landing.
Before Peter Barton was a media mogul, he was a ski bum. Like every ski bum, Peter needed money to buy food and lift tickets. After weeks stacking firewood and shoveling snow, he found a better way to make money: freestyle exhibition skiing.
As it turns out, people love to watch daredevils attempt stupid feats, and equipment makers were willing to pay daredevils to attempt those feats, so long as they wore the sponsor’s equipment.
In Peter’s first event, he had to fly from a ski jump, perform a crazy trick, and land in a pool. The eight people before him all did flips. Peter decided to do a double backflip.
He barreled down the ramp, hit the jump, watched the ground fly beneath him as he spun twice through the air, and landed softly in the pool, his skis gliding across the top of the water like a stone skipping on a river.
Peter recounts this story in his book, Not Fade Away. He goes on to explain:
I tell this story mainly as a way of illustrating something I said a while ago—about the importance of recognizing the difference between an acceptable, life-enhancing risk, and one that’s just plain dumb.
I realized that doing a double back flip off a ski jump could well be put into the latter category. But think about it. Eight people took the leap before I did. All came through okay. I’d gone to school on how they’d done it. And I’d be landing in water—a pretty forgiving substance.
True, I might have messed it up, flailed my skis, and looked like an idiot—but so what? You’ll never accomplish anything if you’re afraid to look bad trying.
➡️ That’s the first lesson I learned from Peter Barton. If you want to be successful, you can’t worry about what other people think of you.
Peter goes on to talk about his other ski competitions. He knew guys who would ski blind off cliffs because the crowds loved it. They’d come rocketing down the mountain and send it off a forty foot cliff with no idea what lay below. This, Peter thought, was an unacceptable risk.
But Peter saw how the crowds loved it, and he wanted to wow the crowds. That’s when he came to a powerful conclusion: “It’s not the leap that’s dangerous, it’s the landing.”
Equipped with this wisdom, Peter started scouting the cliffs before the competitions. He checked the landing areas and planned his leaps to avoid danger. To the crowd, he was still taking crazy risks, but in reality, he was making calculated decisions with low risk of injury.
Since no one gets hurt in the air, he thought, plan the landing, and you’ll be fine.
➡️ This is the second lesson I learned from Peter Barton. If you limit the downside, risks that loom large are actually not that risky.
I’ve applied these same principles to big decisions in my life. Some have been successful. Others haven’t. But true to Peter’s tactics, even the failures weren’t fatal. When you plan the landing, the leap isn’t as scary.
The first meaningful risk I took was buying a rental property. Actually, I didn’t buy one rental property. I bought four in less than a year. Also, I was 25 years old, and the properties were hundreds of miles from where I lived. What could possibly go wrong?
Was the experience all sunshine and roses? Of course not. But it wasn’t a life altering disaster either. It was actually overwhelmingly positive. After holding the properties for three years, I sold them for an 80% cash on cash return. My net worth increased by 15% overnight. It was a risk with an exceptional outcome, but I planned the landing before taking the leap.
I spent a year learning about rental properties—evaluating deals, buying, owning, managing—everything from beginning to end.
I partnered with a friend who had spent at least as much time studying as I did.
We set strict purchasing criteria, and only bought properties that hit our metrics.
Then we stopped buying when those metrics became harder to hit.
We bought four properties instead of one, which probably seems more risky to most people, but it actually spread our risk. Instead of one property with two paying tenants, we had four properties with 12 paying tenants. Our experience held true to the Pareto Principle—80% of our profits came from 20% of our units. Unfortunately, when you’re buying, you don’t know which units will be the profitable ones. If we had only bought one property, we would’ve lost money.
My partner and I both had full time jobs, and we never took distributions from our rental property business. This gave us a double cash cushion—one from our W2 jobs and one from the rental income—to weather any storms we faced. And we certainly faced storms. Everything from nightmare tenants to busted furnaces to broken sewer pipes and COVID non-payments. But we planned the landing before the leap. The risk wasn’t as big as it seemed to people on the outside, and we touched down softly in the fresh powder.
It’s easy to peddle this philosophy with tales of success, but I promise it works with crash landings too.
In early 2021, I was ready for a career change. I’d spent eight years working in financial compliance, and I wanted something more creative. After searching for jobs and taking many interviews, nothing seemed like a fit. Then one day, via Twitter DM, I met my next employer.
The position seemed perfect—Director of Operations at a young company. I’d have the chance to run a team and build the infrastructure to support a growing business. It was a leadership role at a startup in a creative industry—exactly what I thought I wanted. There was just one major catch: the salary was 43% of my current job.
The founder promised a big raise within a year as long as the company was growing like he expected. And I knew if the company was growing, I would grow with it. The role had the potential to be career changing, so it was a risk I deemed worthy of taking, but it was a risk nonetheless. Before I skied off the cliff, I made sure to scout the landing.
Some of this scouting took place before I even had the job offer. I lived in a way such that my income significantly exceeded my spending. This allowed me to build enough savings and investments to take risks like this one.
Next, I knew my wife was starting a job after finishing school, so we would have two incomes where we only had one before. This also removed some risk from the decision.
Finally, I left my job on good terms. I framed the move as a desire to try something new. I wasn’t leaving for a competitor. I didn’t speak poorly of my experience. I didn’t burn any bridges. And when I left, I had an open invitation to return whenever I wanted.
As I was skiing full speed toward the cliff, my mind was at ease. I knew I’d be landing in a pile of fluffy fresh powder below.
Fast forward six months, and the risk turned out to be a bad one. The company wasn’t going to be a unicorn. I wasn’t going to receive that raise. I wasn’t even sure if we’d still be in business by the end of the year. Worst of all, I wasn’t enjoying the work.
I was about to find out if the landing was as soft as I expected. I left the new job in September with no idea what I would do next. My savings, my wife’s income, and our modest lifestyle made for a soft landing. It led to a three month vacation that I spent reading, writing, playing golf, hiking, and thinking about what I wanted to do next. Ultimately, I returned to the industry I was in before, through contacts I had made eight years prior.
And here’s the best part—I’m now making more money than when I left to join the startup.
So it turns out the risk I took didn’t play out how I’d hoped, but because I’d “scouted the landing,” everything turned out fine.
As Peter Barton used to say, it's not the leap that kills you, it’s the landing. And when you plan the landing, almost every leap is worth taking.
Photo by Clement Delhaye on Unsplash
