I Jumped Off a Cliff Because an Entrepreneur Told Me To

It was 5 a.m. and I was sneaking out of the house. As the taxi pulled up, I quietly threw my suitcase in the trunk and instructed the driver to take me to the airport. I looked back at my house to make sure all the lights were still off.

My first flight was to New York. My second flight was to Puerto Plata, Dominican Republic. And this was my first time going out of the country.

I don’t know what made me more nervous: the fact that I lied to my parents about going to New York to work on my summer storage company, or the fact that I was on my way to a Third World country.

When my first flight took off, there was no turning back. I received the first stamp in my passport book in an airport that was almost entirely outdoors and made my way to the arrivals gate. That’s where I spotted him, the man I had come to see: Mr. Z.

Mr. Z was my best friend’s dad. He also happened to be the founder and CEO of a successful Internet software company—and he had sold his firstbusiness for millions of dollars before he was 19. He’d invited me to the Dominican Republic with his son and friends to spend the next week working and strategizing on a growth plan for my storage company.

I took the trip because I looked up to Mr. Z—he was successful, opinionated, powerful and seemingly carefree. But perhaps what I liked most about Mr. Z is that he took me seriously. As an 18-year-old businessman, that was something that meant everything.

The next week flew by. Every morning, I’d wake up at sunrise to have breakfast and talk business with Mr. Z until lunchtime when my friends awoke. Then one afternoon we all ventured off into the jungle with a local guide. We hiked through the tropical forest for an hour. I wasn’t sure what our destination was, but it didn’t matter, as Mr. Z and I had a great conversation as we hiked through the picturesque jungle. When we stopped at the edge of a massive cliff, we were 25 feet above a small pool of water. As we stood at the top of this waterfall, I looked for a way to get around it.

Then I saw our guide run toward the end of the cliff and jump. Seriously? I quickly looked over the edge—my stomach dropping—as I saw him splash into the pool of water. It took a few seconds for us to learn his fate (it was a big jump). But soon he surfaced and looked up at us, grinning and shouting, “VAMOS! VAMOS!”

One by one, my friends leaped after him. I couldn’t believe their bravery. They seemed fearless—while I was paralyzed by the idea of jumping. After a few more jumps and a few more successful splashes, it was just me and Mr. Z at the top. HOLY S*#@! I thought. I didn’t sign up for this. Mr. Z looked at me with a smile of encouragement. I knew he could feel my hesitation. He knew I was terrified.

He put his hand on my shoulder and said, “Jordan, here’s a secret: Nobody knows anything! We’re all just trying to figure it out and make our way. Sometimes you just jump and take a leap of faith. Now, are you going to jump?” Then he walked to the edge and jumped.

I might not have grasped the depth of it then, but the “secret” Mr. Z shared with me wasn’t just about jumping off that cliff. It was about way more. That secret would forever alter my view of the way the world works—because the truth is, no one really knows what the point of this is.

We have adults all around us as we’re growing up, but all they can really say is, “I’ve been around a little longer than you and here’s what I’ve gathered the point to be….” And a lot of their advice is valuable, applicable, helpful—like Mr. Z’s mentorship on that trip was to me. But they’ll usually point us in a certain (safe) direction and tell us to follow certain (safe) rules.

The most basic track? “First, you have to go to elementary school, then junior high, then high school and college. By graduation, you should have figured out what you’d like to do for the next 50 years, get a stable 9-to-5 job, and after that, if you’re lucky, you get to retire.”

Most of us get pushed onto that safe career track and never look back, satisfied with “the way it is.” But there are off ramps all around you. You can walk in another direction if you want to. There are people who will always tell you that the odds are impossible. The truth is, the odds are only impossible until you do it. And that is what Mr. Z was saying that day on the cliff.

Today, I’m a 26-year-old self-employed entrepreneur running two companies. Before you roll your eyes, I don’t say this to brag. I say this because I used to think that was impossible. And maybe it would have been had I followed the “rules.”            

My point is this: You can stay inside the lines and follow the rules made by people no smarter than you, or you can make up your own. Regardless of what you decide, decide to create a life for yourself that you want to live. When you do that, magic happens.

The people who get what they want are totally normal people, just like you and me, who just didn’t give up. So relax. And remember that everyone around you is also just operating on their best guess. We’re all just winging it.

Oh, and by the way… the 25-foot waterfall? I jumped. Will you?

“When you grow up you tend to get told that the world is the way it is and your life is just to live your life inside the world. Try not to bash into the walls too much. Try to have a nice family life, have fun, save a little money. That’s a very limited life. Life can be much broader once you discover one simple fact: Everything around you that you call life was made up by people who were no smarter than you. And you can change it, you can influence it…. Once you learn that, you’ll never be the same again.” Steve Jobs

Check out 4 secrets of insanely successful people—and put them to work.

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Jordan Fried

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