Entrepreneurship: myth vs. reality

Let me tell you a little story about an entrepreneur.

We’ll call him Bob.

(I think you’ll feel this hard if you run a business, but it’s got a solid lesson even if you don’t.)

Bob’s grandpa started a cookie company long before Bob was even born. Grandpa worked his tail off—nights, weekends, just scraping by. There were a few times where the business almost failed and a few breaks (which Grandpa always said were pure luck) that kept the business alive. Slowly but surely, the business grew.

Grandpa had a son (Bob’s dad), who started out at the bottom of the business. You know—sweeping floors, early mornings baking cookies, late nights making deliveries… that sort of thing. Dad was basically the corporate janitor, doing whatever had to be done because that’s what you did back then. But Dad sticks with it a while, works his way to the top, and has a son. Bob.

By this point, the cookie company is really successful. Bob coasts through high school, never goes to college, in fact, never has a real job in his life. One day, he starts working at the cookie company. Nobody even knows his title or what he does, but eventually, Dad gets old and retires, and Bob takes over.

A year later, Bob sells the company for more than $10M. It won’t surprise you to learn that now Bob walks around like he’s got an "S" painted on his chest, drives a Tesla with “DSRUPTR” on the license plate, and talks about entrepreneurship (he’s a #publicspeaker, of course) as if all you have to do is plug some numbers into a formula and be really smart. And, oh yeah, hire Bob to be your coach.

The funny thing about the way Bob tells the story is he doesn’t talk about the lucky breaks, the late nights, and the early mornings. Sure, he talks about hustle and crushing it and hardwork… but there’s nothing about the four times the business almost went bankrupt, and somebody stepped in at the last minute to help them out. To hear Bob tell the story, the business’ growth was all up and to the right… like a hockey stick.

Cool story, right?

That’s the myth of entrepreneurship (and success stories of all kinds)… Bob and the Hockey Stick.

The reality is that building a successful anything is messy and unpredictable, and success is anything but linear. You have good breaks and bad breaks. Anyone who says there isn’t luck involved is a liar. Sometimes it feels like you take ten steps backward for every step forward. You hit walls, challenges arise, people disappoint you. Things never go as planned… it doesn’t matter what your license plate says.

These cute stories we make up after the fact are nothing more than narratives. And it’s fine. It’s not a problem. Bob can go tell that story all he wants.

But that doesn’t mean you have to listen.

Eventually, I just had to learn to tune out all the Bobs of the world… and there are lots of them. I know by now that another Bob story won’t make me feel inspired, it will just make me feel upset and depressed. Like I’m doing something wrong.

Instead of fighting against the reality of entrepreneurship and constantly wondering what I’m doing wrong, I’m trying to learn to revel in the mystery of what comes next.

That has made a world of difference when it comes to how I feel about business and life.

So stop listening to Bob’s cute story and start surfing.