Why You Should Learn To Paint Over Your Masterpieces

My family spent last summer in Vancouver, BC, and in the weeks leading up to our trip, we found out that my wife was pregnant.

And, as any recently pregnant couple knows, there is nothing more deeply discussed in those early days than which pregnancy announcement photo pose from Pinterest is going to make the biggest splash in your social circles.

Do we go with the cute sibling photo? Or the tiny shoes in a row? Or something themed? Well, my wife had a plan.

There is a boutique hotel in Vancouver that for months had been featuring photos of a mural on their exterior brick wall. “It’s love baby,” it said.

Expecting mothers lined up down the street for the coveted Instagram shot.

But, when we finally arrived at the building, it was gone.

GASP!

‘Why would they do this? It was so popular. And now there’s something stupid there in its place’, my wife said. It was a cool new mural with colors raining over an umbrella, but that’s not what she wanted.

And it’s okay. In the end, we got a pretty great photo! Not the one we planned for, but there was a lesson in this.

More and more, I’m realizing, you need to be willing to paint over your masterpieces if you ever expect to surpass them.

Like that brick wall mural, you need to be willing to kill “pretty good” to get to great. And you need to be able to murder “great” to get to extraordinary.

It’s a tough concept, and it’s scary as hell.

When I was 27 and running my first company, I decided to make the leap out of the day-to-day and hire a President to replace me. Of course, I couldn’t afford to pay him AND still pay myself, so I found myself without a salary. It was terrifying.

But, as I look back, I realize that I was complacent with my role, and not being challenged anymore. There was no room to grow, and I needed to manufacture a situation for myself to create under pressure again. And it worked.

A year later, I was making double my previous salary, and excited enough about my newest “side project” that I sold off my first business.

Five years later, I find myself standing in front of another masterpiece, paint brush in hand. Only this time, I have a wife and two kids. I have a mortgage. I have two cars, ten employees, and a life that by all standards is definitely “great”.

But, comfortable is where entrepreneurs die.

So, as I step back and admire this “mural” of my second company, I appreciate all the people that have interacted with it. And I know that next week, someone is going to show up and GASP when they see our old services aren’t there. They’ll think what we’re doing now is stupid and wish they came sooner.

But I know that to build extraordinary, I have to let go of great. Just like that wall in Vancouver. I have to roll up my sleeves and start painting all over again. I’m pretty confident this new venture is going to be that much better in the end.

Here goes!