WHY SO SERIOUS?

by Matt Thomas

I am in a group with six other business leaders. We meet once a month for 5-6 hours. The reason we meet regularly is that we all believe the opportunity to lean into each other, learn from each other, and have some dedicated space where we can discuss what’s working and what’s broken in our personal lives and our businesses is a net positive. It’s that simple and it’s great. Each month we invite a guest to join us. Usually, a gray hair who has been extraordinarily successful in business. We give this individual two hours of our time, half of which they use to tell us their story, and the other half we use to pepper them with questions. Nothing is off-limits. It is a gift.

Our thinking is that we can save ourselves a lot of heartache and stress by learning from someone else’s mistakes.

Our thinking is that we can save ourselves a lot of heartache and stress by learning from someone else’s mistakes. The focus isn’t so much on how to be wildly successful as it is on how to not screw everything up! Amongst the many nuggets of wisdom I’ve picked up during our time together, I’ve come to realize that there are two common threads through each of their stories. First, these guys have all gotten incredibly lucky at one point or another. Truly, like the stars aligned and they hit the one in a million jackpot. Sure they are bright and work hard, but they would be the first to admit that there are better ideas out there that never get traction. The second thread is that none of them take themselves very seriously. They all have had a fantastic sense of humor and are aware that it’s a minor miracle things have worked out the way that they have. In short, despite the tens and hundreds of millions they’ve raked in over the years each of them walks in a boatload of humility. It’s amazing.

They all have had a fantastic sense of humor and are aware that it’s a minor miracle things have worked out the way that they have.

Nothing creates pause more quickly for me than a young entrepreneur who thinks their idea is bulletproof. Last year a good friend of mine asked me to meet with a young guy with an idea he was considering investing in. His request was two-fold, should he invest, and if it is a good idea would I consider investing as well? We sat down and it was clear out of the gate this guy was sharp, motivated, and hungry. All key ingredients for a young entrepreneur. He walked me through his business plan with passion and conviction. I noticed some holes and started to poke. He got defensive. Red flag number one. If you can’t handle criticism of your idea then you aren’t going to be able to pivot when something isn’t working like you thought it would. It didn’t hurt that he was planning on launching into a space I had tried and failed in over a six year run. Did I know how to make it happen? Maybe not. But I sure as hell knew all the ways it could fail. When we started working through the financials I was alarmed by how much he planned to pay himself right out of the gate. Cashflow is a challenge for any start-up but especially for a seasonal business like his. Revenue goals pre-launch aren’t worth the paper they’re printed on. I asked him if he had considered ramping up his income alongside an increase in sales and he shut the idea down quickly. Red flag number two. He believed he was worth “x” and that was going to be true regardless of how the business performed. I asked him where he came up with that number and his response was that it was the amount he made in a previous job with a large company plus twenty percent to account for the risk. I tried not to laugh.

If you can’t handle criticism of your idea then you aren’t going to be able to pivot when something isn’t working like you thought it would.

In the workplace, there is no bigger inhibitor to building strong relationships than taking oneself too seriously. It is no wonder that researchers have identified a strong correlation between emotional intelligence and a sense of humor. And more and more companies are rightly placing a premium on EQ as they consider new hires, promotions, etc. A discipline I picked up from a mentor a long time ago that has served me well I call “The Worst Case” exercise. I put pen to paper and write out all of the things that could go wrong with an idea and where these pitfalls will land me and those I care about the most. Outside of death or prison, more often than not I can stomach these unlikely scenarios. I can even envision a path up and out of them should the wheels come off. This exercise does two more things for me. First, it helps me identify and mitigate risk where possible. Something anyone looking at a new opportunity should do. The second is that it brings into focus all of the things that are outside of my control. It’s a fresh reminder that the list of things I can actually control is pretty small. It also brings renewed focus to those things and a new lens for looking at the idea.

For most of us facing down a career change, launch of a new business, or other significant life decision the world is not going to come crashing down if it doesn’t unfold perfectly according to the plan.

For most of us facing down a career change, launch of a new business, or other significant life decision the world is not going to come crashing down if it doesn’t unfold perfectly according to the plan. Right-sized, we can engage the world around us and the people in it with the appropriate amount of gravity. One of the biggest gifts I’ve ever received was the realization that I’m just lucky to be alive. Anything I get to do, or build, or add value to is icing on a cake I didn’t deserve in the first place. Life is short, and it can be sweet. Don’t take yourself too seriously. Go get ‘em.