The Blade

Let’s not take ourselves… or our businesses… too seriously

Once when travelling who knows where, who knows when, who knows why–a young flight attendant was taking us through the safety precautions and says, “There may be fifty ways to leave your lover, but there are only four ways to exit this aircraft.” Ahhhh, clever– throw in some Paul Simon lyrics. I like.

Image credit: Stuart Miles

The flight attendant strolls by me, and I exclaim, “You just slip out the back, Jack!” No reaction. She strolls by again, I add, “You don’t need to coy, Roy!” No reaction. A few minutes later, “Just drop off the key, Lee!” Nothing. At this point, I’m not even trying to be funny; I’m just looking for some sort of reaction. The flight attendant eyes me as if I’m crazy. The man seated behind me is belly laughing – so I believe this exchange is somehow funny. But she’s not amused and instead is clearly irritated. Now I’m just confused.

The man behind me finally explains why he’s laughing: “She’s only 25 years-old and has no idea what you’re talking about. She’d probably heard another flight attendant use the phrase ‘50 ways to leave your lover…’ and so she copied it.”

I tried to explain myself to the flight attendant, but the damage was done. The more I tried to clarify what had occurred, the less she cared and the more awkward the situation became. Passengers are just shaking their heads.

Truth be told, I’ve done some pretty stupid, silly, embarrassing things during the time I founded two companies. Here’s a partial list:

• I inadvertently sexually harassed the sexual harassment trainer (that story is for another blog post).
• I broke my assistant’s nose playing an impromptu soccer kick-around.
• At a cocktail party meet-and-greet with customers at a very nice restaurant, I showed everyone in the room my geographic tongue.
• I requested my salesperson and intern help me clean my house in exchange for pizza. What was I thinking? This one became legendary.
• I once went postal on a few customers – shocking the room.

If you are a startup founder, I recommend you make your own list. How many times have we heard someone tell a work story that makes their boss sound like a complete moron (think: Michael Scott from The Office)? The reality is that, as a startup founder, embarrassment and vulnerability are inevitable. Best to go with it—laugh about it, be yourself, and enjoy the ride.Tweet this

I would never trade these stories and red-faced embarrassments for anything. The stories are a culmination of who I am and how I remember my startup experience. What would be sad would be looking back at eight years of me trying to become something I’m not. I could never be the CEO of a large publicly traded business; my personality would never lend itself to the necessary political correctness. But I can successfully create a positive atmosphere and grow a thriving small business by simply being myself.

So as Paul Simon advises, “’The problem is all inside your head,’ she said to me; The answer is easy if you take it logically…” Sometimes the problem is easy – Just don’t take yourself too seriously. You’ll be amazed by how much more fun your startup culture will become.