A lot of what I do doesn’t work. It’s been part of my job description for a long time. It started when Bob Polik the incredibly kind Vice President of Marketing who was my first boss in corporate took me in and tried to reform me from the life of an advertising agency executive.

Make some mistakes

On my first day, he told me I should deliver 12 bad ideas to him by year-end. He wanted some small bad ideas, some medium sized ones and one super-duper of a doozy bad idea. He asked me to consciously make mistakes and present him with them.

What he really did was give me permission to use my brain without trying to evaluate the odds of its contents forming something useful. It was quite a challenge.

Failing more than you succeed

As I researched markets, competition, and our company’s resources, I failed Bob more than I succeeded. Meaning, I came up with a lot of really good ideas that helped transform the business. So much so that our business unit had record performance, we became a standalone division and then promptly got acquired. Bob and a lot of C-suite people walked away never having to work again. The rest of us lost our jobs.

Nothing in business is more counter-intuitive than the concept of good and bad.

Bob Polik changed my brain, and that is the genesis of a significant component of my personal brand. Invention defines me. I have the ability to poke around, make mistakes, work in the dark, hold things up to the light, and wonder what they could mean or do.

Michael Jordan missed a lot more end of game shots than he sank to win the game. He had the ability to fail. He knew that failure is the greatest predictor of success. I am buoyed by his approach to the game.

It’s pretty typical that when I sketch out a new website concept, I can’t get anyone in my company excited about it. I buy a cool new domain (or ten) and think it might inspire us to reach out to a likely joint venture partner. No, we’re all working too hard now, I hear. I sign up for what could be a life changing course or conference, and come away with one small new idea – and the same life. Smirks all around from people who can’t believe that’s how I spend my days off.

I also hit the business version of tennis’ grand slams and racing’s triple crown, which is a lot of successes one after another in a short period of time. Not insignificant to me, I also get a lot of thank you notes, which is an important metric that we all talk too little about getting and giving.

Not everyone is going to have the same ratio of winners to losers as Michael Jordan. Not everyone can earn a living thinking, as I have been able to do for much of my career.

But everyone can do better by first doing worse

Personal brands: what permission do you need to take a class that has no chance of increasing your earning power, mind map a bad idea or build something that will undoubtedly lead to nothing? Remember plastic was an inventor’s error.

As they might say at 3M: I wish you post-it notes.