Michael Flannery was a comedy peer of mine back in the day.

I’m in Cincinnati visiting for Christmas and coincidentally have been invited to the First Annual Cincinnati Comedians Homecoming Show. I’ll be going to Funny Bone Newport, KY tonight and hope to see a few of my old colleagues from the early 80’s, back when I was doing stand-up. People often ask me what doing stand-up was like, so, here’s the story, but with a twist. I’m going to relate it to starting anything creatively challenging.

In the late 70’s and early 80’s comedy went from a somewhat quaint and staid art practiced mostly in the Catskills and New York City to something more akin to rock and roll. The influence of Saturday Night Live and the late, great, seminal comics George Carlin and Richard Pryor had clubs sprouting in all major cities. Growing up, I’d been the class clown, could do some impressions, and had informally studied stand up, so, I thought, I’d be a natural, it would be easy. I decided to give it a try.

My Hero, George Carlin

My first few performances were, to say the least, unsuccessful. Frankly, they were humiliating, I was sooo bad. What I thought was funny was clearly not according to my audience. I was booed, heckled, and at least once yanked off stage. My ego took a major hit. I tried various things to improve, but it was so bad I was, for a time, banned from the main venue of the day in Cincy, the DWI. I worked other clubs and tried writing material which I found nearly impossible — staring at a blank page in my typewriter. I didn’t know what I was doing and was swimming in self-doubt, fear, anxiety, and — excitement. It drove me to drink, and yet I was obsessed by the challenge.

Friends advised me to quit, they didn’t want to see me embarasing myself. It was worse than I thought even. One night I pushed record on my cassette tape deck and caught some “friends” whispering about my act. Mercy, it was brutal to hear their cutting remarks. But it was a gift — I was faced with the reality I had to change everything if I was going to be any good at all.

I did consider quitting, but for some masochistic reason I didn’t. I rethought what was funny. I looked at everything with a new set of eyes (could this be material? is this funny? what aren’t people noticing?) I started doing something radical — telling the unvarnished truth. Things started to work. I also tried to get away from jokes and instead leverage my natural goofiness. I had a bit of a breakthrough when I did a parody of the Patty Duke theme song. My first successful night. My material went from trite to, frankly, a bit sick, but at least it was authentically sick AND funny. I was never a great standup, but I did achieve a sort of respectability. I did a few good video bits on Warner Cable. My peers gave me some grudging respect. When I got to that level, I quit, but with my head held high.

So, the life lesson in all this? Doing creative things can be very, very difficult, and emotionally crushing, particularly at the start when it is likely you are going to be Bad. When I think of the nerves, stage fright, and then humiliation when I “died like the Hindenberg” — I wonder why I put myself through it.  When you try to do something really new and different some of your friends will advise you to stop, quit, be reasonable, be smart — and it will really feel like they are right. They’re not, there is a big payoff to this suffering.

The payoff to starting in on the difficult creative journey of a whole new thing is, holy cow, will you ever learn fast. You’ll learn about yourself, you’ll learn about your content, topic or area of interest, you’ll learn what the market wants, and you’ll learn process. Then there are those around you — you’ll learn who supports you in your creativity and who would prefer you stay the same so they can be more secure. It’s good to know who wants you to Stay in-the-box.

By the way, all this applies, in spades, to innovation in start-ups and big organizations.

The things I learned from my brief stint in stand-up I’m still using today? I learned that if you’re not interesting in the first six seconds you’ll lose your audience. I learned that surprises are essential to speaking. I learned that confidence and commitment to your message are essential. I learned that imaginative stories are the vehicle for being compelling. I also learned that being nervous is a good thing because energy is Everything in public speaking.

So, it’s nearly 2013 and many of us want to start something creatively new in the new year. I urge you to jump on that horse and ride — you will learn like mad. Don’t listen to the naysayers. And prepare for very rough trails. But oh, at the end of the day, I promise, they will be Happy Trails!