David McElroy

What would it take to make you happy? To feel content? To feel satisfied with life?

We use different words to talk about this, but almost everybody instinctively knows what I’m talking about. Most of us have some story we tell ourselves about what it would take for us to feel at peace with our lives.

Some people think more money would make them happy. Others care little about money but crave the love and acceptance they’ve always needed. Others want power or social status. They want others to see them some particular way. They think if they had a particular house or car or boat — or something — they would be able to be content with the world and at peace with their lives.

I’m no different. I’ve had money in the past, but found it brought little peace. At this point in my life, I’d love to have more money, but I know it wouldn’t change my satisfaction with life. It wouldn’t give me the peace I crave.

My holy grail right now is connection — to be loved, accepted, valued and understood. Some deep part of me believes I would be happy — would have peace, find contentment, whatever you want to call it — if I simply had a family and some deep community connection. I have a beautiful and loving picture of what that life could look like. And I feel as though it would change everything.

But I have the nagging intuition that I’m wrong. In my gut, I have the terrible feeling that if I can’t be happy or content or at peace right now — when I’m alone and lack many of the things I want — I wouldn’t find those things if all my dreams suddenly came true.

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When I was in college, a morning television show debuted on NBC with a comedian I’d never heard of. His name was David Letterman.

I was soon skipping class to watch this show. It was unlike anything I’d ever seen. The comedy was original and irreverent. I kept trying to get other people to watch it, but nobody I knew was impressed. Pretty soon, it became clear that very few people anywhere were impressed. NBC quickly canceled a brilliantly funny show.

After Letterman eventually became a big star on late-night television, I read about why the morning show failed. Those inside the business said the comedy was simply too new and different for the audience that was watching morning television. Viewers who had grown accustomed to tuning in for game shows and soap operas weren’t ready for David Letterman’s wacky comedy.

Maybe you eventually liked Letterman. Maybe you didn’t. That’s not my point. It’s just that by the standards of the market he entered, his work was too different. It wasn’t what the audience wanted. And he failed.

But Letterman didn’t change his work after that to make the audience happy. He kept doing his wacky and irreverent brand of comedy. He worked hard and eventually earned a late-night spot on NBC. By then, a younger crowd had found him — and he became a wildly successful entertainer.

As I get ready for the debut of my own show on YouTube — The David McElroy Show — I keep thinking about Letterman. It’s not that I have his talent or that I’m even trying to be a comedian. It’s simply that I’m making something that’s different from the rest of what I see on YouTube — and I strongly suspect that a lot of people are not going to “get it.”

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When I launched this website 12 years ago, I didn’t have a clue what I wanted to do with it. As I’m going through another startup — a YouTube show called David McElroy Live — I remember how lost I felt when I started here.

Tom Briscoe had done political cartoons — very good ones — for a newspaper I had owned many moons ago. In early 2011, we got together for lunch to catch up after not seeing each other for a long time. Tom told me that I really needed to start a website to put my writing online.

I was intrigued, but the idea also scared me. What would I write about? What if nobody ever read what I wrote? Would I be humiliated if I failed?

With Tom’s help, I got my site set up. The first things I wrote were awful. I had no audience. I had no concept for what I was trying to do. I averaged 66 page views a day during that month. I was afraid I’d never find an audience or a niche that made sense.

Now I’m starting a live YouTube show and I have the same fears.

I don’t have a clear concept of what I’m going to do. I’m afraid I won’t be interesting. I’m afraid I won’t be able to attract an audience. For the first time in a long time, I’m a clueless beginner once more.

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