My old fear of looking foolish is strong incentive to do good work

When I named editor of my high school newspaper, I was too ignorant to be scared.

I knew very little about producing a newspaper. I had joined the staff of my high school newspaper — the Viking — only because the newspaper sponsor asked if I wanted to join. I spent a year on staff as a junior before finagling my way to taking charge as editor the next year.

The guy flanking me in this photo was my best friend, Larry. I named him as news editor, but it didn’t matter what his title was. He was simply my partner in making everything happen.

As my senior year approached, I realized that I was afraid of looking foolish. I realized how little I knew. I set up a meeting in the summer with the publisher of the newspaper which printed our paper. I got him to set up meetings for me with the typesetters and camera room departments which I would be working with. I threw myself into learning technical details so I could do things which weren’t normal for a high school newspaper.

As I face another big transition in my life right now, I realize that my fear of looking foolish in that role pushed me in a way that nothing else could have. And I realize that I was setting a precedent for how I would handle every major change of my life for decades to come.

The first issue of the student newspaper normally came out a month after school started. That wasn’t good enough for me. I had a printed newspaper ready for distribution on the first day of school.

Newspapers back then rarely used color, but I decreed that every single issue of our newspaper would have at least spot color. When I was told we couldn’t afford that, I doubled our ad prices and recruited fellow staffers to work during the summer to sell ads with Larry and me.

Those things might not sound like a big deal, but they were very big deals to me. I did outrageous things at times, but we were actually selling more newspapers than had ever been sold before. By the middle of the year, we actually sold out of an entire press run. In a school of 1,200 students, we sold 1,000 newspapers. Typical sales before then had been a few hundred.

By the end of the year, we were actually making a profit. For the last edition, I did a 48-page tabloid in four sections, with full color on the front and back of each section. (The biggest that had ever been done before was 16 pages.) At graduation, I was still managing a sales force at the ceremony — selling copies of the paper to parents and visitors.

I’m telling you this for a simple reason.

I did something better than anybody expected with that newspaper. Nobody who came afterward matched our achievements, either. All these years later, the 18-year-old version of me puffs up with pride about the way I handled my job. I realized I knew nothing, so I threw myself into the details and surpassed everybody’s expectations.

And it was all because I was running scared.

Every time I have faced a new opportunity in life, I have been terrified of looking foolish. So I’ve worked hard to do something 10 times as good as what people expected. I always fell short of my “10 times better” goal, so I always felt a failure — but by striving to do that well, I still have typically surpassed others’ expectations, even when I felt that I had failed.

I went back and listened to all six of my new podcast episodes tonight. I listened in a normal podcast app. I heard them one after another. I know where the flaws are. I know where there are things I had meant to be different or better. I know the things that ought to be improved. But tonight, I was able to listen more like a typical listener.

I don’t really want to say this — because it sounds like ego speaking — but I liked what I heard far better than I expected to.

It didn’t change what I thought for the long term. My writing and performance have to dramatically improve. I have technical issues to fix. I need subject matter that will appeal to a wider audience. All of that is true.

But what I heard was better than most podcasts I listen to. That’s an admittedly low bar, but it made me feel as though I was once again on track to follow that same old pattern of pushing myself to do something decent — out of fear of looking foolish.

For years, I didn’t make a podcast because I knew how little I knew. I realized that I didn’t have broadcasting skills or audio editing skills. I didn’t know how to write or structure a show, much less did I have the right equipment or technical skills. But I’ve spent the last few years digging into ridiculous details of learning just enough to do something at this level. It’s not professional. It’s not good enough. But it’s better than I had any right to expect.

My work on my high school newspaper got me a job at the newspaper which had printed the Viking. Just a few years later — after working there all through college — I had become managing editor of that daily newspaper. I was the youngest managing editor of a daily in the country at the time and I was younger than any of the staffers I managed. I wasn’t good enough, but my fear of looking foolish drove me to do better things than anybody had a right to expect.

As I’ve thought about all this tonight, I’ve realized that I followed that path with everything I’ve done. I did things which I wasn’t ready to do — wasn’t prepared to do — but made them work because I threw myself into things out of fear of looking foolish.

I did that when I started my first company when I was 25. I did it when I started a couple of publications in the next few years.

When I worked on my first political campaign, I was so ignorant that I believed winning an election was about ideas. I quickly realized how naive I had been. This scared me badly — because I was scared of losing elections — so I learned the nuts and bolts of running a modern campaign. I made friends with a political consultant who had learned under GOP operative Karl Rove in the early 1970s and I picked his brain repeatedly until I had learned his system inside and out. As long as a client had the money, I could reliably get him elected if he obeyed my plans. (It usually would have been easier if we could have just locked the candidate in a closet for a couple of months.)

When I made a short film 15 years ago, I threw myself into the steep learning process because I was terrified of failing and looking foolish. I was laughably unprepared to make that short, but I somehow managed to make something which got into 20 film festivals and had a run of online success for a few years. (The last time I checked, it had been viewed more than 300,000 times on YouTube.)

I’m thinking about this tonight because I’m facing another huge transition. By this summer, I’m going to be doing something other than real estate. I know it’s going to be something I’m not qualified for. Something I’m not prepared for.

And I am terrified of looking foolish when I do that. I’m also terrified of not making enough money.

But as I look back at the history of the things I’ve done, I see that I’ve always done things I wasn’t qualified to do. I’ve always done things I wasn’t prepared to do. I’ve always been terrified of looking foolish, but that fear has driven me to do things which were beyond what I could have reasonably expected of myself.

I’m going to be making media of some sort for a living very soon. I need to make films. I might need to do some other media-related things to make a living, too. I’m not sure.

All I know for certain is that I am once again horribly unprepared for the things I’m about to do. I’m terrified of looking foolish in the things I’m about to do. I have absolutely no idea how I’m going to make any of this happen. I have no plan. I have only blind, foolish faith.

But I’ve been scared of everything I’ve tried to do so far in life. The truth is that things have always worked out far better for me than I had any right to expect.

I’m going to face this fear, too, and I’ll somehow make money doing it. For now, though, this new challenge terrifies me — but I know I’ll throw myself into it and conquer the fear.