From the Editor’s Desk: Doubt (Premium)

I’m not sure where the self-doubt comes from or, in my case, when it started, or whether it’s always been omnipresent in the back of my mind, waiting to spring out as needed to cut me off at the knees. I just know that it’s there. And that it can be difficult to suppress, even when the topic at hand is something I feel reasonably educated about.

There are certain people in my life who can summon my self-doubt seemingly at will. My wife, of course, but also others whose opinions and intellects I admire. One of my clearest memories of this dates to the start of my writing career, literally 30 years ago this year. I was working at the home of Gary, the mentor who had convinced me to become a writer, and I had come out of his home office with a printout of a chapter I had been working on so that he could edit it.

There’s more to unpack there than may be obvious. Gary is still, to this day, the smartest person I’ve ever met. The book we were working on was our second together, but the first for which I was the primary author. It was a technical book about Visual Basic 3 that targeted the education market, not so subtly raising the bar on the need for accuracy. And, yes, the editing occurred on paper. It was 1994.

I handed him the small stack of paper and sat down across him at the kitchen table, and I watched, nervously, as he read what I had written. I could visually seem him scanning from line to line, something nodding to himself, and it seemed to be going well. Maybe I could relax.

“Are you sure about this?” he suddenly blurted out.

Uh-oh. I looked down at the paper. He had hit a source code block. And had stopped.

“I mean. I was,” I stammered, weakly.

Gary got up silently and walked into the home office I had just left. There were two computers set up in this office, both with giant (for the day) CRT monitors and tower cases. Again, it was 1994. There were no laptops, not yet.

Sitting down at the bigger and newer of the two PCs—I had been using the other one—Gary brought up Visual Basic, started a new project, and finally started typing some code. It didn’t last long. After staring at the screen for a few seconds, he handed me back the papers and told me to try again. Then he walked back into the kitchen. I think he had been eating lunch, I don’t recall. I just remember standing there with the papers in my hands, wondering what I had gotten myself into. I felt so … exposed.

That I had landed in Gary’s orbit was a matter of both circumstance and blind luck. 10 years earlier, in high school, I was an award-winning artist and the only major decision I faced before I graduated was to choose which art school to attend. I applied to and was accepted to all three I considered, and then almost immediately realized what a mistake this career choice was, unless the goal was to never make any money. So I dropped out at the end of the first year, confused and directionless. I didn’t have a Pla...