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 Plan B. It had just never occurred to me, or my parents, that I wouldn’t be an artist.

Two years later, I was going to school part-time for an English degree, going nowhere, basically, and an ex-girlfriend’s father I was still friendly with convinced me to apply for a job as a teller at the bank he worked for. This also didn’t feel like a career to me, and I knew I had no business doing anything math related. But I got in on his recommendation, I’m sure, went through a two-week training program in Boston, and found myself working at a branch of the bank in the Dedham Mall.

Here, too, there’s more to unpack there than may be obvious. It was 1988, and malls were still very much a thing in the United States. This mall had a permanent if fake red barn in its center, a Hickory Farms store, plus a Chess King, a Bradlees, and a Wordsmith Books I cherished. And though I was still living with my parents, I’d soon be engaged and had turned into a curiously speedy and accurate counter of money. This unexpected skill came in handy given all the commercial accounts—retail stores—that banked there. (Oddly, I still retain this skill today. Less oddly, it has never come in handy again.)

The tellers and our imperious leader, the head teller, were separated from customers by glass that extended from our desks all the way to the ceiling, with just a foot-wide air gap so we could pass money and other paper items between the two sides. This head teller had trained me, and I still looked to her each time something new and unfamiliar came up. (And, to be fair, we became friends.) In that world, there was the manager, who was unassailable, and her. I trusted them both.

Until one day, weirdly, I didn’t.

I don’t remember the exact conversation, only that the information that this head teller was giving a customer, next to me and through her glass gap, was not correct. Sitting there, young and inexperienced, I was unsure how to proceed. I couldn’t and wouldn’t interrupt her as she spoke. But the more she continued, the more nervous I got. I had to do something. Say something.

When whatever transaction was occurring had concluded, the head teller walked to the back of our area and the customer turned to walk out of the bank. So I called the customer over quietly, apologized, and explained that what they had just been told was incorrect. I recommended that they speak to the manager, perhaps immediately. And I somehow orchestrated this all without tipping off the head teller. In the end, everything worked out, and the customer—who had indeed spoken with the manager—later thanked me for the intervention.

This was interesting because I didn’t necessarily know all that much about banking per se, not at that early date. But I knew enough to know that something was incorrect, and that incorrect information in banking can be devastating. It was weird watching someone I trusted just be so wrong about something so important, almost an out-of-body experience. And I surprised myself by speaking up, given how easily I doubt myself. But was happy I had done so. It’s nice to be certain, but it’s even better to be right.

Aside from several bank robberies, most of my tenure as a teller was inconsequential. By the time I had met Gary several years later and started down the career path that somehow stuck over 30 subsequent years, everything had changed. I had gone back to school again, this time for software development, and I was just starting to develop a technical knowledge base, a foundation, for that coming career.

Today, I’ve probably forgotten more about personal computing and this industry than I remember. There are people—Rafael, Richard, Mary Jo, Leo, George, and others—who I look up to and whose opinions I respect. But I still struggle with self-doubt, still find myself ignoring literally decades of experience from time to time. So I try to remind myself of the young teller from time to time. And of how important it is to speak up when you know you’re right.

Like all advice, easier to give than to receive.