headshot of George Dinwiddie with books he's written

iDIA Computing Newsletter

April 2025

Questioning Yourself

Many years ago, I had a job working with, and directly for, an incredibly insulting man. He would gratuitously insult people, from shop clerks to politicians, for no apparent reason. When working with him, sometimes I would offer a suggestion about a better way we might do a task. This was always met with some insulting remark, questioning the worth of my suggestion and me for suggesting it.

In my defense, I took to thinking about my suggestions from as many angles as I could before offering them. If I couldn't find a flaw in the suggestion, I would offer it. And I would receive an immediate insult, but in a few minutes we would often be working in the way I had suggested. One such day I offered a suggestion and he looked at me and said "Dammit, George, why are you always right?!"

I didn't answer, but I knew it was because he had trained me to question myself before speaking in vain hope of avoiding his insulting question. Over the course of a year, I developed a strong habit of questioning the value of my ideas.

Overthinking

I've heard many people equate questioning themselves with overthinking, and worry that it will undermine their self-confidence. Ironically, the very term "overthinking" can have that effect, as it identifies that there is something wrong with your thinking. I've seen this lead to a desire to project confidence at the expense of thinking, and this can get people into trouble.

Most of the time "overthinking" is used to describe revisiting past actions over and over looking for what you did wrong in the past. While examining the past can be useful for understanding how perceptions, actions, and consequences are related, it is fixed in time and cannot be changed. Nor can the understanding achieved by exploring it be reliably trustworthy. We are limited by the fixed nature of our past perceptions.

Other times "overthinking" is describing anxieties about the future, particularly aspects about the future over which you have no control and little influence. It can be useful to prepare for potential possibilities, but worry is not preparation. Rather than start with future catastrophes, it's likely more fruitful to start with the current moment, and what you'd like to have happen.

The Current Situation

What is the current situation? At best we have an incomplete understanding of the universe around us. What salient aspects do we feel most confident that we understand? And what aspects are more speculative? These can be teased apart by asking ourselves what observations support our understanding? And what other observations would give us more confidence? We can focus on these observations, checking the validity of the ones we have and seeking others that would give us a fuller picture.

After zooming in on these details, perhaps it's time to zoom out and see how it fits in the larger world. What is the larger situation in which this focus is a part? Are there other overlapping situations that fit this criteria?

Often we look at things from a single point of view, emphasizing what we want and what we don't want. Who else is affected by this situation? Can you name some individuals or classifications of people who are involved with it, or who might be affected by changes in the situation under consideration? How might the situation look to them? Do they want and not want the same things as you, or might there be some differences, even if just differences in emphasis or priority?

These sorts of questions will go a long way toward making your choices or proposals more acceptable to others, without giving up your own needs. That can lead to happier circumstances, even if you do get accused of being "always right."

For what it's worth, I stuck it out because I had a lot to learn from this insulting boss. One bonus thing I learned was that he viewed his insults as humor. Getting past that allowed me to understand many other more positive qualities that he had.

We never have a complete understanding of the situation we're in.

/signed/ George

P.S. What's your experience with questioning yourself? I'd love to learn from you and would appreciate it if you could reply with a few words about your reaction to this newsletter issue.

And if you'd like to talk further about this topic, you could schedule a Zoom Session with me to talk about it.

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