Bosses are inherently intimidating, even though most of them aren’t actually big, or bad. Still, they are “the boss” and they have a great deal of control over your life, which can make them scary.

I met my first boss when I was eighteen. He seemed nice enough, but did expect a day’s work for a day’s pay. I had a summer job as a stock boy in a warehouse, unpacking, stocking shelves, and filling orders.

About a month into the job, my family was leaving for an extended weekend vacation. Being...