Many leaders start their careers with hopes of reaching the top as quickly as possible, skipping past lower-level positions as they scale the corporate ladder. This is particularly true in the startup scene, where founders essentially choose their own titles and begin their careers in management positions.

My career did not have such a direct trajectory. I meandered through the insurance industry for decades before I finally secured a leadership role. I started out working for my parents’ company, doing the grunt work of the office. I generated invoices, processed mail, and even handled janitorial duties. I was the youngest person in the office and the lowest on the totem pole, so I didn’t have a problem earning my stripes. Some people mig...