My great-great-grandfather started our insurance company. At 27, I sit where my 90-year-old grandfather once did.

Evan O'Dowd left his job to join the family business. Courtesy of Evan O'Dowd Evan O'Dowd wanted to start his career outside his family's insurance business. Last year, at 26, he moved home and started working with his mom and dad. Cultivating a connection with other young people has helped him adjust, he says. This as-told-to essay is based on a conversation with Evan O'Dowd, business development manager at Avery Insurance. It has been edited for length and clarity. When I was about 10, my...