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 younger sister lost one of her Webkinz — popular stuffed animals at the time. I offered to sell her Webkinz insurance to help protect her from any future losses. She took me up on it, and that was my first foray into the family business.
My dad’s great-grandfather started an insurance company, and both of my parents work there today. Avery Insurance has been part of my story since I was born. In the car driving to sports practice, or at the dinner table, business always came up. I didn’t mind: I was a little obsessed with running a business from a young age.
Yet, I wanted to start my career somewhere else. At my core, I felt I needed to do that. I wanted to build my competencies and find success for myself outside Avery Insurance before I considered whether to become the fifth generation to join the company.
I realized I could impact the family legacy
I left New Hampshire and went to school in Denver. I did a stint in tech sales, then joined a startup that I worked for in Colorado and New York City.
Working for a startup in New York, I was surrounded by the best and brightest. I learned so much by osmosis, just existing in this ecosystem of other young entrepreneurs. I loved it.
Still, I was always talking with my parents about the family business. Last year, I could see that — based on where the business was — it was the right time for me to join. My parents needed reinforcement.
They never pressured or even asked me to come work with them, but I thought if I wanted to have an impact on the family legacy, this was the time to do it. I wasn’t thrilled about leaving New York, but I knew I would regret not taking that shot.
I worked to connect with other young leaders
I lived with my parents when I first moved back. We get along great, but having them as parents, roommates, and bosses — that triple threat was a little much. Finding my own place was a priority.
Working with my mom and dad was great, however. I have a huge respect for the work they’ve put into the business, because I’ve seen it firsthand. And they really respect everything I’ve learned, so they give me space to implement new ideas. Insurance is an antiquated industry, but I’m passionate about modernizing our company.
Although work was going well, I missed the community of peers I’d had in New York. I’d been able to feed off the energy I got from other business owners. In New Hampshire, I found I had to muster that energy and enthusiasm on my own.
I started building a community here for young people, and it’s paying off. Last week, I helped host an event for entrepreneurs under 40. I’m proud that I’ve helped cultivate that.
My sister isn’t in the business, and that’s fine with everyone
Sometimes I’ll be in the office, and my grandfather, who is almost 90, will come in and see me sitting where he worked for much of his life. I’m sure that’s crazy to him. It’s just one way that working here has made me closer to my family.
Not everything in the family is about business, however. My sister was never interested in joining the company, and that’s fine with everyone. She runs wellness and yoga retreats. To me, it’s impressive that she recognized the family business wasn’t her cup of tea, then built something she’s passionate about.
I’m only 27 and don’t have kids. But hypothetically, if I did, I would take the same approach my parents had with my sister and me. They just wanted us to be the best we could be, whether we were in the business or not. Running a fifth-generation business isn’t easy, so I wouldn’t want to pressure anyone into doing it. If you’re going to take that on, you’ve got to really want it.