Finding Purpose in Petoskey: Ashley DeCarteret's Journey from Insurance Legacy to Industry Leadership
Meet Ashley DeCarteret, owner of Harbor Brenn Insurance Agencies in Northern Michigan. If you ask her, she’ll say she was “born into insurance.” That’s because her journey began long before she officially joined the family business in 1998—it really started in childhood, growing up around the agency her father founded in 1977.
Today, with more than two decades of experience, Ashley reflects not only on a fulfilling career but also on the people, places, and pivotal moments that shaped who she is—both in and outside of insurance.
Growing Up in Petoskey: Community at the Core
Ashley was born and raised in Petoskey, a picturesque town in Northern Michigan. Life in a small, close-knit community profoundly influenced her values and priorities. “You know a lot of the people. A lot of the people you went to school with are still there,” she says. That sense of familiarity and accountability shaped her view of leadership, community involvement, and service—values she now applies daily as an agency owner, mom, and community member.
After graduating from Smith College in Massachusetts with a degree in Political Science and a minor in International Relations, Ashley returned home—unsure of what the future held. Serendipity stepped in when a role opened at her family’s agency. Though she had worked summers there during college, this was different. This was the beginning of her full-time career. “I was technically born into insurance, but I also kind of fell into it,” she jokes.
Lessons from a Life in Insurance
Looking back, Ashley can trace much of her personal and professional growth to her years in the industry. “I feel like I've changed a lot since I was a child,” she says. From being a single mom to running a business and becoming an active community leader, life has been a constant evolution.
Her advice to her younger self?
- Don’t be afraid to say yes. “You don't have to walk into something knowing everything. You can still provide value while learning along the way.”
- And don’t be afraid to say no. Protecting your time and aligning with your values is equally important.
Outside the Office
While she’s deeply passionate about her work, Ashley carves out time for hobbies that help her recharge. She’s an avid reader (favorites include Atomic Habits, The Nightingale, A Court of Thorns and Roses, and Ready Player One), and she’s equally fond of hiking, biking, boating, and yes—even video games.
Books are such a passion that she jokes, “If anybody wants a book recommendation, come find me.” You’ll likely see her at the Navigator Narratives Book Exchange with a few favorites in hand.
College: A Window to the World
Attending Smith College was a major shift for Ashley—a Midwest girl stepping into an East Coast liberal arts college. “It was a big culture shift for me and it opened up my eyes in a lot of ways,” she recalls. While she didn’t pursue a political career, the study of diplomacy and collaboration has served her well in business, especially in navigating complex client relationships and mentoring others.
Mentorship and the Power of Community
Though Ashley never had an official mentor herself, she has taken on that role for others—and she finds it just as rewarding. “I learn as much or more than the person I’m mentoring,” she says.
Her involvement in organizations like NetVU and local leadership programs has helped her build a robust professional network. Through events like Accelerate—her first being in Orlando in the mid-2000s—Ashley has found friends, collaborators, and endless sources of inspiration. “I walk into the conference and it’s like, ‘Oh, I know them! It’s so good to see you!’” she shares.
Embracing Innovation
Ashley’s agency has always leaned toward the tech-forward side of the business. From breaking computers in the early days (thanks, Dorlene, for all the fixes!) to exploring the data and technology aspects of insurance, she’s embraced the idea that every policyholder is unique—and that cookie-cutter solutions don’t work.
“People think insurance is a commodity, but it’s not. Every person and business has something unique about them,” she explains. That’s what keeps her work dynamic and rewarding.
A Legacy, Continued
Ashley’s story is one of returning home, leaning into opportunity, and redefining what it means to carry on a family legacy. She didn’t just take over the business—she brought her own perspective, passion, and purpose to it. And in doing so, she’s become a respected voice in the insurance community, in Northern Michigan, and beyond.
As she puts it, “Getting involved has generated a huge network of people that I know in the industry… and even when I don’t have questions, I meet up with them and they say something and I’m like, ‘Oh! I never thought of that.’ That’s hugely valuable—to me and to my agency.”
Ashley DeCarteret isn’t just running a successful business—she’s building something bigger. A life rooted in service, connection, and community. And it all started in a small town called Petoskey.