Client Spotlight: Craig & Diane Pollock

Craig and Diane’s story is one of family, resilience, and a life well-traveled, all rooted in

strong values learned early on.

Diane grew up in the western suburbs of Chicago as one of five children in a

hardworking, middle-class family. Her father worked for Pepsi, and her mother later

returned to work at a bank after his passing at a young age. Watching her parents work

multiple jobs to support the family left a lasting impression.

“I grew up learning that if you wanted something, you worked for it,” Diane shared. She entered the workforce straight out of high school and built her career as an administrative professional, eventually landing at Toyota, where fate would step in.

Craig’s childhood unfolded in Bettendorf, Iowa. An only child, he lost his father at age

nine and was raised by his mother, who went back to work as a schoolteacher. He later

earned degrees in business and automotive marketing from Northwood University,

which led him to a career with Toyota, and ultimately to Diane.

Although they didn’t know it at the time, their paths were crossing long before they met. As a child, Craig often visited his aunt and uncle in the Chicago suburbs, and during those visits, he was just ten minutes away from Diane’s home. Looking back, it feels like the universe was quietly nudging them toward each other all along.

The two eventually met while working in the same Toyota office in the Chicago area and were married in 1987. Their lives together would become one of movement and adventure, following Craig’s career across the Southeast, before eventually settling back in North Carolina for retirement.

Together they raised two sons, Ryan and Neal, and today enjoy a growing family that includes grandchildren and step-grandchildren.

Family remains central to their lives. Every year, they organize two big family trips, a summer getaway to places like Cape Cod or the North Carolina mountains, and a fall weekend in Chicago filled with deep-dish pizza, Bears football, and shopping on Michigan Avenue.

Chicago holds special meaning for them: it’s where Diane grew up, where they first met, and even where their very first date took place at the historic Drake Hotel.

Travel has always been a shared passion as well. Thanks to Craig’s career, they’ve seen much of the U.S. and Europe, with favorite destinations including London, Italy, and Venice. Now in retirement, they’re rediscovering the joys of slower travel, from trips to Blowing Rock and Banner Elk to future plans for another anniversary adventure abroad.

They also share their home with Harper, their rescue dog, a sweet Siberian Husky

mix who has quickly become part of the family.

When it came time to get serious about long-term financial planning, Craig’s path

to Milestone Wealth came through friendship. A longtime friend was neighbors

with Dave in Greenville, and the two were introduced years ago during football

weekends in Florida.

“I wasn’t quite ready back then,” Craig said. “But when I turned 50, I started thinking seriously about what I wanted retirement to look like.”

What resonated most was Dave’s planning-first approach. “He didn’t just talk about investments,” Craig explained. “He talked about life, how we wanted to live, what we wanted retirement to be, and how to build a plan around that.”

Today, Craig and Diane value not only Dave’s guidance, but also the broader Milestone team and the continuity they provide for their family’s future. “I like knowing this is a long-term relationship,” Craig said. “Something our kids can grow into and rely on someday. It’s

thoughtful, detailed, and built around education and trust.”

Now settled just outside Chapel Hill, Craig and Diane are enjoying retirement the way they planned it, spending time with family, traveling when they can, and savoring the everyday moments that matter most.

From Chicago to Iowa, from Toyota to retirement, their story reflects a lifetime of hard work, love, and intentional choices. And a future still full of family and adventure.

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Want to build a plan for your family that helps you achieve the retirement you envision? Please contact us to schedule a conversation.