Turning the Page: From Family Business to My Own Path

Life has a way of throwing curveballs when you least expect them. After 26 years of dedication to my family’s business, I never thought I’d wake up one morning and make the decision to walk away. But sometimes, circumstances force you to take a hard look at where you are and where you want to be.

The breaking point came after an altercation at work—one that made me realize I couldn’t stay any longer. It wasn’t an easy choice. Leaving something that had been a part of my life for over two decades felt like stepping off a ledge without knowing if there was solid ground below. But in that moment, I knew I had no other choice.

However, I refused to let that moment define me. Instead of dwelling on what I lost, I focused on what I could build. The very next day, I took the leap and launched Chesapeake IT Services LLC.

Starting my own business wasn’t just about moving on; it was about taking control of my future. Technology has always been my passion—from the first computer I broke (and fixed) at age 10, to the countless hours helping friends, family, and teachers with their IT problems. Now, I get to do what I love on my own terms.

This transition hasn’t been easy, but I’ve never been more motivated. Challenges will come, but I know I’m on the right path. Walking away was hard, but building something new is exhilarating.

If you’ve ever faced a crossroads in life, I hope my story reminds you that sometimes, the best way forward is through change. Bet on yourself—you might just surprise yourself.

This year, my birthday weekend was one for the books! It all started on Friday night when Nicole and I attended a special catered dinner hosted by the organizers of Wings & Wheels. The highlight of the evening was listening to the captain of the USS Cole recount the harrowing events of the bombing, describing the incredible efforts the crew made to save the ship and minimize casualties. It was such a moving experience. To top off the night, I bid on—and won—a delightful wine and cheese basket during the auction.

Saturday was a day I had been eagerly anticipating. I got up bright and early to get myself and my Mustang over to the Wings & Wheels car show at Georgetown airport. By 8 AM, I was all set up and ready to enjoy the day. But the real thrill came at 11:30 AM when I climbed aboard a PT-19 WWII airplane, with a German pilot at the controls. For 45 exhilarating minutes, we soared over Rehoboth Beach, flew up the Delaware coastline, crossed Cape Henlopen State Park, and ventured over Prime Hook before heading back to the airport. It was my very first time flying in a non-commercial aircraft, and I can confidently say I’d do it again in a heartbeat!

Later in the afternoon, around 3:30 PM, the car show organizers began handing out trophies. To my surprise and excitement, my Mustang won 2nd place in the Millennial class! It was such a proud moment. After the show, Nicole and I celebrated by heading out to do some Halloween decoration shopping—a fun way to wrap up the day.

On Sunday morning, we continued with our Halloween prep by picking up pumpkins from Home Depot and grabbing some corn stalks from How Sweet It Is. That afternoon, the weekend festivities concluded with a fantastic dinner at The Red Roost in Whitehaven, MD, where all my friends gathered. We ate, drank, laughed, and made great memories before parting ways.

It was an absolutely wonderful weekend, filled with good company, exciting experiences, and plenty of fun!