The Barbershop

In the spring of my sophomore year at Wesleyan, I finally felt like I was settling into Middletown, Connecticut. After months of searching, I found the three things I needed to make the transition smoother: a group of friends, a spot for authentic Mexican food, and, most importantly, a barbershop. As a Black man, the barbershop is much more than a place to get a haircut. It’s where I catch up on local news, talk about the latest NFL games, and sometimes even get a free therapy session. After trying shops as far as New Haven and Hartford, I finally found the right place—Mike’s Barbershop, a family-owned business in the heart of downtown Middletown, passed down through three generations.

Over time, I became familiar with the Whinn family, who ran the shop, particularly my barber, Marquay. One day, while waiting for my haircut, I overheard Marquay offering his nephew a job to help promote the shop on social media. His nephew wasn’t interested, but I saw an opportunity. After my cut, I approached Marquay with a proposal. I explained that I could set up an Instagram account and manage the shop’s social media presence, given my experience with platforms like Instagram. He liked the idea and offered me free haircuts in exchange for weekly content creation.

Six months into this arrangement, I realized it was about much more than free haircuts. The business opportunity helped me gain valuable insights into marketing, community engagement, and entrepreneurship. What began as a way to save money turned into a rewarding experience where I could support a local family business and become a part of their extended community. Each visit to Mike’s Barbershop became more than just a business transaction; it became a time to learn from the Whinn family and bond with the people who came in and out of the shop. This opportunity not only saved me money, but it also opened doors to new relationships and a deeper connection to Middletown.