If I had to describe Chicago in a word, I think I would pick ‘comfortable’. What I mean by that is that everything—the food, the people, even the buildings—seem completely comfortable in their own skin. It’s not trying to be something different; it’s collected, smooth and cozy. Don’t believe me? Eat a burger at Au Cheval and try hard to not fall asleep as you nestle into a meat coma. Or embrace the winter winds on Michigan Avenue where people are passing like it’s business as usual, because it is.

Diggy Moreland shares a similar philosophy. Having grown up in the suburbs of the Windy City, Diggy is more rubber than glue, effortlessly letting negativity bounce to the side like the chilly fall rain that glides off his Tech Terry Hoodie. We took some time to ask him a few questions about life, basketball, and his perfect Chicago day. 

Pictured: White Delta Polo and Black Street Joggers

 

R: You were an avid basketball player in high school and college and now a ref for highly competitive leagues in the mecca of American Basketball. How has the transition from player to ref helped you in your life?

DM: When I was a player, every game was the most important thing in that moment, so it was easy to get wrapped up in the moment and the emotions of the game. As I officiate, I have to manage the expectations of coaches and players from before the whistle to long after the game. Coaches have jobs, promotions, everything on the line and so it’s easy for them to react emotionally. For a ref, it’s another game. For a coach, it’s everything. One thing I constantly remind people of is that refs, like players, coaches, and fans, are human. So I always tell coaches, ‘I am gonna miss a few shots tonight but so are your players, so act accordingly.’ As a ref, you have the ability to see both sides of the issue, so it’s taught me a lot of people skills: how to set expectations, manage different emotions and keep everything in front of me, so to speak.

R: What is something you have recently worked hard to improve and why did you pick that specific skill or area to improve?

DM: Recently, I have really focused in on my organizational skills and how to improve that broadly across the board. What I mean by that is keeping my apartment clean, balancing my time at work with time at the gym, preparing for a marathon, being on time. Just taking some time to plan my days, weeks, etc. and a real focus on being on time, or rather early. It just makes surprises less stressful and helps you get so much done every single day. I am always working on little things to make my life better organized and always looking for areas to improve, but recently this has been a major focus.

R: What was one thing your parents taught you?

DM: I had amazing parents. My dad taught me a lot about being a man, but one of the most important things he taught me was the value of being on time. He always connected it back to integrity, saying that if you tell someone you are going to be somewhere at a certain time, your word is relying on that commitment. My mom taught me the true value of a dollar. We were always financially secure, so as a kid, I assumed that we could spend money because we had it. She was purposeful with money, making it work for her and not against her. It was a critical lesson to learn early on and has helped me tremendously during the time in my life where it would be easy to spend without thinking.

R: Describe your perfect Chicago day. 24 hours in your city? What are we doing?

DM: It’s gotta be summer and I always start the day at my favorite gym, Equinox Gold Coast. The facilities and training staff are amazing and you always see a few big celebs in there. From there, we can take in a day game at Wrigley. Even if you HATE baseball, you will love a Cubs game, and Wrigley is more of a national monument at this point. We catch a few foul balls, have some beers and hot dogs and of course, we heckle the other team. Nothing out of bounds, but some good old-fashioned trash talk. Then we are on some patio surfing, and finish the day with a nice dinner at one of my favorite BBQ joints, either Green Street Smoked Meats or Smoque and some bar hopping in the West Loop.

R: What’s a recent realization that has changed how you see the world?

DM: I have been working with a local group called “I Mentor” and have been mentoring a high school age kid from inner city Chicago. [I’m] trying to help him with whatever he needs, giving career advice, helping him with homework, etc. It’s amazing to step out of your circle and see what’s going on in someone else’s life. I had no idea kids had to worry about getting home from school safely or didn’t know if their friends would show up the next day. You hear those stories on NPR or read about them in a newspaper but once they become real, it makes you empathize in a completely different way. Using my position and my stability to help someone else from a very different station has given me a new perspective and now when someone, anyone, is struggling, I tend to judge less and empathize more.

 

To follow along with Diggy's Chicago adventures, follow him on Instagram: @diggymoreland

Shop his collection