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I grew up in the Chicago area for 17 years before I moved away for college. After ten years, and a great deal of difficulty in convincing employers to give me a chance, I came back to Chicago for my career. I bleed red and black when the Blackhawks play, blue and orange with the Bears and there is very little I like more than a Friday afternoon Cubs game. The people in Chicago are the friendliest, hardest working, most genuine folks that I’ve ever had the pleasure of meeting. The city offers culture, fun, diversity and authenticity that rivals the greatest cities in the world. I have two tattoos that incorporate the Chicago flag, and I’m considering one that includes the skyline. In short, Chicago is my home. It’s where I belong. It’s who I am. It’s what I know. And those are the reasons I am leaving.
I’ve been back in Chicago now for 18 years. But for the ten years I was gone, when I would fly home, I would get chills when I would see the skyline. I’d be antsy to get into the neighborhoods, to eat the food, to see the teams, to connect with my friends over drinks and truly experience Chicago. I was infatuated. I would brag about my city to anyone who would listen. Chicago was my pride and joy.
I no longer feel that way. Right now, Chicago feels more like the place that I live than my home. Part of that may be Chicago’s fault. It certainly hasn’t weathered the pandemic well. The politics of lore are less a memory than most residents would like to believe. The violence is rampant and seems to be escalating. The taxes are astronomical, and the educational system can be bleak. But all places have shortcomings, so I put more of the blame on myself.
A few weeks ago, my good friend Eric told me that a lot of us, maybe all of us, are back in Chicago because “it’s familiar.” Familiar … that word isn’t a compliment in this context. It means we’ve become complacent, comfortable and saturated with the routine. I don’t want routine. I don’t want complacency, and maybe I need uncomfortable. Without debating the merits of the movie, in The Internship, Owen Wilson’s character says something that has always stuck with me: “The thing in life that frightens is the most? Change. I think most people are set in their ways. I know I need change to come along and kick me in the ass to get me moving.”
I am clearly at a point in life where I need change to kick me in the ass to get me moving. I thought I would move back to Chicago, get married and raise a family in the only place that ever truly felt like home. Does that make any sense if I can’t even appreciate this amazing city anymore? Where it doesn’t feel special? When it doesn’t give me chills? When it has become routine? Absolutely not. I need to leave so I can appreciate Chicago again, its culture, its people and have those magical moments when I come back. I need to get out of my routine, to shake things up, to embrace a monumental life change.
Good enough is never good enough
Still, let’s confront the obvious. Change is scary — scary as hell. Uprooting everything I know and everything that makes me feel comfortable in favor of the unknown is scary. It would be a lot easier to sit still and settle for “good enough.” But I don’t know if I will ever get better, ever push forward, ever appreciate where I’ve been if I don’t keep changing and evolving. If you take one thing from this article, let it be this: “Good enough is never good enough.” Not for me, and not for you.
By the time this is published, I will have left Chicago. I’ll be in Colorado taking on new challenges, meeting new people, and most importantly, being uncomfortable. Discomfort forces adaptation, which creates growth and in turn, progress. We get better not by doing things we want to do because they’re comfortable. We get better because we do the things that aren’t comfortable — things that test our limits and push us beyond our thresholds.
I have a tattoo on my arm that says “The only risk you regret is the one you don’t take.” I got this tattoo for a reason, and to be candid, as the title of this article indicates, it’s because my biggest fear in life is not mattering. If you want to matter, you have to take risks. You have to get comfortable being uncomfortable. You need to push your limits and boundaries and dare to be great. It doesn’t mean you won’t fail. To the contrary, you will fail. You will likely fail often, but there are learning moments in every failure, and every failure will make the successes all the more sweet.
I’m not leaving my roots behind. I will be back often and fully expect I will see all of my friends routinely in exchange for the cheap lodging I can offer for skiing. I love you, Chicago. I love what you stand for. I love what you are. I love the promise of what you can be. Most of all, I love the people who make you what you are. I will always be a Chicagoan. You will always be my home. And while I have to go for now, I’ll be back soon. And when I see that skyline through the airplane window, and I feel that magic and those chills again, I’ll know I made the right choice in leaving you to see what can happen when I embrace change, the unfamiliar and the uncomfortable.
Related: How to Thrive on Change
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