AJ Hellow

Yesterday, I finally had surgery on my wrist. I broke it about 14 years ago playing flag football. I wore a wrist guard, let it heal enough to get back on the field, taped it up, and kept playing. I didn't want to miss football. Now, at 39, with a national championship ring on my finger and my playing days behind me, it was finally time to fix it. Here's the story behind that ring, and what it taught me about never giving up. I started playing flag football at 20. I started my own team. We didn't win a single game that first season. But we got better. Quickly. Playing in the second largest flag football league in the country, and maybe the most competitive, we quickly became one of the top teams in Chicago. Eventually, some teammates and I started playing in out-of-town tournaments and traveling to Florida for the national championships jumping aboard a "tournament team" constructed of players from multiple teams from Chicago. We weren't very good at first, but held our own. We learned. We got better. We kept going. Soon after, my team was getting older and I was recruited to a young team from Chicago loaded with athletic talent, including mostly former Division I and II football players just out of college. They wanted me not just for my ability, but to lead the team. They made me team captain the first season with the team. A new playbook and new strategy that I brought with me was just what they needed. The year before I joined, they went 2-8. Our first season together, we went 9-1 and won the Chicago league championship. We thought we were pretty good. Then we went to nationals and got bounced without winning a game. That was a humbling experience. The following year, a handful of us joined another team for nationals. We finished third. That team had less talent than ours, but it had something we needed to learn: leadership, organization, and players who put the team first. We took that lesson back with us. The next year, we got organized, got serious, and finished fifth out of 36 teams. We lost on a field goal attempt as time expired that could have won us the game. It was blocked. The following year, we came back believing we were good enough to win it all. We ran through teams and reached the championship against a two-time national champion. We were up 14-6 late in the game. We sacked their quarterback on third down. They needed a miracle. They threw a Hail Mary. They caught it, converted for 2, and sent the game to overtime. We lost. That was January 2020. Absolutely heartbreaking. Then COVID hit. Our momentum disappeared, but we came back in January 2021 and finished third. Still a good result. Still disappointing. We knew what we were capable of, and we hadn't finished the job. By 2022, a lot of us were getting older. I was 34, and some of the younger guys who had once seemed like kids were approaching 30. We thought it might be our last run. That tournament, injuries on Friday and Saturday to our defensive line forced me out of my normal position at nickel corner/linebacker and into defensive line. At 6 feet tall and about 175 pounds I was lining up against offensive linemen weighing 250 pounds or more. Not exactly an ideal matchup. In my first game at defensive line on Sunday, I dove for the quarterback's flags and collided with a teammate. I got the sack but separated my shoulder. I thought it was just a stinger. I took a painkiller and kept playing. Four games that day. I had Six sacks, including two in the national championship game. We came from behind late to force overtime in the Championship Game. Again. And again, we lost. Sudden-death field goal. I was gutted. I thought that was it. But the younger guys weren't ready to quit. One of our defensive backs, who was also our back up quarterback, stepped up and took over the offense. We recruited young, athletic players and started building again. In 2023, we made it back to the national championship game. And lost again. This time, we got beaten pretty badly. We could have called it quits. Instead, we used it as motivation. The next season, we won the Chicago league championship, won multiple local tournaments, won a tournament in Ohio, and absolutely dominated. Then came January 2024. I was 36 years old. I'd basically promised my wife that this was it. If we couldn't win with this team, I was finally hanging up the cleats. I went down to nationals one last time. And we won the whole damn thing. We ran through the competition and won the national championship in blowout fashion. My role had changed by then. We had younger, faster players who were better suited to nickel/linebacker, so I rotated at defensive end for roughly 30% of our defensive snaps. But I played every special-teams unit: gunning down on kickoff coverage, blocking on kick return, long snapping on punt team, blocking on punt return, long snapping on FG, and rushing on FG defense. I helped with strategy, shared my experience, and contributed however I could. I didn't need to be the star. I needed to help us win. Only a handful of us from those earlier championship runs were still on the roster. Years of work. Heartbreak. Close calls. Rebuilding. More heartbreak. Finally, a national championship. There is no better feeling than working toward something for years, coming up short over and over, and finally achieving it. That ring means more to me because of everything it took to earn it. And that's why I'm sharing this on a business account. I grew up with a single mom who worked two or three jobs to support us. We didn't have much. When it came time for college, I considered playing football. I wasn't great, but good enough to get interest from Division II and Division III schools (probably just wanting my tuition dollars), but I chose University of Illinois Chicago because I could attend for free. It was the financially responsible decision. I didn't play college football. Instead, I built a career in tech sales. It was a great career. It helped provide for my family and gave my wife the opportunity to be a stay-at-home mom for our kids for more than seven years. I'm incredibly grateful for that. But I wanted to build something of my own. I wanted to take a bigger swing. So a couple of years ago, I started my cost reduction consulting business. Building a business isn't the same as playing football, obviously. But the mentality carries over. You get told no. You face setbacks. You put in work that doesn't immediately pay off. You question whether you're making progress. You have to keep showing up when the results aren't coming as quickly as you'd like. You have to adapt when your original plan doesn't work. You have to trust other people, learn from your mistakes, and sometimes accept a different role than the one you envisioned. And you have to be willing to keep going long after the easy motivation wears off. Football taught me that you don't win a championship in one game. You earn it through years of preparation, failure, adjustment, and persistence. Business is no different. I'm not building my business because I want to coast. I'm building it because I have bigger goals for my family and my future, and I'm willing to put in the work to pursue them. I don't expect every attempt to work. I don't expect every prospect to say yes. I don't expect every year to be a winning season. But I'm going to keep learning, keep improving, and keep showing up. Because I've seen what can happen when you refuse to quit. The cast on my wrist is a reminder of what I put off for 14 years because I wasn't ready to stop competing. Playing every fall and spring season in that tough Chicago league, traveling every summer to tournaments, then in the winter to Florida for Nationals. There was no time off to take care of it. The ring is a reminder of what can happen when you stay committed to something long enough to see it through. I'm done playing football. I'm not done competing. And I'm just getting started in business.