Television was unlike anything Strahan had ever experienced, and once again, it was on him to figure it out. “They don’t tell you how to be on TV—they put the camera on you and they turn it on, and you sink or swim,” Strahan says, his tone taking a somber turn. “For the first three weeks I swear I was sinking, and I remember thinking, I should’ve gone back for that one year and played football. I should’ve played as long as I could, because I don’t know about this.” It’s the first time since his retirement that Strahan has admitted regretting his decision to walk away from football when he did. It’s the kind of statement that makes news, one that he wouldn’t usually let slip. Then again, this isn’t the kind of interview he’s used to. He’s not being swarmed by sports reporters waving recorders in his face. Right now, we’re just two guys having coffee, except one of us happens to be a national celebrity—and he’s starting to attract attention. At two points during our interview fans approach Strahan to shake his hand. One woman in her mid-20s recognizes him from TV. An older man comes over to greet him enthusiastically and then calls out to “Big Man Strahan” before disappearing into a restroom. Strahan is happy to give fans what they want, but he stays focused. When approached for a third time, this time by a young man asking to take a photo with the former Giant, Strahan shakes his hand, then points to me to explain that he’s actually busy doing an interview, but tells the guy to stick around for a photo afterward. Later, Strahan follows through, as promised, posing for a photo and even offering to take another if the lighting wasn’t 100% in the first shot. He’s genuine.

The realization that moments like these eventually stop happening is a tough one to come to terms with for any retired celebrity, especially after a career as long and successful as Strahan’s. At the same time, it’s a realization that Strahan tells me motivated him to find success off the field and gave him the energy he needed to box out a cavalry of A-list candidates for the industry-coveted co-host spot on Live! Ending his career on his own terms gave Strahan the mental advantage of being able to think of his next move as one of choice rather than necessity. “We’re our own worst enemy,” he says. “You doubt yourself more than anybody else ever will. If you can get past that, you can be successful.” It’s reassuring to hear a man who’s accomplished as much as Strahan talk about how doubt is only natural when we’re faced with life-changing decisions. We will always wonder what would have happened had we gone a certain way, he tells me. “I’m always curious, and sometimes, I’m not going to say regret, but definitely think maybe I should have [played another season]. Maybe I should have.” The key to moving on, for Strahan, was realizing that there was more to him than a Giants uniform.

He may have left football, but, judging from Strahan’s appearance, you’d never know it. At one point, while changing T-shirts on set during his Men’s Fitness cover shoot, at least one female visibly gawked at the former athlete’s chiseled torso that is currently carrying in the neighborhood of 8% body fat. Working out may have come into Strahan’s life as a means to earn a new nickname—or at least shake an undesirable one—but it never left, and it continues to be a core part of who he is, regardless of what he does for a living.