In 2011, after Chris Halpin had rejoined his colleagues back at Providence Equity Partners’ New York offices at the completion of a 3-year stint in Hong Kong, he found himself being confronted by something he had rarely experienced before: boredom.“I had this kind of existential angst—that I didn’t want to die and have my obituary say that I had worked 40 years at Providence Equity,” recalls Halpin, who notes that it was at this point that he began to think about different operating roles in business and the possibility of landing a CFO position.Still, Halpin tells us that he reviewed and pretty much rejected the different introductions and job opportunities that quickly surfaced: “I was like, ‘No, I really don’t want to do this’—and then I almost joined another private equity firm, but that would have been just changing politics for politics.”Then, October 2012, Halpin added to his calendar an entry that seemed to all but eclipse previous possibilities and instantly loomed large on his autumn agenda: “Coffee with Roger Goodell.”Goodell, the much-revered National Football League commissioner, no doubt usually prefers to honor the prescribed time limits of his appointments, but, as it turned out, his 30-minute coffee talk with Halpin ended up going on for more than hour before Goodell ended it with an offer to introduce Halpin to a number of his lead deputies.      “Roger makes no promises, that’s for sure,” remarks Halpin, who adds that prominent Providence alum and former Comcast CFO Michael Angelakis helped him snag the initial meeting with Goodell.In June 2013, Halpin accepted a position with the NFL that kicked off an 8-year career inside the league’s business operations. Along the way, he served in a succession of strategy-oriented roles before being named executive vice president and chief strategy and growth officer in 2018.Looking back, Halpin tells us that he originally pitched Goodell for a bigger initial role with the league.  “Roger told me, ‘No, that’s the wrong way to come into the NFL—I’ll bring you in and have you get grounding, and then we’ll move you around to give you different experiences,” reports Halpin, who points out that his decision at the time was not an easy one, in part due to his prospective NFL compensation being a drastic reduction from his Providence pay.“In April or May of 2013, I came to the conclusion that if I didn’t do this, I was going to regret it—so I decided to make the jump,” comments Halpin, whose 8-year tenure with the NFL ended in January 2022 when he was named CFO of IAC, the media holding company headed by media executive and dealmaker Barry Diller.Today, having landed in a more traditional finance leadership role, Halpin says that his years with the NFL will always likely trigger conversations that allow him to continue to reflect on past decisions. It seems that career decisions have seldom been easy for Halpin—even when they’ve involved the opening of a door at the NFL.   Says Halpin: “This was not some sort of courageous jump into the breach without any reservations.” –Jack Sweeney