During the early years of his finance career, Dan Fletcher was accustomed to being the executive from somewhere else.

When he first joined the asset management team at Allstate Investments, he was “the auditor from Price Waterhouse,” and when he landed in an interim management role as a private equity advisor, he was a former investor now turned operator.

Fletcher’s early career journey stands out not just for its navigation of the financial triad of auditor–investor–operator but also for the speed at which he was able to leap from one to the next.

“I did not look like everyone else,” recalls Fletcher, who doesn’t try to cloak the burdens of his first pivot.

He continues: “These are two totally different disciplines. Whereas from an auditor’s perspective you’re viewing the business from the outside in and mainly trying to validate financial statements, from the investor’s perspective you’re mainly concerned with returns.”

Meanwhile, Fletcher makes it clear that his ability to transition was dependent on regular outreach along the way.

“Having people place a bet on me required the careful fostering of a lot of relationships beforehand,” comments Fletcher, who tells us that his switch to the operations side required both individual initiative as well as passing muster with a rigorous future employer.

“In addition to completing a lot of prep research on my own, I underwent a lot of vetting—I think I interviewed with probably 20 different people,” remembers Fletcher.

Reflecting on his research, Fletcher adds: “Thanks to the Internet, there was no shortage of material out there with regard to how to thrive in different roles—from both the hard skills and soft skills points of view.”

Still, one career pivot that Fletcher put in motion had more to do with narrowing his focus than widening it: Nearly a decade into his career, he decided to interview exclusively with private equity technology firms—thus ending his days as an industry agnostic.

Says Fletcher: “I just slowly fell in love with tech. I started to understand how technology was really where more innovation—and therefore more value creation—was happening relative to what was going on in older industries.” –Jack Sweeney

Barbara H. Rosenwein, "Winter Dreams: A Historical Guide to Old Age" (Reaktion, 2025)