In the 1986 comedy Back to School, Rodney Dangerfield’s character—a brash, wealthy businessman—enrols at his son’s university and approaches higher education like just another corporate venture. He hires experts (including Kurt Vonnegut himself) to ghostwrite assignments, only to be handed a failing grade. While the movie played this academic-business culture clash for laughs, in real life, many retiring financiers are finding out that transitioning from the boardroom to the classroom is no comedy—it’s a complicated reinvention.
For some high-achieving professionals, returning to university in later life sounds like the ultimate escape. They imagine trading deadlines and board meetings for lecture halls and quiet reading sessions. It’s a way to revisit the intellectual curiosity of their youth—without the pressure of grades or the fear of failure. But reality, as many have learned, often falls short of this idealistic vision.
Former bankers and executives who’ve tried to pivot into academia often encounter jarring cultural and generational differences. After decades of senior leadership, adjusting to taking instructions from professors—sometimes younger than their own children—is no small feat. One former financier enrolled in a master’s program in computer science with the dream of co-founding an AI startup with a faculty member. But the professor lacked any interest in commercialization. Another banker began a PhD in economics, only to leave early, disillusioned by the narrow focus and political dynamics of the academic department.
There are also challenges in simply understanding and adapting to the academic system. While concise writing and practical communication are prized in the business world, academia values dense, citation-heavy prose and theoretical abstraction. Bullet points and executive summaries don’t carry the same weight in a university seminar.
The generational divide adds to the friction. Group work with classmates 30 or 40 years younger can be both enlightening and frustrating. Retirees may see the world in shades of gray after decades of experience, while younger students often argue with the certainty of ideological purity. For those used to directness and efficiency, the meandering nature of academic debate can feel like a step backward.
Then come the logistics. Unlike in their twenties, returning students in their fifties or sixties are more likely to have families, homes, and caregiving responsibilities. Uprooting one’s life to attend a full-time program is often unrealistic. And while some retirees initially see academia as a fresh launchpad for a new career, the job market rarely welcomes older graduates with degrees in obscure fields. Age bias in hiring remains a quiet but persistent obstacle.
Despite all this, the draw of intellectual engagement and purpose remains powerful. Many former bankers and executives aren’t looking to restart their careers—they’re looking to reframe them. Elite programs like Harvard’s Advanced Leadership Initiative and Stanford’s Distinguished Careers Institute are designed specifically for seasoned professionals seeking renewed purpose, not employment. With tuition hovering around $70,000, these programs are exclusive, but for some, the cost is justified by the meaningful experiences they offer.
For those more inclined to teach than to study, adjunct or visiting lecturer roles are a viable path. But even here, full-time faculty appointments are rare unless the applicant holds a PhD—something most ex-bankers don’t. Still, for those who land a spot, teaching can offer a rewarding way to pass on hard-won wisdom. One former banker turned business school professor even keeps plaques from old deals—known in the industry as “tombstones”—in his office as conversation starters for curious students.
Ultimately, while retiring financiers may find their way back into the classroom, they cannot reclaim the youth they once had. What they gain instead is perspective—an opportunity to view education not as a means to a career, but as an end in itself. And as Rodney Dangerfield’s character eventually learns, even if you can hire the author, you still have to understand the book.
Source: Financial Times
