Retirement Planning and Entertainment: A Growing Concern
It seems that many Americans might be overlooking some crucial factors in their retirement plans. They’re thinking about how they want to spend their days, the activities they want to engage in, and what kind of entertainment they hope to include during this phase of life.
A survey by Lincoln Financial in 2025 revealed that a significant 77% of Americans in their 50s and 60s consider retirement to be an opportunity for new beginnings, a chance to pursue passions that the demands of work didn’t allow. However, while there’s enthusiasm for planning more enjoyable activities post-retirement, only 38% reported actually putting specific plans in place. A large number still seem quite unprepared for how they’ll occupy their time once they stop working.
To inspire pre-retirees, Lincoln Financial connected with Rich Roll, who hosts a wellness podcast. They produced a four-part video series titled “Action Plan,” where Roll speaks with tennis legend Andre Agassi and Morgan Housel, the author of “The Psychology of Money.” Roll, now 58, shared some thoughts on how generations today view retirement differently than their parents did. He noted, “We don’t have a job to look forward to; we just mark that date on the calendar, but it’s more complicated than just playing golf.”
Indeed, lifestyle expectations and life expectancy have shifted quite a bit. “We’re living healthier for longer, which raises questions about how to continue enjoying what we love, and let’s be honest—many of those enjoyments can get pricey,” he added.
Interestingly, Lincoln Financial also found that a sizable 39% of retirees over age 50 underestimate the costs associated with entertainment during retirement.
Thinking about hobbies and entertainment expenses is essential. People need to take time to reflect on how they truly want to spend their days post-work, whether that’s picking up sports, learning music, volunteering, pursuing education, gardening, or hosting social gatherings.
Roll finds inspiration in Agassi’s philanthropic efforts and his focus on creating opportunities for others. “It’s a powerful lesson, especially for those nearing the end of their careers who still want to make an impact, either personally or commercially,” Roll shared.
Timing Your Retirement Plans
If you’re nearing retirement but feeling uncertain about your plans and savings, you’re not alone in this. Many retirees lack a clear grasp of their potential daily costs. It’s crucial to start your planning now. “Today’s the day to begin thinking about it,” Roll emphasized.
Having transitioned from corporate law to an ultra-endurance athlete, Roll mentioned he considers himself a “late bloomer” when it comes to finances. Reflecting on what he could have done differently, he said, “In a perfect scenario, I would’ve saved a bit every month since I was 21, but that wasn’t my reality.”
Despite the challenges, he doesn’t see himself retiring anytime soon. When asked about it, he simply stated, “I don’t plan to.” However, he is currently establishing a foundation that would allow him to take a step back if he wishes. “I don’t envision that day arriving, nor do I desire it, but I know that nothing lasts forever. So, on my podcast, I pledge to keep being engaged and excited about life.”
