I recently had coffee with a former colleague who spent his entire career living by the motto “work hard, play harder.” At 67, he confided something that stopped me cold: “I saved plenty of money, but I never saved any energy for actually living in retirement. Now I’m too exhausted to enjoy what I worked for.”
His words captured a paradox I’ve been observing since entering this phase of life myself. The “you only live once” philosophy that drives so many successful careers often creates habits that make retirement profoundly difficult. Not financially difficult, but psychologically and physically difficult in ways most people never anticipate.
After decades in negotiation rooms where leverage mattered more than logic, I’ve learned to recognize patterns in how people set themselves up for future regret. The YOLO mindset particularly interests me because it sounds like wisdom but often functions as permission to ignore uncomfortable truths about our future selves.
Here are seven signs your version of “living once” might be sabotaging the decades you’re supposedly working toward.
1. You’ve confused intensity with sustainability
Think about your current pace. If you had to maintain it for another twenty years, could you? Most people operating under YOLO principles treat their bodies and minds like rental cars, pushing hard because they assume they’ll trade up later.
I spent years in environments where 70-hour weeks were badges of honor. The unspoken rule was simple: those who couldn’t keep up were weak. But here’s what nobody mentioned: the colleagues who burned brightest in their forties were often barely flickering by sixty.
Nathan A Heflick Ph.D., a psychologist, notes that “The catchphrase ‘YOLO,’ (you only live once) has become a bit of a cultural sensation.” What he doesn’t say directly, but what I’ve observed, is that this sensation often masks an inability to imagine ourselves as older. We live once, yes, but that once includes being 70, 80, maybe 90. The habits you’re building now are the foundation you’ll stand on then.
2. Your identity is completely tied to your professional status
Ask yourself this: if you couldn’t mention your job title or company for an entire month, what would you talk about? How would you introduce yourself?
The YOLO approach to career often means pouring everything into professional achievement. Every hobby becomes networking. Every vacation includes checking email. Every conversation somehow circles back to work victories. This feels like living fully until the day that identity card gets turned in.
I’ve watched too many people discover at retirement that they’d become their business cards. Without the title, the corner office, the busy calendar, they didn’t know who they were. They’d optimized so hard for professional success that they’d forgotten to develop a self that could survive without it.
3. You’ve traded relationships for transactions
Living by YOLO often means prioritizing experiences and achievements over mundane relationship maintenance. That college friend’s birthday dinner gets skipped for a work opportunity. Family gatherings become obligations to endure rather than connections to nurture.
In my negotiation days, every relationship had a purpose, a potential value. Even social events were about positioning and leverage. It took entering this phase to realize I’d trained myself to see people as assets rather than, well, people. Now I watch others make the same trade, believing they’ll have time to rebuild those bridges later.
But relationships atrophy differently than muscles. You can’t just start exercising them again after decades of neglect and expect them to support you.
4. You mistake motion for progress
The YOLO mindset loves movement. New projects, new ventures, new experiences. But constant motion often prevents the kind of deep engagement that creates lasting satisfaction.
I know someone who started and stopped fifteen different retirement hobbies in his first year. None stuck because he’d trained himself to chase novelty rather than develop mastery. His whole career was about the next thing, the bigger deal, the better opportunity. That served him well professionally but left him unable to find satisfaction in steady, patient development of interests.
5. Your body is an afterthought until it becomes an emergency
“I’ll get healthy when things slow down.” How many times have you said some version of this?
The YOLO approach treats health as something to optimize later, after the important stuff is handled. Meetings trump medical checkups. Deadlines override sleep. Exercise gets scheduled only when nothing else conflicts. The mentality is that you’re investing your health now for freedom later.
Except bodies don’t work like bank accounts. You can’t make deposits after decades of withdrawals and expect the balance to recover. The neglect compounds in ways that no amount of retirement yoga classes can fully reverse.
6. You’ve eliminated all margins from your life
Efficiency is the YOLO virtue. Every minute scheduled, every resource deployed, every opportunity maximized. But this leaves no room for the unexpected, for recovery, for simple presence.
I remember keeping my calendar so packed that a flat tire once triggered a cascade of failures lasting weeks. No buffers meant no resilience. In retirement, I’ve watched people bring this same mentality forward, unable to enjoy an unscheduled afternoon because it feels like waste.
The cruel irony? Shoba Sreenivasan, Ph.D., and Linda E. Weinberger, Ph.D. observe that “Retirement is a stage that transforms an individual’s life.” But if you’ve eliminated your capacity for stillness and reflection, that transformation becomes torture rather than evolution.
7. You treat future you as a stranger
This might be the most telling sign. When you think about yourself at 70, do you feel any real connection to that person? Or is it like imagining someone else entirely?
YOLO thinking often creates a disconnect between current and future selves. We make choices assuming future us will somehow be different, more capable of handling the deferred maintenance we’re accumulating. We’ll want different things, need less, be content with whatever we’ve managed to salvage.
But future you is still you, just older and dealing with the compound effects of today’s choices. The habits, patterns, and capacities you’re building now are the tools that person will have available.
Closing thoughts
The tragedy isn’t that people live by “you only live once.” That’s actually true and worth remembering. The tragedy is misunderstanding what that one life includes and treating our future selves as strangers who’ll somehow prefer the leftovers of our current choices.
After decades watching people navigate power dynamics and face-saving behaviors in business, I’ve noticed something consistent: those who thrive in retirement are those who treated it as a continuation of life rather than a completely different existence.
The practical step you can take today? Pick one habit you’re currently maintaining through YOLO logic and ask yourself honestly: would I want to still be doing this at 75? If the answer is no, the time to change isn’t someday when things slow down. The time is now, while you still have the energy and flexibility to build something sustainable.
Because yes, you only live once. But that once is longer than most of us are honestly preparing for.
