Last month, I sat across from my father in his study, watching dust particles float through the afternoon light while he considered my question. The leather chair creaked as he leaned back, fingers steepled, that familiar look of careful thought crossing his weathered face.
“What would you do differently if you could go back?” I’d asked, expecting maybe one or two regrets about career choices or investments.
Instead, he pulled out a worn notebook—the same one where he’d been writing that question I’d seen before: “What am I optimizing for now?” He flipped through pages of observations accumulated over eight decades, then looked at me with surprising intensity.
“John,” he said, “I’ve been thinking about this for years. Not because I’m drowning in regret, but because I see you and your generation making the same miscalculations I did.”
What followed was the most valuable conversation we’ve ever had. His seven answers weren’t about missed opportunities or roads not taken. They were about fundamental misunderstandings of how life actually works versus how we think it should work.
At 64, having retired recently myself, I finally understood why he’d waited until now to share these insights. You need a certain distance from the game to see how it’s really played.
1) Stop trying to win arguments that don’t matter
“I spent decades proving I was right,” he began, “in meetings, at dinner parties, even with your mother about which route to take to the grocery store. You know what all that correctness got me? A reputation as someone exhausting to be around.”
He explained how he’d learned, far too late, that being right is a pyrrhic victory when it costs you warmth and connection. The people who disagreed with him didn’t suddenly see the light—they just stopped inviting him to discussions that mattered.
This hit home. In my own career, I’d prided myself on surgical precision in debates, on cornering flawed logic. But he was right.
The biggest lesson I’ve learned myself is that you can’t negotiate someone out of what they’re committed to misunderstanding. People dig in harder when challenged directly. They change their minds quietly, privately, when they feel safe to do so.
“Pick your battles,” he said. “Most hills aren’t worth dying on. Save your energy for the two or three principles that actually define who you are.”
2) Learn to disappoint people gracefully
This one surprised me. My father, the consummate diplomat, wishing he’d disappointed more people?
“I said yes to everything,” he explained. “Every committee, every favor, every weekend obligation. I thought I was building social capital. Instead, I was teaching people that my time had no value.”
He described how his fear of letting people down had paradoxically made him less reliable. When you’re overcommitted, you end up disappointing everyone a little bit instead of protecting what matters most.
The real insight was about power dynamics. People respect boundaries, even when they initially push against them. They don’t respect martyrs. When you say yes to everything, you’re not being generous—you’re avoiding the discomfort of watching someone’s face fall when you say no.
3) Stop waiting for the perfect moment to have difficult conversations
“Your mother and I almost divorced at year seven,” he said quietly. This was news to me. “We spent two years avoiding one honest conversation about money and ambition. Two years of resentment building because we were both waiting for the ‘right time’ to bring it up.”
The perfect moment never comes. Meanwhile, the small irritation becomes infected, spreading into every interaction. He learned that difficult conversations get harder with time, not easier. The anticipation is almost always worse than the actual discussion.
“Have the conversation when it’s a problem, not when it’s a crisis,” he said. “And definitely not when it’s too late.”
4) Recognize that loyalty has an expiration date
My father spent 15 years at a company that treated him progressively worse, holding onto outdated notions of corporate loyalty. They counted on that loyalty to keep him in place while promoting around him.
“Institutions don’t have memory,” he said. “The company you’re loyal to doesn’t exist—it’s just whoever happens to be in charge right now. And they don’t know or care what you did five years ago.”
This wasn’t about becoming cynical or transactional. It was about understanding that loyalty should be reciprocal and based on current reality, not historical precedent. The most successful people he knew renegotiated their relationships regularly, ensuring the exchange of value remained fair.
5) Invest in your body like it’s a retirement account
“I treated my body like it was rented,” he laughed, but there was regret in it. “Figured I’d start taking care of it when I had more time. Turns out, your body keeps score whether you’re paying attention or not.”
He spent his 40s and 50s prioritizing everything except his health—closing deals, attending meetings, sacrificing sleep for marginal productivity gains. Now at 80, he spends a significant portion of his retirement managing preventable health issues.
“Every workout you skip in your 40s, you pay for twice in your 70s,” he said. “But everyone thinks they’re the exception until they’re not.”
6) Stop believing your own performance
This was perhaps the most philosophical of his regrets. He explained how he’d gotten so good at playing certain roles—successful executive, devoted husband, wise mentor—that he’d forgotten they were roles.
“I optimized for appearing successful rather than defining what success meant to me,” he said. “I was so convincing in my performance that I convinced myself.”
Getting married at 35, later than his peers, he thought he’d avoided this trap. But work had already shaped his identity so thoroughly that even personal relationships became performances. Only in retirement had he started asking himself what he actually wanted versus what someone in his position should want.
7) Understand that competence is a depreciating asset
“I defined myself by being useful,” he admitted. “By solving problems, by being the person people called. When that stopped, I didn’t know who I was.”
This resonated deeply with my own retirement struggle. So much of our self-worth gets tied to our usefulness and competence that we forget these are temporary states, not identity foundations. The transition from “person who handles things” to “person who lives” is harder than any career change.
He wished he’d developed identity anchors that weren’t tied to performance or productivity—curiosity, creativity, connection. Things that appreciate with age rather than depreciate.
Closing thoughts
As I left his study that day, I realized why these insights felt so different from typical life advice. They weren’t about doing more or being better. They were about recognizing the games we play without realizing we’re playing them.
My father’s regrets weren’t really regrets—they were clearheaded observations about how human behavior actually works versus how we pretend it works. At 64, I’m finally old enough to see he’s right. The social pressures and power dynamics that drive our decisions are invisible until you step back far enough to see them.
The question he writes in his notebook—”What am I optimizing for now?”—has become my own daily practice. Because the tragedy isn’t that we make wrong choices. It’s that we make choices based on rules we’ve never questioned, playing games whose prizes we’ve never actually wanted.
Start with one uncomfortable truth from this list. Sit with it. Notice how it shows up in your next interaction. That awareness alone will begin to change how you navigate the world. Sometimes the most profound changes come from simply seeing clearly what was always there.
