The 40s are a turning point in life. That blind optimism that stayed with you throughout your youth finally fades, and it’s replaced by a nagging sense that you’re not getting any younger. In fact, you’re sort of on that slow march towards death (though hopefully not for a long while). That being said, for many men, this is when those postponed dreams and unaddressed missteps morph into regrets. Here’s what they often wish they’d done differently.
1. They wish they’d taken better care of their bodies.
The metabolism slows, old sports injuries twinge, the consequences of late-night pizza catch up. The body they took for granted in their 20s starts sending warning signals. Regret isn’t just about vanity, but realizing that health is the foundation of enjoying the years ahead, as the National Institutes of Health notes. They wish they’d prioritized exercise and a good diet way earlier.
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2. They regret not traveling more adventurously while younger.
The lure of “settling down” clashes with a lingering thirst for adventure. Mortgages and school schedules replace backpacking through Southeast Asia. While responsibilities are real, many men in their 40s mourn that lost window when they were freer to ditch the itinerary, sleep in hostels, and embrace the unknown before those possibilities narrowed. That’s not to say they can’t still see the world, but roughing it when you’ve got a bad back isn’t such an alluring idea.
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3. They regret working too much and missing out on family life.
Chasing promotions, logging those 60-hour weeks… ambition in overdrive blinded them to what truly mattered. It’s those missed bedtime stories, absent dads at soccer games, and the slow fading of connection with a partner that fuel deep regret. The corner office loses its luster when you realize the price paid in family time was too steep. There’s nothing rewarding about being a workaholic.
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4. They wish they’d nurtured their friendships more deeply.
In the frenzy of early career and family-building, friends get relegated to the occasional beer, if that. By their 40s, men often realize those bonds have atrophied. They miss the camaraderie, the easy laughter, the support system beyond immediate family. Regret sets in, knowing that revitalizing those old friendships takes effort they’re no longer sure they have the energy for.
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5. They regret not taking enough risks.
Playing it safe has a cumulative cost. The business they never started, the move to a new city they talked themselves out of, the creative passion left on the shelf – all of these linger in the “what if?” section of their minds. Mid-life brings a pang of dissatisfaction knowing they prioritized comfort over stretching themselves, and the nagging feeling it may be too late for bold leaps.
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6. They wish they’d been more emotionally open and vulnerable.
Toxic masculinity teaches men to bottle it all up, per Verywell Mind. But by their 40s, the weight of unspoken burdens becomes heavy. They regret missed connections, unresolved tensions with loved ones, and not knowing how to express themselves beyond anger or surface-level banter. They wish they’d learned to embrace their full range of emotions and share them authentically.
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7. They regret letting fear dictate too many choices.
Fear of failure, fear of judgment, and fear of the unknown all add up to a life smaller than it could have been. Looking back, men in their 40s see those pivotal moments where anxiety, not rational assessment, held sway. The path not taken due to fear is a potent source of regret.
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8. They wish they’d worried less about what other people thought.
The desire for approval runs deep. But four decades in, they start seeing the heavy cost of prioritizing external validation over their own values. They regret the career path chosen because it looked good on paper, the hobbies dropped due to social pressure, the version of themselves they performed to please other people rather than embrace who they authentically were.
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9. They regret not learning the importance of saying “no” sooner.
People Pleasers reach a breaking point in their 40s. The exhaustion of always saying “yes” to commitments they resent, to avoid letting anyone down, becomes unsustainable. They wish they’d mastered the art of setting boundaries earlier, realizing that selectively saying “no” is how they create space for what truly matters to them.
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10. They wish they’d saved more money and been smarter about finances.
Retirement looms larger. Impulsive spending in their younger years haunts them. The nagging worry of whether they have enough socked away grows stronger. A reckoning occurs where they regret not taking financial planning more seriously, or the frivolous purchases made instead of building a solid foundation for the future.
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11. They regret not pursuing hobbies and passions that fulfill them.
Work-life took over, leaving little room for the things that spark genuine joy. That guitar collecting dust in the attic, the half-finished novel manuscript, the dream of learning to sail – all symbolize untapped potential. Regret sets in as they realize life became routine, and they forgot to actively cultivate the things that make them feel truly alive.
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12. They wish they’d been more present in their relationships.
Even if they were physically there, were they truly mentally and emotionally present? Multitasking, distracted by work worries, they went through the motions of relationships without being fully engaged. They regret those missed opportunities for deep connection, for making the people they love feel truly seen and cherished.
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13. They regret not making amends with those they’ve hurt or drifted from.
All those old grudges, unresolved conflicts, and unsaid apologies weigh a bit heavier with every passing year. Men in their 40s often wish they’d found the courage to address those fractured relationships sooner, realizing that life is too short to carry the burden of broken connections they could potentially mend.
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14. They wish they’d forgiven themselves more easily.
Everyone makes mistakes, of course, but dwelling on past failures holds men back from enjoying the present. In their 40s, many reach a point of wishing they’d been kinder to themselves. The energy spent on self-recrimination could have been channeled into growth and making the most of the time they have left.
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15. They regret comparing themselves to other people.
The social media age exacerbates this, sadly, but even without it, that nagging voice comparing their accomplishments to their peers runs deep. By mid-life, many men realize it’s a pointless and exhausting game. Regret sets in over wasting time looking sideways instead of focusing on their own path and celebrating their unique journey.
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16. They wish they’d appreciated the good moments more while they were happening.
The 40s bring a bittersweet awareness of how quickly time flies. They regret the times they rushed through happy occasions, stressed about the next thing, or let negativity overshadow the present. They wish they knew then, as they know now, to savor the simple joys, being fully present in moments of love and laughter because those moments are fleeting.
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