9 Life Decisions Men Regret Most After 40

January 28, 2026

I’ll be 37 this year, closer to 40 than I am 30. For many men, their 40s are when the consequences of earlier choices start to show up… physically, emotionally, and financially. The distractions of youth fade, and what’s left is a clearer view of what really mattered. Some regrets are loud and obvious; others are quiet and persistent. Here are nine life decisions men commonly regret after 40, and how to course-correct before it’s too late.

1. Ignoring Their Health in Their 20s and 30s

Many men treat their bodies like machines in their younger years by pushing through pain, skipping checkups, and living off caffeine and convenience food. But by 40, the wear and tear starts to show. Old injuries ache, energy dips, and preventable issues become chronic. The regret isn’t just about appearance. It’s about mobility, longevity, and quality of life. Prioritizing health earlier could have saved years of discomfort and thousands in medical bills.

2. Letting Friendships Fade

Life gets busy. Careers, kids, and responsibilities take over. But many men realize too late that they’ve let meaningful friendships slip away. After 40, it becomes harder to build deep connections from scratch. Loneliness creeps in, even if life looks full on the outside. You’ll regret not making the effort to keep your friendships.

3. Staying in the Wrong Career Too Long

Climbing the wrong ladder faster doesn’t make it the right one. Some men spend decades in careers that drain them, only to realize they stayed out of fear, comfort, or obligation. By 40, the golden handcuffs feel tighter, and change feels riskier. But the regret of not trying often outweighs the fear of failing. Passion doesn’t always pay more, but it pays differently.

4. Not Investing Early Enough

Compound interest is a powerful thing, but only if you start early. Many men regret not taking saving and investing seriously in their 20s and 30s. By 40, the missed opportunity becomes painfully clear, especially when retirement feels closer than expected. Even small, consistent investments could have made a big difference.

5. Avoiding Emotional Vulnerability

Bottling things up might feel strong in the moment, but it builds walls that are hard to tear down later. Men often regret not opening up to partners, friends, or even themselves. Emotional suppression can lead to strained relationships, missed intimacy, and mental health struggles. After 40, many men wish they’d learned that sooner.

6. Prioritizing Work Over Family

The hustle is glorified, but the cost is often hidden. Many men look back and realize they missed too many dinners, games, and quiet moments chasing promotions or paychecks. Kids grow up fast, and relationships don’t maintain themselves. Time is the one thing you can’t earn back.

7. Not Taking More Risks

Playing it safe feels smart until you realize how much you missed. Whether it’s travel, starting a business, or saying how you really feel, many men regret the chances they didn’t take. Fear of failure often wins in youth, but after 40, the fear of regret takes over. Risks don’t always pay off, but they always teach. The biggest regret is often not trying at all.

8. Letting Their Identity Be Defined by Others

Trying to meet everyone else’s expectations (parents, partners, society) can leave men feeling like strangers to themselves. After 40, many realize they’ve been living someone else’s version of success. Authenticity takes courage, but it also brings clarity. Living on autopilot is easy until it’s not.

9. Not Learning to Say “No”

People-pleasing feels noble, but it often leads to burnout and resentment. Many men regret the years spent saying “yes” to things that didn’t serve them, like extra work, toxic relationships, and unnecessary obligations. Learning to say “no” is a skill that protects your time, energy, and values. After 40, boundaries become essential, not optional. And many men regret not being honest and just saying “no.”

Regret Is Not a Life Sentence

These regrets aren’t meant to shame. They’re meant to shine a light. Every man has made life decisions he’d do differently with hindsight. But the beauty of midlife is that there’s still time to pivot, repair, and grow. Regret can be a teacher if you let it guide you, not define you. The second half of life can be your best chapter if you write it on purpose.

Which of these life decisions hit home for you, or what would you add to the list? Share your thoughts in the comments.