The older we get, the more we look back at our lives and wonder if we made the right decisions. We think about the road not traveled. Most people look at their pasts and are pretty satisfied. We feel fairly confident in our choices and like where we ended up. But it’s not all roses and sunshine. We have all asked ourselves “what if” at one time or another and have let our minds drift to the possibilities that these decisions could have led to. That’s a normal human emotion to getting older and reflecting on life. But there are some choices that haunt us more than others. We look back and really regret the choice made or the path not taken. These regrets shape and color our lives and our perceptions from that point on. They are big turning points that help create the person we become, but we may regret the decisions. I’m going to take us down the road of some of the biggest regrets men face in their lives. We’re going to visit the top fifteen regrets that men say they have experienced in their lives and still live with. We’re going down the long, winding path of “what if” and “why didn’t I?” as we look at the things men regret most.

15. Losing touch with friends – Life takes over

We all try and stay in touch with friends. We vow to keep up our friendships and not lose track after high school and college. But, then life happens. Work, family and daily life fill up your days and we lose touch. We meet up for lunches and coffee if we can, but the closeness disappears. Many men as they get older look back at the relationships they had and regret not making more of an effort. They regret not taking the time to build and maintain the friendships that meant so much at a younger age. Many men, when asked what they would do differently, agree that they would definitely try harder to work on their friendships.

14. Being more open emotionally – showing the softer side

We all know the image of the typical man. Quiet, unemotional and logical…these were the traits that were considered ideal for years. Men were expected to be more stoic and reserved. They were considered weak by society if they showed too much emotion. Luckily, this outlook is very outdated and not as prevalent any more. But men who were raised with this upbringing are now facing the regret of not learning how to share themselves more. They may have withheld affection from people for fear of being judged. Many of these men look back on their lives and wish they had been more open. They feel that their relationships may have been stronger and deeper for it. Luckily, we’re finally teaching men that it is okay to feel and to share those feelings.

13. Not spending time with loved ones – Waiting too long

This reserved attitude goes hand in hand with this next regret. As we get older and we start losing loved ones, we realize that we will always regret not spending more time with them before they passed. Men definitely notice that they regret not spending time with parents and grandparents. The loss of our connection to family history and stories when these loved ones are lost is very obvious. Many men remark that they regret not taking advantage of that time before these special connections are gone. They live with the regret of time lost. They often wish that they would have taken advantage of those last days.

12. Missed career opportunities – hindsight is 20/20

We all look back on our lives and see the doors we should have opened. We can see these missed chances so clearly in hindsight that we don’t understand how we missed them. Men are more likely to regret missed career opportunities. They will look back and wonder if they could have gone further, made more money or achieved even more promotions if they had taken the chances and looked for the opportunities when they presented themselves. When men don’t make the career goals they set for themselves, they may feel unsuccessful and unhappy. These missed chances become a major source of regret when they evaluate their lives.

11. Being a workaholic – why am I sleeping at my desk?

We have seen that men historically tend to be bigger workaholics than women in a lot of cases. This probably stems from the desire to be the breadwinner or the main provider for the household. In earlier decades, it was expected for men to go out and earn the money and for women to stay home and take care of the home and family. With the entrance of women in the workplace and a huge rise in the cost of living, the days of single income households where everyone is home by five are gone. Most households consist of two incomes and often have at least one person working overtime to make ends meet. The pressure to advance and build a career can create a situation where men spend more time working than they do at home. As they get older, many men look back at the many hours they spent away from home and all the things they missed. They find themselves truly regretting being so focused on work.

10. Staying in a job or career that you hate  – get me out of here!

Although men may regret not pursuing all the options they have in their careers, this is not the only regret that they have. There are many men that work for decades to care for their families and maintain the life that they have built. But they hate their jobs. Men and women both have regrets when they stay with a job they hate. Most do it out of fear or uncertainty regarding the loss of an income. But many older men admit that if they could go back, they would leave that job and look for something that was much more fulfilling. They would tell their younger selves that the income isn’t reason enough to stay in a job they hate. We could all use the advice to follow your passion and don’t end up looking back on work with regret.

9. Not taking risks – always on the sidelines

This is a regret that covers so much. We all look back on our lives and see things we wanted to do but were too afraid to try. Be it a career change, a new hobby or a relationship, we look at the dream and just can’t take the leap. We’ll see that bright and beautiful desire but we stand back and let it pass us by. As they get older and spend time looking back, men often find themselves regretting playing it too safe in life. They may pass up a promotion or decline a trip that takes them out of their comfort zone. They know that these chances could lead to incredible things, but the fear of failure gets too strong. We’re all going to have those times in our lives when we just don’t take the chance. We can only hope we don’t have too many. Don’t be the man that has more “What ifs” than “look what I did” when you recall your life.

8. Not traveling when you get a chance – missing the train

We all have dreams of traveling and seeing the world. We want to see places that expand our horizons and let us meet new people. But as we get older, we find reasons not to do it. We get out of high school, go to college, start working and building a family. This is what society says we’re supposed to do. But we never stop to wonder if we’re shortchanging ourselves. We should take the time to really enjoy what the world has to offer. Men are conditioned from a young age to go to college, get a job, build a career and take care of their families. The pressure to be what society considers a success is unbelievable. But this doesn’t allow time for men to mature and experience the world before settling down. It’s no wonder that many regrets center around not experiencing things. Men often look back and wished they had seen more of the world before they settled down. They regret not taking that little time of freedom to truly figure out who they are.

7. Marrying too young – I do, don’t I?

When we get married, we all hope for the proverbial “forever”. We don’t enter a lifelong commitment with the intention of leaving it. But there are times when it just doesn’t work. One of the most common things men mention when talking about regret is marrying too young. This goes hand in hand with the whole societal view of what a successful man does. We all know the stories of high school sweethearts graduating, marrying and settling down with their children. Unfortunately, these aren’t common happy endings anymore. We are seeing more marriages come apart at the seams simply because the two people who got married are not compatible. This can really happen when you marry too young. Many men who married right after high school admit that they regret it and wish they had chosen something different.

6. Staying in a broken relationship – hanging on too long

Although many men who realize they are no longer happy will divorce, there are many that try for way too long to make it work. I’m not an advocate of giving up on marriage just because it gets tough, but there comes a time when you have to admit when it’s over. When both people are miserable and all attempts have been made to change it, it’s time to separate. Many men who have been divorced admit they stayed longer than they should have. They may have been determined to fix it, or they may have stayed for the kids, but they stayed. This is a major relationship regret men admit to.

5. The one who got away – she’s always a dream

Men often look back on their lives and remember all the things they did. The relationships, the parties, the friendships all make us who we are. We all have those memories that stick with us. But we also have the memories of the ones that go away. The friendships we lost, the things we didn’t do and the people we never dated. Many men look back and wonder about those missed chances. They remember that one woman that they either let go or never asked out. The woman that sticks in their mind as the prize they never achieved. This is one of the most common and biggest regrets that men mention.

4. Partying too much – where did I leave my pants?

Teenagers and young adults often spend a lot of time partying. It’s almost a rite of passage to spend time hanging out with friends, drinking and going wild. We go through phases as we mature and head out into the world as responsible adults. This behavior is understandable and to be expected to a certain amount. But there are some that carry it too far and the destructive behavior goes into adulthood. Many men, although they straightened themselves out and went on to have a successful life, look back at the decisions they made and the destructive behavior they engaged in and realize how much different things could be. The childish and dangerous decisions are looked back on with a lot of regret. 

3. Not taking school seriously – Do I really need Trig?

Along with the poor decisions that we make as young adults, our decisions regarding school are not always the most responsible. It amazes me that we are expected to make a decision about what we want to study and ultimately build a career around at such a young age. We spend thirteen years in school and then head straight to college. It’s no wonder that many students don’t take the first few years of college seriously. We blow off classes, don’t study hard enough or just take classes we don’t need. Many men look at their college years and regret not taking college seriously enough. They regret wasting those years and the money it cost.

2. Ignoring their health – paying attention to the signals

We all have those aches and pains that appear as we get older. We don’t want to become the worrier that runs to the doctor for every sniffle or cough. As we get older, we try to watch what we eat, maintain our weight and get a good amount of sleep. We know that taking care of ourselves is necessary. But many of us put off going to the doctor. We don’t get the check ups we need and we procrastinate. Men may suffer in silence and not acknowledge when they aren’t feeling well. It could stem from the “strong, silent type” impression society seems to want or it may be a fear of something really being wrong. But men often look back and wish they had paid more attention to their health and dealt with issues that came up before they got bad. They often regret ignoring something that should be taken seriously.

1. Worrying too much – Just let it go

For all the stress and anxiety that life can throw at us, it’s hard not to worry. Adulthood brings on an enormous spectrum of things to worry about from finances and relationships to careers and retirement. Life provides plenty of stress without us adding to it. Many of us struggle to learn how to reduce stress and manage it. We have to figure out how to relax and take things in stride. Men and women both feel the physical effects of stress and suffer from health conditions made worse by it. Men look back on their lives and regret not relaxing more and worrying about things that didn’t need to be worried about. They find themselves constantly worrying and stressing to a point where they can’t even enjoy anything. As they get older, they wish they had taken time to just relax and enjoy what they have worked for.

We all try and live our lives to the fullest and enjoy every experience that comes to us. We want to make sure that we can honestly say that we never hesitated to try new things. But we will all have regrets of things we did or didn’t do. We can only hope they are outweighed by the positive things that we did and learned.