Your Mistakes Make a Man of You


“There was a long hard time when I kept far from me the remembrance of what I had thrown away when I was quite ignorant of its worth.” ― Charles Dickens, Great Expectations

She was the best. In every way, the best. She made you cry with laughter or laugh through the tears. She kissed you like she meant it. They were the best of times, even during the worst of times. And who could forget the sex? Mind blowing. Porn has nothing on what you had with that girl. Later in life, it’s often the one that got away that occupies our minds before we shuffle off this mortal coil.

We all leave this earth some day. Many of us try to put that thought to the back of our minds so we can focus on the mundane necessity of dragging ourselves out of bed at 6.45am to get ready for work. Sooner or later, we have to face up to our mortality and it’s often with the death of a loved one, or perhaps in the a case when one receives word that they are terminally ill. Every person deals with this in their own unique way; yet there is huge commonality in how humans handle this process. Denial (this isn’t happening), fear (I’m scared shitless), anger (why me? why now?), remorse (on the mistakes you made in your life), denial again (no, seriously, this isn’t happening to me), finally giving rise to acceptance (ok, this IS happening. Nothing I can do now).


In her book, ‘The Top Five Regrets of the Dying’, Aussie palliative nurse Bonnie Ware posits that the single deepest regret facing dying men is that they spent too much of their time focused on their career and not enough time focused on the people in their life. It’s often said that we work to live but the truth is many of us live to work. Putting in that overtime to try rise the working ladder often comes at the expense of being sat on a sofa with a loved one. Working through lunch to finish that important task often comes at the expense of calling your mother to check in on her. And perhaps, simply to tell her you love her. Friends drift away with the passage of time and we are left with a handful of regrets that we didn’t live life to the fullest.

When the end gets very close, when your breathing slows down, your final fleeting thoughts may turn to just how you let life slip by and was all that work truly worth the consequences. Regrets are a funny thing because often it’s what we failed to do that really cuts to the bone, whereas the things we did (and messed up) are easier to internally forgive – at least we tried. Better to shoot for the stars and miss than not shoot at all.

Some recent research suggested the typical man makes half a dozen disastrous decisions during his lifetime, six ‘I truly am an idiot’ moments that often lead to years of trying to right the wrong and make things good again. These decisions give rise not merely to transient regret but to deep reflective remorse in our dying days.

Most reading this will think “only six? Jesus, I could count six since breakfast, never-mind during my lifetime”.

Therein lies the distinction between a mistake and a MISTAKE. The former is trusting a friend with a loan of 20 bucks only to be stiffed on it. The latter is cheating on the love of your life because, well,…’why the fuck did I do that again?’. It’s those life-altering bad decisions, those ‘Sliding Doors’ moments, that often leave dark clouds hovering over us. Clouds that never seem to drift away.

The bad decisions that leave lasting remorse are not the type associated with embarrassment. We’re not discussing that time you tried to bed your married boss at your Christmas Work Party nor are we talking about the time you brought up your friend’s sexual past while delivering a Best Man speech at HIS wedding. No, they are deeply mortifying but hugely trivial in the bigger picture. The epic-bad decisions are the ones that change the flow of the river of your life from a calm straight line to twisting white-water-rapids. The type of decisions you enter into your own personal ‘I’m a complete moron’ Hall-of-Fame.

Most of these big decisions, and mistakes, revolve around women. Sure, picking one job over another is important. The cocaine you sniffed endlessly one summer is important. That time you decided to move to the suburbs instead of maintaining city life is important. Ultimately though the decisions we reflect upon the most revolve around women. Your childhood sweetheart who dumped you for cheating on her. Your first fiancee you thought was the one only to discover she was having an affair with your best friend. It’s the decisions we make with women that truly leave lasting feelings.

Later in life it all seems so simple. Hindsight is described as 20-20 yet often hindsight is three-dimensional and in technicolor. Your mistakes become all too obvious through a prism of hindsight. Of course she was cheating on me! Did I really believe she was out shopping with her friend four days a week? Why did I choose to skip so many classes in school, would it have killed me to suck it up? Why did I marry HER? I never loved her, not truly. Why, oh why, did I agree to move with her to the suburbs and lose a part of my soul, I’m a city type-of-guy?

This truly separates regret and remorse, even if sometimes they are the other side of the same coin. Never ticking off that bucket-list holiday of visiting the Caribbean will pale into insignificance compared to that train-wreck marriage that ended so nastily. Promising to read more books but exiting this life having read a handful of sporting autobiographies won’t hurt half as much as flunking high school because you couldn’t be bothered. Never driving your dream car will seem a complete irrelevance compared to getting blind drunk and cheating on your true love.


That’s when the paradoxes start to appear. Most of our bad decisions seem like damn good ones at the time we made them. School sucked, you literally could not face another science lesson. That night out with the guys that led to being busted for cheating on your true love, was a damn good night. Man, that was one for the books. Marrying your first wife seemed like a no-brainer, boy could she cook and, hey, the sex was pretty good for a while. It’s really amazing how you can convince yourself that you are happy in the moment.

Then again, hindsight when faced with mortality becomes crystal clear and reflection becomes a lot easier. Of course flunking school was terrible, you struggled for years in dead-end jobs before finding something you enjoyed. You should have stayed home with your sweetheart instead of getting hammered and ending up doing a walk-of-shame from a random girls apartment the next morning. Straight up, that first marriage had alarm bells ringing from day one and no amount of gourmet cooking ever actually equaled happiness.

If you’re a couple of years from hitting 30, look away now.

28 is around the age where men usually make their worst calls. It’s normally when we start to make the biggest of decisions – whether it’s marriage, quitting a job to take another job, moving from city to suburb or vice versa, waking up beside a woman who is not your wife or partner, cocaine going inside your body as opposed to something like a productive vitamin. Close to thirty seems to be the age we make our biggest moves, on average. However, truly mind-numbingly bad decisions are not the sole property of the young.

Mick Jagger is 73 years old. He’s rich, he’s a rockstar and has a 29-year-old partner most of us wouldn’t have a hope of hooking up with. He’s doing something right. He also has a new baby called Deveraux Octavian Basil Jagger. Now that’s a name. When little Dev’ is 18, the chances are a 91-year-old Jagger won’t be able to perform any jumping jacks – flash or not. The wisdom of having a child you’ll never see grow into a man is questionable and perhaps a sign that even the old can make pretty bad decisions. Most of us would prefer to be around to see our child grow up (and grow old) but you can’t always get what you want.

How many of us would do things differently in his shoes? Hot chick in her 20’s, working body parts to allow you to have sex often? We’d probably all do the same thing. Which more or less goes to show that stupid, life-altering decisions are made at all ages by all men.

The real question is would we have made our many good decisions in life if we hadn’t have made our bad ones first? It’s really a question straight out of The Matrix, does the vase fall if she doesn’t mention it first? The likelihood is that making our terrible decisions often leads to making our best decisions.

That first wife you married and divorced acrimoniously? You’d never have met your 2nd wife without that decision. Skipping school and working a dead-beat job for most of your early 20’s? It did eventually lead to a career you loved and worked for 35 years. Cheating on your childhood sweetheart after a night of heavy drinking? It did force you to look at your drinking and change your habits.

We all walk our own paths yet it’s stunning how many men walk similar paths. At some point in your life, you will probably walk out on a woman who deserved you and end up loving a woman who didn’t. You will probably quit a job, trudging out of the office one final time vowing that you’ll show them; when in reality staying and showing your worth was the right call to make. Those years of heavy drinking, nights out and parties were so good but caused so many terrible decisions, not to mention hangovers. Maybe you loved too easily or were too hesitant in loving at all.

Whatever the case may be, the only way you learned from all of this was by living through it.

You might be reading this thinking ‘Hold up, I’ve never been married, I don’t drink and I’ve definitely never cheated’. The most common mistakes men make are not applicable to all and your own mess-ups might be diametrically different. One thing is for sure – whatever you come to regret on your deathbed, there’s a strong likelihood it’ll involve a woman or sex. Perhaps both.

Can we actually attain a happy ending without going through these litany of mistakes? For some, sure. But if you’re like the rest of us, then no. It’s through our complete fuck-ups that we learn. We find our dream job after working a bunch of jobs that frankly sucked the life out of us. We find our dream woman after trial-and-error, break-up and regret. We find our happy home after living in a bunch of dumps and bad areas.

Irish superstar Mixed Martial Artist Conor McGregor has a coach by the name of John Kavanagh. He wrote a fantastic book called ‘Win or Learn’. The premise of the book, in general, is that it is through mistakes, poor decisions and, ultimately, losses that actual growth occurs. It’s only through losing that adjustments, corrections and improvements can be made. Losing your childhood sweetheart or your first marriage going badly awry or making the wrong call on a career path are all painful processes. They all sting and sometimes for a long time. And then you move on. It’s through mistakes that we learn and grow.

The biggest mistake of all our lives is the mistake we never learned from and constantly repeated. That, in itself, is regret in its truest form.

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