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Midlife Regret: Coulda, Woulda, Shoulda

January 01, 2012   •   By Master Hobbit

Posted under: Mind, Relationships


Midlife Regret: Coulda, Woulda, Shoulda

It appears that many midlife men live under a cloud of regret. I’ve never really framed my life decisions in terms of regret or its opposite, whatever that is. 


Google indicates that the opposite includes such words as contentment, satisfaction, and applause. Regret is defined as a “feeling of sadness, repentance, or disappointment over something”.


I’m not even sure why I would spend much time regretting a decision I did or didn’t make in the past. And that is not to say I didn’t make plenty of poor decisions.  And it doesn’t mean that when I look at different aspects of my life that I can’t see other ways I could or even should have done something.


For example, I can look at my failed marriage and see key areas where I could have done things much differently, if it weren’t for the fact that I was such a bonehead at the time. Or, I can look back and see that how we chose to raise our kids was not in all ways the best. But, the fact is that I was pretty bullheaded and couldn’t see that at the time. I could go on.


I was who I was. And I did what I thought was right and best for all concerned at the time. I was unable to be a different kind of man at those moments of decision.


I first began to notice this as I engaged my parents over the years since I’d left home. I can say that my parents made some choices with raising us kids that were just not the best.


Don’t let your imagination run wild here, my parents were good people.  And they certainly did the best they knew how. But, like most of us, they were bound by their own history, experience and context. Call it handicapped, if you will.


But as I interacted with my parents over the years and observed their lives, I found that I saw them more and more with eyes of understanding, and of grace.


I can still see my younger self in his context, making his decisions, and charging through life. I have to chuckle as I watch him in my memory and hear his words and recall his rationale for his choices. He was so zealous and driven, often about the wrong things.


It seems we have a tendency to examine past events using today’s eyes, and at times, to cast rather harsh judgment on the actors and their decisions. It seems to me that this is the basis for feeling regret about our own choices. Starting sentences off with “If I had only been more…” or “I wish I hadn’t been so …” are looking back into situations with eyes you simply did not possess at the time the choices were made. And how can such a process be helpful?


The point of all this is that it does little good to bemoan yesterday. Like the ‘60s song by Chad and Jeremy, “that was yesterday and yesterday's gone”.


The man I am today was not present yesterday. I might regret that he wasn’t, but the fact remains – I wasn’t there. 

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About the Author: Master Hobbit

Master Hobbit is the creator of 4060men. After a marriage of over 30 years ended in divorce, he journeyed for over 5 years as a single midlife man. He remarried in 2012. He is also the owner of the blog platform,, and a blog platform review site,

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