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Life's Journey: Should Have, Could Have, Would Have

Updated on June 10, 2014
Have you climbed the highest mountain?
Have you climbed the highest mountain? | Source

How many times have you heard yourself say it? “I should have done that”. “If only I could have been there”. “I would have but…”. You can fill in the blank with whatever excuse you used. We’ve all done it.

The truth is, the past is the past and we can’t change it. We’re wasting our time living with the “should have, could have, would have” syndrome. So how do we move forward without regret?

“Sometimes in your life you will go on a journey. It will be the longest journey you have ever taken. It is the journey to find yourself.” ― Katherine Sharp

Meet my friend Bill, the inspiration for this article.

My friend Bill Holland (aka Billy Buc) published an article that started my wheels spinning. He’s a terrific writer and always writes thought-provoking articles that make me re-examine my past and contemplate my future. Bill and I are baby boomers, born in the same decade on opposite sides of the country. Our journey through life has been similar in some ways and vastly different in others. The foundation of our friendship is built on our mutual desire to leave this world better than we found it and our love of writing.

Bill is a much better writer than I am. He was an experienced writer long before I ever thought of writing. When I stumbled on a web site called Hubpages a couple of years ago, Bill was the first to welcome me to the community and to help me navigate the site. Without his encouragement and guidance, I doubt I would have lasted more than a few months. I’ve learned a lot about writing from Bill since we became friends, but sometimes I think I’ve learned more about life from him than writing.

To read Bill’s article that was the catalyst for this article, click on the link above. It will open in a new window for you..

A summary of my life

After reading Bill’s article about never feeling quite good enough, I started thinking about my own life. As a child born in the 50’s, I was blessed to have parents with strong moral values and a commitment to raising their children to be caring, responsible adults. As a teenager, I rebelled against everything they tried to instill in me. I hung with the wrong crowd and made some bad choices, but I was lucky. None of my bad choices had any real serious consequences.

As a young woman, I fell in love easily and married young. It was a short marriage for one reason only. I was too darn young and I should have waited a few years. For the next ten years, I worked hard and played hard too. I was single, stubborn, and foolish enough to think life was all about having fun.

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My plans for a college education were traded for a paycheck. I had stumbled into a good job right out of high school and once I started making money, I had no interest in going in debt for an education. If given a chance to do it over, I would have made a different decision.

Time passed and in my late twenties, love struck again and I married for the second time. Like my first husband, this one was a good man. We both had good jobs, a strong foundation, and we enjoyed many of the same things. Life was good, for a while. Without going into all the details, I’ll just say that things changed. Alcohol destroyed our relationship and, my trust. The time came when I chose not to live with the unpredictability of life with an alcoholic. Sure, I could have stayed. I could have kept my mouth shut. I could have, but I didn’t.

Bill inspired me to look at myself.

Bill’s article talked about his feeling of never being good enough; having never won the highest award or not having climbed the highest mountain. He offered that he wasn’t telling his stories from a place of ego and I know that to be true. Bill, was simply using his gift of teaching and once again, I was his student. I began thinking about my own accomplishments or lack of. I asked myself what the regrets were in my life. This is the short list of my “should have, could have, would haves”.

  • I should have joined the service.
  • I should have gone to college.
  • I should have pursued a career instead of a job.
  • I could have had children.
  • I could have been more responsible.
  • I could have learned more and given more to others.
  • I would have made better choices about relationships.
  • I would have saved more money.
  • I would have traveled more.

These are pretty generic but I think they offer enough for you to understand the thoughts that followed. As I look at my list, I found myself thinking how different my life might have been if any one of my “should have, could have, would haves” had been different. Even a slight detour in any one of them would have changed the direction of my life. My life experience would have been very different if, for example, I had joined the service. That decision would have exposed me to strict discipline and travel. I would have met different people and learned new skills. Perhaps I would have settled in another state, missed those special moments with my family, or become more attached to money than core values. I would be a different person, wouldn’t I?

Bill's gift

When Bill shared his own feelings of inadequacy and missed opportunities, he gave me the chance to examine my own journey. I was reminded of my choices. As I was contemplating what I might change if given the chance and the answer was clear. I would change nothing. Although far from perfect, the result of my life experience is that I am content. I like where I am now.

It may have as much to do with age as it does wisdom, but my journey so far with no kids, two marriages, a modest income, and a loving family and circle of friends has been good, I am satisfied with my life. Oh sure, I still have goals and things I want to do, but if I never get there or do them, I won’t spend a minute in that rut of “should have, could have, would have:. Instead, I’ll trade them for “maybe I will or “I might”. Then, if I don’t, there will be no regret. I am where I am supposed to be and, I am who I am because of my failings and because I didn’t climb the highest mountain. I can wonder what I missed, but I will always, always, be grateful for what I've earned and learned by climbing the smaller one.

Thanks Bill!

“Sometimes a "mistake" can end up being the best decision you ever make.” - Mandy Hale


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