Coulda, Woulda, Shoulda

Often times, what I enjoy most about travelling are the people I meet along the way


And every once in a great while, when the stars align just so, I’m fortunate enough to cross paths with someone who is truly remarkable and ends up changing my very view of life itself! These chance occurrences are rare indeed, so when one does present itself, I make sure to take in all I can and listen intently to what is being said.

What follows is one such meeting I had with one of these special people, a 91 year-old man named Tom.


I met Tom while visiting Citrus Park, Florida a few years back. He was seated on a bench surrounded by an assortment of his WWII buddies, each proudly displaying blue baseball hats with “WWII Veteran” emblazoned in bright yellow letters across the front.

I struck up a conversation with these gentlemen, who were more than happy to speak with me. One of these veterans was Tom who, during his youth, had parachuted from airplanes behind enemy lines during the second Great War. At 91, Tom was full of wisdom and good charm and was an absolute pleasure to talk with.

After a while, Tom and I broke away from the others and we engaged in a conversation about life that changed a lot of how I view things today.


I asked Tom when he looked back over his long and storied life, did he have any regrets. He said for the most part no, he didn’t. But when we continued talking it became apparent to me that he did, especially when he started talking to me about his deceased wife, whom he loved dearly.

He admitted to me, “I do wish with all my heart that I had spent more time with my wife. I was so busy all the damn time trying to make money, and it was at jobs that I didn’t much like. I guess I always thought that there would be time for us later, after I earned enough.” I noticed the change wash over him as he continued with the story. The smile ran away from his face and his head tilted slightly, the way one tilts their head when they are looking upon a long ago memory.

“You know,” he said, “If I had it to do all over again, I would chase my dreams with the fury of a Texas tornado. I’d go after them with everything I had. And if they never came to be, that would be alright, at least I would have given it my best shot, and there wouldn’t ever be that feeling of wondering if I could, I would know.”

Momentarily lost in thought, Tom again stared out to a time long past just as the late afternoon sunlight illuminated his face with a warm golden hue, showing the etchings of nine decades worth of living.

Then he continued, “I would have lived my life the way I wanted to live it, and not have someone else dictate it for me, so they can realize their dreams. I guess what I’m trying to say is, I would have tried harder to make a living doing what I had a passion for instead of working at jobs that only meant a paycheck. So many years were wasted while my wife and I were in the prime of our lives, so many years wasted drumming away mindlessly at work I found uninteresting and monotonous.”

He turned to me and looked me straight in the eyes with a seriousness that was palpable and said, “If you don’t have a passion for the work you do day in and day out, if you wouldn’t do it for free, I say run and run quickly! Get the heck out of there and get to doing something you know feels right in here,” he said tapping his chest.

He continued with, “If I could do it all over again, I would have loved more and criticized less. I would have helped more people in their time of need, instead of being so worried about my needs. And I would have built more things, things that would be here long after I’m gone. These things don’t have to be physical structures; what I’m talking about is a legacy, something to be proud of, and something that loved ones can be proud of too. Your goal in life shouldn’t be to live forever, your goal should be to create something that will.”

This conversation with Tom, the WWII vet, had profoundly changed me; I could sense the difference inside. It was a fascinating feeling. I knew that I had just been taught a very valuable lesson, one I’d never forget.

I thanked Tom for his time and for the wonderful advice, wishing our talk wasn’t over yet. His face lit up immediately and the smile I was used to seeing was back on his face. He vigorously shook my hand and as he did he bestowed one more shiny jewel of wisdom onto me – he said, “JP, if there is something you really want in this life, something you think about at night in bed before falling off to sleep, then son, chase it like your pants were on fire! Because before you know it, you’ll be an old man like me who can only look back and say – I shoulda, coulda, woulda…”

Tom has since passed away, but his lesson that day lives on in me, and I can only hope it will live on in you too.

Remember, right now is tomorrow’s past. Rather than sow the seeds of a future regret, why not sow the seeds of a budding legacy?

A Few Tips I Took Away from our Conversation:

  1. Choose to be happy, because happiness isn’t something you find, it’s a choice.
  1. Don’t let others dictate how your life unfolds.
  1. Don’t work your life away.
  1. Don’t look at past mistakes as failures, analyze the mistake and learn something from it.


JP Twitter Pic2Hi my name is JP Chartier and I write for Gutter Pup where you can expect to read well-written and entertaining articles about the people and places that often get overlooked at many popular vacation destinations around the world.


  1. Nice description you shared. Such a great experience to talk someone while your travelling.
    Thanks for sharing it.

  2. This is a amazing story.. Congrats! Awesome article and post. Thanks for sharing it.

  3. This is a touching tale. It is truly inspiring to talk with a WWII vet, JP.
    Agness of eTramping recently posted…Into the Unknown: Preparing for the Trip of a Lifetime to North KoreaMy Profile

  4. wow, this is one of my best articles I will ever read online about starting a travel blog, I start implementing this great tips to my blog, this article really helps, thanks for this amazing write-up.

  5. What a terrific story. It’s these unique meetings that make a trip so memorable. I once met a man who was one of the carvers on Lincoln’s face on Mount Rushmore — easily one of the highlights of my trip to South Dakota.
    Stephen Garone recently posted…Christmas at Steigenberger Metropolitan Hotel in Frankfurt, GermanyMy Profile

  6. What a beautiful post. Just goes to show that most times we are chasing after things that we think would make like all that much better but its really about the people around us. Spending time with loved ones. You cant put a price on that and we are not guaranteed that time. So we need to make that more of a priority as hard as that may be.
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  7. This is so awesome. I just love hearing these veterans stories of how they look back at the war and their life afterwards. My grandfather recently passéd away, he was in WWII, and his attitude towards every ethnicity was just amazing. He had such compassion and not one bit of hate or resentment, even after living through such hell. I am glad you made time for this man and hats off to you.
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  8. Great tips you got out of a wonderful conversation!
    Though I find the first one a little hard. I hope to believe happiness is a choice, but I feel I am also in a luxury position being able to say that. I can imagine some situations that make the choice for happiness so , so hard 🙂
    I always tell myself to not let my life be determined by fear. Which works for me 😉 Every time I am not willing to do something I ask myself: is this because I am afraid? If the answer is yes, I still do it. And don’t regret!

  9. Fantastic! Lessons learned from a man who’s lived a full life! There is no better insight in to looking back and reflecting on what might have been.
    We can all learn something from Tom and from this interesting piece!

  10. Truly amazing story thank you very much for sharing. I agree whole heartedly with it and have spoken myself passionately about the idea that we chase jobs and money because we think we have to. We shelve our passions for someone else’s profit because everyone else does. Screw that! Go for what you really want, be broke but happy, full of time and experiences!
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  11. What a fascinating and capturing story. It´s one thing we enjoy a lot too when traveling. Meeting fascinating people and their stories.
    “Choose to be happy, because happiness isn’t something you find, it’s a choice.” — How true!
    Christina recently posted…HotRod CityTour in ViennaMy Profile

  12. Tom actually sounds a lot like my grandfather. They’ve both lived through some crazy times, have a bit of humility, a little bit of resentment, and lots of wisdom.
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  13. Beautiful description of what sounds like a beautiful experience, JP. Isn’t it funny how the places fade into memory but the people we meet stay with us forever?
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  14. “If I could do it all over again, I would have loved more and criticized less”…what better advice could there possibly be. Love stories like this and meeting people along the way.
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  15. Your story is inspiring, I must say. It would be a great if I could ever meet someone as wise and as old to tell me that life goes forward, and therefore there’s just no chance for me to go back. I’m in my sophomore year now and I’ve been looking for degrees that I’m most passionate about, and it really isn’t easy going against your parent’s wish. But just like what Tom said, I can’t let someone else dictate my life. This is a really great story, thank you for sharing!
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  16. It’s really true that many times the people you meet traveling are actually more interesting than the place you visit. It sounds like a cliché, but it’s really true. A great story this one, thanks for sharing!
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  17. I love the random people you meet when travelling! It can really make a trip sometimes. Great post.
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  18. It’s nice to meet people that have interesting stories to tell when we travel. I certainly enjoy it a lot, and I have enjoyed your story!
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  19. Hahah great story! The people you meet on the road are the best. I just made so many good friends when backpacking in Iran lately. What an experience!!

    • Hey Clemens, I bet that was a hell of an experience to backpack through Iran! I hear the folks there are very friendly to foreigners, it seems they get a bad wrap.

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