What is Your Biggest Regret?

Each month, we upload a new writing prompt on our sidebar, encouraging people to write in on the topic. July’s writing prompt is REGRET.

Do you think there are benefits to having regrets, or do you think we should leave those feelings in the past? What is your biggest regret and why? How has your regret(s) changed your or shaped your life? 

Here’s how our staff answered…

I hate the word regret. Something about it just doesn’t roll smoothly off of the tongue. My philosophy for life has always been to live a life without regrets, which is not as impossible as it sounds. I think that we all make decisions that we aren’t proud of. We all have, at one point or another, woken up the next day and thought “Man, that hair color was a horrible idea” or “What did I do last night (and where are my clothes)” or “White Russians and Margaritas do not mix”, but rather than carry around regret I try and make the most of whatever situation my original poor decision landed me in. My hair turned out a bit more colorful than I originally intended, but it makes my chin look sharper and more attractive. I can’t remember all the details of the night before and I am pretty sure I vomited in a bath tub…oh well, I will know not to do that again, or at least what the consequences will be. I believe we only get this one life. Why waste it on feeling regret for every bad decision? We cannot hope to ever control or even know all the consequences of our actions.  – Jessie

Every day I think am I doing the things right now and living the way I wish to be so that my tomorrows are happy? I’m a perfectionist, so every decision is thought through to the extreme. In short, the idea of having a regret worries me so I plan as much as I can. Some would say to loosen up and not worry so much about decisions, but that’s easier said than done. I think of it like this: If our lives are roads, I want to take the scenic route, even if it means it has a few potholes and comes to a detour. It’s the dead ends I’m trying to avoid. For the most part, we can plan that route for ourselves, so I do to the extent that I can. A piece of me always wonders in a daydreaming sort of way how my life would be if I took a different turn in various spots: choosing a different college, choosing a different major, taking a different job, etc. How can you not when the reality is these major decisions did shape us? I wonder, but I do not regret these types of decisions as I know they were conscious. Even so, some days I wake up and wonder philosophically, “how did I get here”? These 10 things are great reminders when life doesn’t go as planned. – Stephanie

I used to find myself regretting a lot – that I wasn’t prettier, that I wasn’t funnier, that I wasn’t smarter, that I wasn’t thinner, that I didn’t do this, that I hadn’t tried that. But as I grew, I realized regret was something that sucked up a lot of my precious time. Although it can be hard to shake regret all together, I’ve stopped regretting the big stuff I can’t change and instead focus on the here and now: here is what I can focus on, now I’m going to either appreciate it, or change it. That goes extra for the mishaps in life that are inevitable; these things happen, and instead of regretting them, I do my best to forgive myself and learn from them. Life’s much simpler when I allow myself the ability to a make mistakes. Nobody’s perfect – not even Beyonce. – Crystal

winding road


4 responses to “What is Your Biggest Regret?

  1. I was 29 when my mom died. I’m 53 now. I used to feel regret that I didn’t spend a lot more time with her in my twenties. Don’t get me wrong – I saw her a lot, but after she was gone, a lot just didn’t seem like enough. Even when I told myself that mom and I both knew I was doing my best just to be a wife and mother of two while working a full-time job and a taking care of a house, somehow still that regret appeared in the form of a knot in my stomach, a lump in my throat, an ache in my heart, or a tear in my eye. Then one day, sort of recently, I realized that more hours with my mom wouldn’t have changed the wonderful relationship we had. It wouldn’t have changed the huge impact she had on me and who I am today. It wouldn’t have changed how much she loved me. It wouldn’t have changed how much I love her. It wouldn’t have changed how much our love and mutual respect for each other has been passed on to my daughters and grandchildren. So, there’s no place in this story for regret!! And I hope that my girls know the same is true for them and our relationship. Love cannot be measured in minutes, hours or days spent together. It’s everything we share together – – the incredible memories, the laughter, the tears, the hugs, the clothes, the recipes, the phone calls and text messages. It’s the occasional anger and it’s the forgiveness. It’s the singing and dancing. It’s the silliness and the warm fuzzies from the Muzzy!!
    Note: Only my girls will get this, but as I sat here writing this comment, a cardinal landed on the tree outside my window. They’re pretty rare in my yard so that fact that a symbol of my mom appeared outside my window reassures me that there should be NO REGRETS!


    • Wow, thank you for sharing this honest reply. I can imagine how “a lot” never seems like enough. I love your realization that more time wouldn’t change any of the important things. That is something I never would have thought about, but it is so true and it must bring comfort. There isn’t a piece of me that thinks grandma would have ever thought you didn’t do enough with her. And I know you mean it when you say the same to me and Danielle. “There’s no place in this story for regret” xoxoxo


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