A Week’s Worth of Journaling Prompts: Regret 7

I received the suggestion for this week’s journaling prompts from Marlene Samuels, who wrote:

I’ve been enjoying receiving your newsletters … Currently I’m working on a series of essays pertaining to decision making for the 3rd quarter of our lives, especially as seen by baby-boom generation women. I think it would an interesting journaling topic: the notion of regrets – how women make peace with them and moving on but particularly how we can use past regrets to make positive choices about our futures.

Yes, I agree! But before we jump into our week’s worth of journaling prompts, let’s take a moment to explore the concept of regret. According to my computer’s dictionary, the verb to regret means “to feel sad, repentant, or disappointed over (something that has happened or been done, esp. a loss or missed opportunity).” To have a regret (noun) is to have that feeling.

That rings a bell with me, especially the part about feeling sad about lost opportunities. How many times in my life have I not taken the opportunity to do something because I thought I was too old, didn’t deserve it, had to take care of others first, or some such thing — all, which I realized much later, were simply excuses for not having the courage to take whatever risk might have been required. Oh, how I have regretted the lost possibilities!

And yet, who would I be now, if I had done those things? Would I be a better person? Perhaps. Perhaps not. Would I want to give up any of my life experiences, trade them for something else? Theoretically, maybe, but what if it meant forgetting something I’ve learned?

Whether you’re sixteen or eighty-two, I think everyone has felt regret about something. I put these questions to you, dear reader, so  you can explore these ideas on your own:

  1. What, if any, are your regrets in life? What action would you undo, or what opportunity would you take if you had it again?
  2. What would you trade of your current experience and worldview in order to make that change, and why?
  3. Describe the life you would have now, if something you regret never happened. Can you imagine your life lived differently? How would it be different? How would it be the same?
  4. Do you think that forgiveness and regret are inter-related? How or how not? Can you forgive yourself or someone else for a past action and still regret that it happened? What is the difference between “making peace with” and “forgiveness for” as it relates to regretting?
  5. Do you think that women of the baby boomer generation are more or less inclined to harbor regrets? Why and/or why not?
  6. Write a letter to yourself in the past, giving advice regarding how to handle that decision or event you now regret.
  7. At any point in your life, has regret for the past changed your decisions for the future? What decision did you ultimately make, and did it have a positive impact? If so, would you say that the original reason for your regret ended up to be a positive thing? Why or why not?

Bonus prompt: Perform a word association with the word “regret.” Write a poem using words that you generated during the exercise.

Do you have ideas for upcoming weekly journaling prompts? If so, I’d love to hear from you.
Image Credit: Toni Blay

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7 thoughts on “A Week’s Worth of Journaling Prompts: Regret

  • Sharon Lippincott

    Thanks to Marlene for the inspiration and to you, Amber, for another thought-jiggling post.

    Here’s another slant on that powerful “excuse for not having courage” thought. I’m of the firm belief that we each do the BEST WE KNOW HOW at any given moment, so ignorance is often the root cause of failed courage. Isn’t it great that we become so much wiser with the passing years? Pleading ignorance doesn’t do away with regrets, but at least for me, it makes them a little easier to bear.

    • Amber Lea Starfire

      Sharon, I agree that we all do the best we can, given our knowledge level and understanding. How could it be otherwise? For me, insecurity and lack of confidence probably contributed to my lack of courage, more than ignorance. We each have our own strengths and weaknesses — exploring how we have made past decisions in unconscious ways, and making conscious choices for our future, is one of the powerful aspects of journaling.

  • Davis

    Regret is quite often only a thought-experiment, as it is based on an assumption that things could have been different than they were — that we could have acted differently than we did — when it has often been my own experience that that either I never really had that option in the first place or things would likely have come out badly had I done so. If you must go through regret to realize that, so be it, but make such amends as you are able and don’t beat up on yourself for not making a choice that might not have been possible in the first place.

    In place of regret, ask if there is any way you could now make the situation better now, and accept that you often won’t be able to do much about it.

    If you want a regret-based thought-experiment, ask yourself what good things that have since happened would not have happened had that unfortunate matter not occurred.

    Reality is enough for us to deal with as it is, without torturing ourselves with what might have been.

    • Amber Lea Starfire

      Davis, yes … the “would have’s, could have’s, should have’s” are all in our minds. I hope you don’t feel that I’m advocating regret in this piece — only that most people carry some kind of regret, and that it’s worth thinking about, if only to discover that you wouldn’t do anything differently. Journaling is all about where we are today and how we make choices for our future. Exploring regret is not the same as “torturing ourselves with what might have been.” It’s more about taking an honest look at the factors that have contributed to who we are and making conscious, positive decisions for our future.

  • Davis

    Amber, You’re right, of course. I never would have understood how illusory were so many of those choices I regretted not making, had I not worked it out in my journal.

    My 1981 travel journal evolved into a daily journal which evolved into a parallel writing project of stories about growing up on a farm in Southern Illinois and then another parallel project (i.e., all of these being carried on at the same time) of my great grand father in the Civil War with another story line of my other relatives and eventually my wife’s relatives (her family was much more interesting than mine) and so that very simple travel journal has grown in thirty years to a swarm of journal projects, any one of which I can pursue as the inspiration strikes me.

    I used to be mired down in my own life, but now I have so many other lives and times to occupy myself with that my own problems are just passing inconveniences.

    In keeping a journal you can wind up attending to so much more than just yourself.

    I hope I haven’t wandered too far off topic.

    Best wishes, D