Dealing With Regret
- LouAnn Clark

- Jan 10
- 5 min read

What have you done that you later lived to regret? Conversely, have you ever decided not to do
something and then lived to regret that decision? Regret is something most of us live with, but it is also something we fear, and that fear can keep us from acting, even when we know action is
needed.
Fear of making mistakes that you will regret can keep you stuck. It can turn into the classic
damned if you do, damned if you don’t situation. You are unhappy where you are, but if you
change something and it doesn’t work out, then you may regret making the change. Being stuck
between a rock and a hard place is a rotten place to be, but what if you move the rock, and it
starts an avalanche? It’s natural to want to avoid making things worse.
Taking a Risk
If you want change in your life, you are going to have to risk regret in order to take action. If you change something—your job, your relationship, your location, your attitude, your heart—things
may not turn out the way you hope. You may make a change and succeed in a big way. You
may also make a change and end up unpleasantly surprised, disappointed, or heartbroken. No one
wants these things, and they can seem so painful that the mere thought of them keeps you from
doing anything to change. I wish it were otherwise, but there is no reward without risk.
I don’t know if it’s possible to live a life without regret. There are times when I can wax pretty
philosophical about things that haven’t turned out the way I wanted. I wish I could say I succeed all the time, but unfortunately, I don’t.
I have suffered many losses over the last dozen years, and as I move forward, I can fall into looking back and longing for places, things, and people I have lost. I can spend a lot of time and energy analyzing what went wrong and trying to figure out how to keep those same things from happening again.
Ultimately, though, I have to go forward, because it is the only direction available to any of us. We can choose to go forward dragging our regrets with us. We can also stay stuck in fear of making new regrets. Or we can choose to let go of the negative feelings of regret but retain the wisdom of the lessons we have learned.
Trying to move forward while dragging your regrets with you hardly feels like going forward at
all. It feels more like going in circles, replaying the same old movie with the same old ending. If
you keep telling yourself things will never be any different, guess what? They won’t.
Constantly looking at your regrets won’t do anything to change the past. You can spend all day saying, I wish I had…If I could do it over again…or I should have known…and the past still will not be
changeable. As long as you keep dwelling on the past, nothing will change, because you won’t
do anything to create change.
The "S" Word
So many times, when we say, “I should have known, or done, or said…” we could not have
known. We could not have done anything differently, we could not have said something
different. Because we didn’t know. Why do we insist on beating ourselves up with that word
should?
When I say, "I should have known better," I am feeling regret. A decision I made or
an action I took didn’t turn out the way I wanted. I think we mean well; we want to do better the
next time a similar situation comes up, and by saying, “I should have done this or that,” what
we really mean is, “I will know better next time.” And that is okay! You probably will know better
next time. But you could not, and you SHOULD not, have known better without the experience
you regret serving as your teacher.
Staying stuck in fear of making new regrets can seem like a reasonable choice. We often refer
to this option as “playing it safe.” You don’t look for a new job or file for divorce or finally get your
finances in order, because maybe if you stick it out just a little longer, something on the outside
will change, and you won’t have to make any changes yourself. It will be like magic. Maybe you
will win the lottery.
If you make moves to change your life for the better, you may not get the perfect outcome you dream of, but if you do nothing to make things better, you are virtually guaranteed to get nothing better.
You know that old definition of insanity: Doing the same things and hoping for different results.
Letting go of the negative feelings but retaining the wisdom of lessons learned is the way to
make regret work for you. As you go forward, you can remind yourself that it is important to
choose what you might regret in the future.
Several years ago, one of my friends took a solo trip to France, and I admired her courage so much that I wrote down what she said about it. She said, “I don't want to look back in ten years and think, I wish I had gone, but I let my doubts and fears stop me. I may or may not love the
experience that awaits me but I will for sure regret not making this trip. By the act of going, it's
already a win.” You probably won’t be surprised to learn that the trip was worthwhile.
Looking Back With Wisdom
Another thing to consider as you move forward is the growth and maturity that has occurred in
the time since you made a choice you regret. Some members of my family used to remind me
frequently of some financial mistakes I made when I was nineteen. Nineteen! Yes, I regret what
happened, but that’s been a long time ago.
Now I can look at myself with compassion and say, you were only 19. You did not have the life experience and the wisdom to know better then. But you do now. Would I make the same decisions today that I made at 19—or for that matter, at 29 or 39 or 49? Maybe, because some of them were good, but when I think of the bad ones, I remind myself of a quote attributed to the late Maya Angelou: “I did then what I knew how to do. Now that I know better, I do better.”
I forgive myself for making human mistakes and consciously choose to give myself the gifts of optimism and hope. You know now what you know now, so take that knowledge and build on it. Decide what you want to be, do, and have in the future.
Going back and getting what you lost isn’t possible. Even if you rekindle an old romance or go back to a job you once had or move to a city you once loved, they will not be the same as they were in the past. And here is the important thing to keep in mind. You are not the same as you were in the past. You do know now what you id not know then. Denying those changes is just another way of choosing to suffer.
If you did something you regret, here is a new story to try: Yes, I did a terrible thing or I made a
terrible mistake. I wish I could change the past, but I know that I can’t. I could continue to brood
about this mistake and make myself miserable, but I recognize that my misery still can’t change
the past. My misery can only change the future for the worse. I choose to forgive myself, and I
resolve to move forward. Keeping the lessons I have learned firmly in my memory will help me
create a better future.


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