Today we share 21 tips about how to stop living with regret as you get older. In the spirit of Lifestyle Fifty we want to age fabulously; and the art of ageing and living the good life has no room for living with regret.
According to Wikipedia, regret is the emotion of wishing one had made a different decision in the past, because the consequences of the decision were unfavorable.
When you’re over 50 (or older as I am!) there have probably been a lot of life decisions made, some of which you regret.
It’s natural to have regrets, which at worst, we carry around with us like a heavy suitcase. I know I’m guilty of this about some things. Especially as the years progress.
I often silently ask myself, “Why didn’t I do such and such back then when I could?” “Why wasn’t I more forceful when such and such was happening?” or “Why didn’t I study harder when I had the chance?” and other niggling thoughts about living a life overseas and not being nearer my extended family as we all age.
And so, in my deepest darkest moments thoughts like this can go on and on. They can spiral down and drag me with them.
But if thoughts like this get out of control then they can weigh us down and drain the energy we could put to good use moving onwards and upwards in life.
It really is a case of, “Get busy living or get busy dying!” This is a quote from one of my favorite movies, The Shawshank Redemption and it really does sum things up succinctly!
It perfectly spells out what regret can lead to, because wallowing in regrets about the past can stop us from being busy living.
In his novel, The Midnight Library, Matt Haig has this to say:
“It is easy to mourn the lives we aren’t living. Easy to wish we’d developed other other talents, said yes to different offers. Easy to wish we’d worked harder, loved better, handled our finances more astutely, been more popular, stayed in the band, gone to Australia, said yes to the coffee or done more bloody yoga.
It takes no effort to miss the friends we didn’t make and the work we didn’t do the people we didn’t do and the people we didn’t marry and the children we didn’t have. It is not difficult to see yourself through the lens of other people, and to wish you were all the different kaleidoscopic versions of you they wanted you to be. It is easy to regret, and keep regretting, ad infinitum, until our time runs out.
But it is not lives we regret not living that are the real problem. It is the regret itself. It’s the regret that makes us shrivel and wither and feel like our own and other people’s worst enemy.
We can’t tell if any of those other versions would of been better or worse. Those lives are happening, it is true, but you are happening as well, and that is the happening we have to focus on.”
Matt Haig, The Midnight Library
While it’s true that we should learn from our mistakes, rather than just discount them, it gets unhealthy when we start to dwell on the things we can never change.

Some people live in constant fear and anxiety, regretting many of the choices they made in life.
But if you allow yourself to dwell on, or worse still, be consumed by your past actions, then you aren’t able to experience happiness and joy.
Table of Contents
Stop Feeling Sad about Things You Can’t Change
As we get older of course there are always regrets, because our lives have been lived longer, and we have yardsticks by which to measure our actions.
Yet even if we’ve lived the most amazing and happy life, it’s still easy to get sucked into a pity party of “I shouldn’t have done that,” or “I shouldn’t have said that,” or “I wish I’d learnt the guitar,” or “We should have moved to Canada,” and even perhaps “I should have become an astronaut!”
“Each existence available to us is a smorgasbord of trials and tribulations. What can look like the shiniest, happiest package from the outside, once unwrapped can look very different.”
Harpers Bazaar: Matt Haig: The reason we’re obsessed with regret
And getting old is a mind game.
Oh I know it’s a physical game too, and that we can’t alter.
But the whole idea of mind over matter is a thing, and how we view what we have, what we had, and what we’re going to do with what we’ve got in the future is really important.
How to Stop Living with Regret
- Keep positive, and learn to let your regrets about the past lead to better choices for the future.
- You can’t go back and change things, so try to live in the moment and enjoy life NOW.
- It’s much harder, but much more meaningful to understand why your regrets make you feel bad, and then find a way to either be a better version of yourself in the future and not repeat them, or make amends in a positive way for what you feel you might have said or done in the past.
- It’s all too easy to look back on your life and regret some of the decisions you made, but every decision we ever make comes with a bunch of other sliding doors that we could have opened. So be thankful that you had choices, and embrace the decisions you made at the time.
- Shift your perception and change your mindset – Look for the good in the situation you’re in now.
- Make sure that any self recrimination is followed by a corrective action.
- Nobody leads a perfect life, so don’t beat yourself up if yours isn’t perfect either.
- In reality, there’s no such thing as a bad decision – as long as you learn from it.
- Think about your life as a series of experiments, some of which you’ll get right and some you’ll probably get wrong.
- Be kind to yourself.
- Realise that everyone is fighting elements of both good and bad within themselves to some degree, and regret is one of those negative feelings..

Most of the time in making decisions we would have chosen what we could, with what we had, according to knowledge we had available at the time.
The thing is as years drip by our perspective changes; new insights come into focus; better gut feel develops; and then there are those moments when everything seems crystal clear – like looking through a pair of prescription glasses for the first time!
We begin to realise that it’s not what you see, but how you look at things.
If a situation is not going well, we can change it, or we can view it in another way and look for the positive aspects.
If a relationship has soured and there’s no going back, don’t regret it, look at some of the wonderful things you did together and the fun times you had.
If you didn’t do something that was right for you, don’t regret it – if the opportunity wasn’t there in front of your face, then perhaps it just wasn’t meant to be.
Life is about taking risks and sometimes they pay off; other times not so much! You can always learn from past experiences.
10 Reasons to Stop Living with Regret
- Regret eats away at your energy and produces negative emotions.
- It means you are spending to much time thinking about something that only brings pain and suffering.
- You never get the chance to grow in wisdom, or experience new things if you focus too much on regrets of the past.
- Wallowing in regret will mean you’ll miss out on lots of fun times in life.
- Dwelling on past mistakes is not good for the soul. Take action and make amends.
- Regret is like a heavy weight keeping your down.
- It makes new relationships difficult, because you are often looking at why they might fail based on your regrets of past relationships.
- Think of regret as a bad decision from which you’ve learned, and can now move on.
- Regret is a waste of time. – If you don’t learn from your mistakes how can you grow?
- Regret means you are not living in the moment. Live in the moment, not the past.
Helpful Books about Regret
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We all live with regret of some form. The important thing is to learn from our mistakes, and try to be a better person. It is hard to kick the night-time regrets out of our heads that go over and over and not get anywhere, because you can’t change past acts. Only the other day I said to my husband about something I still regret from 7 years ago when my Dad was in his last weeks. I can’t go back and change it, But if I can give some small advise to someone else in the same situation, I know what I would say. Thanks Jo for another insightful and truly helpful post.
Absolutely Jill 🙂 Learning from our mistakes is so important, but often it’s hard to acknowledge wrongdoings or regrets, and move on without guilt. Somehow they can just keep niggling. But it’s not worth the energy – we have to let go. I understand how you feel about your Dad in his last weeks and perhaps what you said was wrong – but it was surely a very emotive time, and you were probably struggling with many things at the time. Be kind to yourself 🙂 x