How to Unpack the Beautiful Message Embedded Inside Regret

by | Jan 5, 2025 | Anxiety | 18 comments

“Nostalgia is denial – denial of the painful present… The present is a little unsatisfying because life is a little unsatisfying.” – Midnight in Paris

We just returned from nearly two weeks of traveling abroad. It was a rich, meaningful trip, and I’m endlessly grateful for the connection between the four of us.

But it wasn’t perfect. At fifteen and twenty, our sons are at a stage of life where they’re reflecting on some of our parenting choices. My husband and I are very open to hearing their reflections, and grateful that they feel safe enough to share them with us, but it’s also hard not to fall into regret.

We’re at a stage of parenting where the gaps are becoming noticeable. By this I mean that our kids are old enough where we’re seeing both the positive fruits of our parenting choices – most noticeably that our sons have a solid sense of self, real interests, and a clear voice – and also their places of pain and disappointment.

This is part of life, of course, but as a parent we’re wired to try to engineer our kids’ lives to create as much well-being and as little pain as possible. Yes, yes, I know that pain leads to resilience, but try telling that to the parent brain that is primed to protect our children from hardship of all kinds. It’s simply baked into the formula. So when one of my kids expresses emotional pain about a current situation, my mind goes to, “I wish we had
” or “It’s because we made that choice
”

While it’s healthy to ponder the past with curiosity, I also realize that we can’t take full responsibility for the entirety of their pain. Our kids are going to hurt. They’re going to feel lonely. They’re going to be uncomfortable. There is simply on way around that.

The Message Inside Regret

When regret comes in full force, I remind myself that regret about the past is the mind’s way of trying to avoid the pain or disappointment in the present.

Life is full of pain and disappointment. Instead of accepting that, the mind wanders into the past and says, “If I had done X differently, I wouldn’t be feeling Y now.” Maybe. But maybe you’d be feeling Z, which could be worse than Y. Or you would be feeling a different Y, which would also be painful. We just don’t know. The thing about regret is that is always paints the past with gold paint, imagining the most glowing, lovely outcome of different choices. We don’t wander down the daydream of regret and say, “Oh, if I had only made that choice my life would be so much worse now.”

As such, regret is an escape hatch to avoid the pain and disappointment of the present when the bottom line is that we can’t avoid pain, both for ourselves and our loved ones. We make the best choices we can given the information we have at the time, and then we live out how life unfolds.

No Perfect Life

That’s the hard part: the living out life on life’s terms, accepting the inevitable pain and imperfections that arrive. Here we must remind ourselves that no matter how “perfectly” we choose, there is no perfect life.

There is no perfect parenting.

There is no perfect partnership.

There is no perfect place to live.

There is no perfect friendship.

There is no perfect college.

There is no perfect work.

No matter how we choose, there will be both blessings and challenges. It’s just the way life is. Imperfect. Painful. Disappointing. Lonely. Broken. Beautiful. Connected. Joyful. Whole.

 

What’s the solution?

To keep breathing into the hard parts so that we widen our capacity to tolerate pain and discomfort, while at the same time pouring the light and water of our attention onto the blessings.

This is how the heart grows, in tenderness for what hurts and in gratefulness for the good. Breathing in the pain, breathing out the gratitude, the heart, as the muscle that is it, strengthens and deepens, and when we come back to the broken beauty of the present moment, full of all the blessings that we waiting to be seen, we find our way back to joy.

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18 Comments

  1. Thank you, this came at the perfect time. I also wanted to say thank you for the relationship anxiety course. Took it four years ago and it literally changed my life and my approach to romantic relationships and I am forever grateful for this!

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    • I’m so glad the post and the course were helpful!

      Reply
  2. Thank you Sheryl for this important reminder!

    Six years after our move away from the city, my mind is still stuck on how easier our life would have been if we had stayed in the city and how I’d feel less lonely if we had chosen another school for our kids.

    Because the same thought has been stuck on my mind for so many years, I rationally know that it’s a sign I’m off kilter when it returns… but it is so incredibly powerful and hooks me with so much force every single time (and always after Christmas!).

    And yet I know – I know in my bones, as you so rightly say, that if we had not moved, I’d be experiencing Z or another kind of Y… My inner feeling of loneliness would probably be the same, because I know that no external circumstances can really erase it.

    I find it really hard to tackle it though – my rational mind understands it, but my panicked body resists doing the work and feeling the deeper pain. It is incredibly painful to let go of the idea that there is a perfect, or better place for me, which would take my pain away. I think this is what is keeping me stuck – the false hope that if I find this place, I won’t ever have to feel the pain. The work is to accept that there is no such place

    I also imagine how difficult it must be to handle regrets regarding how we raised our own children (which is unavoidable!!). But it is true – we can’t take away their pain. I remember my disappointment as a first-time mom when i realized that my love couldn’t take away the pain my newborn baby was experiencing sometimes. Maybe the powerlessness i felt was a potent lesson about our human condition, and a reminder that the only way out is through 😉

    Thanks again for putting words on this experience – I am re-committing to accepting imperfection.
    Much love

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    • To Emma 1404- your words really help me see something similar in my life. Thank you may our hearts be opened to be with the present (“tenderness for the pain and gratefulness for the good” as Sheryl says) lots of love- Teri

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    • Yes, ultimately we are trying to avoid loneliness, disappointment, imperfection, boredom – and it’s just not possible. How difficult it is to accept this fundamental and existential human truth!

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    • I also have so much regret from moving out of the city. Life was easier there and my family was happier. I do think regret is a teacher. I thought I would enjoy a simpler life but I actually find it boring and my family misses the culture of city life. After living this way for 1.5 years we decided it’s time to move back. Yes life has painful experiences and uncertainty but there is always room for growth and change if the regret keeps speaking to us.

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      • Yes, regret can be a messenger, just like anxiety.

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      • I agree. Acceptance is different from resignation. When there is will, there is a way.

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  3. This speaks so deeply to my heart! My daughter is only 10, but these last few days I have been in floods of tears, heartbroken for the sweetness of all the childhood things we’re leaving behind. The books, toys, experiences, joyful innocence, playfulness, and even more so for the things we never did, that we will never do, and the things I can’t go back to fix or do better. The passage of time in parenthood is an unbearably painful thing!

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  4. So timely Sheryl. One of my children (aged 6) has been opening up to the ways our parenting has impacted his self esteem. It’s so hard when I’d consider us “thoughtful” parents and yet we are still absolutely imperfect. We can do all the learning, all the reflection, and all the praying
yet we will still be human. Granted, we are better parents when we reflect, learn and grow and yet we never “arrive” as I wish we could.

    My husband and I discussed how we are so grateful that they will be able to be honest with us as they grow up, but yes it does sting with the pain of regret. It’s so easy to go into a spiral of shame and anxiety over the future. Thank you for your wisdom, it is so appreciated.

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    • That’s quite remarkable that your 6-year old is already reflecting on this. And that you’re willing to listen.

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  5. Thank you Sheryl. đŸ©· this came at the perfect time for me too. For me, regret often shows up when my interactions with humans are less than perfect (I.e. conflict happens). I can think, “if only I wouldn’t have said ____, we could have avoided ____. And it’s usually focused on what I could have done differently, not on what the other person could have done differently. That overdeveloped sense of responsibility is hard to shake! But what a healing balm your words are. Conflict, disappointment, and pain in life are inevitable. There is no way we can be “perfect enough” to avoid it! Imperfection doesn’t mean that we should have done Y instead of Z. It means we are human. đŸ©·

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    • Yes, exactly right, Amber: imperfection means that we’re human. 💕

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  6. Always spot on, Sheryl! And you quoted Midnight in Paris, I can’t believe it! It’s one of my favorite movies precisely because it made me see in a poetic way how longing for a bygone era is so irrealistic and robs us of the beauties of the present.

    Thanks!

    ♄

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  7. Hi everyone, I know my comment is not directly connected to this post but I just really need advice and a kind word.
    Me and my partner got engaged 2 months ago after a year of dating. A few days before the engagement (I knew it was coming) I started to panic and ask myself if I love him, because I suddenly stopped feeling like it. Ever since then I ve been battling with myself. There are days when I feel like I love him, want to spend time with him and positive about our future. But most days I just don’t know. I don’t know if what I’m feeling is love, sometimes I need to fight the urge to break up. Something inside of me knows that he is the most amazing person and we could have a wonderful life together and that’s why I’m still staying and trying. He is also very supportive and my heart breaks that he has to deal with those emotional rollercoasters of mine.
    I found this page just a day after I got engaged and it really helped me. But it’s been 2 months and I am just so tired and maybe I am just convincing myself it’s going to get better, when in reality it’s not.
    Most of the time I feel so numb and indifferent. It’s hard for me spending time with him (we live together), I don’t enjoy his company as much as I did and it really pains me.
    Did I really fall out of love or I am just tired of all of this? Is this really fear blocking me or do I really don’t want to be with him and just try to convince myself because he is so good?
    Thank you for any advice, I really want to keep trying but I am just loosing hope

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  8. I’m really glad i stumbled upon your work. My struggle with regret relates to my partner refusing to have another child together after our first; he was fearful but wouldn’t explore or share his own internal reasons so I could really understand. I wasn’t in a huge rush, but the years went by and he didn’t shift out of his position. I now feel zero attraction and even repulsion (have read your post about that, and what you say makes a lot of sense, although besides projection, resentment is a huge factor for me rleating to the above.)

    The regret about not responding in ways that helped us connect and really explore it, or that didn’t leave in time to potentially find someone else and have the possibility to be a mother again. The resentment and loss feels so colossal; all the time i see children playing with siblings, and larger families and I feel so angry with my partner – rationally i can see he didn’t intend to hurt me. Anyway, if you have any thoughts or resources I’d be grateful – i’m at the point where i feel cutting our losses would be better as i don’t want a sexless partnership but trying to explore it uncovers rage about the situation that it feels too hard to move through, part of me strongly feels it was simply a deal breaker. But, with a child to consider and the fact he’s not a bad person I feel i ought to try.

    Reply

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