Making peace with the 'what ifs'
Sometimes it’s not the sadness that keeps me awake, but the guilt and regret.
If you’ve ever replayed moments in your mind, wishing you’d done something differently, known something, done something more, somehow changed the ending … you’re not alone.
Guilt and regret often walk beside grief: quiet, persistent, cruelly convincing. A lingering sense of “I should have” or “If only”.
Grief has many faces; guilt and regret being two of the hardest to meet with kindness because the kindness has to come from you.
This month’s letter is for the part of you that carries those heavy “what ifs” and longs to be forgiven, not by others, but by yourself.
Maintaining some control
When someone we love dies, our minds try to make sense of something that doesn’t make sense. And often, we turn inward, looking for things we could’ve done differently. Things we tell ourselves we “should” have said. Times we weren’t there. Words we can’t take back.
Holding onto the thought that we had some input to the outcome gives us a sense of control and agency.
If we tell ourselves that “I should have picked her up, then she wouldn’t have been driving”, or “I wish I hadn’t suggested that we went to the beach”, “if only I hadn’t picked that fight”, then we can keep busy with blame, regret, guilt and not get on with the tricky business of facing the reality and learning how to live beyond the loss.
We wish we could rewrite the story.
We believe we could have done more.
But here’s the hard truth:
The story remains the same and we did the best we could with what we knew at the time.
The power of your mind
In her book The Grieving Brain, Mary Frances O’Connor, explains that your brain will try to protect you and distract you from the huge challenge of facing a loss by allowing you to repeat the story over and over. It’s a way of keeping your thoughts busy and supplies you with some small measure of control. In the same way, the numbness you initially feel following big news is keeping you from dealing with the reality … until your brain and body are ready to start to process it.
Repeating our story of loss is an essential aspect of this journey of healing. Each time we tell the story, there is maybe a different nuance, some new information is revealed, perhaps a different lens.
While this reflection and processing is helpful and to be expected, what is not useful is prolonged rumination which results in no new information.
Breaking free
Guilt and a sense of disloyalty can keep us stuck in this loop of blame, regret, self self-judgment.
This is not easy, it requires time, patience and intention but it is very helpful to try break free from the self limiting loop of our ruminations.
Let me give you some examples of how this might show up for you together with a gentle truth.
When I catch myself laughing, I suddenly feel as if I am betraying them.
Gentle truth: joy is honouring the life that goes on and a love remembered.
I feel as if I should be crying more, does that mean I didn’t love them?
Gentle truth : Grief is love expressed in many ways, no proof is needed.
I never got to say sorry or thank you, and that keeps coming back to me.
Gentle truth: The connection changes but never leaves, it’s never too late to reach out.
I sometimes want a break from sadness but then I feel bad for seeking that.
Gentle truth: Rest is not rejection. Allow yourself moments to heal in small ways.
Moving forward can feel as if you are being disloyal to the sadness, but continuing to love your person, continuing to live your life, taking care of yourself, IS the loyalty.
“The mind holds onto what the heart doesn’t deal with”
David Kessler
So if you’re holding guilt or regret, let me offer this:
Is there a small weight you could set down today?
Not forever. Not completely. Just for now. Perhaps a thought you no longer need to repeat? Or a self-blame story you can speak more kindly to. Can you find a moment to breathe, where your heart is allowed to rest?
You might like to write it in your journal, record a voice note to come back to or simply acknowledge your thoughts around this.
Grief asks so much of us. But you don’t have to carry every part alone.
If you’d like to explore this further, you’re always welcome to reply to this letter or reach out for a one-to-one session. There is space for your story, exactly as it is.
I am here to help, send me a message if you want to talk.
With warmth
Karen
p.s. Have you seen my other Letters for the Heart?
Reset and Rise - gently awakening and celebrating life after loss through solution-focused grief support


