How do we know we’re ready to let go?


In my first few coaching sessions of the New Year, I noticed this interesting theme of loss, fear of loss, and ambivalence about loss surfacing.

Some of it had to do with completing a piece of creative work and feeling the emptiness that can come with finishing. This thing that has taken up so much of our heart space and head space and waking hours is now up and walking on its own and it doesn’t need us the way it did. There’s sadness — and one heck of a void — in that.

Some of it had to do with letting go of a job or a relationship. And the big thing coming up around that was, is it truly time? How do I know?

And some of it was about giving ourselves permission to let a creative project, job, or relationship go — even though it did not feel “complete.” It was about deciding not to continue. (And that’s rough on perfectionists, which most of my clients tend to be. You mean I’m allowed to give up on it? I’m allowed to not see it to completion?)

My “big word” for this year is permission. I need to focus on permission because I’ve noticed that I can go for hours, sometimes days, forgetting that, yes, I actually do have permission to do things the way I need to do them. To feel things the way I feel them.

So I can’t help seeing these issues with letting go through the lens of permission.

And that leads me to this: Often, when we’re afraid of letting go, it’s because we haven’t given ourselves permission to NOT let go.

Some militaristic part of us jumps up and says, “Okay! Time to move on! Let’s get moving here!”

And those parts of us which are not ready to let go, sometimes not even NEARLY ready, get trampled in the stampede.

But, as I’ve written here before, we can’t truly arrive anywhere until ALL of us shows up. This concept came to me from the writings of Robyn Posin, whose beautiful website you can find here. She uses a stoplight analogy: We can race to the light, but if it’s red, we won’t actually move forward until it turns green.

There may be a part of us that is holding a green light, but many other parts of us are still cradling the red, tightly.

So, permission. To be right there.

That part of us that the light has already turned green for will probably be very impatient with the parts of us that need to go slower.

And working with the impatient part of us might mean saying to it, “Yes, I see that you’re really ready to go, and I get that. AND, the whole of us is not ready yet. You’re not allowed to let your impatience run the show. But you’re totally allowed to be impatient.”

As long as there is conflict between the parts of us that want to let go and the parts of us that don’t, we are not at peace.

And when we’re not at peace, when we’re locked in struggle, we’re in a poor place to make decisions about anything big. When we’re struggling, it’s painful, and any decision we make tends to be more about getting away from the pain than moving toward what actually feels right to us.

The questions to ask the impatient part of ourselves are: What’s scary about slowing down? What’s hard about being in the present moment?

The questions to ask the parts of us who aren’t ready to let go are: What’s scary about moving forward? What’s hard about stretching ourselves into the future?

Allow these parts to talk to each other. Write down what they have to say; you might try using a different color of pen for each part. When you can hear them all out (and notice that each of them has wisdom and truth), you can begin to integrate their needs.

And when you have integrity, you have peace. And from peace you can truly let go in wholeness.

What are your challenges around letting go? Do you tend to let go quickly, or do you really hang on? I’d love to know how it works for you, in the comments.

Image is Feathers Against the Sun © Kmitu | Dreamstime Stock Photos

4 thoughts on “How do we know we’re ready to let go?

  1. Loved this post, Jill. (Actually I’m having a Jill Winski marathon this foggy afternoon.) I loved it so much I sent it off to my son who’s struggling with some decision making right now. Thank you for always writing what I need to read. 🙂


    • Mary, I’m so glad you loved the post! I hope it’s helpful for your son, too. And I’m honored you spent time on a Jill marathon. I love it when you stop by! Thanks so much for reading. 🙂


  2. This is very topical for me at the moment as I’ve just let go of where I live, at least I’ve voiced that I will leave in a couple of months, and that was big because of the implications on the person I live with. For me letting go is actually quite easy once I’ve connected with that inner knowing that it’s the right thing to do. Doesn’t mean it’s not uncomfortable or emotionally intense, but that knowing gets me through, There’s a deep acceptance and an inevitability that keeps me grounded in a quiet peace deep down, even if I’m nervous on the surface, because I know when I listen to that knowing life takes care of me. It’s only when i resist that things get difficult. By the way, came across a great TS Eliot quote recently, this is part of it which ties in with this theme, ‘And to make an end is to make a beginning.’


    • Beautifully said, Harula. That’s my experience as well — once I’m clear about letting go, it’s still painful, but if I can accept how things are and what I need, it’s okay. The most difficult part, I think, can be coming to that place of acceptance. I love this: “…when I listen to that knowing life takes care of me.” So, so true. I love the T.S. Eliot quote! Thanks so much for sharing. 🙂


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