Grieving something good

On the sadness that shows up when everything is finally going right

A few months ago, I felt that familiar, unsettling feeling again.

Things were going well. Better than well actually. I’d been stepping into new circles. I was seeing growing success in my business. I was doing the kind of work that felt genuinely aligned with who I am. Yet underneath all of that…sadness.

I recognised it instantly this time, but that wasn’t always the case.

A couple of years ago, the same feeling showed up, and I had no name for it. Things were improving. I was growing in confidence, doing things that made me feel more alive, and more like myself.

So, why did some part of me feel like I was losing something? It didn’t make sense. I couldn’t explain it, so I mostly just sat with the confusion.

Have you ever felt that? Something good happening, and an unexpected sadness sitting alongside it, with no obvious reason for either?

It took me a while to work it out. And once I did, I had a word for it.

Grief.

I realised the grief was actually two things, layered on top of each other.

The first is something I’ve come to recognise as a pattern that repeats every time I grow.

Because there’s always a version of me I leave behind. Not just relationships or roles, but entire ways of existing. The version who needed to be needed. Who managed how she was perceived. Who stayed small in certain rooms because it felt safer than taking up space. Each time I grow, one of those versions no longer fits. And even though I don’t need her anymore, leaving her behind still feels like losing something.

The second layer is harder to put into words.

It’s not really about who I’m becoming at all. It’s grief for the younger versions of me. The ones who spent years carefully controlling how they showed up, performing for self-preservation, never quite letting themselves be fully seen. They didn’t get to experience what I get to now. The ease of being myself without calculating how it’ll be received. The freedom to lean into joy; into the things that make me feel alive, without justifying it first.

I find myself grieving on their behalf. Not with guilt or judgement. Just a kind of tenderness. They did the best they could with what they had. And they never got to feel what I feel now.

I see a version of this constantly in the conversations I have.

People who, on some level, know they’re ready for something different. Maybe it’s a redundancy they secretly hoped for. Maybe it’s the recognition that they’ve outgrown a role, a team, or a way of working that no longer fits who they’ve become. Whatever form it takes, there’s often a sense of relief when the change finally comes. Or even when they finally admit to themselves that it’s time.

And then often, without warning, grief shows up anyway.

The relationships. The rhythm of a place they knew. The version of their professional identity that existed inside of that role. An entire chapter, ending.

Does any of that sound familiar? That sense of relief sitting right next to a sadness you didn’t expect, and maybe don’t even feel like you’re allowed to have?

You wanted this. You chose this. Or maybe on some level you had been hoping for it. So, it often feels like you’re not allowed to feel sad about it. As though gratitude and grief can’t coexist. As though feeling the loss somehow cancels out the relief or means you didn’t really want the change after all.

But I don’t think that’s how it works. We don’t have to choose between excitement for what’s ahead and sadness for what we’re leaving behind. Both can be true, at the same time, without one cancelling out the other.

Here’s how I think about it now: An ending and a beginning aren’t really two separate things. They’re the same moment, just felt from two different angles.

The version of me I leave behind each time I grow? That’s the ending. And the version of me who gets to feel ease, joy and freedom that wasn’t available before? That’s the beginning. The same shift, both equally true.

And the grief I feel for my younger selves, the ones who didn’t get this, isn’t separate from gratitude either. If anything, it’s a kind of gratitude in reverse. It’s only because I can feel how good this is now that I can recognise what they missed out on.

Sometimes I picture them. The ones who didn’t yet know who they were, or what they were capable of.

I hope they’d be proud. Not because of what I’ve achieved, but because of who I’ve become along the way. Someone who finally gets to live without the weight they carried for so long.

Because everything they carried is part of how I got here.

And I guess there’s a younger version of you in there somewhere too.

So, if you’re in a season of change right now, here’s what I’d ask.

What would it feel like to let yourself feel it all? Not just the part that looks good from the outside, but the quiet sadness sitting underneath it too?

You don’t need to pick a side. You don’t need to feel only excited, or only sad, or worry that one feeling negates the other. Let yourself feel whatever’s true, even if it’s more than one thing at once. Especially if it’s more than one thing at once.

You’re allowed to feel both.

If this resonated, I’d love to have you join a conversation Caitlin Guilfoyle and I are hosting this Friday.

From Reaction to Intention is the second session in Rewriting the Playbook, our free three-part masterclass series. We’re exploring what’s underneath the moments we react in ways we later regret, and what it takes to respond with intention instead.

Friday 26 June | 1:00pm AEST | Free | Virtual

If you’d like to be in the room, you can register HERE.