You don’t have to know where you’re going before you’re allowed to leave where you no longer belong. It’s the hardest lesson of this stage of life, and the one nobody teaches.
My friend Chip Conley sent something out this month that I’ve read more times than I can count. If you don’t know Chip, he wrote Learning to Love Midlife, and I had the joy of helping build the workbook that goes with it. He has a way of naming the thing you’ve felt for years but never found words for.
Here’s what he named this time. One of the hardest lessons of this stage of life is learning that you don’t have to know where you’re going before you’re allowed to leave where you no longer belong.
We’re taught the opposite, and for sensible reasons. Don’t quit the job until the next one’s lined up. Don’t leave until you’ve found what’s next. Don’t let go of one handhold until you’ve got the next one in your grip. I’ve given that advice myself.
But practical and transformational aren’t the same thing, and midlife tends to ask you for the second one. Practical advice is built to keep you safe. Transformation asks something else. It asks you to be willing to not know for a while, which is the one thing every instinct you have will fight.
The Space Nobody Prepares You For
There’s a stage in every transformation that has no name in ordinary life, so we treat it like a mistake. Chip calls it the fertile void: the space between what is over and what has not yet begun.
You know this space. You’re between the title you had and the one you don’t want back. Between the version of you that made sense to everyone and the one that’s still arriving. It’s uncomfortable, and the discomfort is not a sign you’ve done something wrong.
Our culture has no good word for it, so it hands you a diagnosis instead. Lost. Adrift. Between things. Every one of those words quietly assumes you should already be somewhere else.
I keep going back to the caterpillar for this, because it’s the truest picture I know. We love the caterpillar. We love the butterfly. Nobody frames the chrysalis.
But the chrysalis is where the whole thing happens. It’s where the caterpillar dissolves into something with no shape yet, and waits, and becomes.
It cannot turn into a butterfly with one foot still in the cocoon. The old story has to end before the new one will introduce itself.
Why This Is the Spiritual Part of the Work
I call this the spiritual terrain in reference to the part of you that lives underneath the roles. Underneath “mother,” “director,” “wife,” “the reliable one.” The part that knows what actually matters to you when the titles are quiet.
Here’s what I’ve watched, in myself and in the people I coach. Your identity loves certainty. It wants the next chapter written before it will let you turn the page. But the soul, call it whatever you like, loves possibility. And the space between is the one place the soul can finally get a word in.
When you’re not busy being who you were, you start to hear who you are. Meaning shows up. So does the honest, unhurried question of what you want the rest of your life to look like. That isn’t a detour on the way to the answer. That is the answer, forming.
The Act of Faith Nobody Mentions
For most of my life I thought faith meant believing you’d succeed. The real act of faith in midlife is smaller and much harder. It’s believing you don’t need the next chapter written before you’re willing to turn the page. Trusting before it explains itself. Leaving the place you’ve outgrown before the new place has shown itself, and refusing to call that failure.
There’s a reason this shows up as a faith question and not a strategy question. Strategy needs a destination. Faith is what you use when you don’t have one yet.
“You don’t have to know where you’re going to be allowed to leave where you no longer belong.”
I won’t pretend it’s easy. Everything in you will want to grab the next handhold before you let go of this one. But you can’t cross this particular terrain gripping the old ledge. At some point you have to stand in the open, unpretty middle and let it do its work.
You Don’t Cross It Alone
Here’s the part I most want you to hear. This is the terrain you are least meant to cross by yourself.
You can white-knuckle the practical decisions alone if you have to. You can even muscle through the emotional ones. But the space between is disorienting by design. There are no landmarks, that’s the whole point. And the human instinct in a place with no landmarks is to bolt back to the last thing that felt solid, even when you’d already outgrown it. That’s not weakness. That’s just what we do when we’re scared and can’t see the trail.
A sherpa doesn’t carry you, and doesn’t pretend to know your summit. A sherpa has simply crossed this kind of terrain enough times to stay calm in the stretch where you can’t see. To say this fog is normal, keep walking. To keep you from turning back one ridge short of the view. That’s the whole job. Not answers. Company, and a steadier read of the map when yours has gone blank.
I know this terrain because I’ve been lost in it myself. That’s the only credential that matters here.
So if you’re in the space between right now, if you’ve left something and the next thing hasn’t arrived, and everyone keeps asking what your plan is and you don’t have one, hear this. You are not behind, and you are not broken. You are exactly where the becoming happens.
You don’t have to know where you’re going to be allowed to leave where you’ve been. You just don’t have to do the middle alone.
With you on the journey,
Holly
PS — Sign up for your free 30-minute clarity call here. No pressure to enroll on the call. We’ll just talk about where you are and whether this is your moment.
PPS — The piece that sparked this one is Chip Conley’s “Leaving Before Knowing,” on his Wisdom Well. Worth your morning.