A Door in the Dead End

How loss, heartbreak, and failure open your way to the second half of life

A painting of a closed door standing alone in a dark woods

In late September of 2013, an old friend forwarded me a mass email.

That’s not something I’d usually remember 10 years later. But it came during a month when my life was going into full collapse. And it had quite a hook…

“There is an incurable wound at the heart of everything,” it said.

Which made plenty of sense to me at the time. After two years of deep burnout I was pulling the eject handle handle on my life, making final preparations to leave everything I’d spent my twenties building:

My business. A beloved group of friends. The country of Uganda where I’d been living…

I had no idea what would come next.

I just knew I needed out.

It was right in the middle of all this that this email—one of Richard Rohr’s “Daily Meditations”—landed in my inbox.

The mention of an incurable wound caught my attention. But what lodged itself in my curiosity was a reference Rohr made to a second half of life.

The email seemed to be saying that we spend the first half of our lives trying to cure that core wound—to fix the world, and to build lives immune to its troubles.

But (and here’s the kicker) those efforts always fail.

The email went on, though, to paint those failures as a kind of rite of passage into the second half of your own life. One where you finally accept that the incurable wound truly is incurable, but you decide to do the work of healing anyhow.

I’m not sure how much of that I fully understood at the time.

But at that moment, when my best attempts to fix the world were falling apart, and my life as I knew it was ending, this promise of a second half felt like a door cracking open in the dark. A sliver of light in what I’d thought was a dead end.

A simple map for an unmappable journey

When I got back to the States, part of me assumed I’d just ease into a wise and successful second half of life.

But that’s… not how it went.

Instead I was a total wreck for three or four months. Then only a partial wreck as I slowly pieced together a new life for myself.

It’s been about a decade now since I first got that email, but the two-halves-of-life lens has only gotten more valuable to me. It’s helped me understand what happened in my 20s. And it continues to guide me into new, more wholehearted seasons of life.

So here’s a quick and dirty field guide to the two halves of life, as I understand them.

I’m drawing on folks like Carl Jung, James Hollis, and Richard Rohr, along with a fair bit of my own language and experience. But I’m not a psychologist, so this isn’t meant to be a reference piece. My hope is that you’ll find some clues to your own journey, just like I found for mine.

The First Half of Life: Becoming the person you need to be

One of the great, unspoken rites of passage is when your parents stop holding themselves responsible for your wellbeing.

You’re standing there alone in your first apartment. All your friends and family have left. And it suddenly feels very quiet as the full weight of your own needs settles onto your shoulders for the first time.

According to author Jerry Colonna, those needs boil down to three simple things: Love, safety, and belonging.

That’s what the first half of life is for. It’s when you figure out how to get yourself the love, safety, and belonging you need.

Think about what felt most important in your early 20s…

  • Getting a job or some way to make money
  • Having a good group of friends
  • Dating and finding a romantic partner

Whatever else is going on, and whatever other motivations you have, there’s a core drive for love, safety, and belonging.

That’s one of the simplest ways I’ve found to understand the ego: 

Your ego is the part of you that’s committed to meeting your own needs above all else.

It tries to shape the world to get what you need. And where that doesn’t work, it shapes you to fit the world.

It exaggerates parts of you that seem to “work.” It covers up parts that don’t. And it tries to take on pieces of other people who seem to be getting what you want.

Eventually it zeros in on a version of you that gets the best mix of love, safety, and belonging that it can manage. That becomes what a psychologist might call your persona.

When you meet people in the first half of life, you’re mostly meeting their personas.

And they’re meeting yours.

For most of my twenties my persona was formed around the role of “humanitarian social entrepreneur.” Which isn’t to say that version of me was false or deceptive. It had a lot of my best qualities in it. And it was as true to myself as I knew how to be at the time.

But your persona is never your full self.

Which means important parts of you get silenced. Some get pushed down so deep you lose connection with them completely.

But your soul won’t settle for half-alive.

As you get towards midlife in your late 30s into your 40s and beyond, a kind of soul-pressure builds up inside you. Like magma under the surface of a volcano.

It feels like restlessness. Dissatisfaction. Some deep part of you pushing against the boundaries of your life.

The unexpressed whole of you refuses to sit quietly any longer.

Between the Two Halves: Stepping through the forbidden doorway

The second half of life promises a profound homecoming, the kind Derek Walcott described in his poem Love After Love:

The time will come
when, with elation,
you will greet yourself arriving
at your own door, in your own mirror
and each will smile at the other’s welcome,

and say, sit here. Eat.
You will love again the stranger who was your self.

But the door to enter the second half is so menacing that many in the Western world—maybe most—never step through it.

It’s a door that looks like death.

And in a way it is.

Because the whole of you can’t fit within the careful bounds of your persona. But your persona is the exact and only way your ego knows how to get your needs met and keep you alive.

To become whole would shatter it.

That’s why most of us don’t even consider a second half of life until we’ve experienced some kind of fracture in our lives.

A profound loss. An unbearable heartbreak. A near-fatal event.

It’s what Richard Rohr calls a necessary suffering.

Something that shows us the terrifying truth: that our personas can’t guarantee our love, safety, or belonging. They can’t protect us from “incurable wound at the heart of everything.”

For me it took a couple years of depression, anxiety, and mounting failure before I could admit that the life I’d built—and the persona I was living—wasn’t working.

But full disclosure: Even now, a decade later, I don’t consider myself a full resident of the second half of life.

I think I’m more in the disorienting transitional time we call “midlife.”

So as I describe the second half below, just know that it’s not a description from a seasoned resident, but from a grateful visitor who’s read a few of the brochures.

The Second Half of Life: Becoming the person you long to be

Moving into the second half shifts the entire axis of your life, according to Jungian psychoanalyst James Hollis.

In the first half, everything revolves around the relationship between your ego and the world. Navigating that tension is how you get your needs met.

But in the second half, your life revolves around a different tension.

It’s the tension between your ego’s hardwired mission to keep you safe, and your soul’s irrepressible longing to make itself known in the world.

As you learn to play in that tension, three profound shifts remake your world. And the first two make the third one possible.

1. First is the shift to complete self-acceptance. 

Not because you’ve finally perfected yourself. Or because you don’t want to change any more.

In some ways you’ll probably change, grow, and transform more in the second half than in the first. As psychologist Carl Rogers put it, “The curious paradox is that when I accept myself, just as I am, then I can change.”

Richard Schwartz describes this kind of self-acceptance in his book “No Bad Parts.” It’s the recognition that even your worst habits and reactions are rooted in the basic human needs for love, safety, and belonging.

Those parts of you aren’t bad. They’re wounded. 

And when you welcome them home with compassion, then they can heal.

2. Second is the shift to complete acceptance of the world, just as it is. 

A few years back I got to spend a weekend with Richard Rohr and a small group of friends. 

We’d sit and listen to him teach for hours. When we’d ask questions, he’d compose contemporaneous mini-essays on the spot.

One of the questions must have been about this exact thing—about how to accept the world with all its inequality and violence and struggle. In his uniquely sincere and earnest tone he answered: 

“You have to forgive the world for being so stupid!”

That doesn’t mean you stop trying to make things better. It just means accepting that the incurable wound really is incurable.

That for better or worse, that’s the nature of things.

Or as Rohr often likes to put it, using a phrase you could only say with conviction from a solid grounding in the second half of life:

“Everything belongs.”

3. Third is the shift into full belonging.

As you allow yourself to be exactly who you are, and allow the world to be exactly as it is, you start to feel how you naturally fit into the whole pattern of things.

Your gifts. Your needs. Your presence.

Depth psychologist Bill Plotkin describes it as discovering your “ecological niche.”

Just like the foxglove blooming in its unique nook of the forest, you can finally give yourself fully to the world. And you can finally receive all the world offers you.

This is the great homecoming.

It’s what your longing has been calling you towards all your life. As Mary Oliver put it in her most famous poem:

Whoever you are, no matter how lonely,
the world offers itself to your imagination,
calls to you like the wild geese, harsh and exciting—
over and over announcing your place
in the family of things.

None of these shifts are immediate, or even complete. You’ll still have moments of self-judgment and being fed up with reality.

But the center of gravity has shifted. 

Instead of getting acceptance and belonging only in glimpses, they become the default you return to.

They become home.

“Only your footprints are the path…”

My goal in writing this isn’t to hurry you into the second half of life. 

In part because I don’t think that’s possible. Our stories unfold on their own timelines. 

But also because the first half is equally good and important.

I’m writing this so that if and when your life hits a dead end, hopefully you can have some reassurance that not only is there life beyond it, but it’s the very life you’ve been longing for all along.

This journey isn’t strictly chronological. You don’t have to hit a certain age before you’re eligible. But nor does getting older guarantee entrance.

And it’s not linear, either.

If your path is anything like mine it’ll probably be circular and frustrating and uncharted. Like the poet Antonio Machado said:

Walker, only your footprints
are the path, and nothing else.
Walker, there is no path.

So if you ever find yourself stuck, confused, unsure where you are or which way to go, please remember that you are not alone. 

Being occasionally lost is one of the defining features of a well-lived life.

If you could use a little accompaniment on this leg of your journey, book a coffee session with me and together we’ll take a compassionate look at where you are, and which next steps are yours to take.

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