Midlife: Anyone Interested?

What if we crossed the midlife threshold together?

TL;DR:

tl;dr: Midlife is not just a crisis. It is a rite of passage. Tuesday and I are exploring the idea of hosting a retreat for those navigating the unraveling and re-forming that happens in the middle of life. We’re not selling anything yet. We just want to know: Is there interest? Who’s out there ready to walk this passage in community instead of doing it alone?

For those of you that know and love our work, we ask that you please take a moment to share this probe with other people who will find it resonant.

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We spend the first half of life building our ladder of success, making our way up a wall of what we believe really matters… only to discover, in the second half of life, that our ladder is leaning against the wrong building.

If the words above resonate… if they make any sense to you… you are probably already here. You are probably hearing a voice inside you say:

“Wait a minute, I thought this would feel different.”

Brené Brown focuses on our emotional development, and she uses much starker terms:

We all grew up and experienced varying degrees of trauma. Disappointment. Hurt. Hard stuff.

We armored up, and at some point that armor no longer serves us. The weight of the armor is too heavy, and it’s not protecting you. It’s keeping you from being seen and known by others.

This is the developmental milestone of midlife. This is when the universe comes down, puts hands on your shoulders, pulls you close, and whispers in your ear:

“I’m not fucking around. You’re halfway to dead. The armor is keeping you from growing into the gifts I’ve given you. That is not without penalty. Time is up.”

So this is what you see happen to people in midlife. And it’s not a crisis. It’s a slow, brutal unraveling. This is where everything that we thought protected us keeps us from being the partners, the parents, the professionals, the people that we want to be.

Our Experience of the Midlife Portal

I used to own the domain name: somethinghappensinourforties.com.

I just felt like we had so much to say about it. Like the forties were the biggest deal and no one was saying much of anything about it. Nothing beyond “crisis” and “slower metabolisms.”

Tuesday (my wife!) and I experienced our lives unravel in our 40s. It was like everything we thought we were was breaking into a thousand pieces.

It was the hardest time.

It was a beautiful time.

It was everything.

Painful. Chaotic. Liberating.

It was not fully in our control. But it definitely demanded choice.

It demanded hard choices. Choices that had impact well beyond us. Choices that brought pain on the people that we love the most.

It was a devastation.

And it was a birth.

It was an initiation.

We thought we could host a great podcast about the process. We even interviewed some remarkable people. But we never launched. It was not time yet.

And now we are in our fifties!

As we moved through our own unraveling, we began to notice how this personal pattern mirrors what’s happening at the collective level.

We’re looking around and we’re noticing a few things.

Things are falling apart.

And here I’m not just referring to the natural breakdowns that come with entering our middle age.

Here I am talking about the metacrisis. The “crisis of crises.” From the rise of authoritarianism to ecological collapse. From technological disruption to economic fragility. From mental health epidemics to polarization to the erosion of trust, and spiritual disorientation.

Things are falling apart.

And there is a dearth of wisdom and elders.

We find ourselves in agreement with Bill Plotkin’s assertion that we live in an adolescent culture.

We have a dismally low number of mature, soul-initiated adults among us. But we don’t even have a process to enter and move through the middle part of life.

We feel the longing for true elders. But we have to move through midlife first.

We are looking around and asking ourselves a couple of questions:

• How can we share what we are learning?

• Why are people doing this midlife thing alone?

• What are we each learning that we can share with each other?

So what we are doing here is sending a small flare to see who else is out there. We are listening for those who feel called to walk through midlife together.

Every time I talk to someone about it, they say: “Yes, please sign me up.” And we want to find out how true that is.

So here we are testing the waters:

• Are you someone who would sign up for a workshop to help you navigate midlife?

• Do you want to be in community with others who are going through some version of what you are going through?

• Do you want to feel supported as you work through some of the scariest questions that come up in a human life?

• Do you sense that there is another way of being that is becoming available to you now?

• Do you long to let go of old ways of understanding and acting in the world?

• Are there long held habits of thought and behavior that no longer apply? That you can no longer tolerate?

• Is there something opening up for you now that you can’t quite explain but you know you want to trust?

Because the way Tuesday puts it:

Midlife is not just a NO but also a powerful YES. Even if we don’t know what we are saying yes to just yet.

Sign up here to let us know you are interested. This is not yet a formal commitment. We just want to find out if we should take the next step and go ahead and schedule this workshop.

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Please do share this probe with friends and people you care about.

(Our friends help us tell signal from noise)

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The way we are thinking about it is as a retreat. Summer of 2026. Likely five days long. Deep. Intensive. Not a small commitment. Something transformational.

We are drawing on 20 years of experience designing and facilitating transformational immersions for leaders around the world.

We are conjuring a workshop that will help you:

• Shed outdated identities. Release the “armor” that once protected you but now limits growth, authenticity, and intimacy.

• Navigate the midlife initiation consciously. Recognize midlife not as a crisis but as a rite of passage. As a descent that leads to wisdom.

• Find permission and courage. Affirm that breakdowns and unravelings are necessary for authentic transformation.

• Discover a deeper “YES.” Notice what is emerging as old ways and patterns fall away.

• Integrate through practice. Learn tools to help you live from presence and wholeness rather than fear or old conditioning.

• Belong in shared experience. Be in community with others walking through midlife. We were never meant to do any of this alone.

The fact is that if we are lucky… if we are blessed… then in the first half of life we get to do what the world teaches us to do: we build. We create an identity, we pursue success, we establish our place in the world.

We construct the outer architecture of our lives: the career, the family, the house, the reputation. We believe this will bring us peace.

Richard Rohr calls this the necessary work of the ego: building the container that can hold a life. David Brooks calls it the first mountain. The mountain of accomplishment.

It is not wrong; it’s just incomplete.

Inevitably, something shifts. Loss and failure. Including moral failure, which I know too much about.

There is disillusionment, or just exhaustion. And these reveal that the very structures that once held us are now the walls that confine us. The story that once gave us purpose begins to feel too small.

Rohr calls this falling upward. The paradox that descent is the path to wisdom. Brooks calls it the valley. The space between mountains, where the old self dissolves and a truer one begins to take form.

In the second half of life, or on the second mountain, we discover a different kind of freedom. We are no longer driven by achievement but drawn by meaning. We give ourselves to relationship, vocation, community, and spirit. Our fulfillment no longer depends on what we build, but on how deeply we belong. It is here, beyond striving, that a quieter joy and a more trustworthy sense of purpose finally take root.

We live in times that demand grown adults, mature adults. Not old people trying to look young. Millennia of human evolution have given us this rite of passage. This potent space for transformation. This time somewhere between being a grown-up and becoming an elder.

Original cultures around the world have always known how to honor the process.

It is not easy. But it is glorious.

It is the passageway to who we are here to become.

And there is no need to do it alone.

Consider joining us.