Midlife as a Beginning, Not an End

Making the pivot from "climbing" to a life of wisdom, depth, and meaning

The Trappist monk and mystic, Thomas Merton, famously said that midlife can feel like climbing a ladder and then realizing, when we get to the top, that it has been leaning against the wrong wall.

This unsettling realization can strike in many ways: when the hard-earned position doesn’t satisfy as you hoped, when a milestone birthday feels more like aging than maturing, when the financial windfall that was supposed to “set you for life” only makes you more anxious, or when a warm family gathering leaves you haunted by the sense that the most important people and moments have quietly slipped past you.

So many professionals, men especially, spend the first part of life building, striving, proving, and achieving. Then our inner critic whispers:

Is this all there is?
Is it all for nothing?
Have I been getting it wrong?
Will my life matter in the end?

Such questions can feel threatening, but they can also be the doorway to a deeper life. Midlife does not have to be the slow decline we imagine it to be. It can also be an invitation - even a summons from God - to shift from one version of strength to another, from one mountain to a higher and better one, and from one fragile identity into a truer and sturdier one.

Arthur Brooks: From Ambition to Wisdom

Harvard social psychologist and “Professor of Happiness,” Arthur Brooks, in his book From Strength to Strength, describes this midlife pivot with hopeful clarity:

“At some point, each of us starts to sense a new calling: to move away from the rewards of success and toward the rewards of meaning. From chasing after recognition, to seeking after wisdom. From grasping, to giving. From self-improvement, to self-giving love.”

The goodness of the first half of life is about growing, building, and contributing. As people created in the Image of God, we need this not only for a sense of purpose but also to steward the gifts and capacities God has given us.

But Brooks reminds us that life’s second half brings a different kind of strength: the kind that prefers depth over expansion and wisdom over hustle.

The apostle Paul - a very accomplished career man in his own right - wrote to the Philippians, “Whatever were gains to me I now consider loss for the sake of Christ. What is more, I consider everything a loss because of the surpassing worth of knowing Christ Jesus my Lord” (Philippians 3:7–8).

This is not Paul resigning himself to “the way things are.” Rather, it is Paul awakening to his true purpose in life - a joyful, hopeful midlife realization that what matters most is not the name he makes for himself, but the meaningful life God has given him.

---

This publication is free to all, and sustained through reader support. If you wish to support Scott Sauls Weekly and receive bonus content:

---

David Brooks: The Second Mountain

David Brooks - no relation to Arthur - offers another picture in his book The Second Mountain. The first mountain, he says, is about building an identity and chasing success. But the second mountain is about something deeper - service, covenant, and love. As he puts it:

“The first mountain is about building up the self, establishing your identity, pursuing happiness and success. But at some point, you realize that joy is on the second mountain. The second mountain is about losing the self in service, in covenant, in love. It’s about pouring into others, and in so doing, finding a deeper and truer self.”

The second mountain is where the fulfillment we’ve been seeking through achievement finds a better, more durable home. It is where ambition is redefined and given new direction. It is where the anxious chase for significance is answered in the freedom of self-forgetfulness.

Tim Keller: Freedom in Self-Forgetfulness

Tim put it well in his little book called The Freedom of Self-Forgetfulness:

“True gospel humility means I stop connecting every experience, every conversation, with myself. In fact, I stop thinking about myself altogether. The blessed rest that only self-forgetfulness brings is not thinking more of myself or less of myself, but simply thinking of myself less.”

The midlife pivot can be summed up this way: it’s not about climbing higher, but about sinking deeper - into God’s love, into the embrace of our family’s desire to have more of us, and into our neighbor’s need that we are able to help meet.

It is an invitation to stop striving for validation and to begin living in the freedom that, in Jesus, grace has already covered us, holds us, and declares us fully approved by God.

Companions for the Journey

Earlier this year, I wrote about the rare gift of having friends in midlife - friends who know both the thrill of the climb and the frustration of its limits. Friends who understand that the gift of midlife is not less ambition, but redeemed ambition.

I have had the privilege of seeing this embodied in the Sycamore Community, a gathering of high-capacity leaders, entrepreneurs, creatives, and influencers from the Nashville area - people who, on paper, have achieved much. In Sycamore, we come together not to compare résumés or trade strategies and success hacks, but to ask deeper questions about life, legacy, love, and what it means to live well in the second half of life.

Our first year was deeply meaningful, and was among the most life-giving experiences of our thirty year ministry. And this coming Tuesday, August 26, we begin Year 2.

Please pray for us!

Over forty leaders - some returning and some new - will again gather monthly at Donald and Betsy Miller’s carriage house in Green Hills to eat delicious food, enjoy deep connection with each other, and consider the claims of Christ on every area of life.

I feel deep gratitude and eager anticipation for the conversations, friendships, and growth that await us in the year ahead. My optimism rests not only on the richness of last year’s experience, but even more on the witness of Scripture itself.

Scripture is full of reminders that the second half of life can be the most fruitful half. Moses was already in midlife when God called to him from the burning bush. Abraham was seventy-five when God told him to leave his country and promised to make him the father of many nations. Sarah laughed when she heard she would bear a child in her old age, but her laughter turned into joy. Caleb, at eighty-five, declared, “I am still as strong today as the day Moses sent me out… Now give me this hill country that the Lord promised me that day” (Joshua 14:11–12).

Wisdom vs. Irrelevance

Midlife, then, does not have to be a slow and defeating descent into irrelevance. It is instead meant by God to be life-giving ascent into wisdom. It is the time of life where fruit ripens, where seeds that have been planted for many years start to reap a harvest, and where the story of our lives shifts from mostly striving to mostly abiding, and from mostly achieving to mostly giving back.

Jesus himself said, “I have come that they may have life, and have it to the full” (John 10:10). That fullness is not found in clinging to the first mountain, but in embracing the second one.

Midlife is God’s gracious invitation to shift: from ambition to wisdom, from accumulation to generosity, from proving ourselves to becoming ourselves, and from independence to interdependence.

This shift is not the end of our story but, God willing, it is instead the beginning of its richest chapters.

As I look toward what lies ahead - with Sycamore, with the friends I get to journey alongside in this new season, and with the disruptive yet gracious and steady work of God in my own heart - I feel gratitude.

Gratitude for the past.
Gratitude for the present.
Gratitude for what is to come.

Because in Jesus, every ending is also the beginning of something new. And that, it seems to me, is the true gift of midlife - and for that matter - all of life.

How Can I Encourage You?

For speaking inquiries, leadership coaching, or team enrichment, visit scottsauls.com.