Is Your Ladder Leaning Against the Wrong Wall?

Since the summer of 2024, I’ve had the privilege of mentoring and shepherding a cohort of over thirty remarkable leaders called The Sycamore Community. These are high-capacity, high-responsibility individuals who are navigating the complexities of leadership while pursuing health and thriving—not just professionally, but also spiritually, emotionally, at home, and in friendship.

At the heart of our work together lies a single, grounding question:

What does it really mean to succeed?

Thomas Merton once offered a haunting warning that echoes through the lives of many leaders:

“People may spend their whole lives climbing the ladder of success only to find, once they reach the top, that the ladder is leaning against the wrong wall.”

This isn’t just a clever metaphor; it’s an unsettling truth. We pour years of energy, sacrifice, and striving into our ambitions, chasing rewards we believe will bring us fulfillment. Yet when we achieve our goals, hit our numbers, and reach the top, we’re often met with an unexpected hollowness. In the zealous pursuit of success, we can lose focus on what matters most—our souls, our relationships, and the kinds of people we are becoming.

Merton’s words compel us to pause and ask another critical question:

Where is my ladder leaning?

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The Allure of the Wrong Wall

From an early age, we’re taught by parents, teachers, professors, and mentors to measure success by what we achieve. Without realizing it, we are programmed to show up in the world less as human beings and more as human doings. Promotions, accolades, financial stability, and influence are celebrated as the markers of a life well-lived. They are the rungs of the ladder we’re told to climb, reinforced by a culture that glorifies hustle and rewards ambition.

And for a time, the climb seems worth it. Though fleeting, each step brings a sense of accomplishment—a bigger title, a higher salary, or a moment of applause. But as the ladder grows taller, the climb becomes heavier, and the view lonelier.

The allure of success is powerful, but it can also be deceiving. The rewards it promises—fulfillment, security, joy—are often temporary. Worse, they can blind us to the cost of the climb. We sacrifice relationships, compromise our values, and exhaust ourselves in pursuit of goals that were never designed to hold the weight of our deepest hopes.

Jesus captured this tension with a piercing question:

“What does it profit a man to gain the whole world and forfeit his soul?” (Mark 8:36)

The wrong wall isn’t always obvious. It might look sturdy, even admirable, from the outside. Unlike other addictions, workaholism is often celebrated and rewarded, rather than confronted and treated. But over time, the cracks begin to show. We wake up restless, despite achieving what we thought we wanted. We tell ourselves the sacrifices are temporary, that they’ll “pay off” eventually. Yet “eventually” never seems to come. Relationships grow distant. Joy becomes fleeting. Anxiety and dissatisfaction take their place.

Unchecked ambition often disguises itself as diligence or responsibility, making it hard to recognize. But the fruit it often bears—strained relationships, spiritual emptiness, loneliness, and fatigue—tells the truth. When our days are marked by anxious striving and our nights by distracted distance, it’s worth asking:

What wall is my ladder leaning against?

Signs Our Ladder May Be Misplaced

The signs that our ladder is leaning against the wrong wall are usually subtle. They don’t announce themselves loudly; they whisper.

It might begin with a persistent ache—a quiet sense that something is missing. Achievements that once felt meaningful now seem empty. We rationalize the neglect of our relationships, telling ourselves that the long hours and sacrifices are “for them.” But those same relationships grow strained, and the distance becomes undeniable.

Ambition, when left unchecked, can masquerade as virtue. We tell ourselves we’re being diligent or responsible, but beneath the surface, joy fades. Our identity becomes so entangled with what we do that we no longer know who we are without it.

These are the symptoms of a misplaced ladder: spiritual dryness, fatigue, strained relationships, and a restless spirit. The warning signs are there, quietly urging us to do inventory and consider a change.

Repositioning the Ladder

The good news is this: it’s never too late to reposition the ladder.

Jesus offers us a radically different vision of success—one that doesn’t demand anxious striving or hollow achievements. His invitation is simple and kind:

“Come to me, all who labor and are heavy laden, and I will give you rest.” (Matthew 11:28)

This rest is not passivity. It’s not a retreat from meaningful work or ambition. Instead, it’s an invitation to anchor our lives in something that lasts. It’s about choosing a wall sturdy enough to hold the weight of our hopes and dreams.

But how do we begin?

1. Reevaluate Your Priorities
   Take an honest look at where your time, energy, and affection are going. Do these reflect the values that matter most to you—the ones you hope will define your life? What would change if you lived today with those values protected, nurtured, and not put off to the future?
2. Focus on Lasting Values
   True success isn’t found in the fleeting rewards of the world but in the character qualities that endure: humility, integrity, kindness, and faithfulness. Such virtues are cultivated not through drivenness or anxious striving but through slowing down, stepping back, and making intentional choices that prioritize God, people, and community over “winning.”
3. Prioritize the Practice of Sabbath Rest
   Set aside time to rest and reconnect—with God, with others, and with yourself. Sabbath is more than a break for the body; it’s a reorientation of the heart, renewal of the mind, and care for the soul. It reminds us that our worth is not tied to our work and teaches us to trust that God—not our efforts—sustains us and those we love.

Transformation often begins with a single step. Zacchaeus, the chief tax collector of Jericho, climbed a sycamore tree to catch a glimpse of Jesus. That one small act of curiosity ignited a comprehensive life change. He discovered that his ladder had been leaning against the wrong wall all along. But in Christ, he found joy, purpose, and a new life built on grace (Luke 19:1-10).

The Wall That is Sturdy

What is the right wall to lean our ladders against?

It is the wall built on Christ—the firm and lasting foundation that will never crumble. When our ambitions are rooted in loving God and loving others, everything else—our work, relationships, and pursuits—takes on a deeper meaning. Success shifts from being about personal gain to being about service, stewardship, and reflecting the character of Jesus. The wall built on Christ does not diminish our ambition. Far from it. Rather, it redeems our ambition and ensures its sustainability and flourishing. Stress is transformed into service, drudgery into delight, and emptiness into meaning.

The apostle Paul captured this perfectly when he wrote:

“I have learned to be content whatever the circumstances. I know what it is to be in need, and I know what it is to have plenty. I have learned the secret of being content in any and every situation, whether well fed or hungry, whether living in plenty or in want. I can do all this through him who gives me strength..” (Philippians 4:11-13)

Paul was ambitious, but his ambition was driven by contentment born from grace, not ego born from insecurity. His ladder leaned firmly against the wall of God’s heart and mission. In doing so, he found freedom—not from effort and hard work, but from striving for a worth that had already been secured for him in Christ.

Imagine reaching the top of your ladder and finding it rests securely against the wall of the truth, beauty, and lovingkindness of Jesus. The view is not lonelier but fuller. The relationships you nurtured remain meaningful. Your work carries lasting significance. And your life is marked, through and through, by grace, truth, and love.

For those who feel they’ve been climbing the wrong wall, take heart: it’s never too late to reposition your ladder. Jesus offers not just rest from striving, but the joy of a life rooted in the stuff that matters and lasts.

May we have the courage to examine where our ladders stand, the humility to move them when necessary, and the wisdom to anchor them in Christ—the only foundation that will never falter or fail.