Why Your Biggest Failures are Actually Upward Moves: 5 Surprising Truths About the "Second Half" of Life

 1. Introduction: The Universal Stumbling Stone

Most of us spend the first half of our lives on a high-speed "cruise control," meticulously maintaining a performance designed to convince the world—and ourselves—that we have it all together. We build our egos like skyscrapers, chasing accolades and security, following a script of upward mobility that promises peace if we only "do it right." But eventually, we all encounter the "absurd stumbling stone": a situation we cannot fix, control, explain, or outsmart.

In our performance-driven culture, we view these moments of failure or suffering as dead ends. However, a deeper spiritual wisdom suggests a radical paradox: falling down is often the only way to move truly "upward." This is the core of the "Hero’s Journey"—not a straight line to the top, but a necessary descent into the depths before a true ascent can begin. We move from an egocentric survival to a soul-centric thriving only when we stop trying to win and start learning how to lose.

2. Takeaway #1: The Architecture of "Falling Upward"

There is a fundamental shift that occurs between the morning and the afternoon of a person’s life. As psychiatrist Carl Jung noted, "One cannot live the afternoon of life according to the program of life’s morning." The first half of life is necessarily devoted to forming a healthy ego—the container or "raft" intended to carry us through a dysfunctional world. The second half, however, is about the courage to go inward and let go of that very container.

We often resist this transition because our culture treats failure as a lack of cleverness. In reality, hitting "some kind of bottom" is the prerequisite for the spiritual journey. What feels like a catastrophe to the ego is often the necessary foundation for the soul.

The bottom line of the Gospel is that most of us have to hit some kind of bottom before we even start the real spiritual journey... The falling became the standing. The stumbling became the finding. The dying became the rising. — Richard Rohr

3. Takeaway #2: Your Ladder Might Be Leaning Against the Wrong Wall

Many of us spend decades successfully climbing the ladder of achievement, only to find, as Thomas Merton famously suggested, that the ladder was leaning against the wrong wall all along. This is the crisis of the "false self"—the collection of roles, titles, and mental attachments we mistake for our absolute identity.

Growth in the second half of life is not about adding more to our resumes; it is what Paulo Coelho calls an "un-becoming." It is the process of shedding our relative identity—who we are in relation to our jobs, our status, and our parents' expectations—to find our absolute identity as we are known by the Divine. We must surrender the "passing shell" of the ego to find the "pearl of great price" hidden within. It is a Great Emptying that makes room for a Great Outpouring.

4. Takeaway #3: True Power is "Off-Script"

The trial of Jesus offers a sharp contrast between two types of power. On one side is Annas, the former high priest, who wields "soft power" through defensive secrecy. His authority is fragile, propped up by a late-night, "black site" interrogation style that circumvents the law to protect the status quo. His power is a performance fueled by deep-seated anxiety.

Jesus, however, demonstrates an "inherent authority" that is entirely "off-script." He refuses to play the game of surreptitious interrogation because he is governed by mission rather than fear. While Peter initially attempts to use "retaliatory violence"—acting as a "willing weapon" with his sword in the garden—Jesus chooses vulnerability as his strength.

To move into the second half of life, we must stop being "weapons" (defensive, judgmental, and coercive) and become "witnesses" (candid, open, and governed by integrity). True power is the courage to remain governed by truth even when it leads to the cross.

5. Takeaway #4: Balance is Learned by Falling Off the Bike

We grow spiritually more by "doing it wrong" than by "doing it right." Just as a child learns the physics of balance by repeatedly falling off a bicycle, we learn spiritual resilience through our mistakes.

Those who have never allowed themselves to fall are actually "off balance" without realizing it. Because they have never faced their own limitations, they often become judgmental and fanatical. As Richard Rohr points out, such people often become "elderly without being elders"—they have aged, but they haven't matured into the compassion that only failure can teach. Mistakes are the building blocks of a life-giving perspective; they make us "hard to offend" and easier to live with.

You learn how to recover from falling by falling! It is precisely by falling off the bike many times that you eventually learn what the balance feels like. — Richard Rohr

6. Takeaway #5: The "I Am Not" Identity Crisis

When Peter stands by the "charcoal fire" (Greek: anthrakia) during Jesus’s trial, he is in a "fire of fear." When asked if he is a disciple, he repeatedly says, "I am not." This "I am not" identity stands in stark contrast to Jesus’s centered "I am." It is here we meet what Jung called the "shadow"—that "another whom we do not know" who speaks to us when our performance fails.

Linguistically, the word anthrakia appears only twice in the New Testament: once at Peter's denial and once at his restoration by the risen Jesus on the beach. This tells us that our failures are not final; they are the exact locations where our healing will occur. We are often "wound identified," using our victimhood as a ticket to sympathy. However, the path of the second half of life is to transform these "shadows of our own making" into "sacred wounds" that liberate us and others.

7. Conclusion: The Hero's Journey Awaits

Everything we have experienced until now has been mere preparation. The successes and the crushing failures of the first half of life were simply the construction of the "raft." The tragedy of many lives is that they fall in love with the raft and never step onto the shore.

When the ego is finally emptied, God—like nature—rushes to fill the vacuum with a "Great Outpouring." This is the "sacred dance" of the Trinity, where power is no longer hierarchical or dominating, but circular and shared. In this state of flow, our driving motives are no longer money or approval, but a state of divine union.

Resurrection is only possible after we have "died" to the false self. As you consider your own path, ask yourself: What are you going to do with your now resurrected life? Or, as the poet Mary Oliver famously asked, “What is it you plan to do with your one wild and precious life?”

Following Jesus: Making Mistakes

Today we make a huge leap in John. Five chapters from Chapter 13’s reading last week of Jesus washing his disciples feet. To chapter 18, today. In these chapters between, Jesus offers his final words to his disciples, where he literally tells them goodbye. It’s where we see Jesus at his most pastoral: as friend, mentor, teacher, lover. The relationship between Jesus and his disciples - the mutual relationship between them - has deepened over the first half of John. This first half spans three years of their life together. The second half of the gospel of John will span one week. 

Most, if not all, of these stories in the second half of John are typically read during Holy Week. But, in this fourth year of the narrative lectionary, we slow it down. Dramatically. Stretching out each of these scenes that we call the passion of Jesus. The suffering of Jesus. We dive deeply into each one of them. As we try to make meaning from them for our own lives.

Then the company of soldiers, the commander, and the guards from the Jewish leaders took Jesus into custody. They bound him and led him first to Annas. He was the father-in-law of Caiaphas, the high priest that year. (Caiaphas was the one who had advised the Jewish leaders that it was better for one person to die for the people.)

Simon Peter and another disciple followed Jesus. Because this other disciple was known to the high priest, he went with Jesus into the high priest’s courtyard. However, Peter stood outside near the gate. Then the other disciple (the one known to the high priest) came out and spoke to the woman stationed at the gate, and she brought Peter in. The servant woman stationed at the gate asked Peter, “Aren’t you one of this man’s disciples?”

“I’m not,” he replied. The servants and the guards had made a fire because it was cold. They were standing around it, warming themselves. Peter joined them there, standing by the fire and warming himself.

Meanwhile, the chief priest questioned Jesus about his disciples and his teaching. Jesus answered, “I’ve spoken openly to the world. I’ve always taught in synagogues and in the temple, where all the Jews gather. I’ve said nothing in private. Why ask me? Ask those who heard what I told them. They know what I said.”

After Jesus spoke, one of the guards standing there slapped Jesus in the face. “Is that how you would answer the high priest?” he asked.

Jesus replied, “If I speak wrongly, testify about what was wrong. But if I speak correctly, why do you strike me?” Then Annas sent him, bound, to Caiaphas the high priest.

Meanwhile, Simon Peter was still standing with the guards, warming himself. They asked, “Aren’t you one of his disciples?”

Peter denied it, saying, “I’m not.”

A servant of the high priest, a relative of the one whose ear Peter had cut off, said to him, “Didn’t I see you in the garden with him?” Peter denied it again, and immediately a rooster crowed.

I’d like you to visualize a place for just a moment. It’s a happy place - the place where you feel most loved and accepted. A place where you are surrounded by those who are your closest friends and family, with whom you have the deepest of relationships. It’s also a beautiful place, a garden that has the loveliest of flowers and green trees. A place that seems Eden-like. Where, when the breeze blows you can hear it gently moving through the leaves of the trees. And feel it cooling your skin. Where, with your loved ones, led by a beloved mentor, you’re able to talk about the most important things of life- to learn from one another. The most stunning thing about this is that you have come to the realization that this mentor, this teacher and shepherd, is God in the flesh.

Now imagine that, one day, while you are there together, one of your group suddenly shows up with a cohort of nearly 600 soldiers, who’ve come to arrest your beloved mentor and teacher. Can you imagine the emotion in that moment? The hurt and the betrayal you feel? The anger that begins to burn inside you? Can you feel the fear in your gut, as you watch him taken away, wondering if you’re next? But, then, your mentor, who seems completely in control of this situation, steps in and convinces the soldiers that he is the one they want. “I am he,” he tells them. Not once, but three times. He convinces them to leave everyone else behind. They take him away. And all the others leave. Except for you. And one other disciple.

You’re name is Peter. That’s right. Peter. Petros. Meaning rock. You don’t know it yet, but you are the one who will become an important leader in building similar communities. These will be so different from other communities in the world, because they will be open and accepting of everyone. A place of deep love and intimacy. Just as you experienced that first time. Communities so countercultural that, in fact, you will lose your life, killed by a world that resists the transforming power of love.

But, you’re not there yet. Because you have mistakes to make. A huge mistake, really, that will make you feel ashamed. For which you will grieve deeply. But, it is a mistake for which you will be forgiven and that will change you in ways you cannot yet fully understand.

That day, friends, after the incident in the garden, Peter and and the other disciple followed Jesus to the home of Annas, then to Caiaphas. Two trials are interwoven in the story of that day. One trial is that of Jesus. But, the other is that of Peter. The disciple in last week’s story who, first, refused to have his feet washed by Jesus. But, then, quickly was “all in.” 

We see these two stories interwoven in our text today, which begins with Jesus being questioned by Annas, a former high priest. Outside, at the same time, another story is taking place. Peter is being questioned about who he is. Three times he’s asked, “Aren’t you one of his disciples?” 

But, back inside, when Jesus is asked about who he is and what his teachings are, he says, “Ask those who heard what I told them. They know what I said.” We see that statement being fulfilled outside. Where Peter, the prime apostle, is being questioned about Jesus at that moment in the courtyard. Here is his big chance. But, instead of confessing Jesus, he denies him. And, particularly, denies that he is a disciple of Jesus, thus, denying his own identity.

Who are you in this story? This story holds a mirror up to each one of us. 

Are you Jesus, willingly being arrested, knowing what is to come? That’s perhaps a little doubtful. But, if you think you are living as Jesus would, perhaps, it’s time to look more deeply inside yourself. At the hubris that exists within you. 

Are you Peter, the disciple that is “all in”? Well, most of the time. But not when it really counts. Who, when the pressure is on, denies his own discipleship of Jesus. His own identity as a follower and seeker of Jesus. Now, for some of us, that’s maybe more likely.

Or are you, perhaps, Annas or Caiaphas? Religious leaders that are so concerned about protecting established religion, established denominations, that they are in danger of denying the very essence of what worship of God is all about. I wonder who of us are guilty of this?

And there’s one more character. The unnamed disciple with connections. Who is able to accompany Jesus, but unable to - or unwilling to - stop what is happening or what will come. To change the outcome.

Perhaps there’s a bit of all of these characters in us. We try to be like Jesus, but are often more like Peter. Or the unnamed disciple. Or like Annas and Caiaphas. 

This is who we are. This is what we do. We try. But we make mistakes. Big ones at times. Denying our own identities in Christ. Unable to fully follow him. Hung up on the trappings of religion so that we lose sight of what it really means to worship God. 

The thing is God knows this. God knows that this is who we are. That we cannot do this alone. That there are deep gaps in our own ability to do this. Not that we don’t try to follow and continuously seek out Jesus. But, that there are times and places where we fail. Mistakes. Gaps. 

God fills in those gaps. And only God can fill in those gaps. Fully. This God we follow, mistakes and all. Who overflows with grace. Who is rich in love. For us. Who fills in the gaps and smooths over our mistakes. And who welcomes us back to that garden. That place of deep relationship and belonging. That place where we might have abundant life. Now. And later. Scars and all.

Thanks be to God!

Preached March 20, 2022, at Grace & Glory, Prospect, with Third, Louisville, and New Goshen Presbyterian, Prospect.

Third Sunday of Lent

Readings: John 18:12-17, Psalm 17:1-7