The Heroic Journey
The Heroic Journey (Adapted from Richard Rohr’s Falling Upward)
For much of the first half of my life, I woke up each morning feeling an unshakable need to justify the very space I was taking up. Like many areas of brokenness in our lives, this feeling wasn’t limited to myself—I unconsciously applied it to others, too.
Each day began as though I was starting with a negative balance in an emotional bank account. The way I handled my morning routine, my commute, my productivity at work—every action either added to or subtracted from my effort to zero out that balance. Rarely did I end the day feeling “in the black.” Occasionally, a major accomplishment—a completed project or reaching a significant milestone—gave me a fleeting sense of relief. But more often, my evenings were riddled with anxiety, second-guessing, and self-criticism. What could I have done better? What did I leave unfinished?
At the core of this mindset was the deeply embedded lie that my value was tied directly to my ability to produce. And it’s no wonder. We swim in the waters of a performance-driven society, where everything we do is graded, tested, evaluated, and rewarded—or punished. Even in our closest relationships, where love is meant to be unconditional, there’s often a nagging thought: “If I screw things up enough, could their good opinion—and their love—slip away?”
This performance mindset drives many of us to extreme lengths, all in the name of being “successful.” Richard Rohr, in his book Falling Upward, calls this pursuit The Heroic Journey.
In the first half of life, many of us are on this Heroic Journey, striving toward some imagined pinnacle of success where we’ll finally feel valuable, accomplished, or “enough.” We are climbing a mountain, determined to reach the summit, which we equate with “arrival.”
But here’s the question: What does “arrival” look like to you? What’s that mental image of finally achieving your goals? For many, this vision drives relentless sacrifices and exhaustive effort. Yet the truth is, very few people ever reach the top.
And for those who attempt this climb, the journey often brings a moment of reckoning—a crisis of limitations. How we respond to this moment determines the path we take:
1. The Old Fool
Some choose to ignore the evidence of their limits, stubbornly pressing on as though they can still conquer the mountain. These individuals keep pushing, working, sacrificing—chasing an ever-elusive dream. They might lose their families, integrity, or health along the way, but they refuse to stop.
Think of someone you know like this. Perhaps they’ve sacrificed everything for their career, their ambition, or some unattainable ideal. No reasoning or evidence can dissuade them from this path.
2. The Embittered Fool
Others respond to their limitations with bitterness, blaming external circumstances for their unfulfilled dreams. These individuals live in a space of woundedness, never moving on or finding peace.
How often do we hear, “I would’ve made it if not for [insert excuse]”? Maybe it’s the high school athlete who insists they could’ve gone pro “if not for that injury.” It’s easy to laugh at these examples, but many people carry deep resentment for the success they never achieved. It’s a miserable place to dwell.
3. The Holy Fool
The third response, and the one Rohr calls us toward, is to become the Holy Fool. This is the person who stops striving to ascend the mountain and instead finds peace in descending it.
Here’s the key: The Holy Fool’s identity is no longer tied to what they do but to what Jesus has already done. They begin what Rohr calls The Wisdom Journey, a shift in perspective that frees us from the relentless pursuit of external validation.
On the Wisdom Journey, we start asking different questions and valuing different things. We no longer need to be the smartest, the best, or the most accomplished person in the room. We are secure enough to embrace insecurity because we know that, in Jesus, we already have everything we need.
This freedom brings rest to our weary souls. It’s what Jesus invites us into when He says in Matthew 11:28–30, “Come to me, all you who are weary and burdened, and I will give you rest... For my yoke is easy and my burden is light.”
When we live from this place of freedom, we experience the joy of living “freely and lightly.”
Questions for Reflection
As you consider your own journey, where do you see yourself today?
How have you responded to moments of limitation or failure in the past?
What would it look like for you to step off the Heroic Journey and embrace the Wisdom Journey?
