Midlife has a way of renegotiating those terms. It’s the time our primary operating system moves from the ego to the soul, yet no one gives us operating instructions for this middle-aged shift.
Somewhere along the road, life began offering me what my dear friend and teacher Richard Rohr once described with a mischievous smile: “We aspire to one humiliation per day—hopefully mild.” At first, I resisted that framing. Humiliation didn’t sound like spiritual progress. It sounded like failure.
But I’ve come to understand what Richard meant. These small, daily humblings aren’t about shame; they’re about surrender. They’re gentle reminders that I’m not the center of the universe—and that’s not a loss, it’s a relief.
Humility, I’ve learned, isn’t thinking less of yourself. It’s thinking of yourself less. It’s recognizing that wisdom often enters through listening, not speaking. That grace shows up when we stop performing and start allowing. That the most meaningful moments in life rarely announce themselves with applause.
As my ego has softened, something quieter—and far more resilient—has taken its place. A deeper appreciation for not knowing. A growing comfort with being ordinary. A willingness to apologize without defending. To ask for help without embarrassment. To be moved rather than admired.
This shift hasn’t made my life smaller. It’s made it more spacious.
Grace, for me, now looks like showing up without needing to win. Like choosing presence over polish. Like allowing my rough edges to remain visible, trusting they’re part of what makes me human, relatable, and real.
I still have an ego. I probably always will. But it no longer gets the final word. Increasingly, I’m guided by something gentler and wiser—a beautiful soul that knows life isn’t about proving our worth, but about expressing our love.
And if I’m lucky, tomorrow will bring another mild humiliation… and with it, another chance to grow.
-Chip
P.S. Speaking of beautiful souls, my favorite Midlife Chrysalis podcast episode of 2025 was my conversation with Ricky Williams, the former Heisman Trophy winner and NFL great, who marched to his own drummer. Imagine spending Super Bowl evening this Sunday with Ricky and me at our Santa Fe campus this weekend as his workshop Evolving Identity: Learning How to Let Go starts and runs from Feb 8-12. Ricky, now known as Errick, has become one of the world’s leading evolutionary astrologers, quite a shift from where he was years ago.