Holy Fools 2026
I’ve always known Diana Chapman to be a Holy Fool.
And it was clear that Chip Conley is as much of one as I am…
just with a bigger budget.
Our conversation was wide-ranging, and the feedback said it better than I could:
“Oozing with wisdom.”
“Great stories.”
“Made my day.”
“Fun, insightful, encouraging.”
“It went deep… and still had a lightness.”
One person asked for more about “the thread”—
and the William Stafford poem I mentioned:
“There’s a thread you follow. It goes among
things that change. But it doesn’t change.
People wonder about what you are pursuing.
You have to explain about the thread. . . ‘
It reminded me what my teacher, Angeles Arrien, used to say to me:
“I love watching you create. You pull on a string, and you pull, and you pull, and you pull… and out comes a hippopotamus!”
That’s the Holy Fool path.
Sometimes the hippo is a dream realized.
And sometimes it’s a public failure of mammoth proportions.
Chip and I talked about both.
What If There’s Nothing to Figure Out
I enter the New Year with a double whammy: a birthday and a new year—both of which can throw my Capricorn mind into overload with all that might be possible if I could just FIGURE IT OUT.
After all, the war cry of the Capricorn is:
“There’s a harder way to do this, and I’ll find it—even if it kills me!”
This pattern is deeply embedded, and I tend to succumb to it before the wiser part of me steps in to remind me of something my great teacher Angeles Arrien often said:
Each day there are two plans.
My Plan.
And the Mystery’s Plan.
I’ve lived enough life to know that the Mystery’s Plan is always the higher road—designed for greater freedom, deeper joy, and a more truthful expression of who we are.
That understanding gave rise to a new program—one that opens us to the Mystery’s Plan.
Is Your Story — Told or Untold — Holding You Back from a New Story?
I’m writing to you today in service of better stories — yours, mine, and the ones we’re here to co-create. After all, the subtitle of my book Transformational Speaking is: If you want to change the world, tell a better story.
Oh, the stories we tell!
- There’s the “signature story” we tell from the platform that defines us (and can become the very thing that holds us back.)
- There are the stories we hold in silence and are afraid to speak. They need to be told — not to an audience, but to someone who can truly hear us — so we can heal and move forward.
- And then there’s the new story, beckoning us to the possibility that awaits.
Recently I heard from two clients — both from 2015 — whose stories are changing. Our renewed connections reminded me of the deep privilege it is to witness new stories as they begin to take form and how agonizing that process can be. We’re attached! These stories — and the identities they’ve shaped — have often carried us to the pinnacle of success. So why must they change just when we think we’ve arrived?! (And really, how could we ever “arrive” when life itself is in constant motion?)
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