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.
Holy Fool Wisdom Nuggets
- The Holy Fool is the one who sees differently, who refuses to play the usual game, and so becomes the bearer of new wisdom.
- Learn how to alchemize gravitas and levity!
- Failure is part of the deck stacked against all humans. If we are going to be fools anyway, why not be a holy fool in service of something that matters?
- If where you are doesn’t make your heart sing, something is saying, “Come on, let’s play! Try this. Why not?”
- The thing you didn’t do but wish you had is twice as painful as the thing you did and wish you hadn’t.
- Failures are just noble experiments.
- Get a sense of humor. Things don’t always work out. If you lay an egg, step back and admire it.
- They say there’s a light at the end of the tunnel, but sometimes it is a really long tunnel.
- The most important question is, “Do you love doing it?” Then, “Does the world need it, too?” If you really love it and you deeply believe that people are being transformed by it and the world needs it, you persevere.
- There is a thread that moves through our lives that is so individual, yet the culture is always trying to co-opt it. But that thread is what enlivens [and emboldens] us.
- The Holy Fool gets over trying to look good because there are lots of times we don’t.
- Our painful life lessons are the raw material for our future wisdom.
- More play, less proving.
- Being wise and foolish at the same time are two sides of the same coin.
- Our to-do list is always outdated. What about the to-be list?
- Become a first-class noticer and observer of yourself.
- Angeles Arrien’s wise counsel “don’t push, don’t hold back” became my mantra. It opened the field to look for what was coming to me that I would otherwise have missed with tunnel vision toward a goal.
- Sometimes our plans get in the way. Relax the plan and invite life.
- Take one step toward something you’d like to explore. If it ends badly, you’ll have a great story to tell at Transformational Speaking!
- We’re all grappling with really big questions not only personally but collectively. When we don’t know what to do, ask: Who are we to be?
- Our answers are in the unseen as much as the seen, and that gives me great hope.
- Anticipated regret is a form of wisdom. Ten years from now, what will you regret if you don’t learn it or do it now?
- So anticipate what you might regret, whether that’s a societal action you can influence or a personal mission you want to do.
May this conversation ignite your Holy Fool to live the life you came to live and express the Medicine that you and only you can bring to the world!
© 2026 Real Speaking LLC
If you want to explore your own thread and listen for where it is leading you now—
we have one spot left in the April 20–24 Transformational Listening Playground
at Rising Circle Ranch in Santa Fe.
Or connect with me here and we can talk.
And if the Holy Fool in you is alive and well and says, Do it!
Trust that impulse. That is the voice of aliveness in you, reminding you there is more.
So much more.
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