Emotional Fluency, Wisdom Wells, and Gratitude for Chip Conley

On shadows

“But they make it hard to see,” explained bear.

“Not if you close your eyes,” replied bird. “Not if you close your eyes.”


📷: Shadowbloom and Shadowleaf Black


At first, he introduced me to the mathematics of my emotions – ensuring I was adding + subtracting those things that actually matter, that truly make a difference. And I couldn’t have been more grateful.

Then, he invited me to try an audacious experiment: to see what might happen if I dared to be myself. The final results haven’t been tabulated, but the ongoing returns continue to exceed expectation.

Before the pandemic, he helped me sort through what it meant to be turning 50, flipping tired midlife memes on their head, a rite of passage worthy of van Gennep.

During the pandemic, we did an online happy hour twice monthly. And those conversations kept my spirit buoyed at a time when I felt very alone.

As I wrote the essayettes in my book, on., he was often in my thoughts as I sought to find the throughline of my life, piecing together those stories that connected little me to big me, seeing how all the years fit together.

I’ve known him for over 13 years. And he has no idea who I am.

Chip Conley releases his latest book, “Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age,” on January 16.

And, while I’m excited to read it, I know it won’t be enough. With Chip Conley, it never is.

Why? He’s infectious and honest, charming and clear. His daily Modern Elder Academy WisdomWell emails offer these nuggets you’ll want to tuck away, especially as he shares openly about the relationship he is developing with cancer.

His most recent conversation with my favorite Rich Roll Podcast (episodes 681 + 806) is emblematic of what Chip Conley embodies: what it means to embrace a life of contrasting emotions, moments, truths; to hold these things lightly; to understand that just because something has been doesn’t mean it has to be - you can rewrite the script.

Chip has no idea who I am. And that’s okay. I’m grateful for his companionship and insights over the years, and am hopeful for many more.

Who is someone in your life for whom you are grateful who has no idea who you are?

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Left Turns, Right Turns, and Finding the Space Within

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Layers, Love, and Cooking Casseroles