The 10 most personal stories on Wisdom Well

At 26, the world was my oyster. To be explored with bluster and boister.

The Dark Night of the Soul was popularized by a 16th-century mystic and Spanish poet who believed that a purification of the spirit comes from facing difficult challenges and surrendering to God’s wishes. In modern, secular times, it is often considered a time when one is going through a series of seemingly-impossible circumstances like the death of a loved one, the breakup of a marriage, or a painful failure.

How does one respond to a cancer diagnosis? For some, it's an all-out war: "I'm gonna beat you, Cancer." For others, it's an acquiescence: "I'm surrendering to you, Cancer… you're bigger than me."

Poop and pop, those are my post-surgery marching orders for the first week after my surgery. All my organs in my prostate zip code are going through some serious “shock and awe” drills which means I careen from constipation to having a very messy sleep - and I thought I was just passing gas all night.

Years ago after one of my every-five-year big birthday extravaganzas, my friend Ben gifted me with the title “Social Alchemist.” He’s right. I’ve spent my life as a mixologist of people as a boutique hotelier, restaurateur and bar owner, as the head of all the global hosts for Airbnb, and as the founder of MEA, a midlife wisdom school dedicated to life-changing conversations.

Last week was a rough one for me. I was a human pin cushion for a few days in San Francisco while I got updates on my prostate cancer.

I might as well have titled this post “Why I Breathe.” Writing has always been foundational in my life, my faithful guide for helping me figure things out—my emotions, attractions, repulsions, and curiosities.

With a twinkle in my wrinkle, I told Ingrid Summerfield I would remember this day for the rest of my life. We were both in Baja just 17 days before she passed away. Ingrid was the one who taught me the hospitality biz. She was a pioneer in seeing the potential of San Francisco's Hayes Valley.

I got to know my great-grandmother for a fraction of a second. My mom’s grandmother, Ethel, was a stately woman, a matriarch who believed that “children should be seen but not heard.” Honestly, I can’t say I remember a conversation with her. And then, poof, she was gone.

This title was the headline of a New York Times story this summer—an evocative headline that has me personally wondering if my body is failing me or am I failing my body? Am I the victim or the perpetrator?