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Some mornings I wake up and feel really down—on myself, and on the world. There’s always plenty I could point to: Will AI eliminate half the jobs? Is a recession coming? What happens when my mom gets sick? There’s no shortage of “looming” things I can grab onto and use as evidence that today might...

Some people drive thirty minutes to sit with strangers and talk about topics that might stir up difficult thoughts and feelings. Others sign up for a thirty-minute Zoom call out of curiosity—and then don’t show up. I’ve encountered both recently. And I’ve been both. What separates those who show...

On Friday, we’re journaling again. If you’re in the Bay Area, and can get out of work a little early on Friday,  I’d love for you to join us. I’ve written a lot in these letters about the magic of having a conversation with yourself on paper. This week, we’re pairing writing with another equally...

As I reflected on my goals over the holidays, I had to acknowledge my very marginal progress. I made some changes, but I am not where I wanted to be. So what, you may say, as long as you did something, that's good enough. I used to believe that too. But looking back, the biggest changes in my life...

Hard to believe another year is already in the rearview mirror. Have you taken a moment to reflect on yours? I began last week during our wonderful journaling gathering, where we “harvested” the moments—big and small—that shaped us this year. This season is always a quieter one for me. I find...

I’ve been thinking about empathy a lot lately. Maybe it was triggered by a parking attendant and a Labcorp employee. I had to get some lab work done and, in my usual fashion, treated it as a nuisance—something to squeeze in before work. And as often happens when we rush through what “shouldn’t be”...

While digging through my old desk, I found two forgotten journals from the time I’d just moved back to California—my self-discovery era. I was hungry for answers then, writing regularly. Those pages are filled with dreams, goals, and quotes from self-help gurus that I discovered during that time....

The world feels heavy, unbelievable, out of order. And many people carry that heaviness with them. Just yesterday I talked with a woman at my gym who thinks we are doomed. I tried to speak of hope, but she had already decided things can only get worse. She—and others I’ve spoken to recently —wear...

You’ve probably heard the phrase “getting off the beaten path” as an expression for taking a risk or trying something new. On a recent climbing trip, I realized how often I literally do just that. Trails to the base of climbs are faint, sometimes disappearing altogether over stretches of rock...

Have you noticed how a single memory or experience, when written down, can become something more than just a thought? It becomes a shape. A doorway. A mirror. It becomes an opening, something you can return to, learn from, and carry forward with clarity. My personal life has been hectic lately and...