For a long time, I approached meditation like a workout. Put in the time, keep showing up, and eventually my mind would get quieter.

Henry Shukman offered a different image that has stayed with me.

Imagine a young horse running around a meadow, with its mother quietly watching nearby. The horse has all this energy. The mother lets it run. As your meditation practice deepens, Henry says, the meadow gets bigger.

Your thoughts can keep moving. You have more space around them.

I sat down with Henry, a Zen teacher, author, and poet, in New Mexico just before heading into a weeklong meditation retreat. We started with the busy mind and ended up talking about awakening, grief, love, and what it means to be fully human.

What struck me about the meadow is how much pressure it takes off. So much of self-improvement gives us another thing to fix about ourselves. Henry’s approach invites us to notice how tightly we’re holding everything. Perhaps peace is something we gradually learn to stop interfering with.

That becomes very practical when we talk about reactivity. Someone says something, a small irritation lands, and suddenly it has taken over our afternoon. Henry describes how practice helps us recognize that reaction and give it room to soften. We can still address whatever happened. We just have a little more freedom in how we respond.

A few other moments I loved:

The pressure to “get” meditation.
We explore how chasing a particular experience can become another source of tension, and why ordinary, consistent practice matters.

Awakening and being human.
Henry talks about cherishing his emotions and feelings. As he puts it, he has no interest in becoming a “heartless sort of Zen robot.”

Grief and love.
We get into what it means to stay open to both, including the parts we’d often rather avoid.

Learning to live from the heart.
Henry shares his experience after a bicycle accident and how his years of practice supported him as he dealt with the effects of a concussion.

We also get into The Way, the meditation app Henry co-created. I was curious about its sequential approach: following one path over time, with each session building on the last.

If you’ve ever sat down to meditate and immediately decided you were bad at it, I think you’ll get a lot from this conversation.

Let me know what stays with you.

Be well,

Kevin

New episode just dropped.

I sat down with Anish Acharya, Partner at Andreessen Horowitz (A16Z) and one of the most plugged-in consumer investors in tech. We worked together at Google years ago, and what I love about Anish is that he’s not just writing checks - he’s a programmer. He’s in the code every day, same as me.

We got into all of it: why I’ll never look at code again, the personal injury lawyer who won the global Claude Code hackathon by building software that rivals a venture-backed startup, why SaaS is getting demolished, and Anish’s wildest prediction - that America will get the 4-day work week the same way it solved obesity. Not through discipline. Through Ozempic. I also made the mistake of pitching my wife on using AI agents to settle our marriage arguments. It did not go well.

Whether you’re deep in the 1% or wondering what the hell we’re all so excited about, this one’s for you.

Listen or watch the full episode here.