Meditation can be gorgeous… and it can be absolutely bewildering. If you've ever wondered, "Am I doing this right?" or "Why does this feel so intense?", this conversation is for you.

In this vintage conversation from 2016, Dan sits down with legendary dharma teacher Steve Armstrong for a clear, compassionate walkthrough of the progress of insight—including why meditation sometimes gets harder before it gets easier, how to navigate the so-called "dark night" phases, and how to keep going without getting lost in the weeds of self-doubt.

Steve has guided thousands of students through the twists and turns of practice with uncommon precision, humor, and heart. And now, the community has the chance to support him in return. Steve is currently living with a brain tumor, and he and his wife Kamala Masters (a formidable dharma teacher in her own right, who has also been a guest on this show) are facing significant medical and caregiving costs. If you feel moved, you can find the GoFundMe at this link. Our company has also made a significant contribution to support Steve and Kamala.

In this episode, you'll learn:

Why meditation can sometimes trigger emotional turbulence
How to understand the "stages" of insight (without clinging to them)
Practical ways to stay steady when your practice feels chaotic or confusing
How to distinguish between a genuine opening and plain old overwhelm
Why equanimity isn't passive—it's powerful

Steve has spent decades helping people wake up. This episode is a chance to receive that wisdom—and, if you're able, to reflect it back with your support.

Related Episodes:

Get Happier Without Losing Your Edge | Kamala Masters

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