Both/And with Jay Michaelson

Both/And with Jay Michaelson

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Both/And with Jay Michaelson
Both/And with Jay Michaelson
Comfortable with Discomfort
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Spirituality & Meditation

Comfortable with Discomfort

Don't fight the feeling that something is wrong. Get comfortable with it.

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Jay Michaelson
May 15, 2025
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Both/And with Jay Michaelson
Both/And with Jay Michaelson
Comfortable with Discomfort
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My father died when I was 26. Somehow, I hadn’t expected it, even though he had spent most of the past two years in and out of the hospital, fighting smoking-related ailments, and even though he had been steadily been getting worse in “rehab” for several weeks. I remember how my mother had typed out a list of questions for our doctor onto a 5x7 piece of paper, and how we sat waiting in his office (over air-conditioned, like every indoor space in Tampa, where I’d grown up) when we got the news. “I’m sorry,” the doctor said, before we could even say hello, “but he passed just a few minutes ago.”

I don’t know why I didn’t expect it, but somehow this came as a shock. Death hadn’t seemed to be on the menu. No one talked about the obvious-to-everyone-else fact that my dad might die, and maybe I was too young to understand the reality. How could this happen? This wasn’t what I’d been told to expect.

I felt similarly in March, 2020. To be sure, I’d grown a lot over the 23 years between my father’s death and the onset of the pandemic. I’d lost my mother, survived a serious car accident, come out of the closet, and spent ten years making up for lost time. I co-founded a magazine, sang in a rock band, wrote books, started a dot-com and two nonprofits, and had a great gay decade. I also spent a lot of time on meditation retreats, in therapy, and in intimate friendships that I’d never been capable of before.

And yet, despite all of that, I recall that same cratering in the abdomen, that same panic in the chest; that same cognitive dissonance. This wasn’t what I’d been told to expect.

And I sometimes feel it now, too, in this age of poly-crisis, meta-crisis, and national spiritual crisis. I never expected to see resurgent nationalism in America and around the world, and no one foresaw the massive changes looming because of technology and AI. And of course the spiraling climate crisis (which so many deny is even happening), the obscene imbalance of wealth and resources in our society, the death of truth, the abject cruelty that at least a third of Americans celebrate — and let’s not forget the extremism, conspiracy thinking, furious rhetoric, and misinformation that infects all parts of our public discourse, regardless of political valence.

Should I put on my meditation voice now? Should I reassure you that, if you take some deep breaths, everything will be okay?

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