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Andy Chaleff

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Substack
PricingOnly free issuesPublishesWeekly
Issues162Founded2 years agoLast Issue4 days ago
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Latest Issues

Gay Friends

I’m in Cleveland this week, doing an assessment of the LGBTQ+ initiatives in the area and putting together a general investment thesis for the region.

It’s the kind of work I’ve done many times. Straightforward on paper.

But something has...

4 days ago
9
3

Forest People

Every year, Rani and I try to find a new way to celebrate our birthdays. As I’ve mentioned two weeks ago, we share the exact same birthday and wedding anniversary, which somehow makes the whole thing feel ceremonial — like we’re contractual...

12 days ago
9
2

Both Sides Now

I want to talk about a song. Quite possibly my favorite song ever.

It came out a year before I was born, which feels oddly perfect — like it was sitting on a shelf somewhere, waiting for me to catch up. Joni Mitchell’s Both Sides Now.

I h...

19 days ago
8
4

Our Birthday

There was a time when my birthday felt like a national holiday. When you’re a kid, the day arrives with the quiet assumption that the universe has been preparing for it all year. Cake appears. People call. You are, for twenty-four hours, th...

a month ago
10
6

The Quiet Car

He said, “Let’s go to London for two days. Take the train.”

It was his birthday, and I was excited. Not just because I like London, but because I like him. He’s one of those painfully conscious people. Not conscious in the crystals-and-bre...

a month ago
12
7

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  • Andy Chaleff

    Author and mentor writing about death, love, and the messy beauty of being human. I share vulnerable stories, hard questions, and quiet moments of grace for people who want to feel more, hide less, and live a little more awake.

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