Working from the Heart — Sunday Letters

Staying Small for You

On keeping a dream at a safe distance, and the loyalty underneath the shrinking

June 21, 2026

She came to the Friday releasing call with a song in her head, Castles in the Sky, and a pattern she’d been circling for years.

“I have these big dreams,” she said, “but I keep them in the sky. It’s almost like keeping them at a safe distance where I don’t have to risk failure.”

Something shifted in the days before. She was approaching 49. She’d sat down and poured it out, the vision, the steps she could see, and made a decision. Done keeping the dream overhead.

“Today I feel heavy and nauseous and resistant. There’s stuff being stirred up by the fact that I’ve actually gone: okay, I’m going to try this.”

Her dream involved the ocean. We followed that image: the creative edge, far enough out to lose the bottom, close enough to see the shore.

She could see people on the shoreline.

“They’re afraid for me. There’s the disapproval. And then there’s the guilt: I’m going to swim off to this wonderful island, and they’re going to be left behind. I feel guilty for choosing something more wonderful for myself.”

I asked whether she felt like a crab in a bucket, trying to climb out while the others pull it back.

“Yeah. I feel like I keep trying to get out, and they’re like, no, no. Or it’s like I do that to myself.”

She sat with that. Then she started talking about loyalty. About what it means to be faithful to people who have given you so much. About repayment.

“It’s like, let me be loyal. Let me be loving. You’ve given me so much. So let me repay. It’s so messed up. Let me repay all your kindness and generosity and support throughout the years by staying small and being unhappy and blaming you as well.”

She laughed.

“Oh my God. That’s hilarious.”

Then, quieter: “It’s also ridiculous. But it’s very emotional.”

There’s a form of loyalty that functions as self-erasure. Stay where you were when they knew you. Repay what they gave by remaining recognizable.

The absurdity and the grief landed at the same time.

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