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The Daily Whatever, May 21: Protecting Our Trans Kids

Plus special guest Stewart Mason to discuss the Chicago Sun-Times AI summer books snafu

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In the days following the election, as I grappled with the enormity of what Trump 2.0 would mean, I had a personal struggle as well: what to do with Pink Hair & Pronouns, my publication for parents and caregivers of trans and nonbinary kids?

I researched the risks by reading Project 2025. I reached out to the CEO of Medium to ask him about guardrails and protections. And in the end, I realized—it was risky to leave my content up. And even riskier to keep writing.

But in the end, I knew: I couldn’t obey in advance.

I wrote this story about the reasoning, morality, and decision. Then I went and recorded it, because I wanted to say the words aloud. And today then I went and podcasted about it with Lawrence Winnerman, to double-extra underline my intent.

I will not obey in advance.

After this heady discussion, we were delighted to welcome Stewart Mason to the Live. Stewart is an incredible music writer on Medium (and elsewhere), and just shared his very first story to Substack, about the Chicago Sun-Times disgraceful misuse of AI that just went down this weekend.

He joins in about 45 minutes into the recording, and offers so many insights about both the power and limitations of AI.

You can read his story here.

(And definitely subscribe or follow Stewart to welcome him to Substack!)

Thank you Kevin Alexander, Füsun Aydın, Brandon Ellrich, Peter William Murphy, The One Minute Daily Boost, Karen Marie Shelton and many others for tuning in. Y’all are the very best.

Join us tomorrow with very special guest Untrickled by Michelle Teheux!

Love you mean it!!

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