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episode 30 / Dec 17, 2025

Claude Silver

It Doesn’t Have to Be This Hard

It Doesn't Have to Be This Hard: abandoning yourself at work

Claude Silver, Gary Vaynerchuk's Chief Heart Officer, once hid being gay at a company where she didn't feel safe. We get into what that costs.

Claude's book opens with her own story: a dyslexic kid who took Algebra 1 three times, ran with bad decisions, bad drugs, bad boys, and got sent to a 93-day wilderness program from Leadville to the Grand Canyon. An instructor there handed her the line that runs her whole life: you better get another song in your head.

Then, years later, after eighteen years out in San Francisco, she took a job where the culture didn't feel safe, and she hid. Invented gender-neutral partners, edited pronouns, at forty years old. The shame that came back was one she hadn't felt since her twenties. She calls it what it was: abandoning herself at work.

She'd promised Gary Vee a decade earlier that she'd write a book about bringing humanity to work; COVID finally gave her the time, and it was five weeks old when we recorded. The same day we talked, a hard DEI conversation with a direct report had gone badly, and she tells that part too, because that's the actual job.

“I abandoned myself at work by pretending I was not gay because I didn't feel safe in the culture I was in.”

Notes

  • Highly dyslexic and written off academically; she now calls dyslexia her biggest superpower.
  • At forty, after eighteen open years in San Francisco, she hid being gay at a workplace where she felt unsafe.
  • Her book, a decade-old promise to Gary Vaynerchuk, was five weeks old when we recorded.
  • She recorded this the same day a hard DEI conversation with a direct report went badly, and shares it anyway.