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September 7, 2026
Heather Holloway speaking to a large group in an auditorium.

Welcome to the School of Life. For me, September has always felt like the start of something new. New backpacks.

August 3, 2026
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I have a confession. I don’t really watch television. I study it. I could probably find meaning in a piece

July 6, 2026
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The Laugh I Didn’t Know I Needed I laughed so hard this week that I started crying. My sister-in-law sent

June 1, 2026
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There is a version of so-called “professionalism” that gets rewarded in a lot of workplaces. It is not always the

May 4, 2026
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Let’s Start Here Let me save you some time. You cannot AI ease. You cannot app your way into peace.

April 6, 2026
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There is a sentence that keeps circling me lately: Capacity is a form of self-respect. And friend, I think a

March 2, 2026
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Your phone lights up. Your inbox pings. Someone says, “We need an answer now.” And even if you know you

February 2, 2026
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Confidence gets treated like a mood. You either wake up with it, or you don’t. Some days it’s there. Some

January 5, 2026
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January has a reputation for noise. New goals. New pressure. New expectations to be more, do more, fix everything immediately.

December 1, 2025
The Soft Yes Choosing Peace Over Pressure This Holiday Seaso

The Holidays Aren’t Just Merry – They’re Messy Somewhere between the peppermint mochas (my fav!) and glittering string lights, the