A few weeks ago, I was walking up Telegraph Avenue to meet some friends. As I approached a crosswalk, a truck pulled up to the stop sign, and a shadowy hand waved me on. I smiled and nodded politely at the driver.
“You should smile more,” yelled a male voice from the window.
Whoa, I thought. Aren’t we past this?
I kept walking. Later, I imagined the responses my friends would’ve had: the witty comebacks I should’ve delivered, the confidence I should’ve summoned. But in that moment, I mostly felt surprised. And a little embarrassed that my first instinct had been to smile anyway.
It made me think about all the ways women are still expected to be pleasant, accommodating and easy to be around. Not just successful—but successful in a way that makes everyone else comfortable.
Thankfully, the women featured in this issue are defining success on their own terms.
They are building businesses, creating communities and proving that ambition doesn’t have to look one particular way. For Bake Sum founder Joyce Tang, success isn’t about making “the most money or the most pastry possible.” For Amy Pence of Piedmont Grocery, it means preserving a neighborhood institution while investing in the people who keep it running. And for Gaia Yoga founder Martina Chavez-Young, it means combining athletic discipline, tech experience and mindfulness to create a space where everyone belongs.
Whether the product is pastry, groceries or mindfulness, these businesses are built around the same ingredient: connection.
Our cover story on Sheila E. offers another perspective on success—not as fame or fortune but as purpose, generosity and doing what you love. At Personal Pizazz, Laura Leventer helps customers find clothing that feels like them, not just what happens to be trending. And after two decades running A Great Good Place for Books, Kathleen Caldwell reflects on knowing when to close one chapter while honoring everything that came before.
These stories are about women building, adapting, leading and caring. They remind us that success is not always about getting bigger, louder or richer. Sometimes it’s about creating something meaningful enough that you no longer need outside validation.
Which might be the real opposite of being told to smile.
