Archive - Jessiwrites

The price of everything

For more than a century, we’ve worshipped at the altar of optimization. But what if the very value that built the modern world is now unraveling it?

Jul 16 •

How to Be a Consultant (and Actually Make It Work)

Real talk on pricing, positioning, and staying sane while building your own thing.

Jul 14 •

June 2025

The Hidden Cost of Holding It All Together

Dr. Judith Joseph joins me to talk about high functioning depression, anhedonia, and the science of your joy.

Jun 30 •

She just got started

How Shannon Watts Turned Grief into a National Movement—and Wrote the Playbook for the Rest of Us

Jun 23 •

What If We Let Dads Show Up Differently?

Masculinity, family, and building workplaces that truly support care

Jun 16 •

Who Needs College Anymore?

The Answer Will Change How You Plan Your Future

Jun 9 •

This year, Pride Is More than a Celebration. It’s a Wake-Up Call

Family Equality CEO Darra Gordon on what it really takes to protect LGBTQ+ families

Jun 2 •

May 2025

Anna Kendrick has earned our applause. Now she is asking for our trust.

After three decades of playing similar roles, a Hollywood talent attempts a career pivot

May 26 •

The Map Isn’t in a Book. It’s in You.

What Caroline Wanga wants you to know about figuring out your next move, even if you feel completely stuck.

May 19 •

Inside one of the most inspiring creative partnerships of our time

Roxane Gay and Debbie Millman talk about hope, shame and discipline

May 12 •

April 2025

The world Is burning. We’re optimizing spreadsheets.

Moral ambition calls us to build careers — and lives — that center our most significant challenges.

Apr 28 •

When the AARP Letter Lands: Rethinking What It Means to Get Older

At 50, I’m finally seeing how ageism—especially for women—shapes our ambition, self-worth, and visibility. This episode of Hello Monday is a reckoning…

Apr 21 •

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