Anthony Romero has led the ACLU for nearly a quarter century—through four presidents, constitutional showdowns, and a political landscape that feels more chaotic every day. And yet, when you sit across from him, you don’t feel panic. You feel steadiness. Clarity. A kind of grounded purpose that’s rare in work shaped by crisis.

In this conversation, recorded inside ACLU headquarters in New York, Romero and Connor talk about what it means to do work that is forged in conflict while still protecting your humanity. Anthony shares how he stays centered amid tragedy and noise, why “slowing things down” can be a form of progress, and how small daily practices—kindness, discipline, honest self-reflection—are what keep him from burning out.

We also zoom out: What does leadership look like when the stakes feel impossibly high? What happens when your work requires you to step into friction again and again? And what responsibility does our generation have for the systems—and the workplace cultures—we’re leaving behind?

For anyone who cares about doing meaningful work without losing themselves in the process, this conversation offers a rare mix of realism, agency, and genuine optimism.

CHAPTERS

Chapters

00:00:00 Intro — Fighting for democracy in a constitutional crisis
00:02:57 Constitutional crisis or opportunity for resistance?
00:04:14 Leading through tragedy and staying centered
00:07:07 Winning by losing — ACLU's litigation strategy
00:10:43 Redefining success and bringing the public along
00:12:20 The but-for test — Would America be worse without the ACLU?
00:16:53 Best case, worst case — America's future scenarios
00:20:48 Looking at the map — Opportunities in every state
00:23:01 The last man standing — Embracing friction
00:27:01 This is a rental car — Legacy and succession
00:29:08 How my generation f*cked it up
00:32:49 Message to young leaders — Keep fighting, it matters

IS THIS WORKING?!

What if the most interesting thing about work isn’t what we do—but what it does to us?

Is This Working?! is about meaningful work and the messy humans who do it. Host Connor Diemand-Yauman talks to the leaders, builders, and creatives navigating the chaos through the moments they question everything and show up anyway.

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