The Hardest Part Isn't Getting Sh*t Done. It's Knowing When to Stop — Dream.org CEO Nisha Anand

Nisha Anand might be the only person alive who's thrown fake blood on the White House and worked alongside Jared Kushner, Newt Gingrich, the Koch network, and Kim Kardashian to build the coalition behind the First Step Act — the most substantial breakthrough in criminal justice in a generation, according to the New York Times. 53,000 people are home from federal prison because of that one bill. Near the end of this conversation, Connor asks her a simple question: after decades of this work, are you tired? "Yes, I'm very tired, Connor. I'm very tired. And I never experienced burnout before in my life." We recorded this a few months ago. Since then, Nisha has announced she's stepping down from her nearly seven-year tenure as CEO of Dream.org. What you're hearing is a leader thinking out loud, before the decision, about what fighting to the best of her ability looks like at 50, compared to when she was 21 and chained by the neck to six other activists in the center ring of a circus. Along the way, she walks Connor through how she actually gets things done: how she names what she won't trade before anyone else at the table speaks, when working with an opponent is strategy and when it's selling out, and the question she asks her own staff when a deal starts to feel like a betrayal — who are we doing this for? If you've ever wondered whether the work is worth what it's costing you, this one is for you. Chapters 00:00:00 Fake blood, arrests, and the woman who gets sh*t done 00:01:08 Growing up rebellious 00:06:05 Punk rock and straight-edge hardcore 00:08:54 The circus arrest 00:14:11 Myanmar prison and five years of hard labor 00:23:25 The elevator with Marjorie Taylor Greene 00:26:18 Finding common ground without selling out 00:28:32 The First Step Act — 53,000 people home from prison 00:39:18 Would young Nisha think you're a sellout? 00:55:58 Exhausted but optimistic — why she can't stop 00:59:50 The trap of working hard 01:14:41 Power, unlikely allies, and what comes next