The Case For... (with Matthew Campobasso)

"I'm just not sure yet" may be one of the most expensive sentences we say. After twenty years of practicing law and watching people make high-stakes calls with incomplete information, Matt Campobasso has come to believe that feeling sure and making the right decision are two completely different things. The first, you can buy with more research. The second, you can't. In this epi...

When someone says "I'm not going to settle," they usually mean they refuse to be the one who loses. But after twenty years inside other people's disputes, Matt Campobasso has come to believe we have gotten settling wrong. It isn't what you do when you can't win. It's what happens when both sides stop fighting for the fantasy of total victory and decide what they'r...

At twenty-nine, Matt Campobasso had a good job. Steady, secure, nothing wrong with it. He also had two hundred and fifty cover letters, a printer that ran for a month, and a question he was afraid to find the answer to. In this episode, Matt makes the case that the question you're afraid to ask is already a no by default, and the only thing that ever changes it is being willing to risk somethi...

Changing your mind isn't weakness — it might be the most disciplined thing you can do. In this episode, trial-attorney-turned-general-counsel Matt Campobasso makes the case for "reopening the record": the courtroom instinct that tells us to keep an open mind until all the evidence is in, and why most of us abandon that instinct the moment it gets uncomfortable. Drawing on two decades...

This is episode fifty of The Case For — and it felt right that it landed on an episode about starting with almost nothing and building something worth carrying forward, one week at a time. I have always been someone who needs to travel light. I could probably fit what actually matters to me into a few boxes. And over three decades, I've owned less every single year — not because of some minima...

I want to talk about the least interesting thing that will ever change your life. It’s not a breakthrough or a revelation or a crisis that forces you to rebuild. It’s the thing you do on a Tuesday that nobody sees. The decision you make at 6am that nobody applauds. The promise you keep with yourself at 10pm when you’re exhausted and the only person who would know if you broke it is you. There is n...

It's late August 2006. I'm twenty-eight years old, sitting in my office on my first day as an Assistant State's Attorney in McHenry County, Illinois. I've been filling out health insurance forms for ten minutes when the Chief of the Criminal Division walks in, tosses a case file on my desk, and tells me I need to be in Courtroom 301 in fifteen minutes to pick a jury and try a DUI t...

I want to tell you about a man I used to work with. His name was Ian Turvill. For several years at the Chicago law firm Freeborn & Peters, our offices shared a wall. Ian was the firm’s Chief Marketing Officer. He was genuinely kind, genuinely funny — the kind of humor that made you feel like you were in on the joke, never the target of it. He made people feel comfortable. He made people feel s...

My seven-year-old daughter came home from school recently and I could see it on her face before she said a word. A friendship had shifted. She’d been left out. She was hurt. And my instinct — the one that fires before I have time to think — was to fix it. Give me a name. I’m calling a parent. Let me email the teacher. I’m a lawyer. I solve problems. That’s twenty years of professional conditioning...

entire life. But at some point, the question stops being hypothetical. It becomes real. And that’s when most people go quiet. Because the honest answer, for a staggering number of adults, is: I don’t know. I’m twenty years into practicing law. I’ve been a prosecutor, a litigator, a law firm partner, an executive director, a general counsel, and a chief legal officer. If you asked me to describe my...

My twelve-year-old daughter came home from a family wedding recently. She’d missed two and a half days of school. She opened her laptop, saw the list of assignments she’d missed, and completely shut down. Eyes filling up. Breathing getting short. She looked at me and said: I don’t even know where to start. I could have jumped into fix-it mode. I’m a lawyer. Give me a list and I’ll triage it in thi...

It’s a weeknight in 2012. My son is three years old. His hair is wild and curly and he’s lying next to me in bed with his hand across my chest. He whispers three words: “You’re here now?” I tell him I am. But my phone is already lit up on the nightstand. I have a hearing at 8:30 the next morning. And lying next to my three-year-old, with his hand on my chest and his breathing going slow, I’m alrea...

I bought a guitar about seven years ago. Beautiful acoustic. I was going to be the dad who plays guitar. I could already picture it — me on the back porch, strumming Damien Rice while my kids listened. I was terrible. My fingers didn’t understand the assignment. My transitions sounded like a cat walking across a broken piano. I tried for weeks. Never got better. So I put it in a closet and that wa...

You’re sitting in a coffee shop on a Tuesday morning. There are fifteen people in the room. Someone two tables over laughs at something on their phone and you almost ask what was funny. They’re reading a book you’ve read. They’re wearing a hat from a city you used to live in. There’s a flickering signal that says this person might be interesting. But you don’t say anything. You go back to your lap...

More than ten years ago, a kid at a Law Day event asked me a question that stopped me dead: have you ever had to represent someone who you knew had done something wrong, and how did that make you feel? I’d been practicing law for more than five years. I’d been a prosecutor and a litigator. I’d represented clients whose positions I didn’t personally agree with. And that question exposed something I...

I woke up on a Sunday morning a few weeks ago and before my feet hit the floor, the list started. Work. Inbox. Calls. The podcast. The book. My kids. Laundry. Mail. Commitments I hadn’t honored. All of it landed in the first sixty seconds of being awake. And what I felt was not motivation. It was paralysis. A chest-tightening anxiety that pinned me to the bed. Because in my mind, everything had th...

Count how many times you say “I’m sorry” tomorrow. Not after a genuine mistake. Just in the normal course of your day. Sorry, can I ask a question? Sorry, I’m running two minutes late. Sorry, but I actually disagree. Sorry, I didn’t see your email. Sorry, can I get by you? Most of us say it dozens of times a day. And in the vast majority of those instances, we have absolutely nothing to be sorry f...

There’s a poem most people have heard but few have sat with. Martin Niemöller wrote it after the war — after — as a confession, not a warning. He was describing his own silence. His own repeated, rational decision that each new injustice was not his problem. By the time he realized they were all his problem, the architecture of his own freedom had already been dismantled. Not by the people who cam...

At the end of Avengers: Endgame, Steve Rogers is sitting on a park bench. He’s an old man. He’s lived a quiet second life. His friend sees the wedding ring and asks: do you want to tell me about her? And Steve Rogers smiles with absolute grounded peace and says: No. No, I don’t think I will. He understood something fundamental. If something is the bedrock of your joy or the center of your healing,...

I spent $45 as a broke law student to have this album shipped across the Atlantic Ocean from Ireland. It was grocery money, textbook money, train money. I had no business spending it on a CD. And more than twenty years later, it remains the single greatest musical purchase of my life. This is not a music review. This is a love letter from a man who has carried every song on this album through the...

My sixteen-year-old son recently told me I was wrong about something. Not with an eye roll or a sigh or something muttered under his breath. He sat across from me, looked me in the eye, laid out his reasoning, and told me — respectfully and clearly — that he thought I was handling something the wrong way. My first instinct was to shut it down. My second, about three seconds later, was to realize h...

In a courtroom, the goal is adversarial. Me versus you. My evidence against yours. There’s a winner, a loser, and a rope that’s pulled until it snaps and one or both sides fall. We’ve been conditioned to think this is the only way to solve a problem — by defeating the person on the other side of it. But what if the problem was never the other person? What if the problem was the rope? Today’s guest...

I have formed opinions without doing the work. I have voted on things I didn’t fully understand. I have nodded along in conversations where I should have said, actually, I don’t know enough about that to weigh in. This episode isn’t about politics, although we’ll touch politics. It isn’t about media, although we’ll touch that too. It’s about a pattern that shows up everywhere — in courtrooms, comm...

When was the last time someone asked how you were doing and you said “busy”? We’ve built a culture that treats having it all as the baseline expectation. Be the best at your job. Be the best parent. Be the most present partner, the most available friend — and do all of it simultaneously. And if something slips, it feels like failure. Today’s guest has lived that. Valeria Gutowski is a Senior Vice...

How many versions of you are out there right now? Think about the version of you that shows up at work. The one that shows up with old friends. The one at the dinner party, the family gathering, the client meeting. How many adjustments do you make in a given week — not to how you communicate, but to who you are? This week’s episode is about the quiet, exhausting habit of performing. Not lying. Not...