Escaping Lawyer Burnout for Legal Tech with Ben Chiriboga

You’ve been in therapy. You’ve talked through your career. You understand, logically, that your boss’s mood isn’t your responsibility, that your worth isn’t measured by productivity, and that burnout doesn’t mean you’re broken. And yet… you’re still panicking every time Outlook pings. You’re still second-guessing every boundary. You’re still bracing for impact.For many lawyers, this is the point where talk therapy hits a wall. You’ve intellectually processed the stress, but your body hasn’t caught up. That disconnect between what you know and how you feel isn’t a failure. It’s a signal.See show notes at formerlawyer.com/282

Today’s podcast episode is an important reminder every lawyer needs to hear. Sarah reminds listeners that nothing about your job is as important as you and your emotional, mental, and physical health. For lawyers, it’s easy to feel their value as human beings is basically in job performance. See show notes at formerlawyer.com/229

2025 is more than halfway through, and if you told yourself this was the year you’d leave practice, this is your check-in. September is basically here, which means four months left in the year. That’s still plenty of time to make progress. And honestly, the start of fall always feels like a reset — school year vibes, even for those of us who haven’t been in school for decades. So if you haven’t taken steps yet, you haven’t missed your chance.See show notes at formerlawyer.com/281

The question comes up constantly - in podcast interviews, on Collab group calls, and in emails from listeners. "What if the grass isn't greener on the other side?"It's tied to this idea that maybe being miserable at work is just what it means to be an adult with a job. Maybe every workplace is toxic. Maybe no one really likes what they do. You'll even hear people outside the law say things like "Well, no one likes their job."There's something almost protective about believing this. If you don't believe it will be better elsewhere, it's easier to keep doing the thing you're doing, even if the thing that you're doing is painful and not great for your mental and physical and emotional well-being.But after six years of interviewing former lawyers, I can tell you the grass really is greener.See show notes at formerlawyer.com/280

There's a partner at your firm. Everyone knows about them. Multiple people have quit working for them. Multiple people have gone out on mental health leave. When people talk about this partner, they use phrases like "difficult" or "has sharp elbows."If you listen to Sarah's episode about the no-asshole rule, you know that “has sharp elbows” generally means they're abusive. But somehow, despite the clear pattern of destruction in their wake, you're supposed to act like this is normal. Like maybe you'll be different.This is not normal. This is nuts.See show notes at formerlawyer.com/279

In today’s podcast, Sarah discusses how to know when it’s the right time to leave law. Many people listening are grappling with this question, and often, when they ask it, they are looking for an external answer. There is no external answer. You are the only person that can decide when the time is right.The reality is that you need to ask yourself two questions to know if now is the right time for YOU to leave the law.See show notes at formerlawyer.com/231

You're exhausted from work and catch yourself thinking, "I wish I could get hit by a bus just a little bit so I could finally get a break." If that sounds familiar, you're not alone - and it's definitely not normal.This disturbing thought is surprisingly common among lawyers in toxic work environments. Sarah and returning guest Kelcey Baker dive into why so many lawyers fantasize about minor injuries as their only escape from work pressure, and why even vacation doesn't provide real relief.If you've ever had thoughts like this, this episode will help you understand it's not your fault - it's your environment. Content warning: Discussion includes narcissistic abuse, self-harm, and suicidal ideation.See show notes at formerlawyer.com/236

You're successful on paper but can't shake the feeling you haven't really "made it" without a prestigious law firm on your resume. Tiffany Obeng lived with that impostor syndrome for over a decade before finally getting her shot at Biglaw in 2023. Nine months later, she was back out. In this episode, Tiffany shares what she learned during those nine months that changed everything about how she views success, plus how she's built a children's book publishing company focused on diverse representation while working full-time in employment consulting. If you've ever wondered whether the grass is really greener at a prestigious firm, this episode is for you.See show notes at formerlawyer.com/278

You're a lawyer who's good at your job but something feels off. You're performing well, making good money, checking all the boxes that are supposed to matter. But there's a growing disconnect between who you are and what you're doing every day. Sound familiar?Ben Chiriboga lived this exact experience. Today he's an executive at Nexl, a legal tech company, but his legal tech transition wasn't linear. Sarah recently talked with Ben about his journey from maritime litigation to legal tech leadership, and his story touches on so many themes that resonate with lawyers considering their own legal tech transition.See show notes at formerlawyer.com/277

You've taken CliftonStrengths. You've done the MBTI. Maybe you've worked through a few other career assessments too. You have pages of results about your strengths, your work style, your preferences. And you're still sitting there thinking, "Okay, but what am I supposed to do with my life?"Sound familiar? Sarah gets emails about this all the time. Lawyers who've done all the career assessments, who have detailed information about themselves, but still feel completely stuck about their next career move.If this is you, there are two possible reasons why you're still feeling unclear after taking career assessments.See show notes at formerlawyer.com/276