In this episode of Legal Off the Leash, we sit down with Chad Aboud, Chief Commercial Officer at Goodlawyer, TEDx speaker, and host of the What You’re About podcast. From his early days in Big Law to helping lawyers design meaningful, fulfilling careers, Chad shares powerful insights on authenticity, purpose, and redefining success in the legal profession. Whether you’re just starting out or reconsidering your path, this conversation will challenge how you think about your career, your values, and what truly matters.
Key Themes In This Episode
- The Early Spark vs. Harsh Reality Chad opens up about how his childhood dream of practising law didn’t match the reality he encountered in law school and BigLaw — a reminder that sometimes our early ambitions need re-examining.
- Redefining Failure Chad reveals why leaving wasn’t failure — but staying without trying something different would have been.
- Creating Space for Clarity A powerful reflection on why stepping out of the “fast river” of expectations is sometimes necessary to build a truly fulfilling career.
- Purpose & Intentionality Chad encourages listeners to ground career decisions in purpose — and avoid relying on one role, organisation, or person to be “everything.”
- Unlocking Your Unique Value Discover why success lies in amplifying your natural gifts, not just outworking everyone else.
- Leading with Humanity A leadership lesson every lawyer (and leader) should hear: vulnerability and genuine investment in others create stronger, more loyal teams.
💬 Memorable Quotes
- “I watched Matlock as a kid. And I was like, solve the crime, wear the gray suit every day. They admit it on the stand. Beautiful. I want to do this. And so that's why I went to law school. only to very quickly find out that this did not feel like what I was going to be doing. And I didn't really like law school that much.”
- “I'm smart enough to figure something else out. And I think the hardest part for me was that I would have felt like a failure if I hadn't tried. So I actually felt more like a failure during the time, not when I left.”
- “Know the purpose for why you're going. And then start being reflective and intentional about what it is you want in the next phase.”
- “Start understanding where your unique value proposition is. For most people, it's not just going to be knowing the law and being there longer. That's a bit of a commodity.”
- “Associates that see you as a human, know that you have some humility and know that you're investing in them. That's how you build a group of dedicated folks who are going to work hard for you on the work and in the hours that you can't or don't want to do.”
💡 Important Insights & Actionable Takeaways
- Challenge the dream vs. reality gap: make sure your path truly energises you.
- Reframe failure: fear not trying more than you fear leaving.
- Step out of the “river” of expectations to design your own future.
- Anchor your career in purpose and be intentional with your next moves.
- Lead with authenticity and humility—it inspires loyalty and better work.
🎧 Tune in for a conversation that’s raw, honest, and packed with insights to help you design a legal career that lifts you up.
You can connect with Chad here: https://www.linkedin.com/in/chadaboud/
