Most professionals are trained to follow a path that looks safe, prestigious and predictable. Law school, top firm, the next logical step. If the funnel is working, it must mean you are on track. But what happens when curiosity starts tugging at you from the side?
In this episode of Outlaws, Kate and Shayla sit down with Sam Flynn, former litigation lawyer and co-founder of Josef, a legal tech company using AI in law to automate complex workflows for organisations like L’Oreal, Bumble and Bupa. Sam shares how a simple volunteer-built tool to help people navigate fines was used by tens of thousands within weeks and became the foundation for a global platform.
Beyond the headlines about legal tech and lawyers in tech, this conversation explores what professionals have to unlearn to build something new. The obsession with risk. The fear of embarrassment. The assumption that burnout is just about long hours rather than misaligned work. For law students and early career lawyers considering their career options, Sam’s story offers a grounded look at what reinvention can actually look like.
If you have ever wondered whether there is more than one way to use your degree, or whether striving might be less embarrassing than staying small, this episode invites you to rethink what a legal career can become.
