Hey there Legal Rebels! 👋

I’m excited to share with you the 88th episode of the LawDroid Manifesto podcast, where I will be continuing to interview key legal innovators to learn how they do what they do. I think you’re going to enjoy this one!

If you want to understand how a business background, an unconventional career path, and a refusal to accept “that’s not how things are done” can reshape legal aid and private practice alike, you need to listen to this episode. Jen is running a statewide legal aid organization and a lawyer coaching network at the same time, and she has a unique experience and point of view.

Building a Legal Career on Common Sense

Join me as I interview Jen Lee, the Executive Director of Legal Services of North Dakota and CEO of the Lawyer Success Network.

In this insightful podcast episode, Jen shares how she went from being written up in corporate America for having “too much common sense” to running a statewide legal aid organization and a coaching network for lawyers who want to build businesses that actually work. She takes us through her path from small-town North Dakota to insurance and financial services, then law school, then twelve years running her own bankruptcy firm in California, and back home to North Dakota during COVID.

Her stories and insights underscore how business thinking, technology, and a willingness to ask “why do we do it this way” can transform both legal aid delivery and private practice. This episode is a must-watch for anyone interested in access to justice, law firm management, or simply building a legal career that doesn’t require burning out.

The Skinny

Jen Lee grew up in a tiny farming town in North Dakota before an unconventional path took her through an au pair stint in Germany, work in financial services and insurance, and eventually law school, mostly because it sounded fun. She built her own bankruptcy law firm in California from scratch, growing it to four attorneys and doubling revenue year over year for five straight years, all while marketing herself not as a bankruptcy attorney but as someone who helps people with debt and credit problems. Along the way she founded the Lawyer Success Network after getting tired of hearing “you can’t do that” from other lawyers, and started teaching attorneys how to run their practices like real businesses. When COVID sent her home to North Dakota, she took over Legal Services of North Dakota with a mandate to modernize it, and has since grown the team from six attorneys to fifteen while overhauling its technology and culture. Throughout the conversation, Jen returns to a consistent theme: lawyers get stuck thinking about their practice areas instead of the problems their clients actually have, and organizations get stuck refusing to change simply because change is uncomfortable.

Key Takeaways

• Market what you solve, not your practice area. Jen never called herself a bankruptcy attorney; she said she helped people with debt and credit problems, which made her services instantly understandable to potential clients.

• A business background changes how you run a law firm. Jen’s experience in financial services and insurance gave her the marketing, cash flow, and problem-solving instincts that shaped how she built and scaled her own practice.

• Feedback loops beat perfectionism. Whether it’s an AI tool, a new workflow, or a marketing message, Jen argues the work is never “done,” it has to be checked, adjusted, and improved continuously.

• Listening to frontline staff is a management superpower. When Jen took over Legal Services of North Dakota, she found a team that had never been asked for its opinions, and simply asking why things were done a certain way unlocked real change.

• Remote and flexible work is a competitive advantage. Firms and organizations that resist remote work or rigid 9-to-5 structures are struggling to attract and keep good people, while those that adapt are winning.

• Career choices are not permanent sentences. Jen pushes back hard on the idea that once you pick a legal path out of law school, you are locked into it forever.

• Collaboration beats competition in access to justice. Jen sees legal aid and private practice as natural collaborators rather than competitors when it comes to expanding access to legal services.

Notable Quotes

1. “I got written up one time for having too much common sense.” Jen Lee [16:57 to 17:06]

2. “It’s not about what you think you do. It’s about what problem your client thinks they have that you solve.” Jen Lee [26:31 to 26:49]

3. “I think your choices can be different tomorrow than they are today.” Jen Lee [23:04 to 23:22]

4. “The best thing a manager and management levels can do is talk to their employees, ask them why they do things and what would make their jobs easier, and listen to them and actually do those things.” Jen Lee [36:26 to 36:59]

5. “I think we fall into things that we enjoy when we let ourselves.” Jen Lee [22:08 to 22:09]

Clips

Written Up for Too Much Common Sense

The Unexpected Path to Bankruptcy Law

Your Career Choice Isn’t a Life Sentence

Helping Lawyers Build Happier Firms

Jen Lee’s path from a seven-mile-spaced farming town in North Dakota to running a statewide legal aid organization and a lawyer coaching network shows what happens when someone refuses to accept industry defaults simply because they are defaults. Her insistence on speaking to what clients actually need, her comfort with constant iteration over one-time fixes, and her willingness to ask frontline staff why things are done a certain way all point to the same underlying philosophy: good ideas do not require permission, and the discomfort of being told “you can’t do that” is often the surest sign you are onto something worth pursuing.

Closing Thoughts

What strikes me most about this conversation with Jen is how consistently she reframes problems that most lawyers treat as fixed. Bankruptcy becomes “helping people with debt and credit problems.” A slow-moving legal aid organization becomes a place where fifteen attorneys now do the work six used to handle. A career path becomes something you can walk away from tomorrow if it stops serving you. None of this is complicated advice, but it takes real conviction to act on it inside a profession that prizes precedent and how it’s always been done as much as ours does. Jen’s story is a reminder that the tools and technology we talk about so often on this show only matter if the people using them are willing to ask why things are done a certain way in the first place. That is the real rebel move, and it is one every legal innovator listening to this show should take to heart.