Lawyer Turned Thought-Leader, Public Speaker and Entrepreneur

Debbie Epstein Henry practiced litigation for six years before leaving to focus on consulting, writing and public speaking. Since exiting law, she has also authored two books and is the co-founder and managing director of Bliss Lawyers, a company that lends out lawyers on temporary engagements.

We recently had the chance to talk to Debbie and learn about her professional journey from the very beginning.

The Road to Law School

Debbie first got interested in law when she took a psychology and law class at Yale. She was a psychology major and after interning at a criminal defence firm, she wrote a senior thesis on the psychological motivations and conflicts of a defence attorney. After graduating, she knew that she didn’t want to be a psychologist so she decided to take a position at the Manhattan District Attorney’s office. In her two years there she learned a great deal about the criminal side of the justice system and ultimately made the decision to head to law school.

In her third year she accepted a clerkship with a federal judge in the eastern district of New York. Her two years as a law clerk gave her a broad exposure to both civil and criminal cases. This then lead to a job at a New York corporate law firm where she would work as a commercial litigator for a year before relocating.

Leaving Law

As a mid-level associate, Debbie moved to a Philadelphia law firm and found it was becoming difficult to balance her work and home life.

“I had two kids and I was struggling with how to play an integral role in my kids’ lives and also be successful as a lawyer.”

Debbie moved to a part-time schedule but still worked hard to stay on the partnership path. At this time she realized that many women felt the same pressure in balancing their work and family lives and she decided to start a brown bag lunch group to discuss these challenges. In 1999, she started by emailing six lawyer contacts and she encouraged them to invite others with similar interests to an event she was hosting at her firm. Within a few days, Debbie had received 150 emails in response. This is when she first realized the demand and interest in this topic.

“Work-life was not a term of art and nobody was talking about these issues yet. Once I ran my first event and loved it, I knew there was a tremendous need for a resource on these issues and I thought about how I could make this my career.”

After that first event, Debbie started running free events on women’s issues in law and work-life balance. For three years she was speaking, writing and advising lawyers while still practicing law. As she gained a stronger following, she began to charge membership fees and transform her passion into a business she could focus on full-time.

Taking on a New Role

Over the next decade, Debbie developed a network of over 10,000 lawyers originally called Flex-Time Lawyers through her speaking, consulting and press exposure. She had expanded her sessions to a wide range of topics including legal industry trends, workplace issues, and general career advice. She also started to focus more on consulting to companies and law firms, accepting invitations to speak at business events and firm retreats.

In 2008, Garry Berger, an old colleague of Debbie’s reached out to her with a problem. Garry owned a small virtual law firm and had corporate clients asking to borrow lawyers temporarily, often for the duration of a merger or project of some kind. Garry and his colleague Suzie Scanlon Rabinowitz did not have enough lawyers to lend to their clients and so they started to lend out lawyers from Debbie’s Flex-Time Lawyers network.

In 2010, Debbie published her first book “Law & Reorder: Legal Industry Solutions for Restructure, Retention, Promotion & Work/life Balance,” which further increased her network. The demand for lending out lawyers continued to grow and in 2011, Debbie, Garry, and Suzie co-founded Bliss Lawyers to better address that demand. Bliss Lawyers hires lawyers as W-2 employees and then facilitates their work in companies and law firms around the country on temporary engagements. The Bliss network has now grown to over 30,000 lawyers nationally.

Today, Debbie has re-branded her consulting and speaking practice DEH Consulting, Speaking, Writing and she generates clients through her writing, thought leadership, public speaking, press exposure and networking. Her role as a co-owner of Bliss is focused on thought leadership, business development, entertaining clients and engaging with the press.

The Transition

Debbie faced many challenges in her transition out of law. Originally just the decision to leave was hard to make because she was two years away from partnership.

“The conservative approach would have been to wait two more years and then leave after securing the partnership title, but I found my passion and I couldn’t imagine waiting another two years before pursuing.”

Other than her desire to leave, Debbie’s decision was also influenced by a health scare. At 26 years old, Debbie had a rare parasite in her brain and had to undergo brain surgery. For five days, they were not sure if it was a tumor or a parasite. That frightening experience taught her to not live in fear and learn to take smart risks.

Another challenge in her transition was learning to balance her work and family life. During her years of practicing law while building a new company, and while also raising small children, Debbie’s time was stretched very thin.

“There was such a premium on my time and I wasn’t going to risk doing lower quality work. I likely sacrificed my sleep the most.”

Not-So-Legal Advice

Debbie’s advice to other lawyers thinking about leaving law is to find what you’re good at and understand that it is a long and challenging path to build something new.

If it is possible, Debbie recommends working on your passion in addition to doing your day job. Her time doing both was immensely valuable because she gained confidence, a following, and was able to test out a new role before fully committing to it.

“To the extent that you can straddle two identities for a period of time and test the waters, it really can make a big difference.”

This time allowed her to see that there was a market for her speaking, writing and consulting, while also discovering her deep passion for it. If you’re happy doing it then you’ve already accomplished a lot.

“People think happiness is a luxury and I don’t believe that. There is a definite correlation between happiness and success- it is a very legitimate priority.”