Liz Brown, JD

In this installment of the 0.1 Billable Hour Interview, we talk with Bridgette L. Hylton.  Bridgette, an ’09 law school graduate, is a former corporate associate who left law to cofound fashion tech startup ShopRagHouse.com with her Harvard Law School classmate Joana Florez.  ShopRagHouse is the place where Project Runway meets Kickstarter. Everyday fashion enthusiasts and designers can submit their design ideas for a chance to have them produced and sold for a share of the profits.  Let’s get to the questions!

1. Why did you leave law?

The short answer is that I left law because I wasn’t passionate about it. It was a hard choice to make since I was learning so much at my firm, the pay was good, I loved being a part of the hustle and bustle in New York City, and I really admired the partner that I worked with. She was and is a powerhouse, but I could tell that we were different. While the creative structuring of deals was something that really drove her, it didn’t drive me. Doing my job, even doing well at my job, didn’t bring me joy. That should have been a big red flag.

Then there was a question of fit. I started to feel like I didn’t fit in pretty early on. I strolled into the office in sky high red stiletto Stuart Weitzman pumps only to have my secretary tell me that I should try to tone down my fashion choices. At some point you have to be honest with yourself about fit or you will never be happy. It wasn’t until a few months later that I realized my dream of becoming a Prada suit wearing M&A partner, wasn’t my dream any more.

After leaving practice, I almost immediately fell back into the things I had cared about in law school and still care about now, politics and startups.  I spent some time exploring what my next move would be and in the meantime became a mother. I knew after having my child that I wanted a career that would allow me the flexibility to be hands on with my son, but would also still challenge me. The idea for ShopRagHouse was born while I was doing some major soul searching about what I wanted to do next – a rough and tumble time where my career dreams swerved between politics, writing, and fashion (I even tried to launch my own dress line!). When my business partner called me with the idea for ShopRagHouse, something just clicked. It fit. I could use my legal education and still wear red stilettos?! Sign me up! We’ve been full steam ahead on trying to launch our startup since then.

2. What was the hardest part of your career change?

One big change is not having the internal structure that lets you know if you are doing a good job or the right thing. At a firm if you do well, you keep your job and if you do really well, you get praised for it; if you do poorly, ultimately, you probably don’t get to keep your job. It’s pretty straightforward. In the startup world, there is no easy validation and when you are your own boss, there isn’t always someone there to pat you on your shoulder and say, “good work, Hylton.” We rely a lot more on intuition now than we do on praise: Does it seem like our idea is building traction? Do people seem excited to talk about ShopRagHouse? The answers to those questions have to motivate us on a daily basis to keep plugging. Luckily we’ve had some great feedback so far and the buzz continues to grow so we are optimistic.

Adjusting to being more flexible about deadlines and timelines was another big change for both of us. We have to remind each other that we don’t have to freak out if we don’t get a pattern back on time every single time, but I’m grateful that we both know how to push things forward when we need to – chalk that up to our legal educations!

3. What advice do you have for other lawyers who are thinking of changing careers?

Be brave! Be confident! A lot of people look at me like I’m crazy when I tell them I left big law to start a startup – especially so because we’re still just getting off the ground. If I weren’t confident that this was the best decision for me and that this business can and will succeed, I might have run back to a law firm begging for forgiveness. I haven’t yet and I look forward to ShopRagHouse being a huge success soon so that I can prove that following your joy to the ends of the earth is 100% worth it.

Readers, have you thought about starting your own business?  Are you doing it now?  Why or why not?

This installment of the 0.1 Billable Hour Interview features Carleton Montgomery, the Executive Director of New Jersey’s Pinelands Preservation Alliance.  Carleton left legal practice in Washington, D.C., where he was a partner in the firm of Fried, Frank, Harris, Shriver & Jacobson, in order to join the nonprofit world and devote himself to environmental protection. 

1. Why did you leave law?

I left the practice of law, but not the law itself, as the environmental advocacy work I do now is deeply tied up in a set of laws. Legal reasoning and argumentation is a critical element in advancing the organization’s mission, and I often work with and against other lawyers – so all the years of training and practice from law firm days does not go to waste.

I left my law firm and the practice of law because I decided my career should amount to more than the firm could offer. I enjoyed the work, for the most part. I liked my colleagues well and most of our clients. The work was intellectually challenging. We even found ways to have a lot of fun. But eventually, I had to face the fact that this work consisted fundamentally in saving or making a lot of money for very large corporations. Since we only go around once, I concluded that wasn’t enough for an entire career. I wanted to do something I believed in as an end in itself. For me, nature provided that end in itself.

There was another important reason: I wasn’t home enough while my children were growing up. Kissing them goodnight after they were already asleep, and being with them most weekends, was not good enough. I’ve been a better father – not perfect, just better – since changing jobs.

The hardest part of the change was also one of the best parts: It is said that the law makes you sharp by making you narrow, and I found that was too true of my own practice. In contrast, running a nonprofit – even a small one – demands a far more varied use of what intelligence, wisdom and creativity I have to offer. In my job, I do legal and policy analysis, navigate a complex political landscape, meet and work with an extraordinary range of individuals, get outdoors, teach children and adults about a place I love, and manage a small business. The job is simply more interesting than corporate litigation. At first, that was intimidating. Now it is the reason I have stayed at it 15 years.

I have three pieces of advice: First, consider working for a nonprofit. We can make a huge difference working for charities, in part because so few people with business and for-profit legal experience put their skills to work for public goods like alleviating suffering and protecting the environment. Second, save enough money to help make the transition less scary, especially if you go to a nonprofit, where the pay is likely to be significantly, even dramatically, less than for-profit practice. And finally, keep your bar membership up to date, just in case.

Readers, have you ever joining a nonprofit?  What do you see in Carleton’s career path that might help guide yours? 

Ebele Okobi has what many people would consider a dream career.  As the Global Head of Yahoo!’s Business & Human Rights Program, she helps an enormous corporation direct its resources toward effecting social change.  She lived and worked all over Europe and in Africa before landing in California with her husband and having three babies and starting the process of adopting one teenager in the span of three years.  But she started out as a corporate lawyer.

Ebele graduated from Columbia University School of Law in 1998.  She worked as a corporate securities and M&A lawyer at Davis Polk in New York and London.  As a third year associate, she realized that she was more engaged by her pro bono clients, including political asylum applicants and battered women seeking no-contest divorces, than by her paying clients.  At the beginning of 2001, she took a year to travel and volunteer in New York, Senegal and France, while leaving open the possibility of returning to law.   

Then came September 11, 2001, when everything changed. “I lost one of my oldest friends. We’d gone to high school together–he was one of the kindest people I knew, and his life touched so many people,” she says. “After that, I realized that for me, life is too short to spend doing work about which I couldn’t be passionate. I also knew that I wanted my life and my work to have some sort of impact, for good.”

She started as an attorney fellow at Consumers Union, focusing on health care advocacy, and then went to work as the director of advisory services at Catalyst, the premiere research and consulting firm focusing on women and business.  When she and her husband decided they wanted to live in Europe again, she persuaded Catalyst to make her its first and only employee in Europe.  Then she fell in love with the emerging field of corporate social responsibility (CSR).

Although she was initially resistant to the idea of an MBA (she cheerfully admits to leaving before actually graduating), Ebele went to business school in Paris in order to develop expertise which would help her move into operational roles.  She then joined Nike’s management development program, where her rotations included a new business concept launch, a manager effectiveness project in Northern Europe, and helping the Africa strategy team align its CSR, sports marketing and distributor strategies. 

When she read about the opening for her current job at Yahoo!, she felt that the position had been made for her.  Yahoo! appreciated her legal background as well as her diverse business experience and education. 

In fact, Ebele has drawn on her legal experience at every stage of her career.  Being an associate, for example, taught her client service skills.  “I’ve found that having been trained to focus on the client is excellent practice for putting the consumer first,” she says. “And the research that I conducted and analyzed as a lawyer proved handy in guiding my thinking around what women want in the marketplace at Nike.”

Ebele loves what she does now.  “I am fascinated by the nexus between doing “good” and doing well. I don’t believe that they are mutually exclusive, and I believe that companies have a responsibility, and a challenge, to do both.”  The process of getting there, while never straightforward, sounds pretty amazing too: “I got the chance to live in Paris, to run in Casablanca, dance in Rio, cheer in Nuremburg, and learn from and work with classmates from every corner of the world. I’m now working for a company I love, in a position in which I feel fully engaged, and from which I am learning what feels like a million new things every day.”  Ebele’s story is a phenomenal example of what can happen when your idealism leads you away from law and, maybe, toward a career in CSR.