Meet Donald K. Sherman, OBABL’s Careers Columnist

OBABL is thrilled to introduce you to our new careers columnist. By day Donald Sherman serves as counsel on the Democratic staff of the House Oversight Committee in Washington, DC. But by night (and weekends) he interviews professionals with interesting jobs for his website, Donald will be brining you the stories of lawyers who chose both traditional and non-traditional career paths. He’ll also be answering your questions, so feel free to send them to him at In his first Q & A with me, Donald offers up advice on dealing with a tough job market (don’t be afraid to start at the VERY BOTTOM), pursuing a non-legal career, and being honest with yourself.

What initially prompted your interest in different career paths?

A few things actually. As someone who mentors college and high school students in my spare time, I wanted to find a way to help broaden their ideas of what careers were possible and encourage them to take risks in pursuing their dreams. Many industries including finance, education, and law have struggled in our current economy, and I hope that my blog, “Somebody Does That?!” will help readers discover that there are a wide range of career opportunities within these traditional fields as well as unique jobs in many other arenas.

My interest also comes from my own experience realizing that attending professional school is not a magic pill that will by itself lead to a rewarding career. Law schools generally work hard to help students find that first job out of school, but I, like many of my colleagues and classmates, had less guidance figuring out the next steps. Through good fortune, hard work, and successful networking, we have been able to secure a range of different jobs putting our legal education to use. My goal in writing about unconventional careers is to provide examples of individuals who have challenging and engaging jobs in law and other fields, as well as to give readers more comfort with the uncertainty that can come in finding their path.

Finally, I’ve always loved meeting new people, and hearing about their personal stories. When I began to have conversations with strangers and friends about their unique careers and career paths, I wanted to find a way to include others in that conversation. I don’t think it takes a lot to inspire a person to find their greatness. Sometimes it’s as simple as being exposed or introduced to someone else who has done the same thing or taken a similar risk. I believe my blog does just that.

You have a pretty impressive resume. Tell us about your day job and how you landed it.

I am a counsel on the Democratic staff of the House Oversight Committee in Washington, DC. I primarily focus my attention on the Committee’s oversight investigations, and the hearings that arise from them. Prior to joining Ranking Member Cummings’ staff, I was an investigative counsel for the House Ethics Committee. In December 2010, at the end of the 111th Congress, I was looking for a new opportunity to expand the breadth of my experience on the Hill and several colleagues recommended the Oversight Committee. After my former bosses passed along my resume and interviewing with the Ranking Member, I was fortunate enough to be hired for my current position.

When did you first catch the legal bug? Did you grow up wanting to become a lawyer or did serendipity play a role in your career?

I’ve wanted to be a lawyer for as long as I can remember wanting to be anything. But of course, serendipity still played a large role. My fifth grade teacher, Stacey Divack, was always challenging my classmates and I with new activities, so of course we rebelled against her. One of these field trips was for our “Constitution Works” unit, mooting a First Amendment case with students acting as Supreme Court justices. After that, I was hooked.

I feel fortunate that I was assigned to Ms. Divack’s class. I have also benefitted greatly from a supportive family and lots of mentors, teachers and institutions in my career. Since I’m asthmatic, my mom always wanted me to become a doctor and find a cure for the disease. Still, I think she’s pretty happy with my chosen profession.

The legal job market is really tough right now. What advice do you have for recent graduates who would like to work as a legal professional?

Don’t be afraid to consider all options. Last fall, I interviewed Kapil Gandhi, a film major who now runs his own company shooting music videos for luxury resorts all over the world. When I asked him what lessons he took away from his career, he told me “Don’t be too big to do something small … in film terms, we say, ‘Don’t be too big to PA (production assistant),’” the most junior person on a film set. Likewise, in profiling engineers that design amusement parks, several Disney Imagineers noted that despite their college degrees, they started out as tour guides and other low level positions. Although Kapil and the Imagineers’ work couldn’t be more different than practicing law, their perspective remains instructive.

In my own career, I have worked with many lawyers that were initially hired into positions for which they were clearly overqualified – legal interns and office assistants, for example. Even now, I know lawyers who are pursuing clerkships and document review positions that they might not have otherwise considered given their law school “pedigree” or class rank. It may add an extra step along the way, but many of those opportunities have opened doors to full-time positions. The economy is still in a period of recovery, so I don’t think anyone can afford to be close-minded about what positions might launch their legal career.

How does this advice differ from the advice you’d offer to someone who is thinking about an alternate career path?

Based on my experience and that of the various individuals I’ve had an opportunity to meet and interview, success in the legal profession requires many of the same elements as success in many other industries – good work, good luck, and good relationships.

When I spoke to Mark Woods, Head of Bituminous Control for the Tennessee Department of Transportation and the man responsible for inspecting all of the state’s roads, he shared with me this advice from his father: “No matter what you do, make sure that you are doing something very specific and that you’re the best at it. Because if you get really specific, you’ve whittled yourself down to a tight category and there is room for you to be the best in the country at what you do.”

I think this advice is particularly applicable to someone contemplating an alternate career path. The only thing I would add is that it’s not enough to find a subject you like and become the resident expert at it – you also have to find some way to share your expertise and make it known. Legal journals provide lawyers and law students with a unique opportunity to explore novel issues and have their scholarship reviewed and disseminated. Although not every industry has such a wide variety of publications, blogging, and other forms of social media enable job-seekers to share their expertise with the world and can often facilitate a career transition. Next year, for example, I plan to interview Steve Kamb, the founder of Nerd Fitness, whose health and fitness blog has become a full-time job that takes him all over the world.

What have been some of the most creative jobs you’ve come across?

In the process of writing “Somebody Does That?!” I’ve been lucky to profile a number of individuals with unique and compelling careers. For instance, my high school classmate Olivia Smith is an aerospace engineer at Lockheed Martin building spacecraft for NASA. She first became interested in pursuing engineering after spending nearly a year working as a research technician in Antarctica.

One of my very first interviews was with Diahann Billings-Burford, who began her career as an associate at Simpson, Thatcher, and Bartlett, but currently serves as the first Chief Service Officer in the nation, using citizen volunteers to help address problems facing New York City. In addition, the blog recently featured my law school classmate Zhubin Parang, who worked in private practice while doing improv on the side, but leveraged his passion and talent into his current job writing for the Emmy Award-winning Daily Show with Jon Stewart.

What are the three most important things a person can do to find the right job fit?

I think like most advice, these are not terribly hard to recognize, but can be challenging to implement consistently.

Be honest with yourself. It’s close to impossible to find the right job, if you don’t spend any time assessing your strengths, weaknesses, and your passions. Even working in a job that is not a good fit can be valuable, but only if you’ve given critical thought to why it’s not the right place. If you are unhappy in your current job, it could be something that is situational about your work environment, things happening in your life at a given time, or any number of other reasons. But you have to take the time to figure it out.

This is actually the one piece of advice that I didn’t follow in my own career path– I just managed to avoid getting burned by it. There was a time when I considered giving up the practice of law because I wasn’t enjoying my work. Looking back on my thought process, I realize that I was grasping at straws and did not fully think through my strengths and weaknesses. Fortunately, I didn’t follow that path or more accurately, the wrong job didn’t find me at that time, and now I am incredibly grateful that I am still practicing law.

Don’t be afraid to ask for help. This is a big hurdle for many job seekers. There are lots of people out there ready, willing, and able to help with your job search, but since most of them aren’t clairvoyant, they can’t help you unless you ask. Although I encourage everyone to ask for help, even the most generous person won’t help just anyone. As Diahann Billings-Burford notes, “You’ve got to make it easy for them. No one is necessarily trying to move mountains, or hire bobos. So you’ve got to work at what you do. What you do, you’ve got to do well.” You have to put yourself in the best position to get the help you need. And it’s a volume business.

When I was looking to transition from private practice to working on Capitol Hill, I told anyone and everyone that would listen. I wasn’t pushy or aggressive about it, but you can never discount someone’s ability to be a resource. I landed my first Hill job because a law school classmate was willing to forward my resume. This friend was living and working in Oklahoma at the time, and didn’t have a lot of connections on the Hill. But he did have a connection to one Hill job that was a good fit for me.

Save money when you have it. Early on in any career, it can be difficult to figure out whether a particular job is a good fit. Especially in a struggling economy, financial considerations cannot be ignored. Your savings may be the only thing that gives you the financial flexibility to take your dream job when it comes along.

Putting money away while I was in private practice enabled me to deal with the substantial pay cut I took when I was finally offered a job on the Hill. I felt fortunate I was able to make that move, because I know many of my peers didn’t have that same flexibility. Ron Han, a former law firm attorney who is now a career advisor at the University of Southern California law school had a similar perspective. Although he acknowledged, that sometimes, “You think you deserve to spend money on nice things,” he said “I was able to avoid the ‘Golden Handcuffs’ and didn’t over-extend myself during my years as an attorney, so I wasn’t carrying too much debt.”

What else do you think our readers should know?

If I have learned anything from writing “Somebody Does That?!” it’s that there is a multitude of ways to find success. This project is about expanding people’s concepts of what’s possible, so I’ve profiled men and women of many different racial, ethnic, and educational backgrounds, in addition to travelling all over the country. In the past year, I have conducted interviews in New Orleans, Dayton, Nashville, Denver, and Los Angeles, in addition to several in my hometown, New York City, and my current home of Washington, DC. The blog also features dynamic individuals who come from a great many walks of life – some who have attended prestigious academic institutions, some who are self-taught in their chosen careers, as well as some who have less traditional formal education.

Future posts include, among others, conversations with Cranston Valentine, a certified saturation diver who spends weeks at a time living and working in a hyperbaric chamber to repair oil wells in the Gulf of Mexico, and Will Pomerantz, a Harvard graduate now working to develop and launch special projects for Sir Richard Branson’s commercial space travel company, Virgin Galactic. My blog provides substantial evidence that there is no one path to finding a rewarding career, and I hope if nothing else, “Somebody Does That?!” can help readers feel more secure in plotting their own course.

Donald K. Sherman is an attorney on Capitol Hill in Washington, DC, and author of the unique careers blog “Somebody Does That?!” Donald graduated cum laude from Georgetown University with a degree in American Studies and earned his law degree from the Georgetown University Law Center. Email him at and follow him on Twitter @somebodydotcom.


Powered by Facebook Comments

Comments are closed.