Ms. J.D. Interviews Lawyer-Turned-New York Times Staff Editor

Ms. Jenee Desmond-Harris

Apart from the fact that we share a name (spelling notwithstanding), thus solidifying her cool in my book. Ms. Desmond-Harris has enjoyed two thoroughly satisfying careers that, to the outside eye, may seem like completely separate spheres. 

Ms. Desmond-Harris is a Lawyer-Turned-Staff Editor for the New York Times. Her resume is the dream for both the law nerd and the conscious writer! 

From Howard-to-Harvard Law- to Stanford as a Journalism fellow, her educational pedigree is nothing short of top-notch. She spent almost four-years at one of the nation’s top firms K&L Gates, practicing law. So, one might ask, how did she end up at one of the nation's most respected news publications? Res Ipsa Loquitur for the legal nerds out there. For the rest of us; lawyers are more than our one-dimensional Law and Order television counterparts.  

The 21st Century attorney has likely had multiple careers either before or after the law and harbors many talents, quirks, and hidden hobbies. Ms. Desmond-Harris devoted her writing talents to The Root, as a senior staff writer and features editor, and The Vox prior to joining the New York Times. 

It is important to note that, there is no right way to have a legal career –or a writing career for that matter. There are roads less traveled, that often lead to unexpecting and fulfilling careers outside of the law. At Ms. J.D., we want to introduce you to the many talents and identities of The Lawyer! And we're thrilled to begin with the multi-talented Jenee Desmond-Harris.

1.     Why the law? What was (is) it about a law degree and law practice that you found attractive when you originally set out to enter the legal profession?

     I think my story is pretty common among a certain set of law students: What I found attractive about getting a law degree was that it would offer me economic security. I didn’t have the option to choose a career that would require luck or connections to land a job with a decent salary, or would leave me needing years of help from my parents until I got on my feet.  At the time I started law school (2003) this path checked all of my most pressing boxes. I saw it as the express route to real adulthood and success.

     I’m sure there may have been other options if I’d thought more creatively (or had any knack for math and science whatsoever). But at the time, it seemed like a safe and smart choice. Plus, I really enjoyed the social approval and the feeling that I was on the right track, that my friends and family were proud of me and that, no matter what happened, I wouldn’t be seen as a failure. There’s something to be said for that! As a bonus, I’ve always loved school, so signing up for three years of intense studying didn’t bother me at all.

2.     In the legal community we talk a lot about how “you can do anything with a law degree.” There has also been much backlash against that theory, with people taking the opposite approach, and going as far as saying do not go to law school if you do not plan to practice. What is your take on that?

     I think there’s some truth to it.  For lot of people “lawyer” translates to “smart and hard-working,” and there’s no question that that can offer a boost to someone with “JD” on their resume when looking for a job in any field.

     But for most careers outside of legal practice, there are more efficient (and cost-effective) ways than law school to get there. And it’s important to remember that (depending on your personal financial situation, the cost of your education, and whether you’re able to make and save a lot of money in a legal job) law school debt can really limit your options when it comes to starting over on a career path that isn’t as lucrative. So yes, you can be an entrepreneur or run a nonprofit or teach dance with a law degree. But the question is: can you afford to get your foot in the door while paying a student loan bill that rivals your rent every month?

     So I would tell someone who was already in law school or practicing, “Don’t worry, there are plenty of other things you can do if you don’t like being an attorney.” But I would tell someone who hadn’t yet applied for law school, “Don’t apply unless you actually want to be a lawyer and you have a solid understanding of what that involves day-to-day.”

3.     Is there “life after law?” How would you characterize your time as a law student and attorney?

     It’s complicated. I think I enjoyed a sense of accomplishment during both law school and my time as an attorney. You get a lot of positive reinforcement for choosing this path.  And I did have plenty of great experiences and good times during those six years. But at the same time, I had an overarching sense the entire time that life was something to be endured rather than enjoyed. I remember being at brunch on a Sunday as a lawyer (after having working most of the morning) and looking around at my friends with an intense sense of jealousy that they weren’t living under the same cloud of stress, dread and dissatisfaction that I was. I felt like they were actually living, while I was just surviving, one assignment to the next.

     I want to be clear that this is not the case for everyone! I know so many lawyers who have rewarding and exciting careers that allow them to live great, happy lives. I also know many who have found jobs that, even if they don’t make them fulfilled, don’t make them unhappy either. And their joy may come from what the salary can do for them and their families. I think there’s dignity in that, and I always want to be careful of sending the message that a person’s life is lacking if their job isn’t also their passion.

     But my reality was, when I tried to picture myself at age 60, as a law firm partner, I felt nothing but depression. So there was absolutely life after law. Despite the stress that came with starting on the ground floor in a brand new career and making much less money, I never looked back. In some ways, it actually felt like that was when my real life started.

4.     Many attorneys, especially those at large law firms, leave the profession feeling resentful; did you ever have similar feelings or do you have any insight into why so many attorneys feel that way?

     Not at all. I was definitely resentful most of the time that I was actually working at my firm! Like, every day (through no fault of my colleagues — that’s just what happens when you have zero passion for what you’re doing, and you have do it for a million hours a week). But by the time I made the decision to leave, I had a sense of peace and gratitude for the relationships I’d developed — and quite frankly, for the fact that I’d earned enough money to spend some time trying something else. I also sort of chuckled at how stressed I’d been the whole time — despite all my angst, I’d never actually single-handedly destroyed a client’s business, or been fired on the spot for a bad memo, or emailed the entire firm by mistake, or even had a bad review. The worst case scenarios that hung over my head had never happened and it did occur to me that maybe some of my misery had been self-imposed.

     One of the most surprising and gratifying things about my transition was that my relationships with a couple of the partners I worked for, who were sort of the bane of my existence when I was at the firm, transformed. One guy is a true genius, and over the years since I left, I’ve leaned on him to check my instincts when I’ve written about legal topics. He’s kept up with my writing, we email about politics, I hear about his kids’ milestones, and he even served as a reference for the job I have now. He went from being someone whose name I dreaded seeing in my inbox, to a peer and a cheerleader — not because he changed, but because I changed into a person who liked her life.

     As a side note: I think it’s important to draw a distinction between people who leave law firm practice because they’re being marginalized there, versus people who leave because they never actually really wanted to be there in the first place. I’m in the latter group (and for what it’s worth, I thought I was treated very fairly and well supported by almost everyone I worked with and for as an associate) so it makes sense that I wouldn’t be resentful. But I’ve heard way too many stories of people in the former group — people who worked hard and wanted to be in for the long haul but were set up to fail, denied quality work, not offered good mentoring, etc. and then blamed for lack of hours or not being a good “fit” — and I’m outraged and resentful for them.

5.     Even still, many lawyers who leave practice leave with, in my opinion, one foot still in the door, so to speak. Meaning, they began a new career path that still has strong connections to the legal field. They become legal correspondents, bloggers, consultants, or enter some other profession that has a strong connect in the law. Would you agree with this? If so, why do you think that is?

     Sure, I can see this. We have skills that are always going to be in demand. And many of these professions provide more than, say, starting a wedding planning business or becoming an artist. They’re a step away from the practice but not a leap to something hugely risky (and of course, being risk-averse is probably the reason many people decided on law school in the first place).

6.     Scratch a lawyer, find a writer?

     Many times, yes. Talent for writing is useful in many practice areas. But I think a deep desire to write -- a passion for writing -- is more common among dissatisfied lawyers. For the people who truly love their legal jobs, more accurate sayings would be: “Scratch a lawyer, find someone who really and truly enjoys doing discovery,” or “Scratch a lawyer, find someone who enjoys any intellectual challenge, regardless of the substance,” or “Scratch a lawyer, find someone who has decided to dedicate their life to civil rights.”

7.     In what ways has law practice affected your writing career?

     I think law firm practice was a kind of boot camp for developing a serious work ethic.

     When I first left my firm, I freelanced for about a year. Coming from an environment where you would never dare miss a filing deadline or even a deadline to get a research memo to a partner, I’d always file my pieces on time or early because I just thought that was the rule and didn’t know there was another option. It turns out there are other options! And writers are infamous for using them, a lot. To this day, if someone owes me a piece and e-mails me with excuses about being busy or uninspired, I’m sort of taken aback. The “get it done by any means necessary” attitude that characterizes law firm culture is something I’ve tried to hold onto at least a little bit.

     Similarly, survival in a law firm environment means not just doing the tasks you’re asked to do, but also obsessively finding ways to be “indispensable.” You want to create a situation where partners begin to think they can’t live without you, so they continue to give you assignments, so you take on more and more responsibility, and eventually the firm itself can’t live without you so you make partner and live happily ever after. Even though I didn’t end up at my firm long term, I do think I absorbed this mentality, which is a useful one to have in any field. I’m pretty sure it’s what took me from freelancer to staff writer to senior writer to podcast host to editor in my first journalism job in just a few years.

     Another skill that law firm associates, at least in big firms, have to have, is the ability to quickly and independently become smart about things that nobody can be bothered to explain — whether that’s a particular statute in a new practice area, a client’s business model, or the internal politics of a firm. My confidence that I get my head around anything came in handy when I was tasked with writing daily pieces in response to news events, and it’s useful now as I edit opinion pieces on a wide variety of topics. 

     Actual legal knowledge has not really set me apart in my field. I’ve realized that lawyers often encourage each other to believe that we’re the only really smart ones and the only ones who can really understand things. But that’s not actually the case. So many journalists are really sharp when it comes to the legal issues they write about — so much so that they might as well have law degrees. There are tons of people out there who are great analytical thinkers and excellent at analyzing complicated issues. Many of them went to law school, but many of them did not. Their brains work the same. I feel like I’m telling one of the best kept secrets of the legal profession by saying this.

8.     You were an attorney for K&L Gates for almost four years. What do you do with all of that practice? Was it hard to “turn it off,” if you did?

     I still sometimes find myself looking at a busy week or a task I’m not particularly enthusiastic about completing and thinking, “At least I’ll get to bill a lot of hours for this!” before I catch myself and realize nobody is keeping track of my life in six minute increments, and if I work late or all weekend, there may be no record of it! That “Thank God I have a lot of work on my plate because that means I won’t be accused of being underutilized and then laid off” attitude is a hard one to shake.

9.     Would you ever return to law practice?

     I wouldn’t rule it out completely. Even though I love my current job and could do it forever, I keep up with my bar memberships just to make sure I have options if I need them.

10.  If you could go back, would you jump straight into writing/editing?

     This is a tough question. On the one hand, it would have been nice to save the cost of a Harvard Law degree, and sometimes I wonder what else I would have experienced and accomplished in journalism by now, had I gotten in the door six years earlier. My late start means I’ve always had people my age and even younger as superiors in journalism (which was at first really weird, after being one of the very youngest people at my firm and not reporting to anyone under 50) and once in awhile I kick myself for what can feel like being behind.

     On the other hand, the reality is that I would have had a very hard time making it through the first few extremely low-paying years in journalism without having the luxury of paying myself with money I saved during my time at the law firm. It wouldn’t have been impossible -- after all, people do it every day. But I was freed up creatively by the financial security I created for myself. Not to mention, I think my years as a law student and lawyer gave me a lot of confidence and grit that have served me well — and, just as important, a sense of appreciation for doing a job that I fundamentally love and believe is meaningful. Journalists are known for being curmudgeons, and when I find myself slipping into that mindset, all I have to do is recall the time I did nothing but doc review for eight months, and I feel like I have a new lease on life. I bring a lot of gratitude to what I do, and, weirdly enough, I have my past life as a lawyer to thank for that.

11.  What do you think about that state of the legal profession as it relates to 1) diversity and 2) progressiveness regarding technology and its response to attorney dissatisfaction?

     The numbers leave no doubt that the profession still struggles when it comes to diversity. That said, I know there is a place for women and a place for people of color in law, and I know deep satisfaction and enormous success are possible even for people who are members of groups that are underrepresented. I see it every day on my Facebook page as my law school classmates make partner, win awards, lead diversity initiatives, win cases, and make TV appearances.

     The law still has a reputation as a dispiriting field to work in. I’m no expert, but I doubt anyone does their best work when they are overstressed, fearful, or otherwise miserable. For that reason, I would think that individual employers who are dealing with dissatisfaction in their ranks would see an incentive to make some changes.

12.  Is the legal profession at risk of losing lawyers?

     There will always be a demand for lawyers, and I think there will always be enough people who either love the law or love the money the law offers to fill that demand. If changes to the field mean it’s no longer a default “safe” career path for people who would be better suited to doing something else, maybe that’s a win-win.

     Ms. Desmond-Harris, thank you so much for your well-thought out and decidedly interesting responses. Look for her as a speaker at Ms. J.D.’s upcoming National Women’s Law Students Organization (NWLSO) Leadership Academy.

This post has been brought to you by the Ms. JD Journalists. If you have suggestions for any topics that you think should be covered on Ms. JD, feel free to email your suggestions to contentdirector@ms-jd.org, and the Ms. JD Journalists will get right on it. 





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