Interview with Jennifer DaSilva

is Executive Director of Start Small Think Big, a nonprofit in the South Bronx. It provides free legal services and financial and business coaching to empower low-income entrepreneurs. The entrepreneurs receive the support typically available only to wealthier business owners, helping them to improve their own financial security, while stimulating economic activity in underserved communities. Last year, Start Small provided more than 1,000 low-income entrepreneurs with access to more than 4,300 hours of free financial and legal services, valued at more than $3 million. You can reach her at Follow Start Small on Twitter @start_small or on Facebook.

  • Was there something that influenced you in college or law school to move into the area in which you are currently working? If so, what was it?

As a college junior, I read Jonathan Kozol’s Amazing Grace, detailing the South Bronx’s crippling poverty. Compelled to action, I contacted East Side House, an established nonprofit in the Bronx, and volunteered to start a parent support program. The following year I was hired to direct its Youth Leadership Program. Later, I left to attend Cornell Law School, but the impact of that experience never left me.

  • How did you find your first job after law school?

I clerked for two years on the DC district court for the Honorable Gladys Kessler immediately following law school. When I graduated from law school, there were really only two routes to take: law firm or clerkship. Most went the law firm route, but a healthy minority went the clerkship route. Very, very few went directly from law school into the nonprofit space.

  • How did you get your next job/opportunity?

Following my clerkship, I started working as a litigation associate at Debevoise & Plimpton, where I had summered my second year at law school. I planned to stay at Debevoise for three to five years, or long enough to get some real experience there, and pay down some of my law school debt.

  • What helped you early in your career to become more knowledgeable/gain skills/experience success?

Clerking for a judge helped me to hone my legal writing skills. Working for a law firm provided me with important experience in the corporate sector. Later, I volunteered for the Lawyers’ Committee for Civil Rights Under Law to coordinate its West Coast Election Protection program for the 2008 national elections. I also worked in Cambodia with a Cambodian microfinance institution to design a new micro-insurance product.

  • Have you ever stepped off your career path for a period of time during your career, or made a significant career change? What was that change, and how did you do it? What influence did it have on your current status?

Four days after I started my job at Debevoise in January 2006, my mother was diagnosed with Stage 4 pancreatic cancer. She died that April. As might be imagined, this changed the course of my life. I continued to work at Debevoise over the next year. (Debevoise, I must say, was nothing but supportive throughout this entire process. I remain to this day truly grateful to the staff and leadership there, who went so far above and beyond to do everything they could for me.) When my husband was offered a job in The Hague, at the International Criminal Tribunal for the Former Yugoslavia, we jumped at the opportunity and moved abroad. I spent the better part of the nearly three years that we lived abroad (first two in Holland, and then one in Cambodia) realigning myself—both emotionally and professionally—after my mother’s death.

At first, I jumped off the career path altogether. I had little idea how to find my way back, and not much interest, either. Time did pass, as it inevitably does, and I began to heal, and I did start thinking about what my next steps for my career could be. This time around though, I was wholly focused on what I wanted to do, rather than what I thought I should be doing. I threw my three-to-five-year law firm plan right out the window and started thinking as big as possible about what might come next. One of the hardest things about jumping off the beaten path is that there aren’t a lot of very clear markers along the way—like, what does success look like? It’s much harder to measure your progress. You can’t as easily compare yourself to what your peers are doing, because you’re doing something totally different from most people. “Status” is a very hard thing to judge and/or measure—to what extent is it about salary? Responsibility? Autonomy? Flexibility? Security?

  • What have been some of the critical turning points in your career including both successes and disappointments?

My time in Cambodia influenced my interest in the intersection between small business development and community development. It helped me gain the skills, perspective, and vision to start an organization. Living in Cambodia inspired me, compelled me to look past those things in my own life that made me afraid to think bigger, and that suddenly seemed so small in comparison. I think that having experience in both the for-profit and nonprofit space is important, as both help you develop different but compatible skill sets and perspectives.

  • What has been the most difficult aspect of the path you are on now? What has been the most rewarding aspect?

Charting my own course has been both the most difficult and the most rewarding aspect of the path that I am on now. It’s the one thing that would be the hardest to give up, should I choose something else. It’s also the thing that makes what I do the most stressful. Sometimes, all I want is for someone else to just hand me a list of things to do and say, “Here you go. This is what’s on your plate. This is what you need to do, and this is when I need them by.” All of that is on me—to identify the to-do list, and to keep myself going. That’s wonderful autonomy, independence, and creativity. It’s also incredibly exhausting.

  • What kinds of obstacles did you have to overcome to make Start Small Think Big a reality?

There were, and continue to be many. The first one was the psychological one: I can’t do this. This is too hard. I don’t know what I’m doing. I’m not qualified to do this. I’m scared. I overcame those thoughts mostly by ignoring them, truthfully. If I paid too much attention to those things, if I thought too long about whether I actually did know how to do all of the things I was going to need to do (no), if it was going to be really hard (yes), if I was really qualified (maybe yes, maybe no), I never would have done this. I really had to just take the plunge. Jump in. I know that sounds very cliché, but it really was true in this case. If I thought too hard about all the reasons why I shouldn’t or couldn’t do this, I never would have done it. So I just did it and I’m still doing it. It continues to be a challenge, like, why do I insist upon doing something that feels so hard all the time? Why don’t I just go and get a normal job?

Money is also a huge and ongoing challenge. I went without a salary for the first two years of operation. I used my personal savings (including money that I had saved up while working at Debevoise) to support myself during this time. Every year I have to fundraise to make our budget, including my own salary. Fundraising is, in many respects, a grueling task—nobody really likes asking anyone else for money. But, as Start Small continues to grow, and we have better and more impressive results to show for our work, it really does get easier. I’m not so much just asking people for money, I’m asking people to join our proven cause.

Less an obstacle and more of a challenge has been to really focus on what exactly our mission is. If we tried to do everything, for everyone, we would end up doing “nothing for nobody.” You have to make some really hard choices—you can’t help everyone. You have to choose. Over the years, we have methodically honed our mission and narrowed our target population. That has included some very, very painful choices about what to do, and what not to do, but the organization is so much the better for it.

  • How has your legal background served you in your current position?

My law degree and training as a lawyer was exceptionally helpful at the very beginning, when I was working to get Start Small off the ground. We had numerous legal issues to deal with—our incorporation and our 501c3 filing and approval, for starters. My training as a lawyer allowed me to more easily identify the legal issues that we needed to deal with, and either address those issues myself, or find the right person to help. Inevitably, for better or worse, I wear my “lawyer glasses” basically all the time—I can’t help but see issues/potential issues (organizational issues, HR issues, partnership issues, etc.) through this legal lens. This better enables us, as an organization, to mitigate the risks that are inevitable in doing business.

My training and experience as a lawyer—one who has worked for a corporate law firm, but also in the nonprofit space—also affords me credibility in my field. Start Small provides our clients with free small business legal assistance, among other things. It helps a lot, in terms of credibility for the organization and the services that we provide, that I myself am a lawyer, and that I hire lawyers to manage our programs and deliver our services.

Finally, my legal background has allowed me to more easily forge partnerships and relationships with the legal community, i.e. private law firms, law schools, and nonprofit legal organizations. While I certainly don’t “practice law” in the traditional way, my legal training and background has served me exceptionally well. I don’t doubt for one minute that going to law school was the right decision for me, even though I have ended up on this somewhat non-traditional lawyer path.

  • If you were advising a young attorney today who was entering your field, what advice would you give them about how to find a job, how to develop their expertise, and how to be successful?

The more practical, real-world experience you can get, the better off/more marketable you will be. Get an internship over the summer. Do an externship during the semester. Take a clinic in school. Try to get a job even before you go to law school. You have to be able to demonstrate clearly that you have practical, real-life problem solving skills. You must assume that everyone who applies for the job you want has excellent grades and has gone to an excellent law school. The only way that you will distinguish yourself is with your real-life work experience. Employers want to know that you will be able to hit the ground running.

  • What are some of the biggest challenges that you see facing new lawyers today?

Law school continues to be extraordinarily expensive. Unless you are independently wealthy, you will exit law school carrying a very heavy debt burden. This obviously has an impact on the professional—and personal—choices you make.

  • What are some changes and challenges you see on the horizon for the practice of law?

So many different tools and applications are now available that make the law so much more accessible to the general public. With these advances in technology, we are seeing that the fundamental methods of delivering legal advice—i.e., conversations between lawyer and client and memoranda—are beginning to change.

  • If someone had offered you some advice about your career early on—what do you wish they had suggested to you?

Someone said something to me early on that I knew was very important, but at the time, I just didn’t really know what to do with it. That is, it’s so important to be able to distinguish between what you should do and what you actually want to do. Unless I really force myself to stop and be totally honest with myself about things, much of what I do instinctively, I do because it’s what I think I should be doing. Why do people go to law school in the first place? Because they should! Do they want to? Totally irrelevant! But if I take just a moment to pause and think carefully about why I am doing what I’m doing, often I will come up with a very different answer—or, maybe it’ll be the same answer that I arrive at, but for entirely different reasons. So really pay attention when you are making decisions: are you doing what you are doing just because you think you should, or are you doing it because you really want to?

  • What role have mentors had on your career? What advice do you have for new lawyers about mentor relationships?

I have been very fortunate on this front. I think mentors are absolutely critical, especially for younger lawyers and women in the legal profession. I’ve had all kinds of mentors; mentors who gave me a swift kick in the butt when I needed it, who just sat and held my hand when I needed a good cry, who let me just watch them be awesome, who always had an open door for all of the above. I think a person can never really have enough mentors, because each of your mentors can and should play a different role for you. You can always, always learn something from someone else, and the more people you have to look to, to ask, the easier it will be to find your own direction.

About the Author

Debra L. Bruce is President of Lawyer-Coach LLC, a coaching business for lawyers. You can follow Debra on Twitter @LawyerCoach.

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