Why I Became A Lawyer: Following A Serendipitous Path

Reflecting from the vantage point of 30 years as a lawyer, I find myself in a career that I love because I followed my passion but also allowed for serendipity. I was not a kid who ever said that I wanted to be a lawyer when I grew up — but, looking back, I can see a clear path that began with being part of a family with a deep interest in politics and justice. This, in its time, led me to get involved in political campaign work, and, from there, I found my way into the legal profession. It turned out to be a great fit for me.

From an early age, I was drawn to questions about justice. I lived on the south side of Chicago and made regular visits to Hyde Park, home to Nathan Leopold and Richard Loeb. I was intrigued by the story of Clarence Darrow’s defense of Leopold and Loeb against the death penalty,  and I looked at his defense of John Scopes in the “Monkey Trial”  as a fight for fact and reason in a community where faith and science could not coexist.

My politically radical grandmother, who immigrated to America as a young girl, gave me Upton Sinclair’s “The Jungle” and a book about Nicolo Sacco and Bartolomeo Vanzetti, to remind me of the challenges that immigrants had to overcome. She instilled in me an interest in politics as a means of accomplishing positive social change.

We were raised to admire all things Kennedy —  and especially Robert Kennedy.  I saw him as a political crusader fighting corruption and promoting civil rights. Yet, while hoping to emulate him when I grew up, the title that preceded his name —  Attorney General —  did not cause me to consider a career as an attorney. And when I attended Brandeis University, where our newspaper was called The Justice, the idea of actually practicing law was never on my mind, in stark contrast with many of my peers.  My path toward becoming a lawyer was serendipitous, rather than strategic.

I made my first move toward a legal career unwittingly in my sophomore year. I began that year by breaking my parents’ hearts when I told them that I would not become a doctor. They never got over it.

My father used to enjoy watching my trials and always showed interest in my cases, but he was disappointed that I did not follow him into medicine. As recently as this past Thanksgiving, my mother noted what a fine job I did carving the turkey and suggested that I should have become a surgeon. But in college, my dream job was neither doctor nor lawyer. Rather, I wanted to pursue a career in government.

My grandma had instilled a conviction in me that government can and should provide access to the basics: health, education, housing and a range of social services. She bought me my first subscription to The New York Times (and to the English-language version of the socialist weekly The Forward) so that I would be an informed adult. To her, government was not the enemy to be reined in. Rather, she was a fan of big government to protect us from the powerful.

So upon my return to campus to begin my sophomore year, I jumped at the opportunity to attend a presentation by Ted Sorensen, a hero of mine due to his work as a speechwriter and adviser to President John Kennedy. Sorensen came to campus to speak on behalf of Sen. Gary Hart, who was running for president.

Prior to that meeting, the only thing that I knew about Hart was that he had managed George McGovern’s unsuccessful presidential campaign. Many presidential candidates came to campus to recruit volunteers to knock on doors for them in New Hampshire. Based on Hart’s affiliation with Sorensen, his work for McGovern, and his youth, I figured he had to be at least okay. And I had the opportunity to actually meet him, as it turned out that many of my peers found the library to be a bigger draw than Sorensen and Hart.

Although I did not know it at the time, that meeting set me on the path to becoming a lawyer. What I did know was that traveling to New Hampshire each weekend to canvass for the “New Ideas” candidate was a great education. It gave me the opportunity to listen to people from socially and economically diverse backgrounds, to learn about their lives and challenges. And I honed my advocacy skills.

At night there was beer, pizza and talk of making a real difference. It turned out that most of the political professionals who gave us our routes and canvassing instructions were lawyers. My interest did not even wane months later when I was visiting the Quincy shipyards at 6 a.m. — very, very early for a college sophomore! — to meet the men who worked there.

Growing up,  “lawyer”  had been the high school career day occupation to which my guidance counselor sentenced me each year. Lawyers showed up in suits carrying worn briefcases: very dry and unappealing. But my college experience on the Hart campaign showed me that if I wanted to follow in the footsteps of Kennedy or Sorensen, I needed to go to law school. I took the LSAT, typed applications and applied.

My senior advisor at Brandeis encouraged me to rethink my plan when I asked him for a letter of recommendation. He assumed that I had been drawn to the legal field by “L.A. Law” and its deceptive presentation of life as a lawyer. And he had a point: A show depicting people staring at computers (or typewriters), banging out briefs and drafting interrogatories would have made for terrible television. I assured him that while I wanted to go to law school, I would not become a lawyer. I was going to become Ted Sorensen.

It turned out that I not only loved law school, but was drawn to a career as a litigator rather than as a political consultant. My senior adviser had been right that practicing law had none of the flash of “L.A. Law” — except, perhaps, during my glory days as a summer associate. But law school trained me to think about and solve problems in a new and exciting way.

I did not pick up the actual nuts and bolts of the practice in law school,  though.  Those were ground into me as an associate. The discomfort of being challenged under the withering interrogation of a law professor employing the Socratic method was nothing compared to the regular grilling we received as young associates. We were not coddled or praised, but we were shown the ropes.

Early on, I was fortunate enough to get to take cases to trial before juries. I learned that trying a case is like writing,  directing,  choreographing,  staging and acting in a play in which some of the actors will improvise in unexpected ways, seemingly without warning. I loved it then, and still love trying cases today.

As a litigator, I am treated to an insider’s view of transactions that went awry by questioning the participants and assembling the “truth.” I get the opportunity to meet many people, learn how things are made and what makes businesses successful (or not), tell stories and solve problems. I often meet people who find themselves in stressful circumstances, and my job is to help them bring order to disorder, to assist in resolving their challenges and to communicate that I always have their backs. It is a great job.

I have been fortunate enough to argue before the Illinois Supreme Court, and to try a number of cases in a variety of jurisdictions in state and federal courts across the country. Yet, as much as I enjoy litigation, it is just one of the tools we can use to resolve our clients’ disputes.

But what I perceived to be an overemphasis on the billable hours at the expense of a client focus caused me to start my own firm. And to make sure that I understood my clients’ needs and could succeed in this new endeavor, a consultant encouraged me to go to my clients and learn from them about their experiences with lawyers and, specifically, with me.

This exercise took me back to my days canvassing for Hart in New Hampshire, where I learned the importance of listening. I interviewed clients to learn about their experiences with our collaborations, and they told me that by listening to them and applying the tools and strategies developed over the course of 30 years of practice, I helped them navigate choppy waters.

I have strayed far from the government service career that I expected to pursue after law school. Yet, as any good litigator will tell you, while planning is really important, the ability to adapt and adjust to the facts as they appear and evolve is critical to a successful outcome. Serendipity has led me to a very satisfying career.

This article originally appeared on Law360 on February 4, 2020.