I have an uncle in Kansas City who is a lawyer, and two of his children are my age, so whenever we visited I spent a lot of time at his house. Over the years, I heard a lot of talk about the practice of law, trials, strategy, and resolving disputes. His life and practice served as a model for what that kind of life could be.
But I never thought that I would become a lawyer. As a child, my interests were split evenly between reading and the arts. I took drawing courses at the Art Institute, pottery classes at Lill Street Studios, and acting lessons at Piven Theater in Evanston. I always thought that I would do something more traditionally creative and expressive. But, when I started to build a life for myself, I wanted more stability than those paths seemed to offer.
I studied design in college for two years and loved it, but felt it was too limiting as a foundational education. I wanted a more classic liberal arts experience. So, I switched my major with the expectation that I would ultimately go to graduate school and work in design. I got my BA in History with supporting coursework in Political Science. After I received my undergraduate degree from the University of Illinois, I started to work in architecture. But after about a year and half, I realized that design was not something that brought me joy in my daily life. I appreciated it but wanted to learn and read more on a daily basis.
At that same time, the 2000 election was happening. I worked in the Sears Tower, as did a good friend of mine, and we met for lunch every day. We frequently discussed what was going on in the election and then in the Bush v. Gore case. When the decision was handed down, I didn’t understand the opinion. It was disappointing to me that there was an act as fundamental in our nation’s history as the decision of who would serve as president and it was couched in a language and a procedure that I didn’t understand. As a citizen, I wasn’t pleased with that.
That same friend was enrolled to go to law school in the fall of 2001. I remember him saying to me that he really thought that I should consider it. He encouraged me to at least take the LSAT and see how I do. So, I did, and I went on to attend what is now named the Northwestern University Pritzker School of Law.
Tell me about your legal career.
My work in the law started before law school. A college friend was working at Jenner & Block as a project assistant around the time I took the LSAT and was considering leaving the architecture firm. Having heard about what she did and the experience she was gaining, it seemed like a good way to learn what goes on in a law firm setting. Using her as a reference, I applied to be a project assistant. I worked there for nine months, before I went off to law school. It was a great and very informative experience. I had a window into the world of Big Law. I saw the challenge, the friendships, and the excitement of the practice. I spent my twenty-fifth birthday in Miami, Florida as a part of trial team seeking injunctive relief for our client in a breach of contract dispute before the Southern District of Florida. It was my first exposure to the practice of law in a commercial way that I had never seen before, and it was appealing.
Did you know that you wanted to go into big law after that experience?
I had no concrete idea of what I wanted my practice to look like. All I knew was that I really liked learning, especially about things I didn’t already know. Growing up, the civil rights movement was a common topic of conversation in my house. Also, since I studied American history, I felt I had a grasp on law being used as a tool to create a social change. But, what wasn’t familiar to me was The Wall Street Journal. I didn’t really understand how Corporate America worked.
The summer before OCI, I took a summer school class (business associations) with Professor Rick Brooks, and I loved it. I loved the concept of the duties to shareholders. The hostile takeovers and the mergers and acquisitions reminded me of politics in the Ancient Greek city-states and the Roman Senate, where you have these poleis comprised of citizens eligible to vote who were tasked with contemplating a larger population that had no say. Personally, for me, it was very exciting to find an analog that paralleled with what I had studied previously.
I finished the class right before OCI, so I was hot on M&A and transactional work, specifically corporate governance. Going into the interviews, I focused on a handful of firms that did top notch M&A work. In the end, I received a summer associate position at Skadden.
In that role, I did nothing but transactional work. At the end of the summer, I enjoyed it and felt that I wanted to continue that type of work once I graduated.
From there, I had the good fortune to clerk for Judge William Bauer on the Seventh Circuit. Elated, I spent the next year doing appellate litigation. After that experience, when it came time to start in private practice, I felt that litigation would be a better fit, so I asked Skadden if I could go into the lit group, and they embraced the idea.
Skadden really took care of me during that transition. It was a warm, welcoming, and caring environment for me. I had great mentors and I learned a lot. Over the course of my years there, I learned how to practice law generally and within the firm. Thankfully, I was also able to take time for my personal life – to marry my wife, Cindy, and start a family. I am very grateful for the experience I had at Skadden and the life I was able to make for myself while working there.
At the end of last year, I joined Sperling & Slater, P.C. Externally, the two firms are a stark contrast. At Sperling, we have about two-dozen lawyers in one office. But the caliber of practice is stellar, and I could not be happier.
Did you have any mentors?
There were partners at Skadden that taught me about the practice of law as a profession and how to be a good lawyer. They taught me how to exercise good judgment, which is something that’s harder to learn than the law. You can always study the black-letter law online or in a book. But learning how to make good decisions is critical for being a good lawyer.
Judge Bauer has also always been a phenomenal model in my career. He’s an incredibly available person. I think so highly of him that, at times, I have hesitated to reach out because I didn’t want to trouble him. But, that’s on me. When I do call or visit chambers, he is always incredibly giving and open with his time and wisdom. I look to him as a standard of how I should be as a lawyer.
What advice would you give to someone starting out as a new lawyer in Big Law?
This may sound trite, but working hard is incredibly important. Say “yes” to assignments without oversubscribing yourself. And when you work through that assignment, be sure to express whatever limitations you may have so that the attorney for whom you are working isn’t surprised or left in the dark. Big Law firms are unique environments. While it’s true in all forms of private practice, lawyers don’t control their schedule. The reality is that if a client calls and needs something in an emergency you’re honored because you are the go-to counsel in that moment. But it creates pressure in your life.
I found that just being able to do the work at the outset and establishing who you are and building capital within the firm, is going to be a challenge when you first start out. I knew there was going to be a crazy amount of work. I knew I would be putting in a lot of time. So, it’s important when you start out in a Big Law setting to manage your expectations.
As a junior attorney, it’s important to recognize that anyone who is senior to you is your boss. Your goal is to not only do the assignment, but to make life easier for whomever assigned you that project. Everything that you do, from how you deliver the project, to communicating about deadlines, should be done in a manner that puts the partner or senior associate at ease, because he or she is doing the same thing for the attorney (or client) above them.
If you can do that, then people will want to work for you, and if people want to work with you, you can develop the ability to manage your own career.
Speak to the importance of civility in the legal profession.
I appreciate that the law is a way to advocate for our clients in a manner that, at times, may be confrontational. But it need not be. The law is a way for people to work out, in a civil manner, very real disagreements that, absent the law, would have to be resolved in a more challenging way.
I had the very good fortune to clerk for Judge Bauer. He was able to address any situation in a level-headed and thoughtful manner. Whenever I do get frustrated in my practice, I like to think back and reflect on my clerkship and think of him as a model of civility. I contemplate what he would do in my situation to handle it.
How do you spend your time outside of the office?
I serve on the Board of Directors for Landmarks of Illinois. I am also the President of the Northern District of Illinois Court Historical Association. Right now, we are planning to honor the Court as a part of the 200th Anniversary of the establishment of the federal court system in Illinois. It’s a really nice way to stay involved with the community over at the Dirksen Federal Building, and to interact with people who are in the court daily.
I am also the father of two girls, one three years and the other three months in age. They’re amazing, and I’m so grateful to be their father.
Martin Sinclair has served on Illinois Supreme Court Commission on Professionalism since 2015. Martin Sinclair currently serves as Vice-Chair of the Commission.