Guest Chapter 22
Name: Ryan Day
Current Position: Senior Deputy District Attorney – 20th JD (Boulder)
Former Post-Law School Positions: Law Clerk, United States District Court for the District of Wyoming; Associate Attorney, Wheeler Trigg O'Donnell LLP
Legal Practice Area: Criminal.
I am the office's primary “appellate” attorney, so I handle all level of criminal work—misdemeanor to homicide—at both the pre- and post-judgment phases.Law School and Year: University of Colorado, 2010
Time between undergrad and law school: None
One or two books I recommend: Dune by Frank Herbert. Because you've likely received enough recommendations for lawyering and self-care books, you can still read for enjoyment, and it's a tremendous book. Also, if you're reading my chapter you might be a trial attorney and all trial attorneys should learn how to tell a good story. Reading is a good way to learn storytelling.
Why law school
I never seriously considered doing anything else. My dad was an attorney and he raved about it: Lawyers solve the world's problems! Lawyers uphold the rule of law! Lawyers keep chaos at bay! (Really.) I should have known better, but I wanted to be like him. Plus, I was always told I could do anything I wanted with a law degree. I suppose that is technically true, even if I've never met anyone who spent three years and several hundred thousand dollars learning to “think like a lawyer” in order to become a marine biologist or basketball coach.
In any event, I enjoyed the work that went into becoming a lawyer—speech and debate, mock trial, the LSAT, law school, moot court, etc. I was pretty good at these, it turned out, and I liked them enough to stick with it.
What frustrated me most about coming out of law school and/or what frustrates me with regards to people I work with or hire who are newly out of law school
Law school did not prepare me for the day-to-day work of being a lawyer.
Knowing the difference between horizontal and vertical privity was great for the bar exam but not for effectively communicating with the five partners I worked for as a new associate. I had no idea how to triage and prioritize when I became overwhelmed. Law school should include less theory and more practice. Medical and trade schools require students to complete a residency or apprenticeship, right? Why don't law schools?As for new lawyers, I would like them to ask more questions. They should ask all of the questions. Ask to borrow my work product. Ask me to review with yours. And they should not be afraid to make mistakes and then ask me how to fix them. For whatever reason, new lawyers believe we expect them to know everything or we expect them to figure out things themselves. We don't expect those things! The hardest thing to do as a new lawyer is to use your time effectively, and the best way to use your time effectively is to ask questions.
How have you used (or not) the core concepts of lawyering as this book proposes: Empathy, Listening First, Asking Questions, and Giving Advice?
Empathy is the most important of the core concepts because it begets the others—we're far more likely to listen first, ask questions, and give genuine advice if we empathize with the person we're speaking to. Also, empathy builds trust and respect.
When I was a civil litigator, I did not use any of these concepts enough. (Civil litigation is, as a field, short on empathy and listening and constructive advice-giving.) Regardless, in retrospect, I would have been happier and found more success had I listened better and asked more questions. I was worried I wasn't a good enough lawyer to make it in that field and I was afraid that asking questions and making mistakes would expose me. For reasons I touched on earlier, I was wrong.
You cannot be a good prosecutor without empathy. Obviously, empathy is what allows a prosecutor to communicate effectively with a victim about the impact of a crime and to understand the victim's desired outcome.
Less obviously, but just as importantly, prosecutors must show empathy toward defendants, who often commit crimes in reaction to their circumstances. People rarely commit crimes on their best day. Prosecutors have discretion to account for this and they should exercise their discretion empathetically.Biggest mistake(s) you made while in law school
My biggest day-to-day mistake was treating law school like school, at which I had always treated with varying degrees of effort. Treat law school like a job—develop a routine and work the same hours every day.
I also wish I had been more introspective and thought critically about what would make me happy in my career. I pursued a clerkship and law firm gig because I thought I was supposed to, ignoring doubts about whether they were the right fit for me. I reasoned that these would give me greater opportunity down the road—and I was right—but the price I paid was several years of unhappiness. Know yourself and find something you like. There's no point in being unhappy because other people expect you to.
Most useful classes in law school?
Right now? Evidence. I'm a trial lawyer. But across my career, I'd say legal writing and appellate advocacy. You know by now that I'm not a great writer, but I was a disaster before law school. No matter your field you will research, you will write, and you will advocate. For me, these classes were maybe the only ones that taught me principles I've used every day in my ten years of practice.
How did you decide what to do post-law school, and in hindsight how good of a job did you do?
I applied to clerkships because I thought I was supposed to, and that they could open doors down the road. I still think that's generally correct, especially for aspiring litigators. I would recommend it for anyone who wants to be a trial lawyer.
It was the next job that I got wrong. I went to work at WTO because it was a premier litigation firm that would get me into court early in my career.
The problem is, as I mentioned above, I should have known that a law firm practice was not a good fit for me on a personal level. I learned a lot and am grateful for that, but in hindsight I did a poor job of selecting a path that would make me happy. Being happy is everything.Biggest mistake at my first job?
I mentioned this earlier, but I should have asked more questions. I was afraid that revealing what I did not know would undermine me in the eyes of my colleagues. The opposite probably was true—when I put my head down and tried to figure it out myself, I was more likely to waste time and make mistakes. I also probably should have been more empathetic toward the partners I worked for.
Best advice I got coming out of law school
This might be silly, but I vividly remember a senior associate advising me to remove the section of a motion that summarized the legal standard and replace it with argument—I didn't need to analyze the problem objectively, I needed to persuade. This was both an obvious and relatively small tip, but it highlighted for me how I had to shift my thinking now that I wasn't in law school or working for a judge. I give the same advice to new lawyers every year. The mental framework you applied to problems in law school likely won't work in the real world.
Worst advice I received coming out of law school
That I had to work in a big or “prestigious” law firm after law school. Don't pursue a job about which you might have reservations because it confers a certain “status” in the legal community. Think hard about what you'd like to do and go do it. Don't worry about what other people will think. (And anyone who tells you that you can't start somewhere small is just wrong. My wife joined a five-person startup after graduation and is now a senior attorney at Twitter. You can make it work.)
How have you remained happy in your profession? Have there been times when you were not? If so, what did you do to improve your situation?
Of course I've been unhappy. I'm a lawyer. I hated working in a law firm. I spent almost four years trying to convince myself that might change, like I'd wake up one morning excited to go to work. And I know people who were equally unhappy but stuck it out long enough that they couldn't leave for some reason—family, the money, clients, whatever. Luckily for me, other life events intervened and gave me a chance to look hard at myself and think about what I wanted in life. That led me to the DA's office, where on balance I'm very happy.
My advice is to be introspective. Lawyers spend all their time solving other people's problems. Make sure you spend time solving your own. Learn who you are and learn what you like. Then go find it.