Second Careers: Law School After the Age of 40 |Koehler Law

I was 43 years old when I started law school.

I’m sure my grades would have been much better had I gone to law school right out of college. I was pretty intense back in college. I read every assignment and obsessed over every detail, never missing a deadline, and I am sure I would have brought this same diligence to the law had I chosen that route instead of graduate school.

I am also pretty sure I would have hated it. Without the life experience, perspective and patience I had as an older student, I would have viewed every reading assignment as a task that had to be performed as opposed to an experience that should be savored. Always in a hurry back then, I would not have taken the time to sit back and allow the content to wash over me. I would have struggled with the law instead of yielding to it.

It was a strange experience socially. My wife and I were friends with many of the faculty members, mostly through our children. They had been to our house for dinner, for school social functions, or to pick up a child. One of the professors told me later she was glad I never took one of her classes – it would have been awkward, she said, to have me sitting in her class.

As for my fellow students, my wife and I would occasionally join the gang out for a night on the town – maybe once or twice a semester the first year. It was only on these occasions that I truly felt the age-difference. My classmates included some pretty hardcore partiers, and that could get awkward. I also thought that many of them were overly deferential to my wife, with a few trying to use the occasion as a job interview. No, I would tell these people, you don’t really want to work for my wife. Although she might seem pleasant now, she can be a very demanding employer.

I found out later that my classmates had speculated about my age. It was like that scene in Saving Private Ryan in which the soldiers form a pool to bet on Tom Hanks’ civilian occupation. After our last exam of the spring semester first year, I went out for a quick drink with some of my classmates and the waiter asked for all of our IDs. One of my classmates found an excuse to look at mine before I put it back into my wallet. I could see him scanning the ID for the birthdate, and there were some knowing looks around the table. Somebody had just come into some money.

Otherwise, with my twenty- and thirty-something classmates every bit as smart as I was, I hardly noticed the age difference in the classroom. In fact, I probably suffered from the overconfidence phenomenon my father had often described from his experience teaching college English. The best grade in the class, he said, never went to the kid in the front row with his hand raised all the time. That kid, believing he already had everything figured out, never put in the time necessary to really master the material. Instead, the top grade almost inevitably went to some insecure kid sitting in the back row who never said a thing all semester. I was the insecure kid in the back row in college; the cocky hand-raiser in law school, a favorite, I am sure, in any “Gunner Bingo” game, or whatever they call it these days.

In addition, identifying more with the professor than with my fellow classmates, I always felt duty-bound to help out a professor who was struggling with class participation. When our professor in employment discrimination brought in his mentor from private practice to speak to the class and nobody had a single question after the presentation, I quickly came up with something I urgently needed to know. Given the look of relief and gratitude of the professor’s face when I raised my hand, I was expecting the honor of “distinguished class participation,” if not an outright A, for the class. I didn’t get either.

After the respite of law school, the transition back into the working world as a neophyte in the practice of law was also a challenge. Although I have never suffered from an outsized ego, I have to admit that it is not easy to start off in a new and completely different career. It can be humbling to have to figure out everything anew.

I also went from the showcase office in the Ronald Reagan Building I occupied during my previous career to sharing a table with three other interns during an unpaid summer at the U.S. Attorney’s Office in Philadelphia. As an office director and then chief of staff at the U.S. Environmental Protection Agency, I was used to people stopping their conversation when I stuck my head into an office. My time was valued back then. And I was accustomed to people laughing at my jokes. Somehow a first-year law student or intern isn’t quite as funny.

I think of George Bush the Elder complaining about how his golf game suffered after he left the presidency. I think of Hamilton Jordan’s dismay at having to book his own travel arrangements after leaving the Carter White house. And I recall a former EPA official’s extreme gratitude when, while still at the Agency, I returned his phone call. What do you mean, I asked him? You used to be the Deputy Administrator. Of course I would return your call. You would be surprised, he said. Very surprised.

I don’t know that I could ever have worked at a law firm after graduation. For one thing, I didn’t have the grades to get a big firm offer. For another, I don’t know if I had the stomach or patience to report to some associate half my age. I am sure this feeling would have been reciprocated; as one person put it, people don’t like ordering around someone who is old enough to be their parent.

From my wife’s experience, I also knew how difficult life as a law firm associate can be. If deadlines for partners come from courts and from clients, associates get their deadlines from the partners. This means that if the partner wants to take the weekend off to play golf, the associate will get the assignment on Friday afternoon, with the product due first thing Monday morning in time for the partner to review it upon his return. Working every weekend to fit someone else’s schedule may be fine when you are a young and ambitious lawyer. It is very different when you are older.

Starting my legal career at the Philadelphia public defender’s office was thus a good fit. Although we were provided with plenty of guidance, training, and support, we were also given considerable autonomy. Yes, there were certain organizational obligations, like doing office or prison intake interviews on the days we were not in court. I tell you, there is nothing more daunting than having to interview 10-15 cranky or scared inmates at the House of Corrections or Riverside Correctional Institute for Women. But for the most part, we were left on our own after we picked up our files for court each week.

I often took my files home in the afternoon so that I could be home when our kids got back from school. I would then prepare them at night while the children did their homework or slept. In other words, I never fell victim to the mentality that you need to have the boss see you working late every night, even if you are just fiddling around on the Internet. Although leaving the office early at the public defender’s office was strictly verboten, my supervisors often saw me on the way out the door with my briefcase full of files and never said anything about it to me.

At the same time, of course, I understood the trade-offs I was making by not being in the office later into the day. I knew from my previous career that the bonds you develop with your co-workers – to say nothing of the impression you can make on your superiors – tend to happen during these hours. During my first or second year at the EPA, we were unmerciful in kidding an older colleague who had left an important memo, due by close of business that afternoon, half-written on his computer so that he wouldn’t miss his carpool. Those boring old people, we thought, with their home lives.

Given my overarching interest in autonomy, the logical transition from the public defender’s office was to solo practice. I never wanted to be a “lifer” at the public defender’s office. Apart from the elite group of lawyers that handled the most serious offenses, I don’t know how anybody can suffer the abuse you get from indigent clients for that long. Not every burnout is quick and public, although we had those too. I think of my office mate – a dyed-in-the-wool liberal who had worked at legal aid prior to coming to the PDs office – hanging up the phone after a difficult call with a client and telling me he had come to the point in which he despised our clients. Three months later he was gone, having found himself an entry-level job in private practice.

Although I wanted to honor the three-year commitment I made to the defender’s office when they hired me, I had always planned on eventually going out on my own. After a first career spent in government, the notion of running my own business appealed to me. I had a good relationship with many of the retained lawyers who circulated the halls of the Criminal Justice Center in Philadelphia, and I often asked them for specifics. I also consulted two public defenders who had returned to the office after having practiced on their own for a couple of years. How was private practice? Why did you come back?

I had no problem making a living, one of them told me. But I did get pretty tired of chasing after people for money. I like it here where all I need to do is practice law.

When my wife and I decided to return to D.C. for other reasons, I initially hoped to hook up with a criminal defense firm in D.C. Although I knew my way around a courtroom pretty well by this point, I was looking for some type of apprenticeship to ease the transition to a new jurisdiction.

When I didn’t have any takers (and in truth, I didn’t look all that hard), I decided to forego the apprenticeship and jump directly into my own practice. The moment of inspiration came to me one afternoon while I was updating my resume. I had a strange resume anyway, and as I was fretting about how to explain the gap on my resume during the time I spent as a stay-at-home father, I thought, why not be hired by one of the few people who wouldn’t require an explanation on anything: yourself. It was a big relief to put aside that resume.

There are many benefits to being older when it comes to solo practice. A younger version of myself would have missed the structure and social aspects of a job within a formal organization. Now I welcome the autonomy. If I don’t like the client or the case, I say no thank you. If there is an illness in the family or if I want to take a vacation, I do not need to ask anyone for permission. I am accountable only to clients and the courts. And, although I spend most mornings at court, the rest of the day is mine. I am home most days when our son – the last of our children still at home – gets back from school.

While having to learn new things can sometimes be hard on the old ego, it can also be reinvigorating. My wife and I are at the age at which our friends who are lawyers have now been practicing for over 30 years. You can only do the same thing for so long – even if it is what you love to do – before it gets old. If some of them are now thinking about moving in a different direction, I tell myself that, although I may be well behind them with respect to the practice of law, I am way out in front when it comes to the second career. Woo hoo. I never like to lose at anything.

Post-Script (March 11, 2023):

Eleven years after I wrote this, this blog entry continues to be among my most popular pages. Recognizing that many of the comments posted here (before comments were disabled) are themselves old, I often wonder what happened to the people who posted them. Did they take the leap? Are they happy they did?

I myself have never regretted my decision to pursue a legal career. As a solo practitioner focusing exclusively on criminal defense practice in Washington, D.C., I make a good income. With complete control over my case load, I have tremendous flexibility. I enjoy the status of being a lawyer — despite the lawyer jokes, there is no need to explain who I am and what I do. And, even though I focus on a relatively narrow area of the law, there is always so much more to learn. In other words, I will never be bored. I will have the satisfaction of knowing that every day I am a better lawyer than I was the day before.

For those of you who are still on the fence about making the leap, let me offer this word of encouragement: Do it!