Sidebar: Regrets, I’ve Had a Few…

Even if I had received some valued career guidance, I would have ignored it. No one I knew ever thought they’d be rolling in dough, and investment banking, that’s like a teller, right? I taught high school English in overcrowded, raucous John Jay High in Park Slope, back when that neighborhood was diverse and working class, before gentrification, organic kale, and $4 million brownstones.

To maintain your teacher’s license, the board of education required that all teachers obtain 30 graduate credits within five years. I figured studying 19th-Century Novels, or Educational Ideas: A Historical Perspective, would not impress anyone in the real world, so I applied to law school. A brilliant choice, I thought. Go at night, obtain the credits, and if the teaching gig doesn’t work out, voilà, I’m Clarence Darrow. I didn’t realize, of course, that the workload in law school was a tad more intense than college. Suddenly I was crazed—marking papers, writing lesson plans, trying to engage teens who hated school and told you so. Then I hopped the F train to Brooklyn Law with its alien language and concepts, myriad cases, Prosser on Torts, and demanding professors. Exhausted, overwhelmed, and traumatized, I somehow muddled through that very difficult and stressful first semester.

Early spring, I stopped by the board of education to make sure that overstuffed bureaucracy added the 11 law school credits to my file. The pleasant, gray-haired lady smiled as she said: “Sorry, we don’t accept law school credits. Graduate school only.” I wasn’t the brilliant advocate then as I am today, but I eventually articulated a simple question: “Are you freakin’ kidding me?” Her smile never changed, nor her answer.

This is how I became a lawyer—by not knowing the rules, not reading the fine print. The veteran teachers at John Jay begged me to continue with law school—don’t stay, the system’s broken, we’re glorified babysitters. So I did, attending both while I taught—four nights of law and one of graduate school. My only hiccup was in The Romantic Movement, a poetry class even more tedious than Property II. It didn’t help that my idea of romance was to pick up the tab but ask my date to leave the tip.

I never regretted stumbling into law. The work is arduous and long, clients difficult and demanding, judges mercurial and less than brilliant. And if you hate it, try something else, but realize that any successful career entails drudgery, endless hours, and rejection. But certain aspects of my career (and life), I wish I had done differently.

Take a chance. I should have tried more cases. I had my share, but if I had plowed ahead on a bunch early, I would have developed greater skill, resolve, and reputation. Today you go to trial with the frequency of a solar eclipse, so maybe that’s no longer possible, but challenge yourself—take a deposition, argue a motion, write a brief. Volunteer for a chance to learn, to be a success.

“Make the weather your friend,” screamed Coach Greg Toal to his football team at New Jersey’s Don Bosco High when the forecast was rain, snow, or bitter cold. Embrace adversity and thrive. Yes, you will fail and slink back to the office embarrassed, even humiliated. But anyone who’s been there will understand and respect you. You learn most by losing. Builds character, as they used to preach.

Calm down—it’s not the end of the world. Lying in bed, unable to sleep, I would obsess over every minor mishap. Years were wasted worrying about stuff that turned out to be unimportant. I couldn’t help it, or at least that was my excuse. My partners were invaluable. I would slink into a chair, embarrassed, and admit fault. Countless times, they would patiently listen and then suggest a solution or, even better, dismiss it as a nonevent. Always be receptive and understanding to colleagues who need support and reassurance. Winning a case is a team effort. No one’s pinning medals on your chest if your initial reaction is always “How did you screw that up?”

Failing to ask a question, cite a case, review a document is no reason to quit and join a convent. No one likes to make mistakes, but they happen and a near universal truth is that no one error is determinative. You and your supportive colleagues will discover a way to recover. No magistrate judge would ever dismiss a wrongful death case because some idiot forgot to serve one doctor’s medical records. Well, no good magistrate judge, and it was overturned on appeal.

Leave the lawyer mode in the office. I always found it difficult to separate work from life. I never discussed the day’s events over dinner since that would remind me of the million problems in each file. I wanted to enjoy my sausage with broccoli rabe without thinking of the brief that was overdue. Wasn’t really fair to my most patient bride, but that was my way to cope. Be better. Leave the stress in the office. Don’t scare the kids with a tirade about the stupidity of the managing partner. Try not to cross-examine your five-year-old about her day in pre-K.

Stop rushing through life. Turn off your type A personality occasionally. Yes, you have three motions to argue in three different courtrooms at the same time. Our days are hectic and demanding. I get it. But learn to relax, shut off the motor that allows you to multitask in your sleep. Not easy, but essential.

Remember those days when people talked to each other, you know, like face to face? Try it with your colleagues, I mean, really. And not just about the summary judgment motion or the amount of this year’s bonus. Ask about family, interests, what they did over the weekend. Have lunch with the young, frightened associate who’s inundated with work. Listen to his complaints, fears, and explain that “everyone feels the same way . . . we all questioned our ability . . . no one’s work is always perfect.” Be truthful and impart experience, wisdom. Baby lawyers could use some encouragement.

Be nice. It’s really not that hard. How often have you witnessed two nerdy lawyers, who would never remind you of Navy Seals, raising voices, belittling each other at a deposition? Or some pompous Rolex-wearing moron seething while standing before some confused clerk? Too often. You’re much more effective when you’re polite and respectful. Snapping at a young associate will make you feel powerful, but only shows your insecurity and poor upbringing. And please, I’m begging you, don’t stand up at your daughter’s PTA meeting and begin with “I’m a lawyer and. . . .”

We live in a graceless age, one where politicians use invective to attack the other party’s person and position. Instead of reasoned dialogue, we have elected officials hurling abuse in an attempt to destroy. Sadly, this pattern has become common in our everyday interactions whether in the office, at the supermarket, or during our daily commute. Because politicians are crass and cruel, some of us believe we also should scream and belittle. Boarding a bus, I feared these two older women would throw a punch or two when they loudly bickered over a seat. I was entertained, then disheartened, when one screeched at the other: “And I bet you’re a Trump supporter.”

Don’t fear change. I recently read a book, Passing the Time in Ballymenone, by Henry Glassie, an anthropologist, about years spent in the 1970s in a small town in Northern Ireland among simple farmers recording their songs, tales, and way of life. It is a marvelous view of a people and a culture that existed for centuries but have since mostly vanished. Economic, political, and technological advances have made this study—not yet 50 years old—seem as if it was from the Middle Ages. Change is swift and permanent. So too with law. I started with carbon paper; now we no longer have books. Adapt or be left behind.

Be well-rounded. Read books. Watch Casablanca or Animal House again. Attend a lecture, learn to knit. Working all day, night, and weekends limits growth, maturity. Life is more than discovery motions, appellate briefs, and the latest Daubert decision. It’s people, family, friends, life.

Learn to sail or play the piano. Study Renaissance art or the evolution of jazz. Listen to Hemingway’s short stories or David McCullough’s histories while in the car. Trace your family’s lineage, or volunteer at a foster home. Develop your talents—you have many. Have some fun.