I never for a moment thought about pursuing a career as a transactional attorney. I entered law school for the wrong reasons. I knew I could think, write and argue reasonably well. I was a liberal arts major (Philosophy and Literature-Writing) and did not really appreciate how such skills could translate into success in the business world. And I did not think I would enjoy a career as an educator.

So, I did exactly what I would urge no one do today: I took the LSAT, got into law school, and went to law school, without having any particular passion about the law.

If anyone had asked back then–and I don’t think anyone did–what I planned to do with that law degree, what area I’d practice in, what I wanted to do everyday, if and how I would make a difference, I wouldn’t have had a clue. When I was interviewing and starting my career, there were vastly more jobs in litigation, so I became a litigator. I started out doing insurance defense, but not the interesting kind, and immediately grew bored with fender-benders (“Was the light red or green?”) and slip-and-fall lawsuits (“Was the banana you slipped on yellow or green?”). Fortunately, I got hired right away at a boutique firm that did more interesting work (at least from my perspective). I quickly became a “specialist” in automotive product liability litigation, specifically suits relating to the performance of automobile air bags, which was an emerging technology at that time.

I remained a “specialist” in this area, with a smattering of other kinds of cases, for about the first 10 years of my career. However, I eventually figured out that, deep down, I’m not really a gear-head, and it shouldn’t be a big surprise that the lawyers who really excel in automotive product liability litigation, and who most enjoy what they do, are those who are interested in cars. Well, duh!?!

I eventually migrated to employment law for a number of reasons. First, and most practically, it was the only area that I was able to get any early traction in terms of developing my own clients. Equally important, however, being the opposite of a gear-head, I found I enjoyed disputes that arose out of (often flawed) interpersonal relationships in the workplace. Also, I had long felt that employment law was fertile ground for building a book of business, since every, EVERY employer, particularly in California, needs an employment lawyer. If they haven’t needed one yet–they will!

I had not intended this post to be a memoir. I recognize that my career path probably makes dry reading. But I wanted to tackle a topic that I think is important for law students, recent graduates and those still in the early years of their career: should you attempt to specialize? Like most people, I’m narcissistic and can only approach a personal question by starting from my own experience.

In any event, I posed this question to someone who has a fair amount of expertise in helping lawyers make the most of their legal careers. Gideon Grunfeld, the President of Rainmaking For Lawyers, was gracious enough to provide this valuable insight:

“Too many lawyers get shortsighted advice about whether they should specialize and what that means. There are substantive areas, such as tax, ERISA, and patents, where specialization is almost a necessity. But there are many areas, such as business litigation, where specialization can be counterproductive. Rather than focusing on the substantive nature of the law and, for example, specializing in trade-secret litigation, it’s better to encourage young lawyers to identify the clients they most want to serve. Thus, for example, if someone has a passion for high-tech start-ups, they can focus on cultivating relationships in that world and position themselves to solve the full panoply of legal issues that arise for that market or audience. For most young lawyers this is a more robust not to say more fun way to practice law and build a client base.”

I tend to agree with Gideon’s advice. I like the notion of letting one’s specialty develop organically. In my case, it developed because someone close to me gave my business development efforts a big jumpstart by referring employment cases my way. I found I liked it and wanted to pursue it further. This is pretty much the opposite approach from deciding I wanted to practice entertainment law because I like to go to the movies (which I do).

What I would really caution against is remaining in a practice that never brings you any thrills. Even though I’m not a gear-head, there were parts of my products liability practice that I found compelling. I recognize that this is not the market for young lawyers to quit a job on a whim. On the other hand, there is nothing wrong with developing a mid or long-term career plan to move away from an area that brings you no joy, with the hope of finding something more fulfilling. If I was still fighting cases about people who tripped on a public sidewalk, I’d have to open a vein. But that’s just me.

I had a great dinner last night with someone I’ve known off and on for several years and who qualifies as one of the true luminaries of the Los Angeles Bar. Part of what made it a special meal was the food (lemon white wine-poached branzino). But a bigger part was our jovial conversation and his stories about his practice and his travels. It was such an uplifting discussion, in fact, that I spent some time today reflecting on it and I think I’ve put my finger on why I came away feeling so good. It’s this: my dinner companion was first admitted to practice law in January, 1969. Yet, now, after more than 44 years of lawyering, he still enjoys it!

He actually said, “I love what I do.” I don’t know about your friends, colleagues and acquaintances, but I don’t meet too many lawyers who’ve been doing this even just 25 or 30 years who still really seem to enjoy it. Or who enjoy it enough to declare, without the slightest hint of irony, “I love what I do.” Do you love what you do?

Like those researchers who desperately want to unlock the secret to longevity in a culture like Sardinia, Italy or Okinawa, Japan, his words caused me to wonder whether he had stumbled upon some little known formula to continuing to find law enjoyable after over four decades. I haven’t uncovered any secret formula, but after some thought I’ve identified a few factors, habits or traits, if you will, that could help explain how my friend has managed, not only to go the distance, but to do it joyfully. Without further throat-clearing, here’s what I’ve gathered:

Balance

As tempted as you might be to snicker at the notion of “work-life balance,” particularly now when everybody is supposed to feel lucky just to have a job and the new buzz phrase is “lean in,” don’t dismiss this too quickly (that includes you, too, Scott H. Greenfield). When my friend described his notion of balance, it did not mean always leaving work at a “reasonable time” so he can enjoy his life and time with family. His practice is litigation-oriented, specialized and in-demand, so he’s not working what used to be called “banker’s hours.”

But he did stress that he both “works hard and plays hard.” His meaning was that, while there may be some nights that he’s responding to emails in the early morning hours, there are lots of other nights when he’s having dinner with intriguing folks like me. This is the kind of balance I, too, have tried to find in recent years, recognizing that it’s not always going to work to leave the office at 6, or 7 or whenever. But for every time I get stuck working into the night, I make sure there are many more nights when I’m doing something I really enjoy–like spending time with my daughter.

Vacation/Travel

When I first met this man in 1996, he told me he routinely took 5-6 weeks off annually, and spent much of it traveling abroad. When I reminded him of this comment last night he smiled and said, “now it’s more like 11-12 weeks off.” Wow. Just wow.

I fully recognize that most lawyers simply cannot, financially or logistically, afford to take 2 or 3 months off every year. So bear with me, because my point is not that we should all make that a goal, but something a little more fundamental.

For my friend, he loves time off and he loves to travel. So he structured his professional life so that it enables him to maintain a thriving practice while taking a substantial (by anyone’s measure) amount of time off. He is also really good at what he does, so he is in demand and charges a premium.

But, here’s the reason I bring this up: he has found something he loves outside the law and he pursues it and will not let anything, including his practice, prevent him from doing that thing. And we can all learn something from that. We don’t have to disappear for months at a time and visit faraway lands. But I do think having a life, interests and activities outside the law–and making time to enjoy them–may be one of the important keys to a long, enjoyable legal career. One that can last over 40 years! But it won’t happen without some serious effort toward that goal.

A Team

If you’re wondering how my friend can escape a thriving law practice for months at a time, the answer is that he doesn’t do it alone. When I met him in 1996, he had an associate and a fantastic paralegal. Now he has a few “of counsel” lawyers and a paralegal. Again, he didn’t build this practice overnight, but as it grew he early recognized the need for help. We talked briefly about his team last night and he was complementary of their skills, which led me to believe that, when he takes time away, he is confident that his clients’ needs are being protected just as if he were in town.

Here, again, vetting and training a team who could competently manage his practice when he travels must have been a challenge. But, knowing he wanted a life outside the law, he spent the necessary time and energy. I don’t know, perhaps he was also very lucky with the people he found and hired. Perhaps he treats them well. But the upshot is that he’s able to take (a lot of) time away and do so comfortably. I’ll leave it to you to ponder whether this is one of the keys to his longevity.

A Practice He Loves

I do relish a good circular argument. But, the fact is, my friend loves what he does because he does something he loves. If you don’t find an area of the law that you “love” to practice now, you’re probably not going to love it in 25, 30 or 40 years. And I don’t think you have to love it at all, but if you’re going to spend four decades doing an activity many hours a week, it will really help if it’s something you find stimulating. I will readily admit I don’t love my practice, but I do find it stimulating, and I’m hoping it will stimulate me at least until my daughter finishes college.

Have I discovered the career longevity equivalent of Sardinian olives? I don’t know. But I can point to one person whose been practicing for 44 years and is still going strong. I hope I will be able to say as much.

My college roommate and Venture Capital Badass Mark Suster maintains a well-respected VC blog, Both Sides of The Table. He recently quoted some advice his wife, Tania (brilliant, beautiful, Wharton MBA, ex-consultant, serious media chops), gave to a friend who was starting his first real job. I have no idea what kind of job. As I read it, however, I couldn’t help thinking it was the kind of sound advice we all wish we’d received (and, more importantly, followed) when we were brand new lawyers. I can’t resist sharing it. With kind thanks to Tania and Mark, here’s what she said:

Secrets of the real world – stuff I learned the hard way

General Advice

1. Don’t expect constructive feedback without asking directly for it. Most businesses have formal programs in place to give you feedback. Most bosses are too busy to put in the real effort to help you. Many just ask you to fill out the forms for them. It becomes more administrative than constructive. If you ask for feedback in a pleasant, non-defensive way you will likely get it.
2. You won’t really have a mentor unless lightning strikes. But if you seek one out, most talented employees would gladly become your informal mentor. This can be your most valuable career management tool so use it. It can be a great way to build advocates that will move mountains for you in the future.
3. People won’t communicate expectations clearly (you must ask, clarify, ask again). Knowing the expectations of your senior employees (and peers) is invaluable to your success and asking people’s expectations is the clearest way to get them to think about it in the first place. The easiest way to beat expectations is for you and your boss to agree them two-ways and check on progress periodically.
4. Constructive criticism stings, but we all need it. So seek it out, push for real feedback and be open to hearing it whether you agree or not. If you’re defensive you’ll never get real criticism. It’s much easier for your boss to avoid the confrontation or putting the time into thinking through what you could do better.
5. Don’t overly rely on HR. Make your boss and her boss your primary allies. Your career is best navigated though line managers. HR should be able to manage the sensitive information you give them separate from your line managers but in my experience they do not so be careful. They are not your free psychoanalysts.
6. Show up early. You may be a morning person – you may not. But nothing gets noticed more than which employees constantly turn up late. Even if bosses say they don’t care – they do. Nothing tarnishes your reputation more quick than being THAT person. The one always slipping in late.
7. Be humble. Nobody cares where you went to school or how great of a student you were. Get over yourself. Don’t be arrogant. Don’t try to act like a managing partner from day 1. It’s OK to be junior. Nobody expects you to be managing the whole division. In fact, they’ll resent you if you try to act like you are.

Working with Your Boss

Sit down with your boss asap and tell her you want to do an amazing job. Ask her:

• What could I do to exceed your expectations? What have past employees done that made your life much easier? What tips would you pass along from the most successful employees who have had this job?
• What is the worst thing I could do in this job that you want me to avoid?
• Whom should I emulate? Who is great in this role that I should learn from?
• How can I best help you?

What to do in Your First Weeks

• Interview your peers, people in your role/team: set up a meeting and ask them same questions as above, plus:
• How can I best work with my boss, what does she love/hate?
• What mistakes did you make that I can avoid?

What is Your Job, Really?

• Your job is to make your boss’s job easier – to help your boss succeed.  Always have that in mind even if it’s not in your immediate job description
• NEVER bring your boss a problem without bringing him a few potential solutions. Be associated with problem solving, not problems, it creates a positive halo around you
• Say “yes” to work even when don’t want to. Everybody loves employees who take on projects with enthusiasm. The world is filled with people who sigh when assigned work.
• BUT if you do become overwhelmed with work it’s ok to say “I need your help prioritizing my tasks because I have too much on my plate.”  Make it a positive thing. The worst thing is to take on too much work and under-deliver.

Other Notes

• Schedule in your calendar and in your bosses calendar a few check in meetings and ask for feedback and make it a formal conversation. Prepare them in advance by providing a list of the things you’re working on developing and tell them you’d love feedback on how to improve at those things.  You might want to preface with ”I want to learn how I’m doing so I can improve, please give me constructive criticism!” Mostly you don’t want them to feel like these meetings are obligations, reasons for hours of preparations or ways for you to be defensive about your job.
• So take the feedback on and don’t get defensive. The more you get positive measurement on your work the more likely your boss will be aware of it at the annual review time. Make sure to thank you for his time (he is likely busier than you are, after all!)
• After you feel stable in your role and with your relationship with your boss – make sure to get to know your boss’s boss. Don’t let your boss love you but his boss not know who you are! This WILL come in handy in your career but you have to manage this cautiously.

If anyone reading this blog has not read–and read often–Associate’s Mind, you must absolutely begin following it. Every post has some nugget of brilliance.

Before I  actually read the blog, I assumed from the title I would encounter either (1) ranting about the misery of being an overworked albeit overpaid BigLaw associate à la the old Greedy Associates message boards;* or (2) posts like “Five Easy Tips To Bill 2,700 Hours Before October!” I couldn’t have been more off-base. Instead, I’ve always found thoughtful, well-written posts offering insight on topics ranging from the profession to litigation strategy to Eastern Philosophy.

And, now that I’ve been a partner in an AmLaw 150 law firm for almost 10 years, I feel qualified to endorse the following observation by the blog’s author, Keith Lee:

“Although frequently people speak of always thinking like a “partner” or “partner-level” thinking when in regards to how one should conduct oneself inside a firm –  reject the notion. Just as in the mind of the master there are few possibilities and in the Beginner’s mind, infinite – most partners have fixed ways of thinking and conducting their practice and processes.

An Associate’s Mind should be flexible and open to new ideas and processes, while being mindful of the guidance of those who have tread the road before him.”

I recognize this tendency in myself to “have fixed ways of thinking and conducting [my] practice and processes,” and I don’t like it. When he refers to the beauty of the “Beginner’s mind,” I think I may know what Lee means: I love to watch how my 4-year-old approaches any new issue, problem or obstacle. Her thinking is always “outside the box” (or whatever cliché you prefer) because she hasn’t yet been trained to think inside the box.

As we gain experience and, hopefully, wisdom in our profession and our life, we should strive to retain the infinite possibilities of the Beginner’s mind.

*Note: I have not read Greedy Associates in many years, so I don’t know if such ranting still persists, though I expect it does.