Growing Old in Your Practice (You Know You’re a “Senior Lawyer” When…)

By Robert L. Ostertag

You know you’re getting old when you think of a BlackBerry as a pancake compote ingredient.

They’ve asked me to write an article on the subject of growing old in my practice. Why me? “They,” of course, are those young colleagues of mine at the ABA who somehow believe that Hoobert Heever (or was it Heebert Hoover) was my classmate at PS 35. He wasn’t. He was president of these United States when I was born. Man, that’s a while back.

Well he’s gone, of course, having died prematurely at age 90 (that’s premature to me these days). I’ve lived now through 13 presidents (coming up to my 14th!) and 16 vice presidents. That’s about one-third of all we’ve had, and I’ve practiced law through 10 and 11 of them, respectively. Only four of each category survive. Perhaps, after all, it really was difficult to find someone older to write this article.

The words “growing old” imply, of course, a continuous passage of time rather than a glimpse at a momentary time bite. Let me start you on my road to old age on the occasion of my entry into active duty with the United States Air Force. It matured me quickly.

I had taken the bar exam on Friday and Saturday, had swigged a few (a few?) hefty celebratory beers through the night, and had driven the following day from New York to Bangor, Maine, where I was to serve for the next two years as a judge advocate. I kind of burned rubber on my way up. I thought being AWOL before I’d even reported in was not a particularly good idea. I reported Monday morning to my boss and later my lifelong friend, Captain Clarence “Buzz” Walters, the staff judge advocate.

I hadn’t yet been admitted to the bar, but by Wednesday I was already on trial. Scared? I almost . . . well, you know. I actually won the case, but the experience matured me at least a decade; I’d actually sent someone to jail.

I spent the next two years trying criminal cases. I made all my mistakes at the expense of the government. The government never knew, of course.

Trial preparation was terribly difficult. We had the Code of Military Justice, various sets of overlapping Air Force regulations, and about 18 volumes of military case law. That was it. No law library, no technology at our disposal, just the good old dependable yellow pad, pen, and pencil. Court reporters took testimony by shorthand. By the time of my discharge, with Buzz’s help and that of my colleagues, I could actually try a respectable case.

I next took my “career” to the Internal Revenue Service in Washington. I had been appointed to the National Office of the Chief Counsel, a distinct break for me, as it turned out. I could have been sent to a regional or district office in Omaha or Boise, or, for that matter, Guam. Again, I came under the tutelage of one of the finest people I’d ever known, Wally Russell, a Harvard Law graduate. Wally saw immediately that I had limited writing skills. He took me under his wing and taught me how to write as an appellate lawyer. There is a difference between writing and composing. He taught me how to compose. What I’m doing here, I think, is writing.

The difference in how I then was lawyering was marked. No more trying cases. Our work was primarily as backup for the Justice Department across the street. And this being Washington, we had access to more law libraries, including the Library of Congress, than any of us could possibly have needed. It was like gold.

Wally invested much of himself in what he thought would be my career with the IRS. When I told him one day that I was leaving to try my hand at private practice, he was personally crushed. I’d become the son he’d never had. In the closing weeks, he wouldn’t speak with me—a terrible learning experience for me. I’ll never forget him and I still have very deep regrets. I left the IRS and never heard from him again. He died several years later.

The lesson learned after my first five years of professional growth was to understand that no matter how long I may practice or how old I may grow to be in the practice, there is always more to learn, and someone smarter, wiser, and better equipped than I who is willing to mentor and be useful. Now that I’m older but still useful, I never turn anyone away who bothers to tap whatever wisdom I may have to impart.

You know you’re getting old when, to stop operating that idiot box, you must click on “Start.”

My next and last stop was in Poughkeepsie, New York, a small Hudson River city in what is one of the best-kept secrets in America, the beautiful Hudson Valley. I had little interest in seeking employment that would involve me with the hard-nosed corporate world. Moreover, I didn’t want to raise children in New York City, my original home. But Poughkeepsie was within commuting distance, and I really didn’t want to be too far away from the Big Apple. It’s the greatest city in the world.

My new firm was a general practice firm concentrating primarily in litigation, estate planning, and administration and real estate. One of my senior partners, Charlie Butts , became my next professional mentor. How fortunate for me have been the senior associations I’ve developed along my journey. Charlie taught me how to be a private practitioner in a small community where so many knew so many others and where lawyers were still respected and could remain so by good work, social contact, and personal familiarity with the community. Another lesson learned on my way to seniority.

My other senior partner, Bill Walsh, was a different sort. As nice and decent as he was, he had little patience for my type of mediocrity, especially for my walking into his office from time to time and asking for his help.His initial response would always be, “Have you looked it up?” Had I spent hours looking up what I knew he could tell me in seconds, I wouldn’t have sought his help, of course, though I’d never have said it. But he was providing me with yet another learning experience. Looking things up involves not only achieving a result, but more importantly, learning how to find answers,and where . I’ve imparted that lesson to my law students for years.

By the time I’d comfortably settled in at my firm, I was 35 or so and gaining respectability. I was indeed growing what I then thought to be old. One of our more respectful secretaries no longer asked me if I had ever gone to law school. And when I asked for something, I sometimes got it. Occasionally the “girls” (sorry, but my partners were an older group) would even share their doughnut holes with me.But I was, after all, moving up the temporal ladder and I realized that Poughkeepsie would inevitably be my place forever.

The years since then have passed ever so swiftly. Soon I was 40 and firmly ensconced in my life and law practice. Then came 50. Somewhere in there I mindlessly decided to run for County Surrogate, our title for probate court judge. I’m a Democrat. I live in a Republican ocean. Never in the history of America has my county ever elected a Democrat to a court of record. I ran nevertheless. What a dumkopf!

Lo, then came 60. Our firmhad grown from four in number to as many as 13. The larger we became and the more successful, the more difficult became the practice of law. Our partners were an unhealthy mix of liberals, conservatives, and middle-of-the-roaders , at least in terms of business practice and ideals. There were few business issues we could agree on. Our semi-monthly partners’ meetingswere deadly. Serious strains developed, particularly in terms of the division of profits. At the same time, the Hudson Valley was suffering a severe economic recession with the downturn of IBM’s economic health. Some 18,000 had been laid off, impacting half as many others, such as suppliers. The bottom dropped out of the real estate market . Everyone here was affected, and the legal community was not excepted.

Ultimately, our firm disbanded and gave rise to four new law firms. That’s a frightening experience for a 60-year-old during a recession. We all remained friends, however. We frequently still call on each other for assistance, advice, or special projects, and we refer clients back and forth where appropriate. Another good lesson. When there comes a time to divorce, it’s frequently better done than not. New starts are invigorating and uplifting and usually healthful. Hanging on can serve as a death knell. But it was difficult.

Since 1994 I have practiced with one of my former partners, together with a relatively new and young partner and a firm associate. They are all women. I’m the only male in the office—aside from the dog. I listen (sometimes) to my co-workers’ complaints about men; they even occasionally speak with me about baseball. But no more partners’ meetings! God, they were awful.

My current partners and I do regularly discuss firm business, usually over lunch and very occasionally over the conference table in our library. We run what we frequently are told is one of the most comfortable working environments in the community with good employee relations and quality results. Rather than staring out my window into someone else’s office, I now look across the street at the tennis courts at Vassar College. Not bad for the morale of a senior citizen. Our practice is of such a social and casual nature (I didn’t say lax or sloven, for we are not) that our three-year-old white standard poodle is part of our office family. Try that out at Milbank Tweed. He contributes to our ambiance. Clients love him and he just loves to receive their attention and their pets. Such is the practice in halfway upstate New York.

You know you’re getting old when everyone in the office calls the others by their first names, except you.

I am now 76, fast approaching 77, and in my 52nd year of practice. I have no intention of retiring. I love what I do. They’ll have to carry me out. I find that being a senior citizen practicing law has its compensations. I sometimes even am looked on with admiration for just showing up. I have the front office. My name is above those of my two partners, although they and I know that’s really because I’m the old man of the office. I kid no one. They think I don’t know. I arrive late each day, but then I generally stay late. I have the respect of virtually everyone I know within our local bar. On the other hand, I know I’m getting old when I go to local bar luncheons and recognize few other attendees, and many I once knew are now gone. Some of the young Turks I see there are “dressed down” and look to me as though they’ve just left a construction site. Others at bar meetings look like college sophomores.

My longstanding and continuing activities with the local, state, and national organized bars have served me well. I am a past president of the New York State Bar Association and know very many lawyers throughout New York. And as a result of my involvement with the American Bar Association for many years, I have come to know attorneys throughout the nation whom I can call on or who can refer me to lawyers they know within their general areas of practice who might serve me or someone I know well. My bar colleagues throughout America are the best our profession can offer.

My seniority even brings respect from the local bench as well and from those who operate within local and state government with whom I deal. They treat me with kindness, and they occasionally go out of their way to keep me out of unnecessary trouble. I’ve learned that a smile directed to these people sometimes means relief from hours of toil and torment in re-drafting or correcting errors or in just dealing with whatever problem I may have that impacts them.

I’ve also learned never to utter dishonest excuses for my mistakes or ignorance, not to the courts, not to my colleagues, not to my partners and associates, not to my staff, and most of all, not to my clients. Why is that lesson so difficult to learn? If I’ve screwed up, I’ve screwed up. We all do it. The way I approach it is to admit the “brutal truth” of my failings, almost always using those very words. People are accepting of mistakes, particularly those freely admitted. Total honesty about them is very much more respected than feeble and phony excuses that frequently are seen for what they are.

I taught at the Fordham University School of Law in New York for some 15 recent years. Mine were third-year law students about to undertake their bar exams. They kept me on my toes. Lord knows, I probably gained more from them than they ever gained from me. It was my practice on the very last day of each semester, however, indeed during the very last hour, to impart to them the following message learned from a wise old friend and from years of practice:

If, when you leave here, you want to be a banker, a business person, or even a bus driver, do it. All of them are honorable endeavors and we need all of them. But if you want to be a lawyer, be one. Act like one. Dress like one. Speak like one. Write like one. Appear as one before others both within and without the profession. Respect members of the judiciary. Be honest and truthful at all times. Respect your colleagues at the bar; they are your adversaries, not your enemies. Be totally respectful of your state’s code of professional responsibility. Act intelligently, but not with superiority. And even in your personal life, be respectful of your professional life as well, for you are a lawyer at all times. Above all, be the lawyer you would wish as your own.

I’d also tell my students of an old Latin expression my dad imparted to me many years ago: “Quidquid agas prudenter agas et respice finem.” Translated (very) loosely, it means, Whatever you do, do it properly or don’t bother.” A good rule to follow.

Readers who live in more tolerant states may find these examples absurd, but lawyers have a duty in the context of planning for an aging couple to discuss the difficult issues that may arise, particularly to guarantee that forethought accompanies plans to retire to “the country,” a far away or unfamiliar location, or a new state, and that the couple is aware of the non-discrimination protections that may exist and be important to them and their plans.

Very frequently, the courts, the administrative agencies, your colleagues at the bar, and your clients know you only or best by what they see and hear of you and by what you write. I try to make my legal writings clear, concise, clean, and neat on good paper. Sloppy work begets inadequate results and a reputation for inferiority. I try never to go there. And that’s my problem with “dressing down.” It doesn’t impress clients, no matter what I’ve heard from some. We maintain a clean, neat office with employees whose own appearance and approach to clients will impress them. The first impressions people have of others is what they see, then what they hear, then, certainly in the case of lawyers, what they read of one’s authorship. The rest follows.

I’ve learned also that reputation is everything. It does matter what people think of you. Once one loses his or her reputation as a lawyer, it’s gone forever, never again to be restored.

The practice, of course, has changed in many ways that only the young can best cope with in its present terms. It’s technology, particularly the computer. Young lawyers have learned the tricks of the computer in school. Almost universally they are competent. The rest of us have learned the hard way or not at all. It’s an uneven playing field. Telecommunications, the fax machine, and e-mail have made the U.S. mail virtually obsolete. Even air travel has had its effect on the practice. The older one gets, the harder it is to keep up with it all. I first heard that saying 30 or more years ago. It’s still true. But I will not flinch. And 30 years from now, today’s young shall have grown older and wiser and will inevitably be repeating it. Such is life.

Robert L. Ostertag is a partner with Ostertag O’Leary & Barrett in Poughkeepsie, New York. He may be reached at .

A Road Map for Winding Up Your Law Practice

As retirement looms on your horizon, you will face myriad issues and challenges in closing or selling your law practice. Last year, the General Practice, Solo and Small Firm Division published The Lawyer’s Guide to Buying, Selling, Merging, and Closing a Law Practice, edited by Sarina A. Butler and Richard G. Paszkiet, which provides a step-by-step analysis of such issues as preparing for a law firm’s closing, preserving your files, and ending client and employee relationships.

The book focuses on the major differences and ethical considerations that distinguish selling a law practice from a typical business. Contributors to the book include such esteemed legal writers as Jay G. Foonberg, Shannon Pratt, Harold G. Wren, Robert Ostertag, Ward Bower, and many others.

Specifically, the book provides an in-depth treatment (with accompanying forms, checklists, and sample letters and agreements) of the following topics:

  • valuation of a law firm;
  • tax consequences of “retiring” a partner’s interest in a law firm taxed as a partnership;
  • selling a niche practice;
  • business responsibilities in closing a law practice;
  • ethical issues (ABA Model Rule 1.17); and
  • client notification and confidentiality issues.

Aside from the above topics, there are multiple other issues that lawyers will face as they grow older. Sole practitioners and their clients are particularly vulnerable to the sometimes complex issues that occur when a legal practice is closed. Doing intensive planning is the first step, and this book is a practical, thoughtful guide about the entire process.

Go to for information on ordering The Lawyer’s Guide to Buying, Selling, Merging, and Closing a Law Practice.

Copyright 2008

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