July 01, 2013

Planning for Seniority: A Baby Boomer’s Playbook

Rosemary C. Byrne

January 1, 2010, marked a watershed moment in American culture and demographics. The first of the trend-setting generation of “baby boomers” would be celebrating their milestone 65th birthday. The generation born between 1946 and 1964 was moving from the “Age of Aquarius” to the “Age of Retirement.”

Given the extent of their representation in society, their massive buying power, and their historic impact on so many facets of American life, it is not surprising that this transition was front page news in the New York Times. As the Times so aptly noted, “[t]his means that the 79 million baby boomers, about 26 percent of this country’s population, will be redefining what it means to be older.” Dan Barry, Boomers Hit New Self-Absorption Milestone: Age 65, N.Y. Times, Dec. 31, 2010, www.nytimes.com/2011/01/01/us/01boomers.html?pagewanted=all&_r=0.

A quarter of our population is now over the age of 55 and, in the next 20 years, roughly 10,000 people will turn 65 each day. There are more of us, and we are healthier and living longer. It is estimated that the average 65-year-old woman in good health is expected to live another 23 years; males of the same age and health can expect another 20.

The statistics for attorneys tell a similar tale. Government figures indicate that 31 percent of attorneys in America are age 55 and over. Other studies by the ABA and various state bars reflect that the number could be as high at 35 percent.

I leave it to others far more erudite than I to describe, analyze, and opine about the economic, sociological, and political impact of the aging of the baby boomer population or its overall effect on law firms and our profession. For me, the bottom line is that roughly one-third of the attorneys in America (myself included) are considered senior lawyers, and we are at, or nearing, what was traditionally viewed as retirement age. We will likely have a life span of at least another 30 years. Yet, as many of us approach or pass the “65” mark, there are few norms or models for active retirement or indeed any retirement that our generation will likely find acceptable. “I never plan to retire” is an anthem I frequently hear from attorneys. We tend to identify ourselves by what we do; if we cease to do it, one wonders, who will we be? Moreover, the counterculture generation that confronted racism and sexism and came to expect (and insist upon) choices and options is not likely to take kindly to “ageism” or to being marginalized or limited by virtue of age. While boomers are not likely to go gently into the retirement of our parents and grandparents, it is not clear where we will go instead.

Hence, as its title indicates, this piece is not so much about “retirement life planning” as it is about “senior life planning”—devising basic strategies to prepare for and “redefine what it means to be older.” I offer you a playbook to facilitate planning for and enjoying senior status. So, even if you never plan to retire (or are not a baby boomer), I hope you will read on.

(Re)Define Retirement

The first strategy in the playbook is to define, redefine, or perhaps even retire the word “retirement.”

As attorneys, we all know that words matter. This is especially true when the word in question is retirement. Its meaning and impact are different for each of us. Dictionaries define “retire/retirement” as, among other things, “to retreat,” “to seek privacy or seclusion,” or “to withdraw from use or active service.” In Victorian days, “I’ve retired” meant you had gone to bed.

These definitions represent the traditional view that retirement is the end of an active life in the workforce, a move into a life of relaxation and leisure, until we die. For many attorneys, retirement has strong negative connotations. One of my clients describes it as “being put out to pasture”; another sees it as “being permanently benched”; a third free associates it with death. In the traditional paradigm, retirement is seen as a fixed point in time—an end—often marked by length of service or a birthdate. At some firms and in some courts, it’s actually a mandatory event.

In fact, the word “retirement” may be more useful to describe what youdon’t do—work full time in the career in which you spent most of your professional life. It is not, however, particularly helpful in describing what you currently do or plan to do.

Consider social or business events and the typical introductory question, “What do you do?” Now, consider what often happens when the response is, “I’m retired.” Depending on the age of the conversants, there is often a pause, the questioner’s voice drops a bit, he or she says “Oh,” and the conversation frequently stalls. The litigator in me can’t help thinking “that answer is nonresponsive,” unless, of course, you take retirement to mean “I do nothing.”

Given the definitions and possible negative stereotypes surrounding retirement, one may reasonably ask: is this what healthy, engaged, 65-year-old baby boomers would see as a desirable life choice? Would they strive to achieve or plan for it? The answer is likely a resounding “No!”

The alternative is to reframe our thinking about retirement, to think more broadly, and to see it not as a single static moment, but as a continuum, a span of time or a stage of life. Perhaps we can borrow the concept of taking “senior status” from the federal judiciary. Some use “encore years” or “next chapter” to describe this period. I’ve opted to side with experts who describe it as seniority or the “Third Age.”

Call it what you will, but recognize that the Third Age (or your phrase of choice) is not a mere euphemism for retirement. The event we traditionally call retirement is about our professional life. I define being retired as “giving up your current full-time paid primary career or position.” The Third Age is about the entirety of our life and best describes “the period after mid-life and before the afterlife.”

This is the period in which we experience normal (and somewhat inevitable) physical, physiological, and intellectual changes associated with aging. It is a time when our personal and professional priorities may change, a time to reflect on how things are and how we want them to be, and a time to weigh our options and consider those we choose to exercise. I define the Third Age as “a changeable stage of life after mid-life that incorporates education, work, life, and leisure in whatever balance we choose.”

In this Third Age, there may be one (or more) retirement events. It is easy to confuse the stage of life with the retirement event(s). They are not synonymous! While the Third Age happens (the alternative is not a particularly desirable option), retirement event(s) need not. So, rather than focusing on the retirement and engaging in (or avoiding) “retirement” life planning, we might be better served by contemplating and planning for “what it means to be older”—what we will do, who we will be, and the work/life/leisure balance we would like to have in the three decades that may constitute our Third Age.

Recognize the Roadblocks and Consider a Plan

Barriers to creative thinking, or perhaps any thinking, about seniority abound. In my coaching practice, I find that many senior attorneys are not preparing for, or even considering, what they will do or who they will be as they grow older because they view aging through a lens clouded by the negative imagery associated with traditional retirement. The social and emotional consequences of old-style retirement can be enormous. We self-identify by what we do. If we retire, we may lose that self-definition and the structure, friends, and colleagues that surround it. We surrender our working persona and environment but aren’t quite sure what will replace them. We may need to redefine ourselves—not an easy task at any age! Placing the emphasis on retirement planning tends to block forward thinking about life planning after middle age.

Given the current economy and impact of the recession on IRAs and retirement assets, money (or the perceived lack thereof) can also be a significant roadblock to seniority planning. Many conclude, perhaps erroneously, that they will never be able to afford to retire, so they believe there is no need to do any other planning for seniority.

Procrastination may delay the consideration of aging and the development of a seniority plan. Among my clients, I find there are concerns about being marginalized, or diminished, or bored. Some fear facing their own mortality or are reluctant to confront the physical or intellectual changes generally associated with the natural process of aging.

Faced with these roadblocks, real or imagined, many seniors opt to take the path of least resistance, i.e., they “stay the course,” expecting to remain employed, conceiving no plan and thereby hoping, perhaps unconsciously, to avoid the negative aspects of retirement or the inevitability of aging. By so doing, they ignore the possibility that mandatory retirement, firm politics or economics, downsizing, or unforeseen health problems may intervene to force the issue.

The first step toward overcoming these road blocks is to recognize them and realize that they may be posing a significant barrier to positive and creative thinking about the joys and options one can have in seniority.

The next step is to take charge of the situation and begin pondering and formulating a plan for seniority. As attorneys, we excel at weighing options and formulating plans. In our careers we have all assisted our clients, our firms, and our friends and family with life and business planning. Consider the plans, choices, and decisions you made throughout your adulthood. You planned for your education (and that of your children), your choice of firm, your area of practice, where you would live, even the make and model of your next car. We often plan our vacations with exacting detail. Why would we do any less when it comes to planning for what we will do in our 30-or-more-year seniority?

Planning for, or at least exploring, our options in seniority has its own benefits. It gives a measure of control and avoids leaving important life decisions to chance or serendipity. With foresight, preparation, and planning, we will have a better chance of having the life we want, rather than accepting whatever comes our way.

Seek Help with Your Planning

Financial Planners

There is much written about the importance of financial planning, and I will not dwell on it here. We all know that any plan for seniority must involve financial planning. Financial professionals help us determine what we will have and what we will need in seniority—how we can have a financially successful future. Don’t leave these experts out of your seniority planning.

Senior Life Planners/Retirement Coaches

The accuracy of financial planning is greatly improved by life planning. The two go hand in hand. It is difficult to determine our economic needs as we age without envisioning our senior life. Will we opt to continue full-time practice or choose something less or different? Will we relocate or downsize to a smaller home or apartment? Will we start a business or pursue a new career? What leisure activities will we pursue? Each of these decisions and preferences will impact our economic needs. In short, simple logic tells us that we need to consider what we want before we can determine if we can afford it.

More and more of those on the other side of 55 or 60 are turning to a new breed of planning professionals—life coaches, retirement coaches, and senior life planners—to seek help in creating that vision. They are comfortable with the concept of seeking professional help when and where it is needed, whether from a tennis or golf pro, a business consultant, or a fitness trainer. Seeking guidance on retirement or seniority is a natural extension of the process.

Many of you may wonder, as I once did, what does a retirement coach do? Simply put, I assist baby boomer (and beyond) attorneys and other professionals to open the door to thinking about their seniority, to explore possibilities and options, to create a vision for their life after 55 and a plan to achieve that vision, to evaluate their work/life/leisure balance, and prepare and plan for their Third Age—which may (or may not) include retirement.

Generally speaking, the coaching process is designed to help facilitate change. It is not therapy! With probing and insightful questions and observations—many of the same skills I rely upon as an attorney—I help clients to identify the changes they would like to make and devise a strategy to achieve them. A coach is an objective, nonjudgmental partner working with a client to create a vision for the future he or she wants and to identify the steps and strategies necessary to achieve it. Together (generally by phone), we analyze how they can best use their time, their energy, their skills, their knowledge, and their assets to achieve their aspirations.

A Page from the Coach’s Playbook

Questions to Ask Yourself

There is no single game-changing strategy for a successful senior life. The plays and actions in the seniority playbook are largely designed by the players, in consultation with spouses or partners and family and colleagues, as well as with financial and life-planning professionals when needed.

To assist in the planning process, I have included some basic questions and suggestions I use in my coaching practice. They are intended to help you focus on your aspirations, goals, and strengths, and to expand your thinking about what you want to do in your life, your work, and your leisure time to achieve a successful Third Age.

One of the keys to successful Third Age planning is continuing to ask the questions I’ve provided here. I suggest you put some time aside. Fifteen or 20 minutes will suffice. Pick a question and think about it. They are not in any order or degree of difficulty. Put pen to legal pad (or fingers to keyboard) and record (and save) your thoughts. Repeat the process with some frequency. It is interesting to observe how your answers may differ over time.

As you continue to go through the process, patterns will likely emerge that will provide insights and help clarify what you want to be doing in the Third Age and assist you in developing an action plan to get you there.

  1. If money and health were not an issue, what would you like to be doing in a typical week when you are 60, 65, 70, 75? How would your response change if money and/or health were an issue?
  2. Complete the statement, “I’ve always wanted to __________.” Consider what one action or step you could take now toward reaching that goal. Expand the foregoing question and add “but __________.” What obstacles do you see, and what one action or step could you take now to overcome that impediment or perceived barrier?
  3. As you consider your life today, what do you want more of or less of, and what would you keep exactly the same?
  4. As you look back on your life, what do you regret not having done? Can you still do it or something comparable?
  5. How do you define success? Do personal and professional success differ? How?
  6. If money were not an issue, what would be your perfect job? What makes it a dream job?
  7. If money were not an issue, would you have a job at all? Why or why not?
  8. What do you like most and least about the work you do and where you do it?
  9. Consider the social/business event conversation I mentioned earlier. If you were asked “what do you do?”, what would you like your answer to be next year and three or five years from now?
  10. What would you do if you took a six-month paid sabbatical?

In the Alternate: Create a Bucket List

Finally, if all of this seems too abstract or just too difficult, consider another alternative. Take a cue from the Rob Reiner film The Bucket List with Jack Nicholson and Morgan Freeman. No matter what your age or place on the Third Age transition journey, create a “bucket list”—a list of items (great and small, serious or fun, easy and hard, adventurous or mundane) you want to see, do, go to, achieve, learn, hear, explore, or experience before you “kick the bucket.” If the thought of kicking the bucket gets in your way, think of it as a life or dream list! Don’t worry about whether you can do them all. Just be creative and keep adding to the list.

Once your bucket list is started, pick an item and either do it or consider what one step you could take toward accomplishing it. Look at your list at least once a quarter (perhaps when filing your estimated taxes) and on January 1 of each year. Note the dates on your calendar to help you remember. The notation may also help remind you of the need to engage in seniority planning.

For more bucket list ideas, take a look at www.squidoo.com/100things.

When I started my own bucket list a number of years ago, I included seeing the pyramids (I have), learning to scuba dive (I haven’t yet), learning to play bridge (I am), and practicing law part time (I do). Becoming a life coach and writing an article for Experience magazine were definitely not on it. Some good things do happen serendipitously! Perhaps that’s a story for another article!


The definitions and measures of success in seniority are very personal. Each of us must determine what we will want to do and what we may be physically, financially, intellectually, and emotionally able to do as we age. For each of us, however, the process starts with thinking about and recognizing the inevitability of change and the need to perceive, consider, and weigh our options and plan accordingly. Ideally, we will each have the work/life/leisure balance we choose and the financial and social support we need to maintain it.

Rosemary C. Byrne

Rosemary C. Byrne (rcb@sbscoaching.com), of Step-by-Step Coaching LLC, is a corporate attorney and former litigator with an encore career as an NYU trained and certified Life Coach and certified Retirement Coach. A frequent speaker on transition and retirement life planning, she is a member of the ABA’s Senior Lawyers Division Transition Planning Committee, secretary of the New York State Bar Association’s Senior Lawyers Section, and co-chair of its Retirement Planning and Investment Committee. She is also a member of the Benjamin N. Cardozo School of Law Board of Overseers and a co-author of No Winner Ever Got There without a Coach.