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This chapter is from the book

Factors to Consider in Making Choices

For most people, finding meaningful work is not so much an inner self trying to get out (revealing your psyche or soul), but simply making the most of circumstances and opportunities as they change. There are often serious constraints on your freedom and capacity to make choices. Circumstances change, in positive, fortuitous ways and also in potentially adverse, impeding ways. You may not be aware of the facts that will affect your future and therefore you need to adopt fresh thinking about your opportunities and constraints. The following are some factors that can affect your decision-making process.


It is often said that money doesn’t matter as long as you have enough of it. Continuing to earn money is important for people seeking to cover living expenses and accumulate savings for retirement. However, the necessity of working for income can crowd out the time you may want to spend in other non-pay activities.

For many, continuing to earn money is meaningful in itself. In American society, being an income producer has long been a mark of productivity—a reflection of accomplishment, self worth, and identity. Income and wealth are also markers in social networks, often determining the social circles and activities in which you participate (that is, whether you can afford to go on a cruise). In this instance, money does matter.

However, for most boomer professionals, whether or not work is compensated is a secondary consideration. Income is not their critical need or objective. Professionals over age 50 are more likely to embrace work that is not for pay—whether community or charitable work or “meaningful” leisure activities. Of course, you can earn income for work in non-profit organizations, but the motive of service is typically as important as or more important than the income.

Sufficient income or wealth permits you to spend their time as you want. You can give your time and donate assets freely for charitable purposes—supporting the motives of legacy and moral or spiritual purpose.


Unfortunately, many persons have physical conditions that constrain the options for work and other activities. As discussed in Chapter 4, “Stay Healthy and Active,” some people have limitations on their capabilities due to injury, illness, disease, or aging. According to a Boomer Project Healthcare Survey, 30% of boomers say they’ve survived a major illness and 3% have changed their diet due to a medical condition. Some boomers are finding that they need to adapt their choices of leisure and fitness activities because of knee or other joint issues. Others find that the stress of extensive travel or full-time work is too much to bear. Are there factors that might limit your choice of activities?

Serious illness or injuries are often a wake-up call for some individuals. Disability and disease remind you how precious life really is. Charlotte, a young boomer, had a burst appendix and was hospitalized for a month as she recovered. Back in action, she saw her priorities differently. Former activities did not seem as meaningful or important as they once were, and she set new priorities, focusing on family and community. A similar reaction occurs among persons with chronic conditions such as heart disease, cancer, HIV/AIDS, or diabetes. You have to decide how you can make the most of your years ahead. Rachel Naomi Remen, a physician, professor of medicine, and therapist, in her book, Kitchen Table Wisdom, offers thought-provoking anecdotes of people’s battles with chronic diseases, reminding us that the challenge isn’t about dealing with illness but rather life!

Many boomers are discovering the merits of fitness and greater personal attention to diet and health care. For them, health is an opportunity and a meaningful area of activity. At 55, Harriet remains steadfast in going to the fitness club for a 90–120 minute workout every morning. It is a “top of the day” priority that she has maintained. The statement that there isn’t time to exercise becomes no more than an excuse when you decide that maintaining your physical well being is at the top of your “to do” list.

Others’ Preferences

If you are living alone, you may make your own choices regarding work. However, if you are married or live with a partner, you will surely want to take into consideration the interests of this significant other in your life. Work schedule, work location, and the demands of work may need to be tailored to provide time and flexibility for travel, to be with grandchildren, and to engage in other activities. More importantly, you and your life partner may have been focusing on different interests and activities or going in different paths and directions over the years. Although working after retiring from or leaving an employer may offer more flexibility, it may also provide you with new or different opportunities to work or play with family members and significant others. Your relationships may also change as you give and take to do different things together.

Caregiving Responsibilities

You may be caring for aging parents, or even grandparents. You may still have children at home, or as often occurs, supporting children who seem to rebound frequently and come home when transitioning to a new phase in their lives. You may have dependent children with dependent children. Many boomers are the sole caregivers for their young grandchildren. Overall, half of all grandparents alive today are members of the boomer generation, and this number will increase as boomers’ kids become parents. Approximately 40% of boomers are grandparents.

The Boomer Project National Study asked boomers for self-descriptions of their status. The responses were as follows:

  • Grandparent:


  • Caregiver:


  • Child at home:


  • Child in college:


Caregiving responsibilities can be a barrier to pursuing meaningful work or leisure activities. If this situation arises for you, you may want to aggressively explore alternative care providers—assisted living, support for dependents in their own homes, or assistance that is explicitly transitional (only for a short time). One couple found that selling their large suburban home and moving to a small condominium simply precluded the options of children or others residing with them. On the other hand, some extended families find great joy and satisfaction in caring for their members, referring to it as a calling or vocation.

Access to Desired Opportunities

You may find it difficult to locate the kind of work or activity that appeals most to you. While you may have some ideal jobs or roles in mind, they may be hard to find. As discussed in this book, employers are often reluctant to hire older workers as employees and are particularly reluctant to provide the flexible schedules or work arrangements that you may desire.

You also may also find yourself competing with others for work, even for volunteer roles. To gain a senior role in a nonprofit, you may need to “earn your stripes” and work your way in gradually. For example, beginning as a docent in a museum, helping out with fund raising, or serving on a project committee may be an entry role, not exactly what you want to do, but a first step.

Another constraint is the availability of the opportunities you desire. Year-round golf is not available in the colder climates. Opera and many of the arts are not usually available in smaller communities far from urban centers. If you have passions for certain work or other activities, you may have to consider relocating. Numerous books are available that ask you to identify criteria that are important to you and then correlate your responses to “the best places to retire” in America or the world.

Your Independence and Flexibility

Are you comfortable working on your own, as a free agent, or do you prefer working in an organization with other people and a management structure?

Upon retirement or leaving an employer, some boomer professionals take a gap year, similar to the year some high school students take off before going to college. They shift into neutral and catch their breath. They play golf, they travel, and they relax. After a year or two, however, most get restless and realize they need to be doing something productive—for mental stimulation, for social interaction, or to earn some money. That’s when they search in earnest for meaningful activities.

Most, however, have not given a great deal of thought as to what might interest them sufficiently to draw them back into work activities. Few have a sense of passion for a new direction. Rather, they test different alternatives—trying out different kinds of activities through projects of six months or a year. It is a slow transition toward being in charge of your own portfolio of activities, much like being in charge of a portfolio of investments. In the same vein of trying out alternatives, some people rent rather than buy a house to check out a community in which they may want to retire. Short-term commitments enable you to retain your flexibility and make different choices if initial decisions don’t turn out as anticipated.

Managers are typically accustomed to a well-defined work pattern—a specific job, an office or place to go to and work, set hours, and a daily routine. Withdrawal from work is a difficult transition. Those who decide to return to the workplace rarely find opportunities with large companies that resemble the ones they once knew. Rather, individuals must adapt to the new patterns of working in a smaller company, in a nonprofit organization, or as a free agent (contractor, consultant, part-time). More often than not, people move into activities that are not like those in their career, although the work may tap their key skills and abilities.

A study by MetLife showed that nearly one-third of persons over age 55 already are self-employed or owners of their own businesses. The current sectors and employers of older persons who work were as follows:

  • Self-employed or owner:


  • Private sector businesses:


  • Education:


  • Government:


  • Nonprofit:


  • Health care:


  • No response:


As boomers leave or retire from large companies, they are more likely to have the flexibility to adopt a portfolio approach for their activities. As a boomer, you are more likely to pursue work as free agents than to pursue full-time jobs with employers. Companies are expected to be more open to part-time roles or gradual retirement, as discussed in the Introduction of this book. Free agency gives you greater flexibility in implementing a portfolio life. You have the independence to make choices, assert your will, and not be confined by decisions of others.

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