Why surrender your career just because you’ve reached senior status? These professionals prove that “older” doesn’t have to mean “over.”

Most modern gentlemen wouldn’t want to be known for, shall we say, “having a way with the ladies.” Dexter Callender, however, proudly owns up to his nickname: “The Ladies’ Man of Lingerie.” And why not? He’s certainly earned it. As a sales associate for UndercoverWear (think Tupperware or Avon parties for ladies’ underwear), Callender helps his clients to find the lace, silk, and satin underthings of their dreams. Not a bad gig for a former electro-mechanical draftsman for Raytheon Corp. Oh, and by the way, Callender is 72 years old.

When asked about his plans for hanging it all up, Callender — who has successfully displayed and sold intimate apparel in women’s living rooms for the past 16 years — responds: “When my knees give out and I can’t carry the luggage [full] of lingerie is when I will retire. But for now, I feel fantastic!”

There was a time when workers spent their entire careers scraping money together, dreaming of the day they’d be given a gold watch, a farewell party, and a one-way ticket into the sunset of life. The luxury of retiring early to enjoy the good life uninterrupted was a goal to which many aspired. But, for most middle-aged professionals, those days are long gone.

“Whether full-time or part-time, seasonally or year-round, self-employed or as employees, tomorrow’s elders will work as long as they are physically able,” writes Ken Dychtwald, Ph.D., in his book, Age Wave: The Challenges and Opportunities of an Aging America. The latest edition is The Age Wave: How the Most Important Trend of Our Time Will Change Our Future (Bantam Doubleday Dell, $14.95). “They will work partly because they want to, because work gives them fulfillment, control over their own lives, and a useful place in society.” In fact, by 2020, it will become normal for 50-year-olds to go back to school and for 70-year-olds to start new careers.”

The U.S. Department of Labor, in its report, Futurework: Trends and Challenges for Work in the 21st Century, details that “between 2011 and 2029, the baby boom generation will be reaching the traditional retirement age of 65.” It continues, “In 1995, 33.5 million people were age 65 or older, and, by 2050, the elderly population is expected to more than double, representing 20% of the population.” With life expectancies higher than ever, coupled with better nutrition and preventative healthcare, older Americans can surely be expected to continue in their professional pursuits until they see fit to quit.

Want proof? The American Association of Retired Persons (AARP) and Roper Starch Worldwide Inc. report in Baby Boomers Envision Their Retirement: An AARP Segmentation Analysis that baby boomers — America’s next crop of retirees — don’t intend to spend their retirement years unwinding in Florida playing tennis. Instead, eight out of 10 baby boomers say they intend to work at least part-time in their retirement. A little more than 35% say they will work-part time mainly for the sake of interest and enjoyment, while almost one-quarter, 23%, say they’ll work for the money.

Some experts wonder how a business world that regards youth as innovative, easily trained, vigorous, and willing to work countless hours for low pay will deal with an older workforce. Traditionally, business has viewed older workers as resistant to change, expensive, difficult to train, and likely to miss work due to health problems. Though many studies have proven such assumptions to be false, experts maintain that these stereotypes and long-held beliefs are hard to overcome.

Individuals such as Callender are happy to shatter the old generalizations. Indeed, he epitomizes the modern retiree’s relentless drive to overcome seemingly insurmountable obstacles in order to remain in control of his professional life. In Callender, Boston-based lingerie maker UndercoverWear — with over 1,500 sales agents throughout the United States and Canada selling merchandise through home parties — has a prime example that the myths surrounding the older worker aren’t necessarily true.

With an all-time, one-month sales record of $12,031 in March of 1989, Callender, who operates out of Roxbury, Massachusetts, has earned just about every single award UndercoverWear has to offer. He currently holds the title of Top Male Sales Agent, having sold $1 million worth of women’s undergarments. He hosts six to eight private parties a week. At the end of a typical night, Callender usually walks away with about $600 in sales and bookings for at least three more lingerie parties. Tiffany James, founder and CEO of UndercoverWear, admits she initially was skeptical a man would be a good fit, considering the nature of the business. (The average sales associate is 33 years of age and female.) But Callender’s sales savvy soon changed her mind.

Unfortunately, not everyone is as fortunate to find an employer who is willing to take a chance on older professionals. Dianna Jackson was an office manager with a 13-year tenure at a community health center in the tristate New York area. After returning to the office from an extended six-month sick leave in 1998, Jackson was shocked to learn that her services would no longer be needed. Confident that her certification in early childhood education would help her land a new career in daycare, she began a job hunt. One year and six interviews later, she was still without employment.

“Those companies all saw more of a future in younger applicants and chose to invest in them, even though my education and experience qualified me for the job,” says Jackson, 55. She is currently working part-time at a health club and is still looking for a full-time opportunity with a daycare provider that will judge her on the quality of her performance, not the length of time she’s been on earth.

If you suspect that you’re currently being discriminated against because of your age, read up on the 1967 Age Discrimination in Employment Act — which protects most workers who are more than 40 years of age from discriminatory practices on the job — and consider consulting a lawyer who specializes in employment issues. He or she will also be able to confirm whether this important legislation can also protect you when it’s time for you to pound the pavement again. The most valuable tool, however, in your search for a new job may be your own mind.

“Even if you are not discriminated against, you may think you will be and not go look for a job,” observes a Bureau of Labor Statistics (BLS) expert. And finding a job once you’re past the age of say, 60, is certainly not as easy as it is (if it ever is) when you are 20 or 30 years younger. According to the BLS, 500,000 professionals ages 55 to 64 and 140,000 workers age 65 and older lost jobs in 1993-94. Though this displacement rate of around 3% (due to company closings, insufficient work, or terminated positions or shifts) is the same across all age groups, considerably more older workers than younger ones are unemployed for longer periods of time — or left out of the labor force altogether.

So what about you? Maybe you’ve been busy carving out your niche, developing your skills set, and perfecting your professional demeanor when, poof! You look up and 30 years have flown by, bringing you close to the traditional age of retirement. Or, perhaps you’ve already, albeit reluctantly, taken that permanent leave of absence from your career because you thought that’s what you were supposed to do.

Happily, the rules of retirement aren’t written in stone. April Gregory, president of Marketing Concepts Unlimited, a human relations development firm that markets and trains professionals in the workforce, contends, “It’s not about age. It’s not about position. It’s all about attitude. The sky is the limit, no matter how old or young you are,” she says.

If you have the ability and the desire to keep working past the age of 65, you can do it. We’ll share with you the stories of two individuals who have turned back the clock on their careers, as well as expert tips and advice to help you pursue your professional passions later in life. Get ready to show the pundits that like that gold watch of old, you can still take a lickin’ in the workforce — and keep on tickin’!

Callender was 56 when he joined UndercoverWear in 1985. He’d been struggling to pay his bills by waiting tables on weekends to supplement his Raytheon salary. “I heard that I could earn a whole lot more doing lingerie parties and I jumped,” he says. In addition to greater earning potential, there was also the lure of other incentives. In his tenure, Callender has earned full-length mink coats, jewelry set with precious gems, and exotic trips around the world. His travel itinerary has included Hawaii (four times), Paris, Athens, Rome, Bangkok, Australia, and Aruba.

Not only does Callender enjoy the incentives that the company has to offer, he reaps the financial benefits as well. His work ethic, coupled with savvy savings and investment strategies, has crafted him a comfortable financial cushion in the six-figure range.

Like Callender, many 50s-and-ups are opting out of retirement. They are viewing the door between work and retirement as revolving instead of one way. Many want to work, but not in the same place or with the same responsibilities. They are ready to try new skills or perfect old ones. They are reinventing themselves, and are once again enjoying the fruits of their labor.

A PaineWebber study of investors found four categories of retirement attitudes: become an entrepreneur/seek a new job (60%), work as long as possible (15%), enjoy traditional retirement (15%), and seek a work/life balance (10%).

As in previous stages of your career, you will need to chart your course to nonretirement. Decide whether you want to work full- or part-time at a new job or enlist with your former employer. Many employers offer work on a temporary, project-oriented basis. “If health is a major concern, some companies offer a flex-place program that allows you to work from home or a recreational hideaway,” says Gregory. She encourages older workers to leverage their age and experience on the job to choose the arrangement that is most convenient for them.


If you’re more than 50 years of age and want to jump on board the train of second (third, or even fourth) career opportunities, continuing education will likely be a desirable — and in some instances, necessary — activity for you to pursue. Frances Wyman Graham, a 50-year-old New Jersey resident, wakes up every day at 5 o’clock to prepare herself and her 13-year old son for school. After early-morning prayer, cooking breakfast, preparing lunch, and sending her son off to school, her day begins.

Graham, who was responsible for transferring million-dollar accounts for individual and corporate clients overseas as a financial customer representative with CitiBank, was downsized out of her position — and her 23-year tenure with the financial firm — in 1997, the same year her husband passed away. Fortunately, thanks to her participation in her former employer’s 401(k) plan, Graham walked away with $35,468, and an additional $45,757 from a mutual fund serviced by Citigroup.

Faced with unemployment, Graham was compelled to reinvent her life. Her determination to carry on has positioned her as a full-time student at Essex County College in Newark, New Jersey. With a double major in physical therapy and social services, she is pursuing a brand-new career in the medical profession. “I decided to further pursue my education because I wanted to choose a new career that was more rewarding and fulfilling,” says Graham. With her double degree, her earning potential would start at at least $65,000 a year.

Nationwide, more than a thousand colleges now actively encourage people over 50 to take classes for credit, and more than 120 schools have adopted special programs just for the older learner. “Returning to school for more education is no longer an oddity but a common practice,” stresses Gregory. Consider taking courses of personal interest at a local college or university that will further prepare you to re-enter the workforce.

You may want to pay extra attention to increasing your tech savvy or refining the knowledge you already have. Due to constant changes in technology and innovation, skills acquired earlier in your career may no longer be relevent. “Remove this possible hurdle by looking into technology training programs offered by government, nonprofit, and corporate programs,” advises Gregory.

Whether you choose to go back to school, or dive headfirst into your next career, remember that as long as your mind and body are healthy, and you have the drive to keep your career going, you still have options. You can still set objectives for yourself — and reach them. “Goals affect your happiness, success, and fulfillment. Never stop setting goals for yourself,” says Gregory.

Personal and professional coach Diane Middlebrooks, president of Chicago-based The Business Coach, offers a four-point checklist for you to consider in planning your nonretirement career pursuits:

  • Take some time to evaluate what your talents and values are so that your new career matches them. Ask people who know you well, both professionally and personally, what they consider your strengths to be.
  • Research careers that appeal to you. Talk to people who are in your targeted business to find out what they like and don’t like about their line of work. Consider all aspects of the work, not just the ones that seem appealing. How well you succeed will have everything to do with your planning.
  • Remain excited about your second career but don’t ignore the financial implications of your new endeavor. Determine what you’ll need to earn in order to live comfortably. After years of working, you should certainly do what you love. Just be realistic about your money expectations.
  • Give yourself permission to enjoy what you do. Don’t make your new career a carbon copy of your last one. For instance, if you tended to be a workaholic, don’t let this carry over. Look for new ways to bring joy into your life.

Never Say “Retire!”