Cover Letter For Retiree Re Entering The Workforce At 50

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by Katharine Hansen, Ph.D.

Career and Job-Hunting Tips for Older, Mature, and Baby-Boom Job-Seekers

Older Worker/Job-Seeker Resume Strategies:

  • Many hiring decision-makers, especially recruiters, are adamant about seeing every job listed from your college graduation to the present. They argue that background checks — or even just seeing you in person at an interview — will reveal your age anyway, so why hide it? Others recommend going back 15-20 years, with the idea that jobs beyond that point are likely not relevant to your next career move. If you have the opportunity to contact the decision-maker before sending your resume, you can always ask his or her preference. Another option is to include your jobs that are more than 15 years old, but list them in bare-bones fashion (title, employer, location) with or without dates of employment (instead of dates, you could give length of time worked at each older job). You may want to title this section Previous Professional Experience. Even if you opt to leave off the dates, the recipient will at least know that you have provided full disclosure by listing all jobs. A similar strategy is to insert a disclaimer statement to the effect that “additional employment history is available upon request.”
  • De-emphasize dates. Certainly don’t list your birth date. Omit college-graduation dates that are more than 10-15 years old.
  • Some experts suggest softening the job titles you list on your resume so you won’t seem overqualified. For example, “senior manager” instead of “vice president.”
  • Be sure to list all courses and professional-development activities that illustrate your willingness to learn and keep your skills updated.
  • Definitely list all the computer and other technological skills you possess that are relevant to the type of job you’re applying for.
  • Emphasize results, accomplishments, and achievements. List accomplishments that set you apart from other job candidates. You will likely have a greater quantity and quality of achievements than will younger workers. In each job, what special things did you do to set yourself apart? How did you do the job better than anyone else or than anyone else could have done? What did you do to make it your own? What special things did you do to impress your boss so that you might be promoted? How did you leave your employers better off than before you worked for them? Accomplishments are the points that really help sell you to an employer — much more so than everyday job duties. For more about how to identify your accomplishments, see our article, For Job-Hunting Success: Track and Leverage Your Accomplishments and our Accomplishments Worksheet.
  • If you are just entering the workforce after a career as a homemaker or volunteer or have large gaps of unpaid experience in your history, learn to portray your skills on your resume as transferable and applicable to your next job. See our article, Strategic Portrayal of Transferable Skills is a Vital Job-Search Technique and our Transferable Skills Worksheet for Resumes and Cover Letters.
  • For an overall refresher on resumes, see our Resume Tutorial and Resume Builder.

Older Worker/Job-Seeker Cover Letter Strategies:

  • Avoid cumulative experience statements. Older workers are justifiably proud of their work histories and have a tendency in cover letters to make statements such as this: “My 25+ years in management would enable me to make a significant contribution in the position you’re advertising.” With that much experience, it’s probably best not to quantify in your cover letter. Stick to expressions such as “significant experience” or “extensive experience.”
  • An “autobiography letter” or one that rehashes the job history you’ve already laid out in your resume is never a good idea, but it’s especially harmful for older workers who will only call attention to their age with such a letter.
  • Include language in your cover letter about flexibility, adaptability, and willingness to learn.
  • Emphasize that you are a proven commodity (in unspoken counterpoint to a younger worker who may be untested).
  • For a general tune-up on cover letters, see our Cover Letter Tutorial.

Older Worker/Job-Seeker Job Interview Strategies:

  • Realize that you will probably be interviewed by someone younger than you, and don’t be unnerved by that situation.
  • Overcoming the obstacles that may be inherent within your resume and cover letter is a major victory, but once you’ve gotten your foot in the door with an interview, you have to do more than younger workers would need to do to show yourself as a value-added employee. “Despite your age, you’ve got to show that you’re still very current in today’s workplace, such as with your computer skills,” says Deborah Russell, who manages information and resources for older workers at AARP, as quoted in the Washington Post. “Tell how flexible, adaptable, creative you can be, that you’re a team player and able to work with multiple-age generations.”
  • Stress your willingness to learn. One of the biggest obstacles to the hiring of older workers is the concern that their skills are outdated and they aren’t willing to learn new skills. Writing in the Milwaukee Journal Sentinel, Margo Frey urges older workers to demonstrate their willingness to learn based on their past record and future commitment to keeping skills updated:
    • If you’ve taken courses and attended workshops, seminars, conferences, and other professional development events throughout your career, be sure the prospective employer knows that.
    • Especially ensure the employer knows your technology aptitude is up to date, particularly as it relates to the job you’re interviewing for.
    • Telling the prospective employer that you sought out and paid for learning opportunities on your own can be especially impressive.
    • Convince the employer that you are more than willing to get up to speed on any skills that may be lagging.
  • Subtly suggest that your work ethic is unsurpassed (in possible contrast to that of younger workers). Be sure prospective employers know that your references will vouch for your reliability and stable work record.
  • Convince employers that your maturity is an advantage because your experience makes you wise in the ways of problem-solving. “Wisdom involves using past experience to help solve a current situation,” writes Frey. “Having successfully survived difficult situations, older workers can apply their knowledge and experience to make better judgments than a young person might make. Wisdom also means keeping an open mind to better or more appropriate ways to solve a problem.”
  • Stress interpersonal skills, especially your delight in working with people of all ages. If you’re interviewing for a job with client or customer interaction, the AARP suggests you might want to mention your ability to identify with an aging customer base.
  • Be prepared for interview questions that are inappropriate, borderline illegal, or downright unlawful. Surprisingly, it’s not illegal for an interviewer to ask how old you are, although it’s certainly inappropriate. If you are asked any question that suggests the employer wants to know how old you are or is concerned about your age, the AARP recommends responding with a question such as: “How do you see my age affecting my ability to do the job?” Don’t be defiant or confrontational as you ask the question; remain upbeat and positive. If you’re asked whether you’d have a problem working for a younger manager, the AARP suggests you respond with: “When I get to the point where I can’t learn from someone younger or older than I am, I will stop working.”

    Read about what questions are legal in an article directed at human-resources practitioners on Can I Ask That? An Interviewer’s Guide To Prevent Employment Discrimination by Miriam W. Berger.

    We had a 55-year-old correspondent who told us that she was asked what year she graduated from high school. At another interview, she was asked for a photo ID and presented with citizenship documentation clearly stating at the top of the page “To Be Completed by Employee on First Day of Employment.” The consensus among career counselors to whom we presented these situations was that they were clearly illegal. Other counselor suggestions:

    • Anyone in this situation should report the company and call the firm’s president.
    • Ask yourself if you would really want to work for such an unprofessional company.
    • In response to the high-school graduation question, say: “Can you tell me how this question applies to my ability to perform the job?” And when presented with the obviously post-offer forms, simply ask if the forms represent an offer of employment.
    • Say: “I am sensing that there may be concerns about my age. Unless there is something I haven’t been told, I can only assure you that there are no aspects of this position that I cannot handle, and I would be committed to bring you a wealth of education, training, and experience that few could equal.”

    (By the way, our correspondent’s story has a happy ending; she e-mailed us a few weeks later to say that she’s landed a promising job.)

  • To review general interviewing tips, see our Job Interviewing Tutorial.

Questions about some of the terminology used in this article? Get more information (definitions and links) on key college, career, and job-search terms by going to our Job-Seeker’s Glossary of Job-Hunting Terms.

Katharine Hansen, Ph.D., creative director and associate publisher of Quintessential Careers, is an educator, author, and blogger who provides content for Quintessential Careers, edits QuintZine, an electronic newsletter for jobseekers, and blogs about storytelling in the job search at A Storied Career. Katharine, who earned her PhD in organizational behavior from Union Institute & University, Cincinnati, OH, is author of Dynamic Cover Letters for New Graduates and A Foot in the Door: Networking Your Way into the Hidden Job Market (both published by Ten Speed Press), as well as Top Notch Executive Resumes (Career Press); and with Randall S. Hansen, Ph.D., Dynamic Cover Letters, Write Your Way to a Higher GPA (Ten Speed), and The Complete Idiot’s Guide to Study Skills (Alpha). Visit her personal Website or reach her by e-mail at kathy(at) Check out Dr. Hansen on GooglePlus.

Have you seen all our career and job resources for older workers? Go to: Job and Career Resources for Mature and Older Job-Seekers (Including the Baby Boomers)


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Return to Work After Retirement

Finding Your Passion Is Key to Work Happiness at This Stage of Life

Return to Work After Retirement

Donald Sayner considers himself lucky. At 69, he's working because he wants to, not because he needs to. For many older workers today, this isn't the case. Rising healthcare costs, inadequate financial planning and rising living expenses are a few of the many reasons people are working longer. 

As someone who retired and then rejoined the workforce, Sayner, a career counselor, understands the mental anguish, depression and frustration older workers who expected to retire may feel. That's why he started Jobs in Transition, a job club for retirement-age professionals still in the workforce. The workshops are offered through St. Paul-based Quality Career Services, an organization that offers job advice, counseling and networking opportunities for job seekers.

"A lot of people heading into their golden years are unable to live the life they thought they would be able to," says Sayner. "This is forcing would-be retirees to deal with an entire set of life challenges they aren't prepared to face.

Follow a New Career Path

Sayner encourages job seekers to reconsider early passions they may not have pursued for one reason or another. He says finding a job or career path instead of just a paycheck can be the key to workplace happiness at this stage of life.

"Sometimes searching for work in the field you spent your life trying to earn a living [in] just isn't going to work out," says Sayner. "Don't get into a rut where you believe you are too old to change direction. Now can be the best time to look at a new career, to do something you always dreamed of doing.

Melanie Keveles, a certified business coach who has helped older workers find passion and meaning in their current jobs or new careers, often follows the theories discussed in The Three Boxes of Life and How to Get Out of Them by Richard Bolles.

In the late '70s, Bolles predicted we would outgrow the idea that there were three stages (or three boxes) in our lifespan -– the learning stage, the work stage and the retirement stage. Bolles suggested that we were moving into a time when those stages would merge, and we would experience lifelong learning, work and play.

"For those people who for whatever reasons find themselves having to go back to work during what they had dreamed would be the stage in the life that they would be retired or playing only, it helps to recognize that such a leisure-only phase is just not always practical anymore," says Keveles.

Get Motivated to Go Back to Work

Keveles admits it's hard for retirement-age workers to get motivated for work when they feel underappreciated or that they are not contributing in a meaningful way while their peers enjoy retirement. But it's important to make the most of the situation, Keveles says. The first step is overcoming the mental barriers. Keveles suggests that by becoming receptive to the idea that working can coexist with learning and playing as you age, you might find that working again can:

  • Provide an opportunity to find meaning and accomplish things that are compatible with your values. 
  • Give you a reason to get up in the morning and a community in which to operate. Isolation can be deadly as you age. 
  • Help keep your mind and body active. 
  • Give younger people an opportunity to get to know more older people, thereby fighting stereotypes that suggest we lose our usefulness, creativity, imagination and productivity as we age.
  • Keep you engaged. Examples of people working into their 60s, 70s, 80s and even 90s have shown us that people who work into these later decades often outlive those who fully retire.

Shifting your perspective is the first step, and it could be the beginning of a new and rewarding career.

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