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3 Challenges of Extending Your Career After Retirement

Joanne Cleaver

The prospect of working past the traditional retirement age of 65 has become a post-recession cliché realized for millions of baby boomers.

Many of them hope to power down, the way Phyllis Snyder already is. After decades of designing educational programs for working adults, the vice president of the Council for Adult and Experiential Learning is transitioning to a consulting role that allows her more time to spend with her grandchildren, do volunteer work and continue her own learning through workshops and other endeavors.

Snyder's downshift enables her to concentrate on one project in particular -- helping America's millennials gain college credit from the learning they accomplish through the military, Peace Corps and other nonprofit, mission-oriented programs.

About 40 percent of retirement account holders expect to keep working past the traditional retirement age, according to a survey conducted in January and sponsored by State Street Global Advisors. The survey included 980 401(k), 403(b), 457 and profit-sharing plan participants and retirees age 30 and older.

Experts cite three main factors that affect your ability to continue working: finding a new groove for continual professional development, calibrating your energy and abilities, and caregiving.

[See: 10 Steps for Retiring Entrepreneurs.]

Professional development is not about continuing to do what you've been doing, Snyder and her colleagues say.

A 2013 CAEL paper, "Tapping Mature Talent: Policies for a 21st Century Workforce," indicates employers have mixed feelings about older workers staying on the job, points out Sarah Miller, associate director for CAEL. On one hand, employers appreciate the insight and maturity older workers bring to the daily work milieu, not to mention their ability to train and mentor others. But employers also assume older workers will be resistant to change and unenthusiastic about keeping up with technology.

It isn't enough to keep up, Snyder and Miller say. You need to show you are a step ahead. "Do an assessment on yourself," Snyder says. "Look at the skills the employer is asking for and whether you have those skills through volunteer, church and community."

For instance, she says, someone who has been a volunteer manager of a youth soccer league probably has both marketing and financial skills. If a course or certification will add an official validation of skills you have picked up informally, make sure to get that piece of paper.

"See where you can leverage your experience and understand where the new roles are," Snyder says. Make sure you are tracking industry trends and anticipating changes in training, coaching and other functions where your experience provides a critical advantage, Miller adds.

You can also self-fund a career change that sends you back to college for new credentials. Kathryn Spica, a senior fund analyst with Morningstar, points out that tax-advantaged college savings plans called 529s are for anyone. If you see a stint in college on the horizon, set up a fund with yourself as the beneficiary, she says. That can include graduate work, Spica says.

[Read: Should Your 529 Plan Be Direct-Sold or Advisor-Sold?]

Energy and ability. Working forever might be a bragging point, but it could also be a drag if your energy lags -- even if you love your job, says Laura N. Gitlin, director of the Center for Innovative Care in Aging and a professor at Johns Hopkins University.

Consider the physical and cognitive demands of your job separately. You might be clicking on all cylinders mentally but finding that deadline work tires you more quickly and deeply than before.

Expect to adapt the way you work to become more in sync with your capabilities, workload and interests, Gitlin says.

Since boomers are the first generation to purposefully work past 65, expect that your final stage will unfold in stages. Gitlins says "we'll see great diversity" in job descriptions, tasks and responsibilities as boomers and their bosses remix how work gets done to accommodate aging.

Taking care and giving care. Most people assume that illness and disability could derail their plan to keep working. They are half right: Often, it's someone else's illness or disability that pulls the career plug, because near-retirees often step in to care for elderly relatives or ailing spouses, senior transition experts say.

[Read: How to Budget for Health Care Expenses in Retirement.]

Even the prospect of an expensive illness is enough to keep some people cemented in their jobs, says Kristine Brown, assistant professor at the University of Illinois--Urbana-Champaign's School of Labor and Employment Relations. ;Once you have left an employer-sponsored health care plan, it's much harder to rejoin another employer-sponsored plan, she says. ;And retiree health benefits are at greatest risk of being trimmed back by cash-starved pension plans, Brown points out.

"Even if you're not the direct primary caregiver, you are likely to be drawn in," Gitlin says. "This will collide with career expectations of family in many directions."

Illness is unpredictable and disruptive, she explains. It's not just a matter of ferrying an elder to scheduled appointments. Daily needs must be met in the moment, and small emergencies crop up continually. Negotiating a flexible work schedule or telecommuting is not a complete solution: You may find yourself working late into the night to offset time spent earlier at the occupational therapist's office.

"You are on call. You are not in charge, and that affects your productivity," Gitlin says. "This definitely affects how one thinks about one's career."

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