MONEY Second Career

The Secrets to Launching a Successful Encore Career

These prize-winning social entrepreneurs built non-profits that make a difference.

“You must do the thing you cannot do,” Eleanor Roosevelt once wrote. It’s the only way to overcome the fears we all face in doing something new, she thought, and take a leap into the unknown.

Kate Williams quoted Roosevelt earlier this week here when she accepted a $25,000 Purpose Prize, one of the awards given annually by Encore.org, a San Francisco-based nonprofit that works to engage baby boomers in “encore careers” with a social impact. The awards, now in their ninth year, recognize trailblazers over age 60 who have tackled social problems creatively and effectively. Cash prizes range from $25,000 to $100,000.

Williams, 72, lost her eyesight to a rare degenerative disease after a long career as a corporate human resources professional. She overcame her own fears, first by moving away from friends and family in Southern California to start over in San Francisco and later by starting an employment training program for the blind. Today, she runs a similar, larger program for the national non-profit organization Lighthouse for the Blind.

Encore.org’s mission is to promote a game-changing idea: Greater longevity and the graying of America present opportunities, not problems. This year’s Purpose Prize winners underscore that point. They’re rock stars in the world of social entrepreneurship, having started organizations that work on issues like sex trafficking, disaster relief, autism and education in impoverished neighborhoods.

The idea of second careers with social purpose has broad appeal. Millions of older Americans want to stay engaged and work longer, sometimes out of economic need but often out of a deep motivation to give back. An Encore.org survey this year found that 55% of Americans view their later years as a time to use their experience and skills to make a difference, though just 28% say they are ready to make it happen.

Many people have trouble figuring out where to start—which brings us back to Roosevelt. Fear of the unknown is a key hurdle in starting down a new path later in life, and I had the chance to ask some of the encore experts gathered for the awards about how they would advise others seeking to begin.

The juices get flowing when people connect their experiences and knowledge with a problem they are passionate about. But first they have to make the leap.

“I had been in the corporate world, not part of the blind community,” Williams says. “I was frightened, but what I thought would be overwhelming turned out to be a beautiful thing. As soon as we started our training classes, I was hooked.”

The Lighthouse for the Blind program has worked with 100 blind job seekers over the past three years, and has placed 40% of them.

David Campbell, winner of a $100,000 prize this year, wanted to help after the Indian Ocean tsunami that devastated parts of Southeast Asia in 2004. A senior executive at several software and Internet technology companies, he figured he could help by creating a Web-based tool to organize volunteer tsunami relief efforts. That led him to start All Hands Volunteers, which has worked on 45 disaster relief projects in six countries and dozens of U.S. locations. The non-profit uses the Internet to route volunteers to places where they can be put to work effectively.

“People just want to know that if they go, they’ll have a place to sleep that won’t be a burden to the local people, and a contact to start with,” he says. “We give you exact instructions on how to get there, and assure that you’ll have a bunk bed, food and someone will have organized work and that you’ll have the right tools to be productive.”

Campbell talks often with people looking to get started on encores. “I always advise people to start by volunteering with some organization with social purpose – it’s an easy, great way to start. But the question many people have is, ‘Which one, and what might I do?’ “

Campbell suggests people consider geography and the focus of the work. “Do you want to work locally, nationally or internationally? Do you care about health, education or some other thing? That starts the conversation and helps people narrow it down.”

Then, he says, visit a non-profit that interests you, and take the time to understand its needs.

“Be willing to help understand the mission, and do whatever it is they need help with. And don’t treat volunteering as a casual activity. You need to commit to a certain number of hours of work a week as though it were a paying job, and take responsibility for it.”

To paraphrase another famous Roosevelt, the only thing you have to fear is fear itself.

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MONEY Second Career

3 Secrets to Launching a Successful Second Act Career

Adele Douglass created the first U.S. humane certification program for farm animals raised for food Robert Merhaut

Adele Douglass built a non-profit that protects millions of farm animals and gives farmers a new marketing niche.

After a three-decade career in Washington devoted to animal welfare issues, Adele Douglass thought she knew a lot about how bad their mistreatment could get. Still, she was shocked when she began to look closely at the conditions of farm animals in the U.S.

She discovered chickens being raised in cages so overcrowded they couldn’t raise their wings, pigs unable to turn around in tightly packed pens, and animals left unsheltered against outdoor elements.

Douglass decided the best way to improve the conditions of livestock was to push for change herself. So in 2003, at age 57, she quit her job as a non-profit executive for an animal rights association and launched her own organization, Humane Farm Animal Care. “The more I knew, the more appalled I got, and the more I wanted to do something myself,” says Douglass, now 67. “Legislation was not going to solve the problem. It took 100 years for the Humane Slaughter Act to be passed.”

Douglass figured out a way to engage farmers and consumers on the issue—by addressing their growing concerns over eating meat from animals being fed antibiotics. She developed Certified Humane, which is the first certification in the U.S. that guarantees farm animals are treated humanely from birth to slaughter. To get this certification, farmers must allow animals to engage in natural behaviors, provide appropriate space for roaming, and food free of antibiotics or hormones. Farmers who are Certified Humane can market to natural food shoppers and get higher prices for their products, Douglass says.

Humanely raised food appeals to American families of all income levels. “Young mothers want to feed their families good food. Poor people don’t want to feed their families junk” says Douglass.” Following humane practices also improves the environment, since fewer animals raised on more space creates less pollution.

To fund the organization, Douglass cashed in her $80,000 401(k) account. Her daughter, who had encouraged her to make the move, gave her $10,000 and worked at the organization during its first few years. Douglass also received grants from the American Society for the Prevention of Cruelty to Animals and The Humane Society. In the first year of operation in 2004, 143,000 animals were raised under the organization’s standards.

Today 87 million animals are in the program, and the non-profit has three full-time employees and two part-timers. Fees for certification and annual inspections cover about 30% of the organization’s costs—the rest comes from donations and grants.

Douglass shares this advice for others hoping to launch a second act career:

Make a plan before you exit. Douglass spent years researching the issue before quitting her job. She was able to get off the ground in just one year because she modeled the certification program after an existing similar program in the U.K. called Freedom Food.

Leverage your contacts. Douglass has a deep list of connections, from animal scientists and USDA officials to fundraisers and academics, as well as contacts in the animal rights movement and veterinary profession. “I had the contacts, knowledge and experience which gave me confidence I could do this on my own,” says Douglass.

Cut personal expenses. Though Douglass’ salary isn’t much less than what she earned in her previous career, her compensation is a lot more volatile. She has willingly taken pay cuts in recent years. Douglass says she hasn’t had to change her lifestyle much. But she reduced her biggest expense—her home—by downsizing to a smaller place, which made it easier to adjust.

At 67, Douglass doesn’t envision retiring. Now living alone, with three adult children and five grandchildren, she says her family is one of her greatest joys. But her work remains an enormously satisfying part of her life too. “Sure, there are days when I am tired and frustrated. But I am doing something that benefits people, animals and the environment. I feel really good about that,” says Douglass.

Adele Douglass is a 2007 winner of The Purpose Prize, a program operated by Encore.org, a non-profit organization that recognizes social entrepreneurs over 60 who are launching second acts for the greater good.

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The 9-to-5 Start-up: How to Launch a Business Without Quitting Your Day Job

How This Former Techie Gave Her Career a Jolt

MONEY Second Career

How to Find the Right Match for Your Second Career

Signing up with an encore career matchmaker can be a smart way to find fulfilling, paid work in retirement.

WANTED: Retirees looking for flexible, paid part-time work in their field of expertise.

Now, that’s a help-wanted ad many boomers dream of running across in their Unretirement years, isn’t it? Well, for Harry Coleman of Cincinnati, Ohio, that’s pretty much what happened, thanks to a “matchmaking” service.

Coleman worked for Procter & Gamble (P&G) for 30 years, mostly in product development, and decided to grab P&G’s juicy retirement package at age 51 in 2008. “The last nine years at P&G were a blast,” he says. “But I wanted more of a work and life balance and you can’t do that if you’re working 50 to 60 hours a week.”

A Three-Bucket Approach

These days, Coleman, now 57, embraces a “three bucket” approach to life.

The first two buckets are for volunteering and charitable activities (mostly through his church) and for “goofing off”—golfing, traveling and taking on projects around the house.

The third bucket relates to that ideal help-wanted ad. In this bucket, Coleman takes on flexible, fulfilling, paid part-time consulting positions he has found since he retired mostly through a firm called YourEncore. “The jobs keep me engaged mentally on the work side; I can pick and choose projects,” he says. “Yet I have the capacity to be more involved in other things.”

YourEncore, based in Indianapolis, Ind., is essentially a matchmaker between large corporate customers around the country looking for experienced brainpower to address a pressing business problem (typically for about 10 weeks) and seasoned, skilled Unretirees who are eager for a challenge and part-time income.

YourEncore was created in 2003 when P&G and Eli Lilly, the Indianapolis-based pharmaceutical giant, asked consultant John Barnard for a way management could draw on the knowledge and expertise of retired employees. Boeing quickly joined the venture to recruit “retired engineers for urgent and complex technical projects,” as an internal company online newsletter put it.

Companies using YourEncore are largely in the food, consumer product and life sciences industries. So far, more than 8,000 people have found work through the matchmaker; 65 percent of them have advanced degrees. The pay is good, although the exact amount depends on the person’s experience, the company, the difficulty of the project and the time commitment.

Encore Career Matchmaking Services Are Sprouting

YourEncore is just one example of the growing number of matchmaking services targeted at retiring boomers. It focuses on private sector work, but many others specialize in the social venture space, creating bridges between for-profit careers and nonprofit encores for the greater good. Some are regional, such as Experience Matters in Maricopa County, Ariz. ESC of New England runs an Encore Fellows program in greater Boston. Other matchmakers like ReServe, headquartered in New York City, have national and international ambitions.

Though the Unretiree matchmaking business is pretty new, it’s already starting to puncture a common stereotype: that the idea of gray hair and creativity is an oxymoron. For example, YourEncore workers have earned a reputation for creative problem solving, says Peter Kleinhenz, manager of the its P&G office. “You can be really productive when you don’t have a career that needs to be advanced or turf to protect,” says Kleinhenz.

New York City-based ReServe offers a very different business model, but it, too, acts as an encore career matchmaker.

ReServe connects 55-plus professionals with local nonprofits, public institutions and government agencies. Aside from its New York operations, ReServe also places candidates — typically former lawyers, doctors, nurses, teachers, accountants, corporate recruiters and the like — in Baltimore, Md.; Miami, Fla.; Newark, N.J.: Boston, Mass.; southeast Wisconsin and New York’s Westchester County. ReServe has placed more than 3,300 workers at more than 350 organizations.

ReServists work for a $10-an-hour stipend, well below their market value during their earlier career. (Another $5-an-hour is split between the company managing payroll for the person and ReServe.) The job is between 10 and 20 hours a week and the average ReServe contract lasts nine months to a year.

“A good proportion—50%—are not really looking to do what they have done before. They want to use their skills in a brand new setting. The common denominator is transferable skills,” says Lorrie Lutz, chief strategy officer at Fedcap, a New York-based nonprofit that combined with the smaller ReServe in 2012.

For example, Lutz says, an accountant with a passion working with kids might spend a stint as a math tutor. A marketing professional might employ her skills at a government agency struggling to get its policy message out.

Giving Back for Your Next Career

ReServe plans on operating in every state and taking its program overseas. “We think we have a great idea here. There’s a generation of talent here and abroad. Boomers are the most-educated generation,” says Lutz. “They have so much to give back.”

That’s certainly the case with Scott Kariya, an IT recruiter for 23 years who “retired” at 52 in 2006. Quickly bored, Kariya reached out to ReServe. He didn’t find an open position at the time, but in 2008 talked his way into a job at ReServe’s main office.

He worked there three days a week using his recruiting skills, spending the rest of his time volunteering at the local Red Cross, managing his investment portfolio and doing other things. “Everyone wants to stay busy,” says Kariya. “But I think a lot of people get tired of the 50-hour workweek.” Today, he heads up ReServe’s information technology operations.

A common denominator among encore career matchmakers is the amount of effort they put into finding the right people for clients’ needs. YourEncore gains an understanding of the proposed project from P&G, Lilly or another corporate customer, and then uses that to find the right experts. ReServe learns about the skills and passions of its applicants so the client partnerships are fruitful.

I’ve witnessed the same matchmaking ethos at Experience Matters in Phoenix and with the national Encore Fellowships Network. Although the infrastructure is still being built, the future looks bright because corporate America and nonprofits seem more aware of the talents and skills of available boomers.

Locating a Local Matchmaker

To find an encore career matchmaker in your area, you might start at the Encore.org site. But you may need to take a more indirect route, by networking locally. For example, in Portland, Ore., Life By Design NW serves as an information clearinghouse. JV EnCorps (part of the Jesuit Volunteer Network) recruits people 50 and older in Portland and Bend, Ore. and Seattle, Wash. In Kansas City, you could check out Next Chapter Kansas City, a grassroots networking group for boomers.

At the moment, the supply of people eager to keep using their accumulated knowledge and creative insights exceeds the demand for their services. But organizations like YourEncore and ReServe point the way toward a model that allows for engagement and compensation for people who’d otherwise have lots of time on their hands.

It’s a model that may well end up defining Unretirement the way Sun City symbolized retirement for a different generation in the 1960s.

Chris Farrell is senior economics contributor for American Public Media’s Marketplace and author of the new book Unretirement: How Baby Boomers Are Changing the Way We Think About Work, Community, and The Good Life. He writes about Unretirement twice a month, focusing on the personal finance and entrepreneurial start-up implications and the lessons people learn as they search for meaning and income. Tell him about your experiences so he can address your questions in future columns. Send your queries to him at cfarrell@mpr.org. His twitter address is @cfarrellecon.

More from Second Avenue:

Manual for an Encore Career

3 Essential Tips to Switch to a Second Career

Dipping Your Toe Into Encore Career Waters

MONEY retirement planning

3 Little Mistakes That Can Sink Your Retirement

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Cultura RM/Korbey—Getty Images/Collection Mix

Big mistakes are easy to catch, but even a small miscalculation may jeopardize your retirement portfolio. Here are three common missteps to avoid.

We think it’s the big mistakes that cost us in retirement, like hiring an unscrupulous adviser or funneling savings into a risky investment that goes belly up. Major errors can certainly hurt. But the smaller seemingly sensible decisions we make without really examining the rationale behind them can also come back to bite us in the…

Assiduous planning is key to a secure retirement, but the effectiveness of plans we make depends on the assumptions behind them. And when you’re making a plan that extends well into the future, as is the case with retirement, even a small miscalculation can take you way off course. Below are three mistakes that may seem minor, but that can seriously erode your odds of achieving a successful retirement. Make sure you’re not incorporating these errors of judgment into your retirement planning.

1. Relying on an unrealistic rate of return. Clearly, the higher the return you earn on the money in 401(k)s, IRAs and other retirement accounts, the less you’ll have to stash away in savings each month to build a sizable nest egg. For example, if you start saving $600 a month at age 30 and earn a 7% annual rate of return, you’ll have $1 million by age 65. Bump up that rate of return to 8% a year, however, and you have to put away only $480 a month to hit the $1 million mark by 65, leaving you an extra $120 month to spend. Earn 9% annually, and the monthly savings required to get to $1 million shrinks to just $385 a month, freeing up even more for spending.

Problem is, just because a retirement calculator lets you plug in a higher rate of return or a more aggressive stocks-bonds mix, doesn’t mean that loftier gains will actually materialize. Shooting for higher returns always involves taking on more risk, which raises the possibility that your aggressive investing strategy could backfire and leave you with a smaller nest egg than you expected. That can be especially dangerous when you’re on the verge of retirement.

For example, just prior to the financial crisis, nearly one in four pre-retirees had more than 90% of their 401(k)s in stocks. A pre-retiree with a $1 million retirement account invested 90% in stocks and 10% in bonds would have suffered a loss in 2008 of roughly 33%, reducing its value to $670,000—enough of a drop to require seriously scaling back retirement plans if not postponing them altogether. No one knows whether recent market turbulence will be a prelude to a similar meltdown. But anyone who has his retirement savings invested in a high-octane stocks-bonds mix, clearly runs the risk of a experiencing a significant setback.

A better strategy when creating your retirement plan is to keep your return assumptions modest and focus instead on saving as much as you can. That way, you’re not as dependent on investment returns to build an adequate nest egg. To see how different savings rates and stocks-bonds mixes can affect your chances of achieving a secure retirement, check out the Retirement Income Calculator in RDR’s Retirement Toolbox.

2. Factoring pay from a retirement job into your planning. It’s almost become a cliche. Virtually every survey asking pre-retirees what they plan to do in retirement shows that the overwhelming majority plan to work. Indeed, a recent Merrill Lynch survey found that nearly three out of four people over 50 said their ideal retirement would include working. Which is fine. Staying connected to the work world in some way can not only offer financial benefits, it can also keep retirees more active and socially engaged.

It would be a mistake, however, to factor the earnings you expect to receive while working in retirement into your estimate of how much you have to save. Or, to put it more bluntly, you’re taking a big risk if you assume that you can skimp on saving because you’ll be make up for a stunted nest egg with money from a retirement job.

Why? Well for one thing, what people say they plan to do in 10 or 20 years and what they end up doing can be very different things. You may find that the eagerness you feel in your 50s to continue to working may fade as you hit your 60s and 70s. Or even if you wish to work—and actively seek it through sites like RetiredBrains.com and Retirementjobs.com, it may not be as easy as you think to land a job you like. Maybe that’s why the Employee Benefit Research Institute’s Retirement Confidence Survey finds year after year that the percentage of workers who say they plan to work after retiring (65% in the 2014 RCS) is much higher than the percentage of retirees who say they have actually worked for pay since retiring (27%).

So when you’re making projections about income sources in retirement, keep work earnings on the modest side, if you factor them in at all. And don’t fall into the trap of believing you can get by with saving less today because you’ll stay in the workforce longer or rejoin it whenever you need some extra cash in retirement. Or you may find yourself working some type of job in retirement whether you like it or not.

3. Taking Social Security sooner rather than later. Although a recent GAO report found that the percentage of people claiming Social Security at age 62 has declined in recent years, 62 remains the single most popular age to begin taking benefits, and a large majority still claim benefits before their full retirement age. But unless you have no choice but to grab benefits early on, doing so can be a costly mistake.

One reason is that for each year you delay between 62 and 70, you boost the size of your benefit roughly 7% to 8%. You’re not going to find a low-risk-high-return option like that anywhere else in today’s financial markets. More important, waiting for a higher monthly check can often dramatically increase the amount of money you receive over your lifetime. That’s especially true for married couples, who can take advantage of a variety of claiming strategies to maximize their expected benefit.

For example, if a 65-year-old husband earning $90,00 a year and his 62-year-old wife who earns $60,00 claim Social Security at 65 and 62 respectively, they might receive just over $1.1 million in today’s dollars in joint benefits over their expected lifetimes, according 401(k) advice firm Financial Engines.

But they can boost their estimated joint lifetime benefit by roughly $177,000, according to the Social Security calculator on Financial Engines’ site, if the wife files for her own benefit based on her work record at age 63, the husband files a restricted application for spousal benefits at 66 and then switches to his own benefit based on his work record at age 70.

Although you may not think of it this way, Social Security is, if not your biggest, certainly one of your biggest and most valuable retirement assets. And chances are you’ll get more out of it by taking it later rather than sooner and, if you’re married, coordinating the timing with your spouse.

Walter Updegrave is the editor of RealDealRetirement.com. He previously wrote the Ask the Expert column for MONEY and CNNMoney. You can reach him at walter@realdealretirement.com.

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MONEY retirement planning

Why I Want a Real Retirement, And You Should Too

Senior on sailboat
Monika Lewandowska—Getty Images

Working longer may improve your finances. But that doesn't mean it will make you happier.

Looking forward to retirement seems irrational these days. Rising life expectancies and the increasing funding problems for Social Security and private pension plans have led to the recommendation that we defer retirement past the traditional age of 65—perhaps into our 70s and beyond. It’s getting to the point where many in my generation have started to assume that they might never retire at all.

It’s true that delaying retirement into your 70s will likely improve your financial situation. Yet in an age when work has come to permeate most of our waking hours, it seems even more important to delineate at least a decade when you’re still healthy enough to both reap the benefits of that hard work and devote your time to other pursuits. And yet the concept of a real retirement has come to symbolize financial irresponsibility or laziness or both.

This was not always the case. Over the last century, the retirement age has gone through enormous fluctuations, mostly dictated by public and corporate policy, not personal preference. In the period of 1950 to 1955, the median age of retirement was 66.9 for men and 67.7 for women, according to the U.S. Bureau of Labor Statistics. But changes in defined benefit plans increasingly encouraged early retirement as a way to cut the work force, and by 1990-1995 the median retirement age had dropped to about 62 for both men and women.

But as defined contribution plans such as 401(k)s have overtaken traditional pension plans, employers no longer have as much sway over the timing of their workers’ retirements. Instead, that decision is more often dictated by savings rates and the financial markets that drive investment performance. Once again employment rates for Americans ages 65 to 69 and 70 to 74 have begun to rise, a trend only accelerated by the Great Recession. As of September, 60% of workers age 65 or older had full-time jobs, up from about 55% in 2007.

Meanwhile, for anyone born after 1960, the “full retirement age” (meaning the age you get full Social Security benefits) is now 67, and there are strong incentives to delay benefits until 70.

The consequences of working longer on our health and well-being are largely unknown, but researchers at the University of Southern California have recently examined data from 12 countries, including the U.S., and their preliminary results are telling. Contrary to conventional wisdom that working longer provides a buffer for mental health, retirement actually reduces depression, their analysis shows. What does increase the probability of depression, and reduces life satisfaction, is not being bored by not working, but health conditions that impact the ability to go about your daily activities. While household wealth, being married and one’s level of education are all positively related to life satisfaction, income alone does not seem to have a significant effect on depression or life satisfaction.

Granted, many of us still won’t have a choice about when we retire. We may not be able to afford to stop working when we want to, or we may get forced into early retirement by the loss of a job. But we may also want to take a look at whether the work-until-you-drop ethos has become more of a cultural commandment then a financial imperative—“I’d get bored if I didn’t work” is the new corollary to the often-uttered “I’m crazy busy.” It’s as if retirement has become so elusive that we’ve decided to tarnish the whole concept. But there is nothing wrong with looking forward to retirement if one has done a decent amount of saving and planning.

I love working, but two decades from now I think I would prefer to downsize rather than stay in the workforce an extra five or 10 years in order to maintain my standard of living in retirement. (From a purely balance sheet perspective, if continuing to work has adverse effects on well-being, then the fiscal savings from delayed retirement may be offset by increased health expenditures.) Medicine may be prolonging our life, but that doesn’t necessarily mean that it’s improved the quality of the later stages of that life. I want to make sure that I have not just the time also but the ability to enjoy more than just a few years when work is no longer the priority.

Konigsberg is the author of The Truth About Grief, a contributor to the anthology Money Changes Everything, and a director at Arden Asset Management. The views expressed are solely her own.

MONEY Second Career

How to Jump from a Second Career to a New Dream Encore Job

Senior painting in studio
Lynn Koenig—Getty Images/Flickr

You aren't limited to a second career. Be ready to embrace a third or fourth career as opportunities come along.

Most of my boomer friends tell their adult children to plan on multiple jobs and careers. The era of corporate loyalty and the organization man and woman is long gone, they (and I) say—due to a hypercompetitive global economy and their likely desire to embrace new opportunities throughout their work lives. Good advice.

But boomers ought to heed this insight, too, embracing multiple acts during the second half of life. I think you shouldn’t just plan on a second career, but maybe a third or a fourth.

Linda Lyman: On Her Third Career

That’s also what Linda Lyman told me with a smile when we met at a Phoenix breakfast event for UMOM, a nonprofit helping families break the cycle of homelessness. She’s exploring her third career in what I call Unretirement (also the title of my new book on the trend).

Lyman moved to Phoenix 31 years ago, eventually managing legal services for a land developer. On the 17th anniversary at this job, a colleague congratulated her and asked: “What will you do for the next 17 years?” The thought of spending another 17 years at one place jolted Lyman, then 46.“I have to get out of here,” she thought. “I am going to do something more meaningful.”

Lyman next began working at a small nonprofit that mentored at-risk kids, New Pathways for Youth, and ran the group successfully for a decade. She loved the work, but decided it was time to “retire” earlier this year. “Ten years is a long time,” Lyman says. “I needed to have more life balance. I left on my own terms. It’s good.”

Now Lyman, 58, is eager to teach in an inner-city school. “I want to do something that I’m passionate about,” she says. “Teaching is what I thought I was going to do when I was in high school. It’s nice to be circling back.” Her husband is 65 (he’s retired from Intel) and the couple is open to relocating for Lyman’s teaching job, with Wisconsin and Minnesota high on her list.

Ginia Desmond: Heading Toward Career No. 5

Ginia Desmond is now on her fourth career and may be heading towards No. 5. My sense is that she has danced from one adventure to another.

Desmond was a serious artist early on, with a Masters in Fine Art. She painted in Argentina while living there with her first husband and then in the Phillippines, where her second husband—Charles Kepner, founder of the Kepner-Tragoe consulting firm—worked.

Desmond brought some Philippine fabrics back when they moved to Tucson about a year later and sold them to a local boutique. The store owner wanted to buy more fabrics, so for her second career Desmond created Sangin, a trading company importing baskets, fabrics, lighting fixtures and similar items from the Philippines and elsewhere in Southeast Asia.

She ran the business for 27 years and sold Sangin in 2003. “I never got rich,” she says. “But we didn’t go broke and I employed a lot of people.”

Time to return to her first career, she thought. So Desmond again picked up her charcoal, oils and watercolors and worked at becoming an established artist.

But Desmond took a screenwriting course at the University of Arizona in 2004 and fell in love with writing screenplays, which led her to career No. 4.

She’s since written a dozen-plus scripts; some have been optioned and she has been hired to write a few others. One of her scripts is Lucky U Ranch, about a bullied boy living in a trailer park in the ‘50s who is helped out by an angel appearing in a Cadillac that’s pulling a shiny silver trailer. A local director liked it and offered to turn the script into a movie if Desmond could find a producer.

She thought about the offer and finally landed on a producer—herself. Could this be career No. 5?

“I could buy a home or I could make a movie,” says Desmond, now 72. “I’ve bought several homes. Why not make a movie?”? She put up the money, is hoping for a winter release and is now working on another screenplay, Singapore Fling, about revisiting the island nation late in life to meet up with an old flame.

While Lyman and Desmond have led very different lives, they’ve both taken a savvy approach in approaching their encore careers.

For example, Lyman took advantage of her retirement from New Pathways for Youth to think through her options. When she kept coming back to becoming a teacher, she reached out to a few that she knew to glean insights about the job.

At the moment, Lyman is thinking about applying to Teach for America. The program is best known for hiring young college graduates and placing them in schools in low-income communities, but the organization has been increasingly opening its doors to midlifers.

Desmond has a talent for finding intriguing opportunities, but was careful to ensure that she could afford her latest venture: movie producer.

She didn’t let her enthusiasm for the project put her finances at risk. An unusual source of income helps: she gets royalties from her songwriting father, whose best known hit is Here Comes Santa Claus.

Turns out that for many of us, our Unretirement may not be our encore career but encore careers. Pretty cool.

Chris Farrell is senior economics contributor for American Public Media’s Marketplace and author of the new book Unretirement: How Baby Boomers Are Changing the Way We Think About Work, Community, and The Good Life. He writes about Unretirement twice a month, focusing on the personal finance and entrepreneurial start-up implications and the lessons people learn as they search for meaning and income. Tell him about your experiences so he can address your questions in future columns. Send your queries to him at cfarrell@mpr.org. His twitter address is @cfarrellecon.

MONEY Second Career

When You’re Bored Silly in Retirement

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Martin Diebel—Getty Images

After taking a break from your career, you may need a break from retirement. Here's how three retirees found their next act.

Ah, retirement! Playing golf whenever you like. Fishing when the mood strikes. Cocktails in the afternoon and barbequing on the patio. But what do you do when you try out retirement and you’re bored stiff?

Ask Ken Howard, 67, of Greer, S.C., who built a successful trash hauling business and sold it to Waste Management in 1997. “I was really looking forward to getting rid of all the everyday headaches that come from running a company,” Howard recalls. So he built a house on a golf course, but soon found that after “playing a good bit of golf I got bored.”

His retirement lasted about five months.

Howard then bought a car wash…and then another….and then another. He now has eight. He has also bought a septic pump business (largely run by his son and nephew) and owns a small real estate investment company.

“I still get excited about cutting a deal,” he says. “Doesn’t matter if it’s $200 or $200,000.” These days, Howard says, he spends a lot of time at his family’s lake house, “but when I am in town I’m usually at the office.”

Even Del Webb Got Bored

Former utility executive Jackie Hauserman, 72, took a retirement package in 1998 when her company, Centerior Energy, was bought. She moved from Ohio to Florida, first to Naples and then to Bonita Bay. Retirement didn’t take, so Hauserman got a real estate license in 2001, at 59, and has been selling for John R. Woods Properties ever since. “I have been really busy. It is fun,” she says.

Even Del Webb, developer of America’s most famous retirement community — Sun City, near Phoenix, Ariz. — couldn’t live the life of leisure. A 1962 Time cover story about him said: “Del Webb, the hulking, slope-shouldered, long-striding 63-year-old who hates to be called Delbert, could not stand the life in one of his own Sun Cities for more than a few days — or a few hours.” He preferred working.

Here’s the thing I’ve learned while researching my new book, Unretirement: Most people desire to live their third age doing something between full-time work and full-time golf. And many new retirees find themselves easily bored without working part-time, even if they don’t need a paycheck.

Certainly, that sentiment was repeatedly expressed at a recent talk I gave at Verrado, a new multigenerational development outside Phoenix, where residents found the initial joy of sleeping in and enjoying an early cocktail faded with time. All were now working part-time or looking for the right retirement job.

The Shock of the New

The swing from racing to embracing leisure to seeking work isn’t really surprising. Put it this way: You spend many years holding down a full-time job (or multiple part-time jobs), so freedom from bosses and job stress is liberating at first. Many people have a bucket list of delayed projects and postponed travel, too. But… Your career and the expertise you’ve built up over a lifetime are also a big part of who you are.

So putting it all behind you can be a shock.

“After awhile, you then wake up and something isn’t quite right,” says Joel Larsen, a certified financial planner at Navion Financial Advisors, in Davis, Calif. “Successful retirement means finding fulfillment and meaning. And a lot of fulfillment and meaning comes from being good at what you do.”

4 Myths of Aging and Retirement

His insight echoes the results from the recent Merrill Lynch survey, Work in Retirement: Myths and Motivations, Career Reinventions and the New Retirement Workscape.” Conducted in partnership with Age Wave, the demographic consulting firm, the survey disputes four popular myths about aging. They are:

  • Retirement means the end of work
  • Retirement is a time of decline
  • People only work in retirement because they need the money (the reality: meaning and purpose matter, too)
  • New career ambitions are only for young people

I’ve grown convinced that most people need to take a break from their careers — they need to retire — before they can Unretire. It takes a break to figure out the next stage.

Adopting a Fresh Perspective

“You have to get out of the work mindset and take a fresh perspective,” says Ellen Griggs, 59, an excellent example of someone who has taken deliberate steps toward Unretirement.

Griggs had a successful career in finance with some storied firms (Paine Webber and Strong Capital Management among them) as Chief Investment Officer, Chief Operating Officer, Client Advocate and Investment Consultant. In 2011, at 56, Griggs took a year off, traveling spending time with her family and working on a 160-year-old home on Cape Cod.

She also hooked up with Boston-based New Directions, a career transition organization focused on helping executives and professionals figure out what’s next. “During my career I had never been introspective about what I was going to do when I retired,” she says. With New Directions, “I got to kick the tires.”

She’s since ended up filling her days with a mix of for-profit and not-for-profit activities, including being a member of the philanthropic trust board at the Boston Medical Center and a board director at Evanston Capital.

How to Beat Boredom in Retirement

So, what should you do when playing golf isn’t enough and you want more meaning and purpose in retirement?

Reach out. Talk to your network of friends and former colleagues who know your skills and strengths; ask them what they think you should do next.

If you’ve decided what field you’d like to migrate into, part-time, attend a local industry meeting and find out how others made their transition. This is a low-cost way to glean information and make contacts.

Potentially even more powerful is hooking up with similarly challenged retirees who’ve decided to put their leisure days aside.

For instance, Experience Matters in Phoenix matches talented private sector workers looking for their next act with community-based nonprofits. Similarly, Shift is a Twin Cities-based organization with a goal of guiding midlife life transitions toward “purpose, passion and a paycheck.” And the Encore Fellowships Network is another path for experienced professionals who want to devote time at social-service organizations.

Another resource: your local community college. These schools are creating courses and meeting spaces for boomers looking for a next act. You can look up programs near you at the website for the American Association of Community Colleges’ Plus 50 program.

It’s a safe bet that in coming years, people will talk less about golf and leisure in retirement and more about preparing for a new stage of productive and creative work in their Unretirement.

Chris Farrell is senior economics contributor for American Public Media’s Marketplace and author of the forthcoming Unretirement: How Baby Boomers Are Changing the Way We Think About Work, Community, and The Good Life. He writes about Unretirement twice a month, focusing on the personal finance and entrepreneurial start-up implications and the lessons people learn as they search for meaning and income. Tell him about your experiences so he can address your questions in future columns. Send your queries to him at cfarrell@mpr.org. His twitter address is @cfarrellecon.

More from Next Avenue:

What Retirement Is Really Like

Avoid Living Unhappily Ever After in Retirement

Know Your Level of Activity for Retirement

MONEY Ask the Expert

5 Strategies for Finding Meaningful Part-Time Work In Retirement

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Robert A. Di Ieso, Jr.

Q: I want to find part-time work to bring in extra income when I retire next year. But I don’t want to be a greeter at Walmart. How do I find a job that’s meaningful but still flexible enough for me to enjoy my retirement life?

A: Working in retirement has become the new normal. Nearly three-quarters of workers 50-plus say their ideal retirement will include working, according to a survey by Bank of America Merrill Lynch and Age Wave. But they also want a job that is flexible and fulfilling. Some 62% of working retirees said staying mentally active was the most important reason to work vs just 31% who said they simply needed the money.

“A lot of people are in the same boat. They need to bring in some income and are happy to work but don’t want to go from a professional career to something mindless or boring,” says Tim Driver, CEO of RetirementJobs.com. Still, it’s often challenging for an older worker to find that combination. If you can, start the hunt while you’re still working and your skills are up to date—that way, you can leverage your current contacts. Here are five more tips to consider:

Look to your employer. If you like what you do and want to still use your professional expertise, a natural place to start is with your current employer, says Nancy Collamer, a career coach and author of Second Act Careers. “It might be possible to downshift into a part-time or seasonal schedule, freelance or be on-call as an in-house temp.” For advice on how to ask for a flexible work arrangement, go to WorkOptions.com.

Line up new clients. Does your career lend itself to consulting or freelance project work? Many fields do, from graphic design and event planning to tax advising and tech services. Consulting or freelancing is an ideal retirement job for retirees because of the flexibility it gives you to choose your projects and how much you want to work, says Driver. There are a number of sites that connect older workers to project work, including Driver’s RetirementJobs.com and RetiredBrains.com.

Fill in at a high level. For mid- and higher-level executives, another option is to temp as an interim executive. Interim execs fill an existing position while the company searches for a permanent replacement. It’s a great option if you still crave the prestige and pace of the executive life, but also want the flexibility to enjoy time off in between assignments, says Collamer. The Riley Guide lists firms that specializing in placing interim execs.

Find your passion. If you want to connect with work that you feel is most meaningful, you may be able to transfer your professional skills to a non-profit that focuses on issues important to you. “While nonprofits depend heavily on volunteers, most have at least a few paid staff positions,” says Collamer. Start volunteering now and see what opportunities are available. Nonprofits with tight budgets may be more open to part-timers. Check out non-profit job sites such as Bridgespan, Idealist and NonProfitJobs. Another good resource is Encore.org, which helps older workers transition to careers with a social purpose.

Seek adventure. Finally, if you’re looking for something totally new, check out CoolWorks.com’s Older and Bolder section. It is aimed at retirees looking for seasonal or temporary jobs at national parks, lodges, ranches and other outdoor destinations.

Do you have a personal finance question for our experts? Write to AskTheExpert@moneymail.com.

MONEY Second Career

This PR Exec Launched Her Second Career by Raising Millions for Wounded Veterans

PHH Co Founder John Gallina and Vicki Thomas
Purple Heart Homes co-founder John Gallina with Vicki Thomas Lynnette Thompson for Purple Heart Homes

Marketing pro Vicki Thomas saw a news segment about a non-profit start up. She knew she could help them—and ended up with a new job and happier life.

Just four years ago Vicki Thomas was a successful public relations executive in New York City with high-profile financial services clients. But she was was growing frustrated. “There was a voice calling me to really make a difference in the lives of others, not just improve a client’s bottom line,” says Thomas. “I wanted to do something more fulfilling, but I wasn’t sure what it was going to be.”

Then one day in 2009, she saw a news segment on CNN about Purple Heart Homes, a North Carolina organization founded by Iraq veterans Dale Beatty and John Gallina to provide handicap-accessible homes to wounded vets. Beatty and Gallina, who also suffered combat injuries, focus on vets who lack the money and resources to renovate their own residences. Thomas felt an immediate connection and wanted to help the fledgling organization raise more money. Improving their marketing and public relations outreach was key.

“I knew they could use professional advice but couldn’t afford the kind of expertise I could give,” says Thomas. She cold-called Gallina and Beatty, leaving a message offering her services pro-bono. “It took them two weeks to call me. But we agreed to meet and we’ve been working together since.”

Thomas left her corporate PR career behind in 2009 and began drawing on her 35 years of experience in fundraising and marketing to bring attention to the non-profit. “When I met them, I couldn’t get a news story in the local paper about them,” says Thomas. A few months later, thanks in large part to her network of contacts, Gallina and Beatty were featured in a 2011 Time magazine cover story about a new generation of veterans bringing their leadership lessons home—they even appeared on the cover. “That opened so many doors. ABC News and Nightline did stories on them, and money started pouring in,” says Thomas.

Today, as the chief communications officer for Purple Heart Homes, Thomas has helped raised millions in financial contributions and material donations. In her first year with the start up, contributions rocketed from $67,000 to $2 million. With that cash horde, the non-profit was able to qualify for grants, including a major donation from Home Depot, which further improved its financial stability. She’s particularly proud of a program she launched that matches veterans with foreclosed homes donated by banks.

After providing her services pro bono for two and a half years, Thomas now 68, began working full time for Purple Heart Homes in 2012 and drawing a salary of $48,000 a year. It’s a lot less than what she earned in her PR career, and she’s fine with that. Her husband still works, but “we’re at an age where we’re not buying stuff,” she says.

She enjoys the different pace of her work life, which is far less hectic than her days in PR. “I have so much flexibility—I can take a play day when I want to,” says Thomas, who works from her home in Connecticut. “I probably have a more perfect balance in my life than I ever had before.”

As for retirement, it’s not happening. “They’ll have to carry me out on a flip chart,” she says. “I believe you remain much more vital and connected if you can work in some capacity, especially if you are doing something you are passionate about.”

Vicki Thomas was the 2013 Winner of the Purpose Prize for Future Promise, sponsored by Symetra. The Purpose Prize is a program operated by Encore.org, a non-profit organization that recognizes social entrepreneurs over 60 who are launching second acts for the greater good.

MONEY working in retirement

Here’s the Best Way to Rescue Your Retirement and Find Happiness Too

A second career can provide income as well as meaning. This advice from retirement expert Chris Farrell can help you plan your next venture.

Chris Farrell has a hot retirement investing tip for you, but it’s not a stock or bond.

Farrell wants you to invest in yourself. In his new book, Unretirement (Bloomsbury Press), he argues that developing skills that can help you earn income well past traditional retirement age offers a better return on investment than any financial instrument—and it can help transform the economy as it continues to heal from the Great Recession.

Farrell is senior economics contributor at public radio’s Marketplace, a contributing editor at Bloomberg Businessweek and a columnist for the Minneapolis Star Tribune. In a recent interview, I asked him to describe his vision of unretirement.

Q: How do you define “unretirement”?

“Unretirement” is about the financial impact of working longer. If you can work well into your 60s, even earning just a part-time income through a bridge job or contract work, you’ll make so much more in the course of a year than you could from saving.

That changes the financial picture—and not just income. You also don’t have to tap your retirement nest egg during those years, and you might be able to add to it. And it allows you to realistically wait to claim Social Security between age 66 and 70, depending on your health and personal circumstances.

Q: What are the essential tools and strategies for people trying to figure out how to unretire? Where should they begin?

The most important thing is to begin by asking yourself what it is you want to be doing—what kind of work. Do informational interviews with people. The real asset that older workers have is their networks—the people who have known them over the years. Talk with them to find out if you need to add new skills.

Don’t romanticize any particular idea—research it. Think about how you can take your existing skills and move into a different sector of the economy with those.

Q: One of the biggest obstacles facing older workers is age bias. Are employers adapting to help older people keep working longer?

The only evidence I’ve seen of that is at companies that face very tight labor markets—typically technology businesses. It’s also true for the nursing profession. For the rest of the economy, I’ve been to conference after conference focused on older workers, where employers wring their hands about all the brain power walking out the door. They’re sincere, but when they go back to the office they really aren’t motivated to do anything about it because the labor market isn’t strong enough

Q: If that’s the case, how will unretirement be able to take hold as a trend?

The economy is getting better, and labor markets are tightening. But this also will be driven by grassroots change. Many leading-edge boomers are negotiating their own deals, starting businesses or setting themselves up for self-employment with a portfolio of part-time jobs. It’s very do-it-yourself.

And attitudes are changing—there will be enormous pressure from society as people push for this. They’re going to be saying, “We’re pretty well educated, and healthier than we were before, and the numbers don’t work for us to go down to Florida or Arizona and retire—and we actually don’t want to do that.”

Q: There’s a great debate under way over whether we are headed for a crisis in retirement security or not. What’s your view?

I don’t think there will be a retirement crisis if we continue to work longer. But we’re going to want to do it with jobs that provide meaning rather than those that make people just miserable enough that they have to continue to work.

One thing that upsets me is that we have a conflation of financial stresses facing the middle class and pretending that the middle class will be in poverty in retirement—and that’s just not true. There is a group that is really vulnerable—they’ve worked all their lives for companies that don’t provide retirement or health insurance benefits. That is the really vulnerable group.

I think two-thirds of our society will be fine, but for this other group, it’s not about investing in a 401(k), because they simply don’t have the money. For them, Social Security will be the entire retirement plan.

Q: That suggests we will need to beef up Social Security, at least for the lowest-income retirees.

Absolutely. If a majority of us are healthy and continue to work and pay into the Social Security system, we will become a wealthier society—and we will be able to afford to be more generous with Social Security.

Chris Farrell’s write columns on second careers for NextAvenue.com, which also appear on Money.com; you can find his articles here.

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