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4 Ways to Make Your ‘Encore Career’ a Success


If you’re like many boomers, you’ve at least entertained the thought of an entirely new career, be it ditching your 60-hour-a-week marketing gig and opening a bakery or kissing your cutthroat finance career goodbye and working part-time for Greenpeace.  And while there’s no shortage of pitfalls for baby boomers looking for a late-life career change, as I reported on Encore Friday, who are we to stand in the way of someone’s dream?

Even with the difficulties and risks inherent in a career switch over 50, it’s possible to stack the deck in your favor. First, you should tip-toe into it, says Kerry Hannon, author of “What’s Next? Follow Your Passion and Find Your Dream Job.”  “Most successful people who made a switch took a couple years to do it,” she says.

Here are four other questions to ask if you’re pondering a 180-degree career change.

Can you afford it?

For most people, it would be a stretch. Nearly half of all boomers are running the risk of being unable to pay for basic expenses in retirement, according to a 2010 study by the Employee Benefit Research Institute —  so it’s important to consider how much this will really cost you. The average small business owner spends $10,000 to open its doors, according to a study by Wells Fargo/Gallup Small Business.  What’s more, “the more resources a new business has to start with, the better its chances,” according to SCORE, a nonprofit group devoted to aiding small businesses. The organization recommends start-up capital of at least $50,000 for most businesses, saying that “businesses that start with less have higher failure rates.” And that’s just to get started — you can expect costs like rent, insurance and inventory to potentially cost thousands, experts say.

Even those hoping to hop to a lower-paying job at another company or have a go at freelancing have to be careful. Not only may you take a big cut in income and face additional expenses like paying your own health insurance, this can also mean that you cut contributions or stop saving for retirement, Hannon says.

Do you really like it?

To get a feel for what this new gig will really be like, “volunteer, moonlight or apprentice in the job you’re considering,” says Hannon. “It might not be all that you think it is.”  Hannon says that even if you have to work at the place for free, it’s probably still worth your time so you can make sure this is what you really want.

Are you qualified?

Some careers, like teaching and real estate, may require a new degree or certificate. Others may require a new set of skills that you might not even realize you need to learn unless you work in the industry. For example, if you open a bakery – or bookstore or furniture shop — you’ll need to learn about inventory management, bookkeeping and marketing to be successful.  Hannon says local community colleges are a good, often inexpensive, place to start looking for small business classes. and also have resources.

Do you have a teacher?

Moonlighting and schooling alone don’t guarantee success, so it’s also important to get input from others, Hannon says. “Ask successful business people what worked for them and what they struggled with,” she says.  And if you can find them, ask for guidance from people who had to close a related business.  You may also want to get assistance from your local SBA office — they can often provide not only start-up resources, but also guidance and contacts.


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About Encore

  • Encore examines the changing nature of retirement, from new rules and guidelines for financial security to the shifting identities and priorities of today’s retirees. The blog also explores news that affects retirement, from the Wall Street Journal Digital Network and around the web. Lead bloggers are reporter Catey Hill and senior editor Jeremy Olshan. Other contributors include The Wall Street Journal’s retirement columnists Glenn Ruffenach and Anne Tergesen; the Director for the Center for Retirement Research at Boston College, Alicia Munnell; and the Director of Research for Pinnacle Advisory Group, Michael Kitces, CFP.