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Matt Chase

Twenty years ago as she whip­ped up peanut but­ter balls for friends, Cathy Churcher never thought she’d wind up making a living as a candymaker. But after a series of deaths in her family—including that of her brother, at age 49—Churcher quit her job as the director of admissions at a nursing school and opened Chocolate Cravings, a 400-square-foot shop in Richmond. “It was about happiness,” says Churcher. “I stepped out in faith that I could make a go of it in a new career.”

Churcher, then 50, wasn’t depending on faith alone. Three years before launching, she began writing a business plan. She studied local candy stores, trying to learn from their successes and failures. She earned a certificate as a professional chocolatier. And two years before she opened her shop, she started selling at farmers’ markets and to local stores and restaurants.

Fifty-five percent of U.S. workers want to change careers, according to a University of Phoenix survey. As Churcher’s story suggests, those shifts take time. To make a switch, you’ll have to learn new skills, make new professional contacts, sock away cash, and more.

Maybe you, like Churcher, want to start a business, or maybe you’d like a salaried job in a new field. While the prospect of starting over may be daunting, it can also be deeply rewarding. So if you ache for a professional reboot—either as your own boss or working for someone else—follow these five steps to learn from experts and people who have successfully made such a move.

1. Make sure your dream has some connection to reality

In 2011, Jennifer Johnson, a general manager at Johnson Controls (no relation) in Plymouth, Mich., had an idea. Noticing an increase in seasoned executives no longer working full-time, she thought she might match them up for project assignments with local companies that could use their expertise.

Was this a viable business? Johnson, then 35, resolved to find out. On nights and weekends she studied other professional-services firms. She cold-called people running similar businesses in other states, asking them everything from how they dealt with competition to how much they charged. And, believe it or not, they told her. “People who have started businesses generally want to be helpful,” she says.

Johnson’s research led her to Patina Solutions, a Milwaukee-based firm already doing what she envisioned. Rather than start her own company, she proposed teaming up with Patina, and in February became managing partner of the firm’s new Detroit office.

Research like Johnson’s is key; you need to learn if the image you have of your proposed career—the routine and the money—is an accurate one.

How to do it:

Get the inside scoop. Reach out to people doing the work you want to do, and ask them all you can about their jobs. How did they get started? What do you need to succeed? And what can you expect to earn, both at first and later on? Because you aren’t asking for a job, the discussion should be relaxed. “Be an inquisitive child,” advises Jayne Mattson of Keystone Associates, a career-management firm in Boston.

Do a trial run. Moonlight or apprentice yourself to someone already in the field. A client of career consultant Maggie Mistal who baked in his spare time did a second-career dry run making cookies on nights and weekends. Over six months he saw how much effort beyond actual baking he’d have to put in, and he decided he couldn’t earn enough to support himself. He kept his day job and now just bakes for fun. “Don’t ruin a hobby that you love,” says Mistal.

If you want to work for a nonprofit in a cause meaningful to you—a common goal among career changers—then volunteer; you’ll not only see what the day-to-day work entails, but also meet people in the organization.

2. Identify the skills you need.

After 24 years as an engineer at IBM, Alan Zollner landed a job as a high school physics teacher in 2009. “I am working harder than at IBM—12- to 13-hour days,” he says. “But my work has a lot more meaning than before.”

To change careers, Zollner, from Cornwall-on-Hudson, N.Y., squeezed in three years of required courses while still full-time at IBM, taking advantage of IBM’s Transition to Teaching program, which paid for $15,000 of his education—nearly two-thirds of the cost.

Be prepared, like Zollner, to spend the time and money to get the skills, credentials, and contacts you need to get relaunched—but don’t assume that you’ll need a costly degree.

How to do it

Find the right school. As you do research, get a handle on the education you need. To avoid wasting your money on a particular school, talk to graduates and the director of the course of study you’re considering. Get a list of employers who have hired graduates too. Ask those employers whether the credential affects their hiring decisions.

Unless you’re entering a profession with specific academic requirements —nursing, say—a degree may be overkill; a certification or training program may suffice. The quicker the training, though, the less value it may have; a certificate that you earn in a few days probably won’t provide the knowledge and gravitas you will need.

Get financial aid. Fifty-four percent of employers offer tuition assistance to employees, reports the Society for Human Resource Management. You may have to repay the funds, though, if you don’t stay with the company for a certain number of years afterward.

Uncle Sam can also help. Depending on your income, you may be able to claim the Lifetime Learning Credit, which can cut your tax bill by as much as $2,000 annually. The credit can cover up to 20% of tuition and expenses for college and graduate courses, or for any class you take to obtain or improve job skills. (The benefit phases out completely for married couples earning $128,000 and singles earning $64,000.) If you’re studying more than half time at participating schools, you can also take out a federal Direct Unsubsidized Loan (see studentaid.ed.gov); the current professional-school interest rate is 6.21%. Go to FinAid.org and Edvisors­ .com for information on scholarships and grants for older students.

3. Get your finances in shape for your adventure

When Churcher quit her day job, she and her husband, Ian, forfeited her $50,000-a-year salary. To prepare for that hit, the couple had put a moratorium two years earlier on big vacations. A year after the store opened, they moved their son from a $7,000-a-year private school to a public high school.

Chances are that you, too, will take a salary cut when you start over, whether you’re starting a business or working for someone else. When you factor in your training costs, health insurance (if you’re going out on your own), and perhaps the loss of an employer’s matching 401(k) contribution, the expenses can ratchet up. “Remove your rose-colored glasses and assess your finances,” says Brian Kurth, founder of the online mentoring service PivotPlanet. Following your passion is great, but make sure you can afford your dream job.

How to do it

Live less large. Chart a personal budget to find ways you can pare back your spending. Discretionary expenses like travel and dining are obvious targets, but also look at costs of housing and other necessities. One option for reducing your monthly nut is to downsize to a smaller home or condo. Another is to refinance your mortgage to a lower rate. Then, beginning at least two years before your transition, pay down any outstanding non-mortgage debt, from credit card balances to auto loans.

Pile up the cash. One big payoff of cutting back well before your switch: You can set aside money to carry you through lean times ahead. Aim to save up at least a year’s worth of living expenses, rather than the three to six months’ worth that’s standard for emergency funds; you may have to live off that money during your transition. To make saving easier, set up a new bank account and make automatic deposits from your current paycheck.

4. Line up more money than you think you'll need.

When B.J. Jones retired in 2009 from her job as director of human resources at Sandia National Laboratories in Albuquerque, she hung out her shingle as a career coach. But for the first six months, Jones, now 56, took on clients gratis. “I looked at these as practice sessions,” she says.

While Jones was prepared to forgo an income, most people who take the entrepreneurship route overestimate their initial income and underestimate their startup costs. Little wonder that half of all new small businesses fail within five years, according to the Small Business Administration.

So at least two years before you plan to launch, get a clear picture of what a startup will cost you and then begin to line up your potential sources of financing.

How to do it

Get real about costs. To get an honest assessment of your likely expenses, consult with the free resources available to you. One is SCORE, a national organization of experienced businesspeople who volunteer their expertise to entrepreneurs. The Small Business Administration and AARP provide online educational resources and webinars to help develop a business plan, among other startup needs.

“It’s a good idea to pull together an airtight budget,” says Edward Rogoff, a professor of entrepreneurship at Baruch College’s business school. “Then add a cushion of 20% to your up­front costs to be on the safe side.”

Raise some cash. Sorry, but the chances that a venture capitalist will shower you with money are slim. Eighty-two percent of funding for startups, according to a study from Babson College and Baruch, comes out of the entrepreneur’s own pocket or from friends and family. Crowdfunding sites like Kickstarter can make it convenient for you to ask people you know for contributions, but don’t plan on the kindness of strangers to launch your business: Most Kickstarter campaigns are for one-off artistic projects.

Homegrown funding has its risks. Pull cash from your traditional IRA, and you’ll possibly pay a 10% extra tax on funds withdrawn prematurely. Dip too deeply and you’ll endanger your retirement. “If you’re in your twenties, you can bet the ranch, because if it fails, you can always start over,” says Rogoff. “But if you’re near retirement age and your business fails, you won’t be able to get the ranch back.”

Borrowing from friends and family, as opposed to getting no-strings crowd­funded cash, can strain relations, so be clear about the terms of any loan and put everything in writing (go to nolo.com for loan paperwork).

The upside of a friends-and-family loan is that you can probably borrow relatively cheaply—say, a five-year loan for 2% (above the rate the IRS currently requires to show that a loan is not actually a gift). A more expensive but less fraught avenue is the Small Business Ad­ministration’s micro­loan program (sba.gov/microloans). Interest rates for these loans, which average $13,000 and are administered by local nonprofits, generally range from 8% to 13%; startups aren’t necessarily disqualified, but you may have to meet training requirements.

Your costliest option is probably plastic: The average rate on new credit cards is 15%, according to CreditCards.com. Proceed with caution.

5. Show people how far you’ve come

For all the effort you made researching, studying, and saving for your new career, you’ll still need to land a job if you aren’t starting your own business.

For Zollner, success took time. First, he got hired as a substitute physics teacher by parlaying a solid recommendation from the teacher he had worked with as a student teacher. Then he sent personalized cover letters and résumés to about 30 school superintendents. Eventually one responded, and Zollner got his first steady classroom gig.

Getting hired can be a challenge for anyone; it’s especially hard when you’re entering a new field—and when you’re perhaps decades older than the usual low-level applicant.

How to do it

Network, network, network. Employers hire people whom they know themselves or who are known by someone in their circle. Check in with everyone from whom you got advice in the early days of your research. If you networked like a pro over the past few years, you’ve kept them in the loop about your progress. “Those are the people who will end up hiring you or referring you to someone who is hiring,” says Mattson.

If you volunteered with an organization, you’re in an even better position. The hiring manager has had a chance to observe your passion and work ethic, and when a job opens up, you’ll be top of mind. This is particularly true at nonprofit organizations, where volunteers and board members are often the first to be considered for paid positions. Last fall, for example, Jones—a longtime volunteer with the United Way and other local charities—was offered a paid fellowship with the Center for Nonprofit Excellence at United Way of Central New Mexico; in addition to her freelance coaching, she’s now helping volunteer skilled professionals advise hunger-relief agencies on measuring their effectiveness and getting grants.

Polish your act. While hiring managers ought to see your age as a marker of experience or wisdom, chances are they’ll wonder if you’re too old for the job. Beyond the obvious moves of updating your skills and knowledge and showing your comfort with new technology, what can you do?

Rehearse your job interview. No matter how at ease you are in business situations, trying to break into a new industry is a special challenge. Like going out on a date for the first time in 20 years, interviewing for a job does not come naturally. Enlist friends to conduct practice interviews, and record the sessions on video to see whether you’re conveying the enthusiasm and vitality that an employer would value. And why wouldn’t you be energized? You’re embarking on a new adventure.