Planning a Second Career? Here's Your Homework

Making your dream happen takes planning and patience

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It's fun to dream about what you really want to do with your work life. Maybe you've always wanted to run away with the circus or start a chocolate company. If you're lucky—and industrious—you might just get to a midpoint in your life when you can act on that inner ambition.

But to start making it happen, you need to go slow and do some homework to make sure you're heading in the right direction. There are dozens of books and websites to help guide you on your path. Some of the best:

Encore: Finding Work that Matters in the Second Half of Life by Marc Freedman. Freedman is the founder and CEO of the think tank Civic Ventures and cofounder of Experience Corps, the nation's largest nonprofit national service program for Americans over 55. His book is basically a self-help guide for people who want to build a better world through their work. Freedman provides concrete steps to finding a meaningful new job, and he profiles people who have succeeded in their second acts.

The Boomers' Guide to Good Work, by Ellen Freudenheim, is a downloadable 16-page pamphlet designed to help boomers think about new careers—whether full or part time—in the second half of life. It includes dozens of websites, books, and organizations that offer information about the nonprofit sector, including job descriptions, salaries, and job listings.

One reason many people make a midcareer switch is they're simply not passionate about what they do eight hours a day. To find something more rewarding, it's vital to match your work to your interests and personality. If you need some prodding to assess yourself, take a self-assessment quiz like the ones found at CareerPath or Monster. Once you start to narrow your potential career fields, CareerBuilder is filled with specific advice.

The Department of Labor's Occupational Outlook Handbook is a bit dry—it's a government publication, after all—but it outlines key info for hundreds of different fields: the training and education needed, earnings, expected job prospects, what workers do on the job, job search tips, and links to information about the job. CareerOneStop is a U.S. Department of Labor-sponsored website that offers sweeping career resources to jobseekers. The website features occupation and industry information, salary data, career videos, education resources, self-assessment tools, career exploration assistance, and more. DOL's America's Service Locator connects individuals to employment and training opportunities available at local One-Stop Career Centers.

You might need some further education to fulfill your new ambition, and that can get pricey. Look into federal financial aid to offset education costs. There's no age limit to apply, and you're eligible as a part-time student. Federal Student Aid, an office of the U.S. Department of Education, is the place to learn about your options. For research scholarships and grants for older students offered by associations, colleges, religious groups, and foundations, try search engines such as FastWeb to find what's available.

The IRS wants to help, too. Take advantage of educational tax breaks. Depending on your income, you might qualify for the lifetime learning credit, worth up to $2,000 each year, and other tax savings; check IRS.gov, the IRS's website, or the National Association of Student Financial Aid Administrators' Parent and Student Guide to Federal Tax Benefits for Tuition and Fees. Not as fun as dreaming about your great new job, perhaps, but it might just help you attain it.