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Money & Career

6 Tips for Finding Your Second Act

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Retirement can sometimes conjure images that may revolve around world travel, sipping boat drinks and living in Hawaiian shirts. The reality, however, may be quite different.

“We’re living longer lives, which means there’s a good chance that you’ll also be working longer, but work doesn’t have to be a four-letter word,” says Kerry Hannon, who is a career, entrepreneurial, personal finance and retirement expert. “Let’s find ways to make it fun.”

Hannon has spent a great deal of time researching and writing about how to do just that. She’s penned about a dozen books, including Great Jobs for Everyone 50+ and What’s Next? Finding Your Passion and Your Dream job in your 40s, 50s and Beyond. In her work, she’s found commonality in later-in-life career choices. Namely, people are seeking to do something meaningful in their second act. She shared this advice on how to plan for your encore career.

Start planning early. Three years is a good number to target, says Hannon. That gives you time to do some soul searching, to consider your talents and the kinds of jobs that might fit well into your life. Do you want to give back and work for a non-profit? Is there something you’re passionate about that you’d like to pursue? Is there a particular market out there for your skills? “A lot of times, it goes back to something an individual liked to do in their childhood, but they set it aside because they felt they needed to go down a certain path to earn an income,” says Hannon. If there’s a career dream or goal that you always wanted to explore, now is the time to consider its feasibility.

Talk to people who are doing the job you’d like to do. Once you’ve narrowed your goals down, start doing your homework. If you know someone who’s involved in the line of work you’re considering, invite them to lunch to talk about it. “People love to talk about their work,” says Hannon. “So you’re not asking them for a job, you’re just trying to find out if it’s a good job for you and how did they get that job?” Other questions to ask include: What is their background? What training did they need? What is the job like? This may help you figure out if it’s potentially a good fit for you.

Try out the job you’d like to do. See if there’s an opportunity to moonlight or apprentice in a similar field to what you’re considering. That may help you to see if your expectation of the job is realistic. If you’re interested in working with a nonprofit, find a volunteer opportunity there using your skills. That way, you can add the experience your resume while also getting a foot in the door. Hannon points out that it’s also a great networking that could help you down the line, whether it’s at that organization or another one.

Keep up with tech and training, within reason. While education and training are important, Hannon cautions people not to break the bank here. “Consider your options and do a little research before investing a lot of money on education right off the bat,” she says. By talking with people in the field, you can get a sense of the type of training that will help boost your appeal as a potential hire. Once you know what you need, you can start doing some online research. Many universities, libraries and other organizations offer inexpensive or even free online courses. Pick and choose the ones that seem most helpful.

Work your network.  At any age, making connections in both your personal and professional life is some of the best arsenal for finding a job. “Often you may get hired by somebody you know, or by somebody who you know knows. And that’s how it’s always been in the job market, but for older workers it’s even more important to use your network—and you have one,” she says. If you find a business where you’d like to work, search social media and LinkedIn to determine if anyone in your network has a connection there, and reach out to that person. It can help if they put in a good word.

Keep your resume short, sweet and skill-based. “Your resume is not your obituary, it’s your advertisement,” says Hannon. She says to keep it to two pages, three max. Highlight the skills you can offer that are relevant to the job, and then list applicable experiences from the last 10 to 15 years. “If you’re switching careers to an encore career, it’s not about the jobs you held before in your positions, it’s about your skills and how they can transfer to what you want to do,” says Hannon.

Hannon says that workers older than 50 often have a fear that they’re going to outlive their money. For them, getting a job is a necessity, but it can also be a challenge, as they compete with younger generations. By keeping up with technology, working your network and showing a flexible, open-minded attitude, you could help alleviate potential concerns and work your way closer to starring in your second act.

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