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How to Snag the Perfect Side Job After You Retire

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Working after retirement may seem counterintuitive, but it’s a reality for many women (and men) who want to supplement their Social Security income. The good news is that a “second act” job you love can not only give you extra cash, but can keep you busy, energized, and even less stressed! You also have the potential to make new friends, enjoy some exciting adventures, and spend time doing things you love. 

Don’t be afraid to seek out a part-time work-from-home job or to start up an exciting side business. After all, there’s no time like the present! Here are all the strategies you need to know in order to snag a great post-retirement gig. Your second career? It starts here.

Network through your hobbies. One of the best ways to find a job you love is by exploring possibilities and trying new things—whether it’s taking a yoga class or visiting a community garden— says retirement expert Catherine Collinson. “Once you zero in on something you like, chat up the instructors or workers there to build a network of friends and contacts that can help point you in the right direction. Ask them how they got started at their job; it could possibly open doors for you!” 

Search the right sites.RetirementJobs.com is designed specifically for job-seekers age 50 and older,” reveals Collinson. “It carefully screens employers who post jobs and certifies them as ‘aging-friendly’ for reasons from shorter work hours to greater flexibility.” Another great site to check out? AARP’s “Back to Work Age 50+” program at AARP.org, which has excellent resources available for people seeking employment.

Make your resume stand out. The skills that’ll set retirees apart? Soft skills! “Tout your experience with things like communication, team work and decision-making,” advises Lauren Griffin of Adecco Staffing, which helps find jobs for seniors. “Despite young people often having a leg up in the digital arena, we’re seeing them struggle with these type of skills, so older workers actually have an advantage.”

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Tap the right adjectives. “When people write ‘seasoned’ on their resume, it can sound the same as ‘outdated,’ and has become something of a cliche,” Cenedella says. “Instead, describe yourself as ‘industry-leading,’ ‘respected expert in my field,’ ‘goal-achieving’ or ‘tested and proven.’ 

Snag a dream job. Instead of pouring your life savings into a boat, you can sail in luxury—and get paid—working on a cruise ship. Just look for jobs like on RetirementJobs.com like event coordinator, workshop leader or even a position as salesperson in a ship’s retail stores. “As a retiree, you have a leg up on the competition due to your years of experience, and you’ll be able to connect better with the typically older demographic that frequents many cruise lines,” says job-hunt pro Marc Cenedella. In exchange, you’ll get free room and board plus a salary—and a chance to cruise around full-time.

House sit—on a private island. Always dreamed of retiring in the tropics? How about getting “paid” to live in a seaside mansion in paradise? Turns out, many owners of private island getaways seek full- and part-time caretakers to make sure their homes stay in top condition while they’re away. “Most jobs simply require that you make sure the house stays clean and deal with minor maintenance issues,” says Griffin. Just search “caretaker positions” on Indeed.com.

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Let your kindness pay.  If you love traveling—and helping people—why not combine the two by becoming an assistance companion? Many folks—including other seniors and people with flying anxiety—often need someone else to travel with them to assist with their bags, medication, customs forms and other needs. Sites like FlyingCompanions.com and FirstLightHomeCare.com can help connect you with travelers in need; in return, you will get free airfare wherever your travel partner is headed, as well as a fee for your services.

Help furry friends. Become a pet sitter or doggie day care operator! The pet sitting business is booming, notes Cenedella, and these days, many pet-parents are looking for someplace safe and fun to send Fido while they’re at work all day or during vacations. With sites like Rover.com or Care.com, you can create your own pet sitter profile and offer to watch dogs and/or cats in your own home on your own time and set your own prices (most folks charge between $20-$30 per pet, per day). As a senior, you also have an advantage, since clients will automatically view you as more trustworthy. “You can always leverage your age as a way to set yourself apart from the crowd,” says Cenedella.

Profit from your love of nature. Check out Cool Works, which features jobs at national parks, ski resorts, dude ranches and retreat centers all over the country. “You could do anything from host campfire meet-and-greets to brush and clean horses to instruct yoga classes by the beach or even help build cabins,” says retirement trends expert Collinson. “One of the best ways to find a job you love is to explore possibilities and try new things.”

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Work your connections. If you enjoyed the work you did before your retirement, consider working for your former employer (or a competitor)! Employers, who hate to lose the valuable knowledge that a long-time employee has, will often jump at the chance to hire you back—on your terms and according to your schedule. Or use those same skills to teach or tutor people looking to gain a foothold in the field you worked in. Every kind of school from community colleges to cosmetology institutes to culinary schools regularly hire retirees with strong skills set to help teach their students the insider knowledge they need to succeed.

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