Nontraditional Jobs Where People Over 40 Are Thriving

These people over 40 proved it's never too late to switch jobs.

Millennials aren’t the only ones who are embracing nontraditional jobs. Older generations are also taking advantage of ways to make money outside of traditional 9-to-5 positions.

From freelancing to podcasting to working in the gig economy, many in the 40-plus crowd are prospering in unconventional careers, proving it’s possible to succeed without following the typical career path.

Try These: 101 Side Business Ideas and How to Start Without Quitting Your Job


Joe Saul-Sehy’s current job didn’t even exist when he entered the working world a few decades ago. “I’m 51 and podcasting, which wasn’t even a thing during the early years of my career,” he said.

The 51-year-old host of the award-winning “Stacking Benjamins” podcast got his start as a financial planner. While working in that job, he had the opportunity to do some media appearances and was hooked. But he didn’t think he could build a career on that. “Only for a very few does ‘media spokesperson’ pay the bills,” he said.

In his 40s, though, Saul-Sehy made a midlife career change. He had sold his financial planning company and was going back to school to become a teacher. He also had started a blog and a podcast — and when that took off, he decided to forgo teaching. Now, Saul-Sehy produces and helps create seven podcasts a week. “I finally get to do some of the creative things I’ve always wanted to do but that didn’t pay at the time,” he said. “With some episodes clearing well over 40,000 listeners, podcasting has thankfully been paying.”

Check Out: Expert Tips on How to Make a Midlife Career Change


Emily Guy Birken became a freelance writer and author by accident. She had been teaching high school English when she got pregnant with her first child and she and her husband moved to another state. She knew she would have to take time off from teaching when her child was born. But then she found herself in a financial pinch. “I decided to see if I could find work I could do from home while the baby slept, and I started looking for paid writing opportunities,” she said. She found one writing for a personal finance blogger, who passed along her name to other financial bloggers.

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Within a few months of landing her first freelancing gig, Birken had about six regular writing clients. “It’s been 8 1/2 years since I first started freelancing, and I am now a Plutus-award winning freelancer in the personal finance sphere, the author of four books and a cited expert in magazines like ‘Redbook’ and ‘Woman’s Day,'” she said. “I’ve also out-earned what I was making as a teacher for the last three years.” On top of that, Birken can set her own schedule as a freelancer, has a better work-life balance and loves what she does.

Options: 20 Best and Worst Jobs for Work-Life Balance

Pet Sitter

Happy senior woman enjoying walk in nature and embracing pet dog in forest park.

If you’re looking for careers to start in your 40s, 50s or later, you might want to give pet sitting a try. Kathy and Craig Chastain began taking care of other people’s pets as a way to supplement their retirement income. They started by caring for a friend’s puppy and then got a few more clients. However, after signing on with — an online service that connects pet owners with pet sitters — the Chastains turned a side hustle into their primary source of income.

“The income we’ve earned through Rover has matched and exceeded most anything available for seniors these days and it allowed us to keep our savings and retirement funds intact,” the couple said. They make more than $34,000 a year watching pets in the comfort of their home.

Keep Reading: 15 Best Work From Home Jobs for Retirees

Mobile App Creator

Lori Cheek made a leap from one unconventional career to another. For years, she paid the bills as an architect, work that was considered nontraditional employment for women because of the small number of women in the field. But in 2008, she came up with an idea to create a dating app. “I completely threw away my design career, and I’m no longer building structures,” Cheek said. “I’m now building relationships.”

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It hasn’t been easy, though, to design and launch Cheekd, her Bluetooth-enabled app that notifies users if someone who meets their criteria is within 30 feet of them. She blew through her savings, sold her designer clothes and got odd jobs to fund it. Her app idea even got shot down by the sharks on “Shark Tank,” but her TV appearance helped Cheekd land investors and become a reality.

“I feel like I’m living the American Dream — I’ve given birth to an invention,” Cheek said. “I’ve gone from 16 years of helping others build their dreams to a life finally dedicated to building my own. It’s the most rewarding feeling.” She just launched a new business networking app — — and is working on another mobile dating app called Wingmom.

Check It Out: Americans Are Quitting Their Jobs But Most Still Love What They Do


As a mom of two, Sireesha Narumanchi wanted to find a way to earn money from home, so she started searching for remote jobs. She managed to find one, then came up with an idea to help others in her situation. Narumanchi created a blog,, to help other remote job seekers find legitimate online work.

“Having researched infinite ways to earn a good income from home over the years, I have put all my research into my blog and this has helped a lot of online job seekers,” she said. She went from earning just $300 a month from her blog to a full-time income in the three years she has been operating it. “It’s amazing how it grows every day as a thriving business and is helping others achieve their financial dreams,” Narumanchi said.

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Keep reading to find out what each generation wants from their jobs.

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About the Author

Cameron Huddleston

Cameron Huddleston is an award-winning journalist with more than 18 years of experience writing about personal finance. Her work has appeared in Kiplinger’s Personal Finance, Business Insider, Chicago Tribune, Fortune, MSN, USA Today and many more print and online publications. She also is the author of Mom and Dad, We Need to Talk: How to Have Essential Conversations With Your Parents About Their Finances. U.S. News & World Report named her one of the top personal finance experts to follow on Twitter, and AOL Daily Finance named her one of the top 20 personal finance influencers to follow on Twitter. She has appeared on CNBC, CNN, MSNBC and “Fox & Friends” and has been a guest on ABC News Radio, Wall Street Journal Radio, NPR, WTOP in Washington, D.C., KGO in San Francisco and other personal finance radio shows nationwide. She also has been interviewed and quoted as an expert in The New York Times, Chicago Tribune, Forbes, MarketWatch and more. She has an MA in economic journalism from American University and BA in journalism and Russian studies from Washington & Lee University.

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