Making Money, Post-Retirement

For most, the thought of retirement brings images of spending time with family, traveling, volunteering for causes you care about and, finally, having an opportunity to take it easy. However, it is increasingly common for people to continue working, either in the career they’ve always loved, or taking a completely new direction. We interviewed three people who are viewing their retirement as an end of one chapter and the beginning of a new one.

Polly Caumartin

retired VP of Central Travel

Polly Caumartin, retired VP of Central Travel

After retiring from her position as Vice President of Central Travel, Polly Caumartin decided it was time for a shift in how she spent her days, leaving the world of corporate travel to work with special needs kids. Since 2013, she’s worked as a substitute paraprofessional, assisting teachers throughout the school day in special education programs for Sylvania Schools.

An incredible perk with substitute teaching: using an app on your phone to look at available jobs and to select them, you never have to go into work if you need a day off. “This job is perfect because it allows me to have flexibility,” says Caumartin. “If I don’t want to work one day, I don’t have to take the assignment. It’s really perfect and offers some extra income. I’m getting paid for what I love to do.”

For Caumartin, working in special education is fulfilling. It’s not just an extra source of income, but a pursuit that has always been dear to her. “I love kids and have a special place in my heart for those with disabilities,” Caumartin says. “Every day is different. I never get bored. I do have a new respect for those that work with special needs kids full-time; they are so caring and extremely good at what they do.”

Dick Sachmann

Truck Driver for Advanced Auto Transport

Dick Sachmann, Truck Driver for Advanced Auto Transport
PHOTO BY Cortney Probert

Retired TARTA mechanic Dick Sackmann has always had a passion for cars and driving cross country, so it stands to reason that he would choose to do deliveries of trucks as his post-retirement job. When the opportunity first presented itself, however, he turned it down.

“I’m a pretty busy person,” Sackmann said. “I had plenty to do!” After a friend of his asked him, maybe for the fourth time, if he’d be interested, he finally said, “‘Sure, I’ll give it a try. I started doing it, and I found that I liked it very much.” He describes his first trip as a “trial by fire,” when he had to drive a cement mixer to Duluth, Minnesota, only to return and find that he had to deliver another truck to Cincinnati.

“It was three days of just driving. They (the company) thought I’d never want to do it again, but I didn’t mind at all.” Having done truck deliveries for almost two years now, he’s travelled all over the country. His longest trip took him through Colorado, Utah, Nevada, and finally Los Angeles where he wound up spending a day on the beach in Santa Monica.

“It’s such a pleasant thing, all the fun things you get to see,” Sackmann says. “There’s nobody with me. It just gives me time to think and enjoy the beautiful countryside.”

Rebecca Booth

Owner of Three Businesses

Rebecca Booth, Owner of Three Businesses

Founder of Arty Parties To Go, Marketing Goddess at Imagine That, and the woman behind Funky Girl Creations, Rebecca Booth is finally trying to slow down. “I’m one of those lucky people who can make money in a lot of different ways,” she says. “I’ve always been interested in different media and design opportunities.”

Booth worked as a designer for various companies over the years, then founded Imagine That in 1998 to provide marketing strategies for small businesses. She loves combining business strategies with artistry. When she was fresh out of college, people asked her, “Do you want to be a designer, or do you want to be a writer?” With a triple major in creative writing, public relations, and graphic design, she knew that she wanted to be both a designer and a writer.

Retiring interests

Though Imagine That is still very active, Booth is looking to slow down the marketing to pursue things she hasn’t had much time for over the years. For her, retirement means pursuing the interests she’s always had.

“I started Arty Parties to Go as a retirement business,” she says. Booth provides instruction on how to create a painting and participants can enjoy wine while painting. The twist, Booth doesn’t have a retail space, so she’ll come to you.

Booth’s motto is “everyone can be an artist,” and she hopes to expand her teaching from beginner level to intermediate classes. She’s also moving away from graphic design to focus on other opportunities, like font development and illustrations. A lifelong dream of hers has been to write a children’s book, so she is working on an interactive nonfiction story about the history of colors and how they are made.

Booth has found in her later years that she much prefers to work for herself, and that won’t change once she officially retires. “I have been on the road for 20 years living in different areas of the country,” she says. “I finally got tired of other people making money off my talent.”

If you want to schedule an Arty Party, find the company on Facebook or give her a call at 419-344-6262.

Suggestions to fulfill that dream after all…

  • Drive for a transport service like Lyft or Uber. Set your own hours and opt which routes to take and which to reject.
  • Buy a piece of property and rent it. Choose to maintain the building yourself or lessen the workload and hire someone to help.
  • Make money selling your wares online. Your hobbies like sewing, woodwork or jewelry making, can earn you extra cash.
  • Walk dogs or take care of them while your neighbors are vacationing.
  • Babysit and advertise on sites like
  • Leverage your expertise and be a consultant in the field from which you just retired.
  • Clean out your basement and sell your stuff on Craigslist, eBay or Facebook Marketplace.
  • Launch a business and become an entrepreneur. With a lifetime of experience under your belt, you have the skills you need to succeed.
  • Become a mystery shopper, blogger or freelance writer (for MLiving!).


Similar Articles

Most Popular