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4 Ways to Start a Side Hustle in Retirement

Tips from Chris Guillebeau, author of '100 Side Hustles'

By Nancy Collamer

If you’re looking for a way to earn money in retirement, you may want to check out Chris Guillebeau’s newest book, 100 Side Hustles: Unexpected Ideas for Making Extra Money Without Quitting Your Day Job. It’s a terrific read that tells the stories of “ordinary” people who’ve found clever ways to make money in the new economy.

Side Hustle
Tanieka Vance Randall  |  Credit: Courtesy of B2ful Photography Houston, Texas

As someone who advises people on switching careers and working part-time in retirement, I’ve long been a fan of Guillebeau, a bestselling author and host of the Side Hustle School podcast.

So, I jumped at the chance to hear him speak recently in New York City as part of his 100 Side Hustles World Tour. “Everything I do is about helping people live unconventional lives,” Guillebeau told the SRO crowd. “I want people to see they have more options.”

Most people launching side hustles use their existing skills.

During his talk, Guillebeau shared strategies for getting started with a side hustle. He acknowledged that starting a side hustle can be scary but, he said, it’s worth the effort.

“Once you start doing this, that mentality can change your life,” noted Guillebeau. “If you have a dream and give it a try, think how good you will feel eighteen months from now.”

4 Ways to Start a Side Hustle in Retirement

Here are four of my favorite takeaways from Guillebeau’s presentation and book (revenue figures cited came from the book and might be different today):

1. To Find a Side Hustle, Use the Skills You Already Have. While it’s fun to fantasize about doing something wildly different in your next act, most people launching side hustles use their existing skills. And Guillebeau thinks that’s smart.

This doesn’t mean you have to continue doing exactly what you were doing before. But there is likely a piece of your expertise that you can leverage.

Guillebeau cites as example, Sumit Bansal, a marketing manager at IBM in New Delhi, India, who turned his proficiency with Excel spreadsheets and PowerPoint presentations into a series of online courses at (no relation to the President). Bansal’s basic Excel course is free, but he earns about $3,500 a month in net income from the sale of the other courses.

Tip: If you’re not sure which of your skills to leverage, Guillebeau suggests making a list of things you know how to do. Then ask yourself: Which of these do I like to do and do well that others could find useful or helpful?

2. Follow a Problem, Instead of a Passion. Not everything you are passionate about can be monetized. But people often will pay you to solve their problems and alleviate their pain.

Often, the best side hustle ideas are found at the intersection between your passion and an unsolved problem.

100 side hustles

For example, Tanieka (Tee) Randall, an oncology nurse from Houston, lost her hair while undergoing chemotherapy treatments for cancer. A self-described “healthy hair junkie” who had enjoyed concocting homemade hair products in the past, she eventually came up with a recipe that helped to regrow her hair. After people began asking what she was using, Randall started selling her products to friends on Facebook.

Over time, she decided to take her side hustle more seriously. Randall started networking, expanded her product line and built an e-commerce website at Her income fluctuates but has been as high as $80,000 a year. She hopes to turn the side hustle into a full-time business.

Tip: Have you figured out a unique solution to a common problem? Perhaps you’ve developed a homemade organic cleaning solution that’s safe for people with allergies. Or you know how to order beautiful wedding flowers at a discount. Sometimes, those solutions can be monetized in interesting ways.

3. Teach What You Know. One of the best ways to generate side hustle income is to teach others what you’ve learned through your life experience.

One example: Jodi Carlson, of Conneaut, Ohio, spent over 20 years as a Girl Scout and troop leader. After the birth of her son, Carlson realized she no longer had the flexibility to continue as a volunteer but wanted to stay involved in some capacity. So, she decided to upgrade the small blog she’d created for troop leaders and renamed it

While most information on the site remained free, Carlson started selling low-cost digital downloads — like activity booklets, games and printouts that she knew other troop leaders would love. The products cost less than $10 each, but the site generates $3,000 to $3,500 per month.

Tip: Think about what you are the “go-to” person for at work and in your personal life. Do people turn to you for help with relationship issues, technical problems or design help? There might be a way to turn that expertise into a profitable course, service or product.

4. Do Good And Do Well.  Lots of retirees want to give back later in life, but not everyone wants to work for a nonprofit. That’s why I especially liked the side hustles in Guillebeau’s book that incorporate a “social good” component.

For instance, Danielle Fang, a stay-at-home mom and former teacher from Washington, D.C., developed a series of YouTube tutorials to help immigrants prepare for U.S. citizenship tests. Fang knew from her experience volunteering that there was a need for this information and that many immigrants couldn’t find time to attend class in person. So she created a website,, and a YouTube channel, where she guides students on this topic.

Initially, Fang had no plans to make money from the videos. But after traffic to the site grew, she learned how to monetize the channel through YouTube’s advertiser program. The site brings in around $2,000 a month, strictly from advertising revenues (the information is free for students). This additional income supplements her household income and lets Fang purchase supplies for her students and arriving refugee families.

Tip: Remember: there are many ways a side hustle can help you give back. You can donate profits or product to charities; sponsor a philanthropic event or provide work to people in need, just to name a few.

Photograph of Nancy Collamer
Nancy Collamer, M.S., is a semi-retirement coach, speaker and author of Second-Act Careers: 50+ Ways to Profit From Your Passions During Semi-Retirement. You can now download her free workbook called 25 Ways to Help You Identify Your Ideal Second Act on her website at (and you'll also receive her free bi-monthly newsletter). Read More
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