Sideline Supplemental Income Opportunities for Retirees

I retired four and a half years ago from my job as a software project manager. Part of my reason for retiring was that I wanted more flexible work hours and wanted to do something different. If you are retired, you want to have more than one source of income available. That way, if one dries up, you have others to fall back on.

Here are some opportunities with which I have personal experience. Some of them I did myself, others were done by folks in my circle and the rest are ones that I wished I could have hired someone else to do.

Although they won’t make you rich beyond your wildest dreams, and although some of them are pretty hard work, they can provide an opportunity to add to your income by capitalizing on your life experiences.

Manage maintenance and cleaning for a vacation home or condo

We own a condo in the Branson, MO area. We are always in need of someone who can come to the condo and do maintenance or cleaning, or for someone who could line people up to do that. Last year we used a man that had prior experience as the grounds keeper/maintenance man for a millionaire family. He lined up cleaners to come in after each visitor stay. He assisted or handled minor repairs and maintenance, such as hanging my new drapes or putting together a BBQ.

If you live close to a vacation area, and don’t mind being on call, you could make quite a bit doing this kind of work. Most individuals charge $25 or more per hour – at least in our area.

Free lance writing

The web demands fresh content each and every day. If you have writing skills, life experience or special expertise, you could make money writing articles for blogs, company websites or ghost writing eBooks. I got started by having my own website, joining several blogging networks and getting to know other website owners via the networks and conferences. You can do the same, or you could compete for jobs posted on such sites as or or

Medical transcriptionists

My son’s Mother-in-law worked from home for many years transcribing medical notes for several doctors. With a bit of training you could do this as well. It is a very detail oriented, time intensive job however.

Newspaper delivery

When my first born was a baby, I earned a bit of extra income by delivering neighborhood newspapers. While today, there aren’t as many papers, there are still flyers and other types of things that need delivering. The pay is not great, but you get a lot of beneficial exercise!


My son, who is a web programmer, earns extra money via side jobs. He programs from home after normal work hours. If you have experience and expertise in a certain field, there is probably someone who is willing to pay you to help them out.

For example, when writing my eBook (Choose Wealth), I could have benefited from someone to edit for me at a reasonable price.

Kid sitting

After I decided to go back to college to learn how to program, I opened a licensed day care home in my residence. I charged $40 a week in the 1980’s per child. Today, folks who care for kids get paid fairly well. I believe my son and his wife pay over $200 a week for before and after school care (as well as school holiday full day care) for their two elementary age children.


My next door neighbor cleaned homes. For the initial cleaning, she charged $300 for a whole house cleaning and thereafter charged $100 for each clean. If you are physically able and need the money, finding clients who want individuals to do cleaning for them may be for you.


If you have experience with the common household maintenance items (such as a leaky faucet, fixing a broken lamp, backed up toilet or drain, painting, gutter cleaning) you could earn money helping out others in need of such services. Lots of homeowners today work long and hard at their jobs and ignore some of the necessary home maintenance chores due to lack of time or lack of knowledge. Get the word out at your church, do some pro bono work and request that work be referred to you. I’m still looking for my handyman.

Dog walker/pet sitter

When we had a cat, I often wished there was a good, inexpensive alternative to taking the cat to the pet boarder. I didn’t want to impose on neighbors, but if I had known someone who would have come over to feed the cat while we were gone, at less that the $200 a week we paid the boarder, I would have jumped on that!

How do you supplement your retirement income?


Sideline Supplemental Income Opportunities for Retirees — 2 Comments

  1. I remember when I was a kid my grandparents would clean a bank every Sunday for extra income. I would go along with them and pretend I was the drive through person while they worked. 🙂

  2. All great suggestions! Although there may be one or two on the list that some retirees may not be too keen on doing. I think it’s important for retirees to still keep active after retirement, and not remain idle.

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