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Money-Making Side Hustles for Retirees

By Jane Bokun

I love a side hustle.

In fact, I started experimenting with side gigs as soon as I started in the working world. Now, in retirement, they are my saviors. I’ve tried almost every side hustle that’s legal and within reason. Why? I can’t help myself. I love a good side hustle and you may too.

The three I’ve worked on include product sampling in big box stores, teaching and heading up six-minute  dating.

The first job is product sampling. It’s a job I still do and  is perfect for anyone who wants to set their own schedule as a contractor. It includes five-hour food and wine demonstrations with companies such as Target, Walmart and many more. The pay can range from $15 to $30 per hour and contractors are paid every two weeks.

Sometimes I’m sampling products such as vitamins or even prunes and wine. I lay out rows of brown, wrinkly prunes and people are sneakily trying to take more than one prune behind my back.

“They’re free,” I have to remind them. People love a free sample.

One the best things about sampling is you meet so many interesting people.

“I’m an opera singer by day,” said one attractive senior who worked with me serving drinks.

“My kids are out of the house and it gives me something to do at night,” she says. “I love the money, too.”

I showcased press-on nails at another event and drew crowds. Having a good sense of humor helps as well. This job was $22 an hour and lasted for five hours with breaks. Kaching!

If you’re looking for something a little more cerebral, substitute teaching can fit the bill.

You can sign up to fill-in while teachers are absent. They give you a lesson plan so there is no doubt about what to do. The only problem may be unruly children in the classroom, and I’ve really only run into that once.

That time the students weren’t listening and didn’t want to listen as I taught them. They then decided to go together to the principal’s office to really express that they weren’t too keen on me. That was a stressful day, but most students are truly easy to teach.

Either way, substitute teaching offers a stable and meaningful job opportunity. Full-time substitute teachers can receive long-term school placements, a steady paycheck, full healthcare benefits, paid holidays, and more. You can get a substitute teaching license in about a week.

Seniors are welcome in substitute teaching and you can do it when you want. It can pay about $150 a day. Some requirements are you are a college grad, but you also can be a teacher’s assistant in the classroom.

Six Minute Dating, my third side gig, I thought of myself, but others do it as well.

First, I partnered with a national dating chain and asked the company if they would join with me to showcase six-minute dating nights. Nowadays, I would use a dating organizer organization.

I pitched the dates as fun and what do you have to lose? I advertised my event in bulletins, newspapers and on social media. It came together nicely and there were no out-of-pocket expenses. That dating company provided some of the accouterments such as signage and a bell and that was about it.

For my first gig, I recruited a local family-owned restaurant and they provided some dips, crackers and cheeses. Those who attended had to buy their own drinks. I curated matching (participants fill out a quick profile so you can seat them strategically).  I then seated ten men and women two at a time and rang a bell. It was off! They got to know each other within six minutes.

I charged $20 per person and promised a night of fun. The couples were all I needed and I had them in excess. It can be a lonely world. Even though in some cities, six-minute dating has fallen off, it was a hit in mine. Now, I would have used themed events with seniors, dog owners, etc. It was rudimentary when I first did it.

By day, I worked on the news and once a week, I was the head of local Six Minute Dating. It worked so well I had to hire another person to help. At the end of a night I made about $500 and two couples got married.

Some side gigs are a mixed bag. One gig showcasing various food products, required me to wear a hairnet, ugh, not me.

Today’s Gig economy has grown by leaps and bounds. It requires taking smaller jobs that offer flexibility but no insurance or benefits beside pay. Most of us use it for extra money. In my case I’m 68 and retired and I still love gigging. It pays some bills and provides me with lots of fun and new friends.

If you’re curious, you too, can find a job doing demonstrations in a big box store, by searching online for companies that do connect people with side hustles, such as https://www.flexjobs.com/ and https://partners.thepennyhoarder.com/. For substitute teaching access https://www.hellosubs.co/. Finally, for Six Minute Dating try Pre‑Dating Speed Dating (https://www.pre-dating.com/).

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Tell me a senior story

By Jane Bokun

Old age tales are rarely true, and I see them all the time. In fact, you might say they are as normalized as the Paul Bunyon story. I may be the only one who didn’t think about retirement in my 20s, but I bet I’m not:

Here’s one: “I’m 63 years old, have $800K in savings and I was all set to retire in four months — but now I’ve just got a fantastic new job offer. Should I take it or stick to my plan?”

Answer: Shut up. Not only do you have some money, but people are also clamoring to hire you? Ugh! Next, you’re going to say you miraculously have no wrinkles on your derriere. Or, your husband’s sex drive is over the top and he NEVER looks at porn because you’re so hot.

You know you don’t have to ask if you can live on $800,000 or $2 million like I so often see.

“I have $25 million. Do you think I can live on it for five more years until I probably die?” Sure, nutcase. You can live on that.

How about the truth? I saved $300,000 and now it’s dwindling because I can hardly remember my name and my old engineer husband, is unemployed and has been tapped out of the system. Sure, we lived it up until about 55 years old, then it was hellish if not hell.

In my current old age, I wonder where the previous woman was in her 20s. Was she dazzling in a $1 million job with no husband while she listened to the latest song from Tears for Fears? Did she date pre-Bill Gates and he left her a bunch of money because she might need it when she turned 63?

We spent most of our money when we were young or needed to pay for high-end schools for a sophisticated kid who will certainly be embarrassed if we become homeless in front of his tony apartment building. My husband drives a small, colorful auto parts car a few times a week and we pray the sale of our kind of nice home will be enough to get us by until our suicide pact kicks in.

According to a recent Northwestern Mutual survey posted by MSN, Americans think it takes $1.46 million to retire securely. But the savings data above reveals that most people don’t have anywhere close to $1.46 million by the time they reach retirement age. The reality is that the amount of savings it takes to retire comfortably depends on your needs and age.

Sure, my needs include a Fiat Spider sportscar, but that’s like $30,000, a mere pittance in the retirement game.