Odd Jobs: Finding Meaning and Money in Unlikely Places

Over the years, I’ve had my share of odd jobs.

As a teenager, I took them to make pocket money for the essentials – glossy magazines with pinups of the day’s hunks and disco dance lessons. I did everything from babysitting to working at a dry cleaner’s to typing invoices for a psychotherapist.

As I got older, I continued to seek out this kind of work when I needed extra cash, also for the essentials. You know, things like the gas bill, food, and rent.

And while I never delivered a singing telegram or developed strangers’ vacation photos in an hour (or less!), I’ve had some curious side hustles over the years. But the strangest had one thing in common: they were disguised as fairly mundane positions. Like the one I had as a call center operator.

A Second Job, Three Clients, and One Line I Wouldn’t Cross

It seemed completely unremarkable at first. I took it as a second job for spare change during the holidays. The hours were flexible, and the tasks seemed simple enough: read scripted greetings, key in orders, and sprinkle in the occasional, “Excellent choice!” or “You have great taste!”

I started with one client – a well-known purveyor of gadgets, memorabilia, and fun, nonsensical stuff. When customers called in, they were asked for item numbers only, not descriptions. Management said this practice helped avoid order mix-ups. It also provided opportunities to say (in my most professional voice) things like, “I see you’ve selected our fart clock. You have great taste!” or “You’ve chosen our ‘How to Seduce Women’ kit. Excellent choice!”

A couple of weeks later, a renowned lingerie manufacturer was added to my list. Taking orders for the items in their catalog provided a whole new set of surprises. It was educational, too. I discovered the demand for French maid outfits, from both men and women, was broader than I’d imagined and that some customers were very particular about their fabric preferences.

But when the call center added a lifestyle company geared to older adults to my roster, things stopped being funny. I was expected to incentivize callers – many of whom I imagined had limited incomes – to purchase add-on products. Operators were told we couldn’t deviate from the script. So, I quit that night.

Filling requests for flatulent timepieces and leather bustiers? I was happy to do it. Talking people into purchasing trees that “grow five kinds of fruit” or commemorative coins? Not okay.

Looking back, I realize how lucky I was to have the freedom to walk away as well as how much that job taught me. Every strange task, every awkward call, reminded me of the power of choice: what we’ll do for a paycheck, and what we won’t.

Why Some Say “Yes” to an Odd Job Today

These days, a number of us – even those who’ve retired or cut back on work hours – consider odd jobs to experience something different, have disposable income, or help pay bills. Personally, I’ve dabbled in areas I hadn’t considered before last year, from consultation opportunities to a short stint working for a matchmaker. Like many women in their 60s, I’ve learned that sometimes the most unexpected work brings the richest perspective.

Whether it’s out of necessity, curiosity, or simply a desire to stay engaged, many in our community find themselves drawn to the idea of taking a side gig. The reasons, as listed below, can vary. But we often learn the most about ourselves when we try something new, even if it’s a little outside of our comfort zone, which is something traditional retirement doesn’t always provide.

A Little Extra Income

With cost-of-living increases, a part-time job can soften the edges without a commitment to full-time hours.

Structure and Purpose

A few shifts or side projects can add a pleasant rhythm to the week and a reason to get out the door (or log on).

Social Connection

Light work brings moments of community you can’t always get at home.

Using What You Know

You’ve built decades of good judgment and skills that others will happily pay for.

Curiosity and Confidence

Trying something new can be invigorating. It’s also a low-risk way to test-drive a path before committing to it.

Not So Unusual After All

“Odd jobs” aren’t really that odd at all; they’re opportunities. They remind us that earning, contributing, and connecting don’t have an expiration date. Whether it’s for extra income, kinship, or the sheer joy of trying different things, these experiences can bring fresh perspective and unexpected confidence. Worst case scenario, you gain a story. (My call center job became storytelling gold!) Best case, you gain purpose, meet new people, and end up with a little cushion.

Every quirky gig, no matter how temporary or unconventional, can teach us valuable lessons about resilience and choice. We may not all find ourselves taking orders for X-ray specs or mystery tomato plants (and thank heaven for that!). But if we want it, there’s something powerful in saying yes to work that makes sense for us where we are right now.

You may also want to read Could a Side Hustle Gig Provide More Financial Peace of Mind in Your 60s?

Let’s Have a Conversation:

Have you taken an unconventional job or side hustle? Is it a decision you’ve been happy with, or do you regret it? Did you ever leave a position because you were uncomfortable with its requirements? Share your thoughts and experiences with our community.