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The Best Side Hustle I've Ever Had

Here's how some of our writers have supplemented their income over the years.

Man on laptop-1
Man on laptop-1

Image source: Getty Images.

Over the past decade or so, the so-called gig economy has exploded. More Americans than ever are finding ways to supplement their income through part-time "side hustles." We asked three of The Ascent's contributors about the best side hustles they've ever had, and here's what they had to say.

A side hustle that led to a career

Matt Frankel, CFP: I've had a few side hustles in my life -- even before that term existed. When I was a high school teacher, I worked at an after-school tutoring center. Before that, when I was working toward my masters and still bartending for a living, I substitute-taught a few days each week to save money.

However, at the risk of sounding like I'm just saying what my bosses want to hear, the best side hustle I've ever had was the one that led to my current job: writing for The Motley Fool (The Ascent's parent company). To be perfectly clear, I'm still a freelancer, but these days, writing on investing and personal finance is my main gig.

Back when I was a struggling high school teacher, I stumbled upon a project known as The Motley Fool's "Blog Network," which was essentially a platform that allowed people to share their thoughts on stocks and, if their content was good, to get paid for doing it. Well, about eight years and over 5,000 articles later, here I am. It's been quite a journey, and it has allowed me to help countless people invest and manage their personal finances better.

The Blog Network isn't around anymore, but freelance writing gigs of many kinds are abundant if you have expertise in a certain area as well as a knack for explaining complex topics in an easy-to-understand way. So if this sounds like you, and you're looking for a side hustle, I highly recommend checking out some freelance employment marketplaces (Upwork is a good one) and seeing what's available.

A truly…interesting content writing job

Maurie Backman: Before I became a full-time freelance writer, I would dabble in part-time writing gigs to supplement my income, build my portfolio, and gain experience in the content field. And while I've certainly taken on my share of random assignments, one gig that stands out in my mind was a stint writing copy about a topic many of us might find awkward, to say the least: sexually transmitted infections.

Now, I won't get into the nitty-gritty of what I wrote about, but let's just say that in the course of that job, I learned more about unsavory symptoms than I care to remember. Here's what I loved about the gig, though: The company would contact me at the start of the week and ask for these short, snippet paragraphs that would get attached to ads for home STI testing kits. I'd then have a good four or five days to submit my work, which meant I could do it at my own pace and convenience.

Some weeks, I'd be given a batch of four or five content pieces. Other weeks, I'd have double the load. The pay was excellent, given the limited time commitment and flexibility, and over the course of about six months (which was how long the project lasted), I earned a few thousand dollars without really having to disrupt my life. That money then went toward paying for a vacation so I wouldn't have to tap my savings.

The best part? The company that hired for me that project was so pleased with my work that my contact referred me to another medical content project -- one that was quite lucrative, too.

If you're in the market for a side hustle, be willing to do something outside your comfort zone. You never know what opportunities it might lead to, and it never hurts to have a little extra money to play with or save.

Helping others to succeed indirectly helped lead to a career

Christy Bieber: The best side hustle I ever had was one I took on in law school: tutoring students preparing for the SAT and the Law School Admissions Test (LSAT).

At the time I took the tutoring job, it seemed like a great gig because of the generous hourly rate and the fact that students would come to my house for their tutoring so I didn't have to try to commute in Los Angeles traffic. It was also rewarding to help people grasp concepts they didn't fully understand and to help them make their dreams of getting into a great school come true.

What I couldn't have imagined was that this side hustle would ultimately lead me down a winding career path that led to my true dream job: writing full-time for a living.

I kept tutoring all through school and for about six months after school, too -- once I figured out I didn't want to use my expensive law degree to practice law. Then, with the tutoring experience under my belt, I was able to land a job writing LSAT and SAT questions.

This, in turn, led to more educational writing, including ghost-writing textbooks -- which subsequently led to writing for websites, including an online dictionary site. Writing for the Web ultimately helped me to develop the career as a full-time writer that I have today.

My career took a winding path and looks very different from what I had originally expected to do with my life. I'm much happier working from home, setting my own hours, and doing interesting work than I would have been practicing law. And it all started because of the transferrable skills I developed through my side hustle.

The Motley Fool owns and recommends MasterCard and Visa, and recommends American Express. We’re firm believers in the Golden Rule. If we wouldn’t recommend an offer to a close family member, we wouldn’t recommend it on The Ascent either. Our number one goal is helping people find the best offers to improve their finances. That is why editorial opinions are ours alone and have not been previously reviewed, approved, or endorsed by included advertisers. Editorial content from The Ascent is separate from The Motley Fool editorial content and is created by a different analyst team.