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.