Side Hustles That Worked For Me (and those that didn’t)

When I became a stay-at-home parent two decades ago, I didn't use the term “side hustle.” But now I realize side hustling was, indeed, what I did when I found ways to make extra cash.  

And most side hustles I tried back then are even more accessible today.

Better online access means more legit and lucrative opportunities to earn additional money!

Back then, there were fewer ways to make a side income. But when I quit my job to stay home, money was tight, and we had debt to pay off.

So I was motivated to find ways to bring in some cash!

Successful Side Hustles & Those That Didn't Pan Out

Below, are brief descriptions and stories of my side hustles that worked – and those that earned me little cash!

Side hustle: Reselling

Reselling has stood the test of time!

When my kids were young, my two best options for reselling were eBay and Craigslist, and I used both.

Craigslist had no fees, so I used it for household items, toys, and clothing. And eBay expanded my reach, so I used it for more niche items, like collectibles. 

I started by selling items we already owned and no longer wanted or needed. Later, I began to pick up things at yard sales, thrift stores, and the curb to flip for a profit.

Did it work?

Yes, it worked then, and it still does. But the landscape has changed since I started, and now I only dabble. 

There are many more selling platforms today.

Now I use Facebook Marketplace to avoid eBay fees and resell only occasionally. Facebook is good for local reach, and people tend to follow through, but it's pretty competitive in my area. 

Also, I don't have much on hand to sell anymore. My kids are grown, so there are no outgrown kids' items to sell! But I still resell household items we no longer want.

And when I find a great thrift store deal or something on the curb, I grab it to resell. From curbside grabs, we made a profit of around $500 last year.

Side hustle: Selling handmade items

Etsy wasn't around 15 years ago when I tried this side gig. So, I used Craigslist and word-of-mouth to sell my homemade baked goods and crocheted items. 

I found a few regular customers for my baked goods (mostly my spouse's co-workers!). And I had a reliable customer for crocheted baby items!

Yet I never expanded this side hustle since it was time-consuming, and my hourly rate was super low.

Did it work? 

No, it didn't work for me. After calculating my hourly wage (low), I decided it wasn't worth the time and effort to continue or expand.

But, Etsy and Facebook Marketplace weren't around at that time. With the help of those platforms, it could work better today. 

Curious about selling printables on Etsy but don't know where to start? Check out this free guide.

Side hustle: Assistant substitute teacher

When my kids were in elementary school, I was a substitute assistant teacher at their school. So, on many mornings I went to school with my kids!

As an assistant, I helped out in the preschool/kindergarten classrooms and the library. I had recess and lunch duty and looked forward to naptime as much as the kids.

Starting this side hustle was easy. I didn't need a teaching certificate to be an assistant. Plus, there was a lot of demand for reliable subs familiar with my kids' Montessori school. So there were some weeks I worked full-time. 

Did it work?

Yes, it did. I didn't earn a high hourly wage, but it was convenient and worked perfectly with my kids' schedules.

Soon, it became less of a side-hustle and more of a job as the school asked me to work more often.

Side hustle: Child care

I spent one school year as a child care provider for a teacher and friend.

It was very convenient since she worked at my kids' school—our schedules lined up nicely, and I love babies! (This side hustle ended when we moved away.)

Did it work?

Yes, it was a great side hustle for that time in my life. The pay was decent, and it was just one child, so I could still get things done while taking care of the baby.

Side hustle: Real estate investing

I've always enjoyed learning about real estate. Add in my love of personal finance, and real estate investing seemed like a perfect fit.

My husband and I wanted to buy a single-family home to rehab, rent, and refinance (the BRRR strategy). So, we bought a fixer-upper and got to work. 

Alan had a full-time job, so he worked at the house on nights and weekends. And I spent nearly every day for 4½ months lining up contractors and working on rehab projects.

In the end, the house looked terrific. But we were ready to get it off our hands, and the housing market was good. So we ended up flipping it for a profit instead of using it as a rental. 

Did it work?

Yes, there's no denying we made a good profit on the house. But, it took up a significant amount of our time—too much time for that point in our lives.

That said, we're not ruling out a future flip. Our kids are older now and don't need us as much. And once my partner isn't working full time, it's something we'll consider. 

Side hustle: Blogging

I started a personal finance blog in 2016 because I enjoyed other money blogs, and I wanted to try writing.

But, after I started, I realized it took more time than I ever imagined. Also, to make money at it takes patience! In other words, there's a lot to learn, and it's a staying game.

My first blog was a wild ride, full of personal growth and connections with wonderful people. I owned it for a year and a half and started earning a bit of money before selling it in 2017.

Did it work?

Yes and no. I sold that blog for a tiny profit when I got overwhelmed with our real estate investing venture. But the payoff didn't cover my investment of time and effort.

Looking back, I should have kept the blog and been more patient!

Blogging is a long-term commitment. And while it can pay off, it takes lots of time and effort!

But I don't regret it.

It didn't pay off financially, but I met some great friends – and the lessons I learned are priceless. Those led to me starting a couple more blogs and earning money through freelancing.

Side hustle: Freelancing

Through my first blog, I connected with wonderful folks online and in my local area. And through that network, I got a few of my first freelance opportunities. 

Since then, I've had various freelance gigs. They include social media management, article curation, writing, WordPress, and SEO, to name a few.

Did it work?

Hands down, this is one of the best side hustles I've had!

It's super flexible, I work with extraordinary people, and it pays well. Did I mention it's often fun?!

For me, freelancing is a part-time side hustle I didn't set out to do; it just evolved from that first blog. Yet, freelancers that are more intentional about finding work often make it a full-time job.

Read: Should I Quit My Job to Freelance? [The Pros & Cons]

Final thoughts on my side hustles

My favorite side hustles are reselling, freelancing, blogging, and real estate investing. But that doesn't mean they're always the most profitable or that they're the best ones for you. 

I had to try many different side hustles to figure out what worked and what didn't. And experience has been the best teacher!

So, to me, the best thing you can do is try different things to see what works for you.

Next: What Do I Need to Be a Successful Virtual Assistant?