How This Couple’s Side Hustles Has Made Them $160K… and Counting

A couple and their infant son pose for a photo.
Public school teachers David and Meg Cahill, who have made more than $160,000 from a variety of side hustles during their eight years of marriage, pose with their son Joshua. Photo by Melissa Nicole Photography

My wife, Meg, and I are an average 30-something couple. We’re public school teachers who live in the Chicago suburbs with our son and two dogs.

On top of our demanding teaching careers, we have pursued several ways to make extra money on the side. Some of them have been one-off side hustles — by our choice — while others have been ongoing opportunities to bring in more cash.

It started slowly, but in the eight years we’ve been married, we’ve made more than $160,000 from our many different side hustles. In 2018, we’re on pace to earn over $75,000 in extra income.

It hasn’t always been easy, but we’ve earned every single penny through hard work, honesty, and integrity.

Sure, talking about how much money you make is a taboo subject for some people, but we’re passionate about sharing because it may help other people replicate our results. Our motto is simple: If our transparency helps others change their lives for the better, it’s worth a little awkwardness.

Here are the exact side hustles we have tried, how much money we’ve earned from each, plus what you’ll need to know to get started with each gig.

Selling Custom Cards, Invitations and Wedding Programs

As newlyweds, we were in way over our heads, fighting to live on just my starting teacher salary while Meg finished college. Our rent was low and we had some money saved, but we needed a cash infusion — badly.

Fresh off planning our wedding, Meg knew that wedding invitations, programs, and thank you cards can be expensive and saw an opportunity. She put to work her artistic skills, years of scrapbooking tools and materials, and an entrepreneurial spirit to undercut the competition and make a quick $300 from just one wedding client.

A few months later, Meg opened her in-home music lesson studio and put her custom card-making business, MC Creations, on the backburner.

Our earnings: $300

What you’ll need to get started: If you have an artistic eye, a collection of scrapbooking materials, and the bravery to advertise your services, selling custom paper products is a side hustle that’s easy to start.

One-on-one Tutoring and Private Lessons

A woman gives a young boy a piano lesson.
Meg Cahill gives a private piano lesson in the couple’s music room. Photo courtesy of David Cahill

Meg and I have always been teachers at heart, which is why we’ve both put our musicianship and teaching skills to work since our teen years. Since 2010, we’ve earned nearly $70,000 combined by teaching private music lessons and one-on-one tutoring sessions.

Many of our musician friends have done well for themselves working for local lesson studios, but we’ve always taught independently in students’ homes and in our home studio. At one time, Meg taught 25 students in our home studio, in addition to her full-time day job, thanks to the flexibility of setting her own schedule.

Our earnings: $69,127

What you’ll need to get started: You need musical talent to give music lessons, obviously, but we believe you can teach and tutor in any subject area in which you are knowledgeable as long as you have good rapport with your target-age students. These days, marketing through word of mouth, social media and referrals from family and friends can make it easy to get started. Our only start-up expense: business cards.

Babysitting and Nannying

Coming from the average-sized city of Norton Shores in southwest Michigan, attending Trinity College just north of Chicago in Deerfield, Illinois, was a culture shock in more ways than one. But the biggest shock came when Meg put her name on a list for local families looking for part-time nannies and babysitters. We quickly learned that the going rate for a regular, part-time sitter ranged from $15 to $25 per hour.

Over time, Meg developed strong bonds with a few families, which naturally led to more referrals. One special family was kind enough to let Meg bring me along to meet and play with their children. Their daughters were later the flower girls in our wedding, and they remain dear friends to us to this day.

Our earnings: $3,000 (approximate)

What you’ll need to get started: Babysitting and nannying are the perfect side hustles for education majors, counselors, and anyone who has a natural rapport with kids. You can create free accounts on websites like, but word-of-mouth referrals and personal referrals are tough to beat.

Pick Up Extra Work at Your Job

When I started my first teaching job in 2009, I was just like most recent college grads: poor, in debt, driving a beater, and living with a roommate just to make ends meet. So whenever opportunities came along to take on extra work at school, I made sure to be the first one to sign up.

Over the years, I’ve earned extra money working a few hours per month as a database coach, student arrival and dismissal supervisor, curriculum writer and summer program teacher.

Our earnings: $6,400

What you’ll need to get started: Bringing in extra cash at work may not be a viable side hustle for many people, but this general principle rings true: Always stay on the lookout for ways to use skills from your current job to make more money.

Online Content Creation and Affiliate Marketing

After I graduated college in 2009, it didn’t take me long to see that I knew nothing about living as an independent adult. And when it came to managing my finances, I realized I knew even less.

Over the next several years, I invested a bit of money and a lot of time to change that. I read books, took courses, listened to podcasts and found a few interesting finance blogs. Finally, in 2016, I gave in to Meg’s encouragement and started my own personal finance blog as a way to merge my interest in writing and money. I never expected to make any cash doing it because I had no idea how to start a business. Instead, I looked at blogging as a cheap hobby.

But I found myself building an audience and getting decent site traffic after about a year. That’s when I began making an effort to monetize my site with a few ads and affiliate relationships.

Today, I spend 10 hours per week, on average, working on my blog. My niche website earns a steady income from a combination of display advertising, affiliate marketing and sales of my online personal finance course.

Our lifetime earnings: $19,460

2018 projected earnings: $25,000

What you’ll need to get started: Blogging is one of the least expensive small-business options of all time and a great side hustle for anyone who enjoys writing. Web hosting is cheap, which makes blogging a pretty risk-free venture. Some people say that there isn’t room on the web for new bloggers, but they’re wrong. If you have a story to tell and can help people solve problems and improve their lives, you have a chance to make money blogging.

Help People Buy and Sell Houses as a Real Estate Agent

For the past two years, Cahill has earned extra income by working as an associate on a small real estate team. Photo courtesy of David Cahill

There probably aren’t any pictures to prove it, but I used to watch the local real estate listings TV channel when I was a little kid. So I’m not exaggerating when I tell people there was always a part of me that wanted to become a real estate agent. It just seemed like a natural fit based on my passion for helping people.

For the past two years, I have worked as an associate on a small but very successful real estate team. I’ve been fortunate to learn the ins and outs of the local market from a great friend who took me under her wing, and we make a great team. This year, just my second, I reached my personal annual commission goal with three months left to go.

Summer vacation and a teacher’s schedule made becoming a real estate agent the perfect side hustle for me. I’m available afternoons, evenings, and weekends — when most buyers want to see homes anyway — and I have the freedom to work full-time hours when needed.

Our earnings: $70,000

What you’ll need to get started: First, you’ll need to choose a real estate study course and pass the required tests in your state to earn a real estate agent license. Courses are available online and at local agencies. Second, you’ll need to choose an agency and local association to join. Smaller, local offices and big name agencies each have their pros and cons, so do your research.

You will also need business cards, professional attire, a reliable car and a healthy dose of patience. It often takes new agents up to a year to get rolling, but the good news is you won’t need a big emergency fund to fall back on if real estate is just a side gig.

Odds and Ends

My wife and I have obviously enjoyed success with a few side hustles, but we truly believe that this success would never have materialized if we hadn’t been willing to try new side hustles over the years. Here is a small sample of the few odd jobs we’ve taken on:

  • Composing/arranging music and performing at weddings
  • Distributing AdvoCare health products
  • Taking online surveys in our free time

Our earnings: $1,500 (approximate)

What you’ll need to get started: Surveys and product sales weren’t the long-term side gigs we sought, but they are very easy to start. If you have the desire and motivation, you can start making money quickly.

Next Steps

My wife and I learned many hard lessons while working our side hustles over the years, but we agree that one in particular is essential for anyone looking to start their own side gig:

You need to go for it with complete confidence and genuine passion.  

In our experience, our biggest side hustle mistakes happened because of our fear of failure. Once we learned to let go of negativity, stop listening to the naysayers, and act confidently, our income skyrocketed.

You’ll never regret taking bold action that could potentially change your life.

David Cahill is the founder of the blog FinanceSuperhero, a Chicago-area realtor, and public school teacher.