I Quit My Job and Turned My Side Hustle into a Six-Figure Business—Here’s How

If elevating a side gig into a lucrative career is on your job vision board, consider these tips—and you just might quit your day job

It was 7 a.m. on one of those chaotic mornings in the early pandemic. I was about to jump on a Zoom call with 30 tenth-grade students and was trying to amp myself up. I needed to both get excited about writing and convince my students to turn on their cameras—all while persuading my kindergartner hiding under the desk to engage in virtual learning. After a few hours of teaching, I’d get to do what I really wanted to: write. I’d fallen out of love with teaching, wishing for better pay and the flexibility that teachers deserve.

Let’s back up though. At 18, thanks to a top-notch high school journalism teacher, I got an internship at a local newspaper and wrote my first reported news story, about a local American Idol–style competition for teens. I was paid $15, and I was elated. My grandparents hung my first clip on their bulletin board, and I went to the movies with my friends. A side hustle was born.

I graduated from college during the 2008 recession, when newsrooms were dissolving and print media was burning down. So I went back to grad school to be a teacher. It was a safe, fulfilling and recession-proof career route. Writing remained a side hustle indefinitely, as I taught high school English and journalism for the next decade. But it took that jarring pandemic moment to remind me of what I knew: As much as I’d loved teaching, it was time to make the jump.

How to turn a side gig into a lucrative career

I’ve always been quite open about making money, for a very specific reason: Few people think writers can thrive financially in a creative field (unless they’re bestselling book authors). But those people are quite wrong, I’ve come to find out, and I want others to know the truth. So I share that my first month in business as a freelance writer, I only made $500 on a few stories. I kept my day job until things ramped up. Three years later, my writing business earns $250,000 annually, with a part-time schedule, working five hours per day. It’s the type of math I questioned originally, but I’ve learned through experience that it’s not only doable, it’s also fun.

Side hustles don’t have to mean career burnout, as long as you have boundaries. And they’re a great option for career cushioning. Turning my side gig into a main source of income now finances my five kids’ futures, supports my own desire for a creative career and offers a flexible part-time workday. And I teach others to do the same. If elevating your side hustle, freelance work, temp job or consulting gig is on your career vision board, here’s what I’ve learned.

Find a mentor, be a mentor

We’ve all heard the sayings about only being as strong as the women (and others) who surround you, and reaching back to pull others up by the hand. This has been done for me, and I’ve done it for others. The first step in making your side hustle your main hustle is to find someone who has done it, and learn from them. Sometimes, this looks like paying them for advice, and sometimes, it’s a cup of coffee and a conversation. Attend events, hang out and network in the same circles as they do. And remember, career advice shouldn’t come from just one person—different people have different strengths and things to teach. You likely have something to offer others as well. Although being a mentor might seem like another to-do, it can be a major source of fulfillment.

Niche down—or not

Some common advice with side hustles is to “niche down” and get really specific with your goals. Niche down means to specialize in a specific area and clarify which niche of your market you fill—and how. It’s the opposite of being a jack of all trades. Maybe your side hustle is making soaps, but your niche might be making organic soaps or products for kids.

This can work in many instances. For others, it’s not necessary. For example, I have colleagues who are only experts in one specific field of writing—politics, foreign affairs, pop culture—and they are quite good at it. For me, I wanted four to five areas of expertise to keep creativity flowing and boredom at bay. So, instead of just one topic, I write about education, health, work, parenting and e-commerce, among a few other things. Make your own rules, and stand by what is fun and lucrative for you.

Craft a stellar statement

What’s the purpose of your business? You’ve created a side hustle—and future full-time gig—that’s flourishing, but what exactly do you or your brand offer? In a few simple sentences, provide a roadmap for yourself or your business so potential customers or clients (or in my case, editors) know what to expect.

Build your online presence

For any side hustle, a clear and helpful online portfolio or LinkedIn bio is essential. From there, a heavy presence showcasing your best work is a must. The how and where and what will depend on your industry, but anyone should be able to head to both those places to see what you’re about. Don’t get caught up in making it perfect from the get-go. Just start, and add a bit each day, week or month. New freelancers I speak to sometimes hesitate to start reaching out to clients because their portfolio isn’t perfect yet. But ironically, your portfolio will only get better as you encounter more success. So just get started.

Make the leap

stack of money on the edge about to take the leapPM Images/getty images

When your side hustle income gets close to or rivals your main income, you have to consider what you are losing by not making the leap. You can only grow so much doing both, and it could be time to consider quitting your main job. This is where it’s often hard for people. To make the leap, I had to get real about intentional business planning and goal setting, and take concrete steps to accomplish those.

One of the biggest pain points in transitioning from a main job to a side hustle is that there can be a bit of a delay in getting enough work. Work doesn’t just materialize. So I maximized evenings and weekends when I was teaching to build up my client base, preparing for the big switch. You can work on padding your savings account or creating a sinking fund with enough backup money to make the jump. For me, the right time was when my day job was costing my side hustle money and opportunity.

Don’t overthink bookkeeping

If you are DIYing your bookkeeping at first, think meticulous, not fancy. You do not have to have an elaborate software program for invoicing or project management (though there are plenty of beneficial ones out there to look into). Instead, simply keep a detailed spreadsheet of your projects, costs, income and expenditures. Work with a qualified accountant who knows how to help freelancers to ensure your taxes are in line. The rest can level-up later.

Start telling everyone you know

Even in a digital age, I’ve found clients chatting outside a boutique fitting room on a weekend shopping trip, at the coffee shop waiting on a latte and discussing career plans with a restaurant server. Start opening your mouth and chatting with anyone you can. Ask what they do—or drop into conversation what you do. The rest often flows simply from there into a new networking connection. Similarly, engage in posting on social media about your side hustle, with specifics about how people can collaborate with you. They don’t know what they don’t know, so tell them.

Know your worth

Some people are surprised to learn that I almost always negotiate rates and terms for new projects and new clients. Knowing your worth (and standing by it) is a vital money tip. It can feel cocky at first, but it’s mission-oriented and should permeate your decisions throughout the day. Simply tell that imposter syndrome to step aside.

One of the challenges of a side hustle (and full-time gig) is figuring out what you should charge. Your first step should be to ask everyone who will share in your industry or at your level what they’re charging. Then determine your pricing model: hourly or a fixed project-based rate. From there, you’ll want to determine a salary or wage that is sustainable and allows you to make a solid living, knowing that it will grow once you’re more established.

Consider other freelance expenses, such as taxes, health insurance, subscriptions, office space or contractors, as well as your savings, vacation and more. Figure out what you need to take home monthly or weekly to make it all work, then divide that by the number of hours you’d like to work, and that’s your hourly rate.

Turning a side hustle into a main hustle can be daunting and disorienting. But it’s worth taking a step every day toward making it happen. Your future self will thank you.

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Alex Frost
Alexandra Frost is a freelance writer and journalism teacher who covers parenting, health, relationships, communications, business, education and more for Reader's Digest and other publications. Her work has been featured in Glamour, Parents, Healthline, Today's Parent, Women's Health and We Are Teachers. Alex has a master's in education and a bachelor's in journalism/communication from Miami University, and she resides in Cincinnati with her three sons under age 5. See more of her work at Alexandra-Frost.com.