How To Turn Your Five-Figure Freelance Career Into A Six-Figure Startup

Here’s your guide to going from solopreneur to CEO.

How To Turn Your Five-Figure Freelance Career Into A Six-Figure Startup
[Source illustration: MaryLB/iStock]

Whatever you call yourself–“freelancer,” “consultant,” or “solopreneur”–you’re getting by just fine as your own boss. You’re regularly pulling in a comfortable five-figure income, and it feels good answering to nobody but yourself. But now you’re ready to think bigger. You want to build your solo operation into a proper company by making a few key hires and expanding your customer base beyond the handful of clients that just you yourself can personally manage. Here’s what it takes to make that happen.


1. Outsource Before You Can Quite Afford It

After two years of running my own business as a solopreneur, I hired a business coach to look at things from an outside perspective and point out a few ways to take everything to the next level. It quickly became clear that if I wanted greater rewards, I’d need to take bigger risks. Most of those came in the form of hiring help–namely a virtual assistant, a video editor, and my own publicist. At the time, these looked to me like expenses I couldn’t easily afford, but I took a chance anyway and it soon paid off.

Other entrepreneurs agree that this type of early investment can be crucial. “There is so much that goes into running an online business, and there’s no possible way that you can do it all,” shares Lori Kennedy, founder of the Wellness Business Hub, which offers personal development and professional training for health and wellness experts.

“I learned that lesson quickly. I didn’t want to waste any time trying to code or figure out how to set up webpages. Even though I wasn’t making enough money,” she explains, “I decided to hire a virtual assistant who specialized in tech development to help me get all of my online properties set up properly. It was like I was buying back my time.”

Related: How (And Why) To Launch Your Own Product Line, No Startup Required

2. Scale Up Your Audience

Once  you’ve outsourced a few key functions, you need to spend the time you’ve freed up strategically. One of the first things you should do is focus on growing your audience.


Every digital entrepreneur has heard it time and time again: the money is in your email list. “It takes 90 days to attract at least 2,400 new people into your audience on an email list,” says Shanda Sumpter, a business coach and CEO of HeartCore Business. “If you haven’t built a list yet and are busy trying to build a website, work on your branding, or create products, then stop!” Sumpter says.

Those are all important projects, but they can come later. When you’re trying to transform your freelance work into a full-fledged startup, your critical next step is to “give your potential clients what they want,” she explains, and “the only way you can do that is to ask them”–ideally by email. “Focus your energy on creating a list of subscribers” before you turn toward any other business-branding projects.

Not sure where to start? Here are a few tips from Fast Company’s own newsletter editor Cayleigh Parrish, on the nuts and bolts of launching a high-impact email newsletter.

3. Focus First On Solving A Problem For Free

As you work on scaling up your email list, don’t forget about the “know, like, and trust” factor; that’s not only the key to actually getting subscribers, but it’s also what the most meaningful relationship with your startup’s customers will be based on. So instead of just pointing people to your website, offer them content upgrades, lead magnets, and opt-ins. Translation: hand out a free download, checklist, training exercise, or something similar in exchange for email addresses.

“You should be able to create your lead magnet within 24 hours,” notes Kennedy. “Pull together some of your existing content, and package it into a guide, report, or checklist.” Chances are there’s something you’ve developed in your previous work that you can repurpose–and don’t overthink it. “Remember,” she adds, “your lead magnet has to tie into your program or service offer. It should provide the reader with a quick win.”


4. Get Really Good At Making Deals Over The Phone

I will admit, until this year, I myself had let this one slide a bit. With 2015’s and 2016’s surge in webinars, online classes, and virtual summits, I’d come to rely exclusively on making sales through digital means. But as Sumpter points out, “Everyone wants to sell through a website, and websites don’t make money.”

“If you want to go from five to six figures,” she says, “you must learn how to sell your product or service over the phone. You build a connection and a rapport that helps you to truly understand their vision, so you can strategize and then share your options that can really make a difference for them.” There’s no substitute for being able to react real-time as somebody weighs a decision, Sumpter adds.

“More often than not, even though they know it’s a good idea to take the next step with you, they’ll usually talk themselves out of making a commitment: ‘I don’t have the time, I don’t have the money.’ You have to hold the vision for the person on the other end of the phone to help them overcome their objections,” she says. “The phone = financial freedom.”

Related: What Happened When I Replied “Call Me” To Every Email I Got For A Week

5. Start Succession-Planning Early

In the first days of our businesses, most of us solopreneurs are pretty scrappy, wearing the hats of CEO, intern, graphic designer, writer, and sales rep all at once. But there’s a reason you don’t see Tim Cook at the Genius Bar in the Apple Store or Elon Musk servicing Teslas. To truly become the head of your own company, you need to develop the leadership skills to delegate tasks and inspire your vision in others.


“In order to stay laser-focused on your key revenue-driving activities, you must have a plan in place to groom a successor,” says Bianca Sprague, cofounder of doula-training company Bebo Mia. That may sound premature, but from the very first hires you make, look for people you could eventually trust to make management-level decisions. After all, if your own duties change when you go from solopreneur to CEO of a startup, they’ll change yet again when your six-figure company adds even more staff–and, eventually, a seventh digit in its revenue count.

About the author

Christina Nicholson is a former TV reporter and anchor who now owns and operates a full-service public relations firm, Media Maven.