Freelance to Small Business: 10 People Who Made the Transition

This article is a reprint of Wise Bread's contribution to OPEN Forum from American Express -- where small business owners can get advice from experts and share tips with each other.

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When you start out as a freelancer, there aren't a lot of options for moving forward: You can increase your rates or land bigger and better clients. But as long as you keep the title of "freelancer," your path can be very limited. Just a name change can make a big difference. Many freelancers start out thinking of themselves as on their own, but when they start thinking of themselves as small business owners and entrepreneurs, the opportunities available to them boom. These business owners started out as traditional freelancers, but have moved far beyond what that title can describe:

1. Andy Hayes

While Andy Hayes may have started out as a freelance writer, he's gone on to become a speaker, a consultant, and the owner of Hayes Media Group. "In the beginning, I was blissfully unaware of the difference between freelancer and entrepreneur," says Hayes. "It didn't take very long for me to realize that I had traded one employer for another (and I wasn't a very kind manager to myself). Being freelance is fairly easy if you've got in-demand skills, but entrepreneurship requires you take risks and leaps. Doing so gives you leverage to start earning a lot more money, dreaming a lot bigger, and most importantly, helping to bring bigger/better change to the lives of your customers."

2. Mason Gentry, Faucet Face

Gentry took the skills he learned as a freelance art director and used them to create a line of artistic water bottles. "I started Faucet Face about 20 months ago, working on it at night and during the downtime in between freelance gigs," says Gentry. Now the business offers artistic drinking bottles that Gentry designed and had manufactured.

3. Nathalie Lussier, Raw Foods Witch

"When I started freelancing I didn't have a bigger business in mind at all," says Lussier. "But after a few months of freelancing, also of seeing what other freelancers and business owners were doing, I realized I could start a business that went beyond freelancing. So the raw food business came out of the 'ashes' of my freelancing business." She made the switch from writing and translating on a freelance business to offering coaching and creating products around raw foods.

4. Lisa Tener

Getting her first book published tipped Tener over the line between entrepreneur and small business owner, but it took talking to a coach to help her see it. "Only when I met (and began working with) my first business/life coach did I begin to see myself as an entrepreneur. As a stay-at-home-mom working part-time, I needed to make around $3,000 that summer and had been making just a couple hundred a week. My coach helped me set specific goals (like the $3,000), which opened my eyes to an opportunity to do some consulting in a previous field (nonprofit management) and make exactly what I'd hoped...$3,000."

5. Brian Casel, CasJam Media

Many freelancers hit a plateau in their ability to keep growing, and Casel is no exception: "My rates are at a comfortable level, so I needed to look for other ways to grow my business. Releasing products was a way to do that. I've been specializing in designing WordPress-powered websites for clients, so I built on that expertise to create and sell WordPress themes that meet the needs of bootstrapped businesses."

6. Chris Davis, The Swizzle Collective

Just because a freelancer becomes a small business owner doesn't mean that he has to change what he's been doing. Davis moved from freelancer to agency without a big change: "I was a freelance copywriter in the advertising industry, working for any and all agencies that needed creative help. One such assignment was to write some radio spots for Velocity Credit Union on behalf of an agency that went out of business shortly after the spots were produced...But thankfully my relationship with Velocity didn't end when that agency went belly up. In fact, it prospered. I become their go-to guy when it came to concepting and producing their advertising work, and eventually I was able to start my own agency because of that relationship."

7. Jennifer Maciejewski, Atlanta on the Cheap

Maciejewski started her blog as a way to brush up on her skills and demonstrate her abilities to her freelance writing clients. But her sites have become her focus. "Once I started depositing checks, I realized that I could potentially grow that revenue into a solid income stream, so I started investing more time into the sites. Over the past year, they've taken over the bulk of my work hours, but treating it as a business has definitely paid off," says Maciejewski.

8. Allison Torneros, Circledot

Starting as a freelancer in high school, Torneros knew she could fall back on her skills when she didn't have a job offer after graduating college. "Since I had been freelancing for such a long time, the natural step was to establish something more permanent. I began to set up my freelance business as a design studio and started building a team, and when I did that, even bigger jobs came in, and the stigma thats usually attached to the word freelancer was gone."

9. Joy Gendusa, PostcardMania

As a freelancer, Gendusa wanted to print up postcards to market her services. A run-in with the printer gave her a clear direction for her business: When Gendusa got the proof back, the printer had listed his own phone number and name on the cards and was asking $50 to remove it. That was enough for Gendusa to set up shop in order offer businesses better services and marketing help — at least as far as postcards go.

10. Heather Whaling, Geben Communication

Whaling took on public relations, social media, and writing projects on a freelance basis before launching her own company. She had to start seeing herself as the client to really succeed with her business, says Whaling. "I knew it would be challenging going from being an employee to being an entrepreneur, so I wrote a marketing plan for myself, had a logo professionally designed, created a website, and implemented a 'launch strategy.' Basically, I tried to think about myself as a 'client' — how would I advise any other small business to go about launching itself? Looking back, I feel like taking this 'formal' approach to launching a company was invaluable. It helped me hit the ground running and secure new businesses far better than if I had just all of a sudden started calling myself a small business owner."