Business Basics

9 Lessons Freelancers Can Learn From Successful Entrepreneurs

Use the advice from these small-business owners to boost your freelance career

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Yes, you’re a writer. But you’re also a business, and the sooner you start treating yourself that way, the more profitable you’ll be. Need a nudge? We asked crazy-successful entrepreneurs to open up about what they’ve learned since day one. Use their lessons as a kick in the pants, as a reminder that it does get better, and as an affirmation that you’ve totally got this.

1. Slow down.

Starting your own business, whether you’re a sole proprietor or a corporation, is a marathon, not a sprint, says Beerud Sheth, CEO of Teamchat and Webaroo and founder of freelance network Elance (now Upwork). “Sprinting can lead to mental and physical burnout,” he adds. “Pacing yourself well is critical to success.”

2. There will never be a perfect time. 

“The best advice I can give is to start today. Start before you’re ready, because you’ll never be ready,” advises former network news journalist Carlota Zimmerman. Now, Zimmerman is a coach for other small-business owners, but she wasted years worrying whether someone like her, with zero business background, could launch a successful startup.

“I was terrified of not knowing all the answers,” like should she become an LLC or how she would pay her taxes. “The search for perfection is a huge waste of time,” she says.

3. The more the criticism hurts, the more it has the potential to help.

Former architect Lori Cheek thought Shark Tank would be the perfect launch pad for Cheekd, her dating startup. However, she ended up not with a deal, but with some biting criticism from the sharks. Though Cheek was tempted to lick her wounds, “I heard what they said and decided to make a change,” she says.

A month later, she and her partner had pivoted the platform—and were pulling in more money than she’d asked the sharks for originally.

4. Understand the upside of a quick “no, thank you.”

Pitching magazines might feel different than working retail, but this doesn’t mean there aren’t similarities. Just like with that pair of jeans that keeps making the circuit from dressing room to sales floor, “not every idea is right for every individual,” Sheth advises. “I’d rather get a rejection quickly, save time and focus on real prospects.”

5. Pass on projects that aren’t a good fit for you.

It’s the first thing Melissa Dowler, co-owner of Long Haul Films, wishes she’d learned when she made the move from an advertising agency to her side-hustle production company.

“You have limited time and resources, and you want to spend that time working on projects that are most aligned with your vision and goals,” Dowler explains. “For a long time, we said ‘yes’ to opportunities even if we didn’t feel the fit was completely right. Trust your instincts.”

6. Learn how to juggle the roles of CEO, CFO and COO.

CEOs, CFOs and COOs run businesses, including the not-so-fun parts, like managing clients and projects, sending out and following up on invoices and seeing to it that your insurance premiums are paid and your taxes are filed on time.

Joe Koller, founder and CEO of digital media firm Slot Right, was astonished by the number of hats his startup supplied him with. “The key,” he says, “was to figure out a disciplined schedule which you need to stick to day to day and focus on the bottom line.”

7. Don’t be precious.

Ellen Jovin, who co-owns her communication skills training business, Syntaxis with her husband, emphasizes the importance of the hustle. It’s not enough to get out there and sell; you have to “get off your behind and think about what the customer needs and values,” she says.

“Audience awareness is key. This is about getting a job done for someone else who is not you and who does not care that you know what a participle is or that you think ‘incentivize’ should not be a word.”

8. Hit up industry alpha dogs.

A year ago, personal branding and online business strategist Kimra Luna was, she says, a digital nobody. She’s since taken her business from $0 to $1 million, but back then, she had no business acumen and no connections—and she was terrified to talk to people who did.

“Connecting with influencers who I admire and look up to has turned out to be way easier than I ever thought it could be,” she shares. “It turns out most people are totally open to hanging out with the new kid on the block once you’ve shown you’ve got chops for business.”

9. Think about the big picture.

It’s easy to think about what you want to do, career-wise. But what do you want your entire life to look like, now and decades from now? These are the questions Matt Urmy, CEO of Artist Growth, a music industry startup that builds data collection tools for artists, wants you to ask.

“Once you understand what you want your life to look like,” he explains, “you can begin the process of building the roadmap to get there. Then it just becomes a question of how badly you want it. If you want it badly enough, you’ll get it done.”

 

Topics:

Business Basics, Go Freelance