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4 Simple Mistakes That Can Crush Your Creative Side Hustle, From an Expert Who Raised $45 Million to Support Independent Workers Ben Huffman, CEO and co-founder of Contra, became a "power user" on Elance and Odesk (now Upwork) and realized freelancers needed more support.

By Amanda Breen

Key Takeaways

  • Huffman built Contra to address the pain points that can make or break any freelancer's success.
  • Huffman also shares four common mistakes that can derail an independent worker's business.
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Ben Huffman, CEO and co-founder of Contra, knows what it takes to run a successful freelancing side hustle. Huffman got firsthand experience in the freelancing space as a music producer, working with small labels and, ultimately, Sony Music. The work was fun but "didn't pay well," he tells Entrepreneur, so he started designing apps, pitch decks and websites. Huffman became a "power user" on Elance and Odesk, which would merge to become Upwork, and soon "became fascinated" with the idea of building a team globally.

Image Credit: Courtesy of Contra. Ben Huffman.

"I would find projects locally in New York and then hire freelancers from all over the world to help me with the skills I didn't have," Huffman recalls. "I loved the freedom and autonomy of working independently, but even more, I loved working with people from different cultures and backgrounds. Early on, I realized the flaws in the business models of the platforms I used."

The world was becoming more connected, Huffman explains, and the "take-rate model" eBay brought to the fore "didn't make sense for people and working relationships," especially as workers increasingly sought flexibility and employers needed more niche skills. So Huffman set out to create a platform that could address those pain points, and after interviewing thousands of independent workers, discovered they need to think about three things to be successful: creating their identity and credibility, managing their business and finding new leads. Contra, which has raised $45 million from venture capital firms, provides support in all of those areas.

Related: How to Start a Freelance Writing Side Hustle

"Contra is commission-free, so our users can keep 100% of their earnings."

"Independent workers can create a profile that showcases their skills and what they can actually do instead of their roles at past companies," Huffman says. "Focusing on projects and skills allows independents to highlight the specific problems they've solved and the value they've delivered. Independents can find new projects from high-quality, vetted clients, manage their business with our free invoices, contracts and proposals, and, most importantly, they can get paid. Contra is commission-free, so our users can keep 100% of their earnings."

Nowadays, nearly two in five U.S. adults have a side hustle, and one in three of them say they use their side hustle earnings to cover everyday expenses, according to a Bankrate survey. Freelance projects can be an accessible, flexible option for people hoping to capitalize on their skill sets, but the most successful will be those who avoid the common pitfalls of the job.

Related: 10 of the Most Profitable Side Hustles You Can Start With Little or No Money

Huffman shares four mistakes that could hinder any side-hustler's success:

1. Underpricing your services to attract your first clients

"Going down this route can devalue your work," Huffman explains, "and make raising prices much more challenging in the future. Before solidifying your prices, get to know the market you're entering, track industry rates, consider your years of experience and outline your unique expertise; these variables will help you determine a price that works for you and your clients."

2. Not prioritizing your projects the right way

"It's important to prioritize projects that fully align with your skill set and politely turn down projects that could be a better fit with someone else," Huffman says. "While many first-time freelancers may regret turning down new projects, taking on too much work can often lead to being overwhelmed and subpar work."

3. Not learning new in-demand skills

"Right now, we are seeing a ton of demand for skills like Framer for building websites, video animation and social media management," Huffman says. "There is also a huge opportunity to upskill in the latest AI tools. So much of the world of work is changing because of AI, and there is a huge opportunity to get ahead of it all."

Related: The Skills Gap Is Rapidly Widening — Here's What We Must Do To Close It.

4. Not going the extra mile for your clients

"Going above and beyond with clients can lead to referrals, more projects in the future and a reputation that will help you build longer-lasting relationships," Huffman says. "To set up any project for success, you will want a well-scoped out set of deliverables and project timeline. Once you have this, you should get everything put into a contract so that you have a framework for your agreement and protection if things get off track."

And one last piece of advice for side hustle success? While growing your network of clients is important, don't forget to cultivate a network of other independent consultants, too. "Having a community of fellow freelancers to bounce ideas off of and get advice from is invaluable and can lead to new leads in the future," Huffman says.

Amanda Breen

Entrepreneur Staff

Senior Features Writer

Amanda Breen is a senior features writer at She is a graduate of Barnard College and received an MFA in writing at Columbia University, where she was a news fellow for the School of the Arts.

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