How To Become A Freelancer With Dorothy Hollabaugh


I’m joined by Dorothy Hollabaugh, the Co-Founder & CEO of The Gig, a digital media company that helps freelancers acquire and profit from high-income online skills. We discuss the number one thing that you can do to bridge a gap in your income, regardless of what’s coming up in your industry. She details through how to leverage your skills (or develop new ones) to get up and running as a freelancer. We dive into how to come up with your rate, where the biggest opportunities for online jobs are, and how exactly to land clients on sites like Upwork. There are so many ways to get scrappy and creative online, and I promise that the tools that Dorothy shares will give you the options and flexibility that you didn’t have during the ‘08/’09 recession. 

Episode Highlights:

( 1:15 ) Welcome back to The Chris Harder Show. Chris is joined by Dorothy Hollabaugh on today’s episode. 

( 5:09 ) Dorothy joins the conversation. 

( 6:36 ) Chris asks Dorothy, “Would you take us back to what you did, the fears you had? And were ran into a couple of hiccups?”

( 13:28 ) Chris asks Dorothy, “How are you feeling in the absolute depths of all of that?”

( 16:22 ) Chris asks Dorothy, “What is that thing that exists today that people could turn to back then?”

( 17:05 ) Chris asks Dorothy, “There’s a lot of things you can do to bridge the income gap so that you don’t have to feel the pain, regardless of what’s coming. You signed up for talking about that?”

( 19:33 ) Chris asks Dorothy to give an example of how a person transitions into freelancing. 

( 21:56 ) Chris asks Dorothy, “The Gig is probably the most popular daily newsletter for gig economy workers for freelance workers. By the way, shameless plug, where can people sign up for it?”

( 23:16 ) Chris asks Dorothy, “Would you talk us through how to get up and running start to finish?”

( 26:05 ) Chris asks Dorothy, “Could you give us a few more examples of what freelance opportunities are out there?”

( 28:10 ) Chris asks Dorothy, “When you say proximity to sale, you’re really saying, be as close to being the person who controls the yes or no with the customer as possible. Is that right?”

( 28:48 ) Chris asks Dorothy, “You said copywriting, or learning how to do paid ads or learning how to do sales, or other people that have high ticket things to sell or funnel building or graphic design. I don’t have any experience with those. So how do they learn that?”

( 30:25 ) Chris asks Dorothy, “So if someone’s like, Hey, I think the challenging economy is going to show up in a few months, could they learn this in 60 days enough to make some good money?”

( 32:02 ) Chris asks Dorothy, “So give us a couple more examples on how somebody could get up to speed real quick.”

( 33:43 ) Chris asks Dorothy, “How the hell do I get clients?”

( 35:32 ) Chris asks Dorothy, “Are there enough people on those platforms that go around for everyone?”

( 37:16 ) Chris asks Dorothy, “So you go on Upwork, you get some clients. How do you really turn it into an income producing machine?”

( 43:07 ) Chris asks Dorothy, “You could be like, Listen, I’m pretty new. I’m trying to build my portfolio. I would love to do this one for free because I think it’s a cool project. Like, how did they approach this?”

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You’re Going To Hear About:

  • The most challenging time Dorothy’s ever gone through as a business owner and how she moved through it 
  • Putting yourself in the position to gain experience working on real projects
  • Simple things that you can do to immediately set yourself apart in the freelancer market 
  • Developing your network of freelancers with people who have similar and complementary skill sets 
  • Cultivating confidence and belief in yourself as a freelancer
  • The power of spending an hour a day in deep study on your skill

Resources Mentioned:

  • Get FREE access to “How to Win Clients on Upwork in 5 Simple Steps” ($47 value) at
  • If you’re going to make more than $500,000 next year, apply for next year’s Elite Mastermind at
  • Text DAILY to 310-421-0416 to get daily Money Mantras or Business Perspective messages to boost your day.