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Ruulmates on the mic: Meet Craig Cannings from FreeU

Işınsu Unaran
December 20, 2022

Running a solo business can be a bumpy ride, but with the right tools and resources you can smoothen your path. Freelancer communities are great hubs for learning, sharing, and networking. Today, we bring you an insightful conversation with Craig Cannings, the co-founder of Freelance University; an online learning platform Ruul has recently partnered with, aimed to teach freelancers the ins and outs of the industry, like how to get clients, which skills to improve to raise your rates, and more. After 20 years of freelancing professionally, Craig and his wife are currently living the “laptop lifestyle” in Canada with their five amazing daughters.Continue reading to learn about how the platform started out, what it entails for freelancers and Craig’s take on the current landscape and the future of freelancing. Welcome to Ruul Blog, Craig. We’re happy to host you. Can you tell us a little bit about yourself? What was your career like before founding Freelance University?While I have enjoyed a remote, freelance lifestyle for the past 20 years, this was actually not my first career! I originally studied Counseling Psychology in University and worked as a Counselor for 7 years, prior to making the shift to freelancing. In 2003, I faced a big fork in the road with one direction continuing in the counseling profession and the other one leading to a freelance contract with a software education start-up!As the poet Robert Frost one said, “Two roads diverged in a wood and I took the one less traveled by. And it has made all the difference!”I chose the freelance path and it has truly made all the difference in my life, more than I could have ever imagined.What made you finally take the leap and start Freelance University?My wife and I had a freelance contract in a remote, fast-growth software start-up company. In the first couple years, we went from a small but mighty team to hiring over 40 freelancers in a variety of areas.One of my roles was to train and onboard new contractors, so I would create guides, short tutorials and do live training. I realized that I had a knack and an emerging passion for training, which was the starting point for the idea of Freelance University.Since we had to learn freelancing the hard way on our own, we wanted to create a supportive learning platform where new and experienced freelancers could come to sharpen their skills and get the help they needed to grow their businesses.Tell us more about Freelance University: Is it only for beginners? Freelance University is a one-stop learning hub for new and existing freelancers to sharpen their technical skills in order to offer high value, in-demand services to clients. Freelancers also have the opportunity to get connected with business savvy mentors who can help them overcome any specific challenge they are experiencing in their business. For a low-cost annual or monthly membership, students get unlimited access to:

  • 80+ skill-based certifications and courses across many popular training pathways including social media, online business management, digital marketing, writing & editing, digital media & events, graphic design, virtual administration, and technology support.
  • Monthly, live, skill-building workshops on topics that are important to a freelancer’s business
  • Regular live Q&A and small-group mastermind sessions to help you work through and overcome challenges.
  • Professional certifications to showcase ongoing professional development in LinkedIn and on website
  • Practical software training that features timely and relevant tutorials on the technology you need to know right now!
  • Job board and Professional Freelance Directory to access some amazing client opportunities!

When you founded Freelance University in 2008, it was a very different time–freelancing wasn’t as popular as it is today. How did you see the landscape of freelancing evolve before the COVID-19 pandemic?Since we started teaching freelancers, the industry has seen strong, steady growth with so many businesses and entrepreneurs recognizing the value of hiring a lean team of talented freelancers over getting offices with full-time employees and all the expenses that go along with that. The laptop lifestyle also became a thing after the dotcom boom which only fueled the freelancing industry.What kind of changes in freelancing did you observe since the start of the pandemic?The world literally went remote during the pandemic with many companies choosing to have a full or partial remote workforce. This remote work revolution has only increased business owner’s interest in working with talented freelancers. Plus with a looming recession, businesses will need to tighten their purse strings, which means freelancers will continue to offer a cost-effective alternative over hiring employees. What do you think makes freelancing such a desirable option for so many today?Many people want more FREEDOM in their lives… the freedom of time, money and location. They want to be able to work on their own terms with clients they love at the rate they deserve and from anywhere they choose! This desire for freedom and flexibility is driving the massive growth in new freelancers joining the ranks!No matter how enticing it is, freelancing has its own difficulties. What do you think professionals should consider before starting freelance work?Yes, becoming a freelancer or starting any business can be challenging with a lot of unknowns. So, a couple things to consider to ensure freelancing is a good fit…

  • You need to be comfortable working in a flexible environment from home (or anywhere you choose)
  • You need to set some structure and a schedule in your day to ensure you are getting things done and not wasting time on trivial things.
  • It is important to be intentional about setting boundaries with your work time and personal time, in order to grow your freelance business in a healthy way.
  • You need to have the right systems in place in order to organize your work and effectively onboard clients.
  • You should be willing to learn new things in order to further your opportunities.

Do you think freelancing will become easier with time? How about market saturation?As long as you are committed to learning new skills and staying in touch with what your clients need, you will continue to find great income opportunities.There are lots of freelancers joining the ranks, so it is important to carve out a distinctive brand and discover your ideal niche audience you would like to target. Your brand, unique services and target client audience can really distinguish yourself from the pack.Finally, what are your suggestions for freelancers who want to grow their solo business and stand out from others?As mentioned, you need to discover your ideal niche service and audience to target. For example; if you are the definitely ghost writer to celebrity chef recipe books, this unique niche will make you very marketable with a specific audience. So, the more you can determine your distinct benefit to a specific client group, the more you will stand out from the rest!

Don’t be afraid to take the leap

We thank Craig and his wife for agreeing to give an interview to Ruul, and wish them the best on their journey to educate the future on the lifestyle and business of freelancing. We are always searching for voices to amplify on our blog! Do you have a story to share about the modern work landscape and tips about the new rules of the game? Maybe even some “don’t”s you had to learn the hard way? Get in contact with us at and join us for an interview!


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