The Design Business Show 168: Thriving as a Freelancer While Working Remotely with Craig Cannings

Director : Melissa Burkheimer | December 21, 2021
Check out episode 168 of The Design Business Show with Craig Cannings to learn all about Freelance University and working remotely!

Craig Cannings is the co-founder of Freelance University with his wife, Kelly. Craig has had the privilege of helping over 20,000 students in 75 countries realize their dreams of launching a portable, freelance business (and lifestyle). He has enjoyed the great freedom of working from home and traveling abroad while raising 5 wonderful daughters.

Here’s what we covered on the episode:

The Launch of Freelance University

  • Craig’s background is in psychology and he was a counselor for a few years before making a pivot and joining his brother in-law who started a software company in 2003
  • In 24 months the business onboarded 40 people – Craig shares that his job was to train every new freelancer and person working with their remote software company
  • How craig realized his talent and enjoyment for training/teaching people which led him and his wife, Kelly to launch Freelance University in 2008
  • Freelance University was launched to train freelancers in multiple different skill areas so they could start their own portable, flexible business
  • The story of how Craig and Kelly were able to onboard their first 7 students into their course by running a small Google Ad and hosting a free teleseminar
  • When they first launched Freelance University, they had 1 course, now they offer 80 courses and have multiple tracks and instructors
  • Craig explains how slow the onboarding process was back in 2003 while working remotely
  • When Craig was freelancing his niche was called web based marketing (now digital marketing) and was doing affiliate marketing, paid advertising, SEO and business development
  • As Craig moved into the University, he got more involved and was freelancing in course design and curation for clients in addition to creating his own
  • Craig says, because there are so many different opportunities in freelancing, where you start is not necessarily going to be where you end up

Offerings at Freelance University

  • Running a business from home while raising kids and homeschooling them requires a lot of thought and strategy, Craig says but explains that he and Kelly were very disciplined with the free time they had and built effective systems over time
  • At the University, they do a lot of the business startup training such as setting up your virtual office, figuring out what your website will look like, your niche, what service you’ll offer, etc.
  • Once people finish up the startup training at the University, they go into 1 of their 8 core tracks like, social media management, digital marketing, copywriting, web design, etc. where the University then gives them the technical skills they need to provide these services
  • Once someone has been certified, the next step is joining the job directory at the University to get plugged in with potential clients
  • On their website, you can find people by searching for what service you need, for example if you need someone to help you with social media management, or you can send a job posting to the board
  • When the University first started, they were offering a la carte courses but about 5 years ago they made the decision to put everything under one hood and turn it into an education based membership, where people can buy annually or monthly and get access to all 80 courses, all 8 tracks, mentorship, the job board and community
  • How Freelance University created, Eight Ways to Thrive While Working at Home as a Freelancer because they saw an increase of remote working after the Covid-19 pandemic – Craig says working from home is skill that can be learned if you want to make it work

Adding Structure + Tools to Your Remote Working Lifestyle

  • Freelancing can make it seem like you’re free from a boss, dress codes, and a work commute but Craig says you still need to have some form of structure
  • Craig explains the importance of building a work schedule to keep yourself on track, having rituals in your day so your work and personal lives don’t become too mixed, and guarding your technology so you’re not constantly on it during your personal time
  • One important tool Craig suggests using when working remotely is a PM app (Project Management App) he shares different PM apps like, Trello, Asana, and ClickUp and says they are great for laying out your schedule
  • If you’re in the freelance space, Craig highly encourages you to get a client management app to create a seamless onboarding process and touches on all the built-in tools they offer for your convenience
  • You might also want to consider using a time management app to help you track your time, or a password management tool that allow you to never forget a password

Popular Niches in Freelancing + Tips for Building Your Business

  • When picking a niche, Craig says to look at what’s going on in the marketplace because you never want to train in an area that no one is hiring in
  • Some popular niches in freelancing are currently, digital marketing, social media management, ad management, copywriting, virtual and digital media space management, virtual assistants, or any technical skill like graphic design.
  • On the Freelance University website they have a free guide, Discover 21 In-Demand Freelance Services to Offer in 2021 to help you find a niche that might be a good fit for you
  • Craig explains that it’s important to understand that you’re not going to build a thriving, full-time business overnight, you will probably have a full-time or part-time job while you’re side hustling, then through babysteps your side hustle will eventually become your full-time business
  • When things aren’t working out in your business, like not hitting your expenses for example, Craig says it’s important to evaluate your business and see if you can reduce your expenses temporarily or see if there’s a free app you can use instead of the paid app you might be subscribing to
  • Craig shares that it’s important to block off time for marketing each week, whether that’s reaching out to potential clients or networking because it’s going to make you more visible which will lead to more potential clients
  • At Freelance University, they have an area called The Client Training Center which includes 9 courses that teach students how to network, make digital cold calls, set up a client-friendly website, etc.
  • If you are someone who is interested in working for yourself, Craig encourages    you to pursue freelancing because the industry is blowing up – don’t miss the opportunity
  • Go to the Freelance University website to learn more and check out the FreeU Blog or Freelance Podclass 


Links mentioned:

Freelance University

Eight Ways to Thrive While Working at Home as a Freelancer

Discover 21 In-Demand Freelance Services to Offer in 2021

FreeU Blog 

Freelance Podclass 


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