August 23, 2021 Genetically Unemployable: Mentorship & Collaboration Among Freelancers

On the Uprisor podcast, we like to look at all different perspectives when it comes to the freelance revolution and the future of work. This week, Topcoder’s VP of Marketing, Clinton Bonner, connects with Emily Leach, freelancer extraordinaire and founder of The Freelance Conference and Freelance Business Week.

She joins Uprisor to discuss the importance of mentorship, collaboration, and human connection among freelancers, and the most important skills freelancers need to be successful. Check out the full conversation and top takeaways from the episode.

Tethered to the Traditional — But Not Forever

What keeps people tethered to the traditional work environment? Emily believes the answer is multi-faceted. Although workplace stability is a primary factor, she thinks that fear also plays a key role. When she started freelancing over 30 years ago, there wasn’t even a name for the kind of labor she was providing; she was just someone working for a few different companies all at once. The path can be fraught with uncertainty, something Emily says people struggle to feel okay accepting.

Over time, freelancing has become more widely accepted and seen greater uptake from Millennials and Gen Z. COVID pushed many people out of their companies, forcing them to find other ways of supporting themselves and their families–and freelancing was often the solution.

Without diminishing the effect this sharp pivot had on peoples’ livelihoods, Emily suggests that it’s actually been an opportunity when viewed through the appropriate lens. She says the transition required individuals to dig deeper to figure out their marketable skills and develop those competencies into something tangible to work in a new way.

Pooling Resources: FreeCon

Next, Clinton and Emily address some of the best news in freelancing for those new to the workforce. In contrast to when Emily started out, freelancers today don’t have to go it alone. 

Emily created a private Facebook group in 2014 designed to help freelancers network. With rules prohibiting self-promotion and sales, the community has grown, sparked relationships, and helped those seeking work and looking for guidance running their businesses. As its popularity grew, Emily realized she wanted the opportunity to connect with other freelancers on an even larger stage. She took it upon herself (in true freelancer fashion) to create one. Enter: The Freelance Conference, and later, Freelance Business Week. 

Now in its seventh year, Emily says FreeCon will be virtual in 2021 with hybrid offerings in the future. The event “strives to find and solve the roadblocks that are holding freelance business owners back from success”, and features speakers and workshops tailored for the freelance community. 

Required Skills & Risky Labels

What are the top skills someone needs to freelance successfully? According to Emily:

  • You have to understand yourself 
  • Make your business your lifestyle
  • Know your boundaries
  • Develop relationships with people that do the same work as you at a different level–and lean on each other

Wrapping up, Clinton and Emily spend time dissecting the implications of the PRO Act on the freelancing community. As written, the bill would prevent independent contractors from engaging in work that has anything to do with a company’s primary business. This would fundamentally change the way that freelancers interact with larger organizations. The two agree that there’s not enough recognition of just how big the freelance element of the economy is in this country, and how much money flows through. The PRO Act is risky because it could bring that to halt.

Thank you to Emily Leach for sharing her take on all things freelancing. As always, check out the Uprisor podcast for more great conversations centering on the future of work. 

“Sometimes we feel like we need to have all the answers. It’s amazing to have a space where people can ask these vulnerable questions and get feedback.” —Emily Leach


Annika Nagy



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