10 September 2023

Season 4, Episode 8. Is Freelancing the Future of Work with Jason Montoya 

“If you're going into freelancing as a way to escape something that you don't like with what you're doing, you may discover that that same thing is in freelancing or entrepreneurship, and it sometimes may even be more severe." - Jason Montoya


Have you ever wondered if freelancing is the future of work? Clearly, the landscape of employment is evolving, and the world of freelancing is opening up opportunities for independence and flexibility that were once unheard of. In today’s episode Natalie Born welcomes Jason Montoya, where they explore the intricacies of freelancing and its growing prominence. Jason, a freelance consultant, author, and podcast host, shares his insights on how freelancing has become a viable career path, especially in the wake of recent global changes. He delves into his journey, from transitioning out of a marketing agency to embracing the freelance lifestyle, all while managing a family of seven.


Jason emphasizes the importance of being fully committed to freelancing, showcasing the achievements freelancers must accomplish for success. He unveils strategies for building a steady stream of paying clients, navigating the challenges of the freelancer-client relationship, and maintaining balance between work and personal life. 


Jason Scott Montoya grows small business owners, teams, and incomes around Atlanta, Georgia as a freelance consultant (since 2014). He's also the author of two books, one for aspiring freelancers (Path of the Freelancer) and another for striving small business owners (The Jump). On his blog and the Share Life podcast — JasonScottMontoya.com — Jason shares stories and systems to live better and work smarter. He also lives with his wonderful wife and five cherished children in Atlanta, Georgia (since 2005).


[00:00 - 14:34] Navigating the Freelance Journey

  • Freelancing's appeal lies in its flexibility and work-anywhere lifestyle, aligning with post-pandemic remote work trends.

  • Key freelance success factors include commitment, steady client acquisition, and efficient financial management.

  • Achieving the eight freelancing milestones, including securing paying clients and integrating personal and work lives, is crucial for sustained success.


[14:35 - 28:05] Exploring the Future of Work: Pros, Cons, and Collaborative Dynamics

  • The future of work is trending towards freelancing, with a projected majority of the workforce being self-employed, influenced by factors like social media and platforms like ChatGPT.

  • Freelancers should weigh pros and cons, recognizing that freelancing doesn't automatically guarantee freedom; it's important to align one's goals and approach with the desired outcomes.

  • Successful freelancer-client collaboration hinges on clear communication, shared processes, and understanding each other's needs, ensuring a smooth interface for productive partnerships.


Key Quote:

“Increasingly, the state of unemployment is self-employment.” – Jason Montoya

Connect with Jason Montoya


LinkedIn: https://www.linkedin.com/in/jasonscottmontoya/

Check out his webpage at: https://www.jasonscottmontoya.com/

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