What if losing almost all your freelance clients wasn’t the end of your business but the bridge to building a stronger one?
If you’ve ever wondered whether a setback means you’re not cut out for freelancing, it’s time to hear a different perspective.
After building up five retainer clients, my student watched his business shrink to just one client, and he had to return to corporate employment and rebuild his freelance business from the ground up. His experience shows what it can look like to keep moving forward when the market is uncertain and your confidence takes a hit.
By the end of this episode, you will:
Learn how to shift from treating freelancing like a side hustle to building it like a legitimate, sustainable business.
Discover why proactive marketing can create opportunities even when your existing clients disappear.
Gain practical insight into overcoming imposter syndrome and using setbacks as temporary bridges rather than permanent failures.
Play the episode now to hear how this student rebuilt his freelance business, overcame his doubts, and ultimately made the leap back to full-time freelancing.
Quick recap
Kiri conducted an interview with Gary, a student from her Flourishing Freelancer Program, to discuss Gary's journey from corporate employment back to full-time freelancing. Gary shared how he started freelancing during the pandemic in 2020, built his business over 4-5 years, and then faced significant challenges in early 2025 when economic instability caused his five retainer clients to drop to just one. Despite these struggles, Gary was able to rebuild his business and recently quit his corporate job after 9 months of proactive marketing efforts. Gary credited Kiri's program with helping him shift from a side-hustle mindset to treating freelancing as a legitimate business, particularly emphasizing the importance of proactive marketing and overcoming imposter syndrome. Kiri highlighted how Gary's experience demonstrates the value of looking at setbacks as temporary bridges rather than failures, and she discussed the structure of her coaching program including weekly group calls and one-on-one kickoff sessions. Podcast Episode Planning Discussion
Kiri and Gary discussed the structure and content of an upcoming podcast episode featuring Gary's story. They agreed to start with Gary's most recent freelancing experience and how it connected to Kiri's Flourishing Freelancer Program. Kiri suggested highlighting how she supported Gary during difficult times and framing setbacks as learning opportunities rather than failures. They also briefly discussed how to handle political references in the episode, with Gary agreeing to acknowledge current economic challenges while keeping the content focused on the story rather than politics.Corporate to Freelancing Career Transition
Kiri and Gary discussed Gary's journey from corporate employment to freelancing. Gary explained that he quit his corporate job after about six months of heavily pitching, starting in December and leaving in June, though they could potentially count from fall 2025. Kiri described how they first met through her Freelancer Corners monthly calls in 2023-2024, and Gary later became a founding member of Kiri's program in 2025. The conversation was cut off as Kiri was about to ask Gary to share his story.Freelancer's Journey and Challenges
Gary shared his freelancing journey, starting in 2020 during the pandemic when he had an opportunity to focus on building his business due to deferred mortgage payments. He grew his retainer clients to five by the end of 2024, but faced significant challenges in early 2025 when political instability caused his clients to drop off one by one, leaving him with only one retainer client by March. By summer, money was running out and Gary had to take on debt, ultimately deciding to return to an in-house marketing role as a temporary bridge while working to rebuild his freelancing business.Business Rebuilding Journey Discussion
Gary discussed his journey of rebuilding his business after going through a difficult period where he had to return to corporate work. He explained that he chose coaching because he recognized gaps in his business development skills that he couldn't identify on his own. Kiri emphasized the difference between running a freelance business and building a stable business, and shared that Gary's temporary return to corporate work was challenging for her as a coach, though she encouraged viewing it as a temporary bridge rather than a failure.Business Mindset Shift Success Story
Gary discussed how the coaching program helped him shift from a side hustle mindset to treating his consulting work as a legitimate business. He explained that through tactical actions and strategic implementation, his mindset evolved to see his work as a valuable business partnership rather than freelance work. When asked about the most successful framework or action step from the program, Gary indicated he would provide more details about specific tactics in response to Kiri's question, but emphasized that the combination of tactical execution and mindset shift was key to his progress.Overcoming Imposter Syndrome Through Marketing
Gary discussed how Kiri's program helped him overcome imposter syndrome and become more comfortable with personal marketing, particularly through proactive rather than reactive approaches. Gary shared his success story of using these techniques to quit his job and transition to freelance work, building relationships with new clients. Kiri announced that Gary would be conducting a workshop with her in the future to share his proactive marketing methods.Program Participant Success Interview
Kiri interviewed Gary, a program participant who successfully quit his corporate job three weeks ago using proactive business development methods. Gary recommended Kiri's coaching program for people seeking honest accountability and constructive feedback to build a viable freelance business, emphasizing the program's value in helping participants develop strong foundations including brand identity and core offers. Kiri outlined the program details including weekly group coaching calls, workshops, and a 90-minute kickoff session, and Gary agreed to promote an upcoming podcast episode scheduled for August 4th.