From Slinging Words to Selling Expertise: A 1 on 1 Coaching Case Study with Josh Monen

From Slinging Words to Selling Expertise: A 1 on 1 Coaching Case Study with Josh Monen

Author: Austin L. Church August 8, 2025 Duration: 34:44

What if you feel stuck not because you lack skill but because you’ve snapped on a pair of golden handcuffs? What if you want to go a new direction but can’t afford to lose the retainers you finally stacked up? 

This new Freelance Cake episode with Josh Monen is the first one to drop in over 18 months, and I can’t wait for you to check it out.

In it, Josh Monen opens up about his transition from senior copywriter who was booked out but working way too much to fractional CMO with productized offers, more time off, and a business closely aligned to the life he wants.

Josh didn’t need more clients. He needed different ones. He didn’t need more ideas. He needed a clear roadmap with action steps he could put in his calendar. During our one-on-one coaching engagement, Josh put in the work.

Listen to the full conversation.


Key Points

  • Booked out, but stuck: Josh was making good money and fully booked, but felt directionless and burnt out. He didn’t need more clients — he needed clarity. 
  • Desire for leverage: He wanted to evolve from copywriting into productized services, consulting, and fractional CMO work to create more time freedom. 
  • Indecision as the real bottleneck: His core problem wasn’t lack of opportunity — it was overthinking and analysis paralysis. Coaching helped him move from ideas to decisions. 
  • Created two scalable offers: Through coaching, Josh developed Funnel Insights and Funnel Blueprint — strategy-first services that led to $30K+ client engagements.
  • From executor to advisor: By leading with strategy and positioning himself as a fractional CMO, Josh changed how clients viewed and engaged him. 
  • Lifestyle improvements: He now protects weekends, takes unplugged vacations, and feels more aligned with the freedom-focused business he originally wanted. 
  • Real ROI from discomfort: Investing in coaching created “point-of-no-return” momentum and helped him stretch into higher-leverage work.


Notable Quotes

“I was booked solid with copywriting and making good, consistent income — but more of my thing was like, ‘Where am I going with this?’ I felt like I kind of plateaued and was in maintenance mode.”

“If you’re making good money but don’t have time to enjoy it — what’s the point?”

“From that very first call, I was blown away. I even told my wife — ‘This guy really listens.’ And that’s rare. That’s one reason I hired you.”


Resources Mentioned

  • Book a strategy call with Austin: https://bit.ly/1-on-1-coaching-pod
  • Austin Church on How and Why to Sell Strategy Engagements to Your Clients [Ed Gandia podcast]: https://b2blauncher.com/episode267/

Josh Links

Listen, rate, and subscribe!

For specific beliefs, principles, and practices you can use right away to make the freelance game more profitable and satisfying, subscribe to Freelance Cake podcast on Apple Podcasts or wherever you listen to podcasts!


Austin L. Church hosts Freelance Cake, a resource built for independent professionals who are tired of the hustle-for-every-dollar grind. The focus here is on sustainable strategy over shortcuts, exploring the underlying mindsets and operational habits that actually create leverage in a solo business. Instead of fleeting trends, each conversation delivers practical, timeless ideas designed to increase both your income and your satisfaction with the freelance life. You'll hear clear discussions on setting boundaries, pricing with confidence, and streamlining client work-all aimed at reducing unnecessary effort while improving outcomes. This isn't about working harder; it's about working smarter, with a focus on principles that remain relevant no matter how the market shifts. Tune into this podcast for straightforward advice that helps you build a practice that feels less like a constant scramble and more like a deliberate, rewarding craft.
Author: Language: English Episodes: 21

Freelance Cake
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