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

• Josh’s podcast, The Way Of Kings: https://podcasts.apple.com/us/podcast/the-way-of-kings/id1743034411
• Website: www.JoshuaMonen.com
• X: @JoshMonen

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!

In this episode, Austin L. Church talks to journalist, freelance writer, and coach Wudan Yan about the art of negotiation. The driving force behind The Writers' Co-op, Wudan tells the story of her transition from journalism to freelance narrative writing and sheds light on the two different cultures with their sets of norms.

Wudan goes on to share how her upbringing and academic background provided very little preparation for the freelance world where negotiation is often necessary.

When teaching freelancers and consultants how to negotiate, Wudan frames back-and-forth as a dialogue or conversation, not a confrontation.

Her personal journey and insights prove that negotiation can be a fulfilling and rewarding aspect of the freelance journey, even if it doesn’t come naturally to you.

If you’ve ever felt uncomfortable during a negotiation or felt like your skills are lacking, you’ll be glad you found this episode.

Key points

• Wudan’s Journey from Science to Narrative Writing (01:53)
• Negotiating a raise for the first time (17:44)
• Wudan's negotiation journey montage (25:37)
• Negotiating rush projects and rush fees (25:51)
• The importance of a conversational approach in negotiations (28:43)
• One simple yet profound tactic to become a master negotiator (36:58)

Notable Quotes

• “You're never going to get what you don't ask for, and you can never get more than the maximum of what you're asking for."
• "Negotiating is a conversation. If both you and I are setting really hard boundaries around things, there's no meeting in between."
• "Ask questions that invite a response.”

Resources & Links

• Business Redesign Group Coaching Program
• $300K Flywheel for Freelancers & Consultants
• The Writers' Co-op
• Jim Dethmer: Leading Above the Line
• Connect with Wudan Yan on Instagram and LinkedIn

This episode of Freelance Cake is brought to you by CrowdHealth

Healthcare in the US is complicated, confusing, and highly personal. Insurance premiums, deductibles, and copays can get really expensive, especially for freelancers and consultants who don’t have an employer paying for anything. Over the last 7 years, my family has saved $60,000+ in premiums, deductibles, and other out-of-pocket medical expenses that we would have paid with our previous insurance policy. Healthcare crowdfunding has been a game changer for us. If you live in the U.S. and you haven’t already explored what CrowdHealth has to offer, take the time to educate yourself. And if you decide you want to give them a try, go to www.joincrowdhealth.com. You can use promo code FREELANCECAKE during sign-up to save $99 per month for 3 months.

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!

In this continuation of “The 4 Stages of Freelancing,” Austin L. Church explores the last two stages: Lifestyler and Diversifier. After they’ve navigated through the Moonlighter and Hustler phases, freelancers reach a level of maturity where challenges become more complex. Meanwhile, opportunities for growth and personal fulfillment expand.

Austin highlights the motivations, challenges, mistakes, and questions at each stage, as well as the key breakthroughs and financial goals.

Are you a Lifestyler eager to earn the same or more while working less? Or are you a Diversifier interested in creating new revenue streams?

Regardless, this episode will help you figure out where you currently are in your journey and what to focus on next.

Key points

• Lifestylers overview (01:53)
• The motivations for Lifestylers (04:35)
• The mistakes for Lifestylers (05:27)
• The questions for Lifestylers (07:23)
• The main breakthrough for Lifestylers (7:56)
• The main financial goal for Lifestylers (08:16)
• Diversifiers overview (10:35)
• The motivations for Diversifiers (12:35)
• The challenges for Diversifiers (13:49)
• The questions for Diversifiers (17:07)
• The main breakthrough for Diversifiers (17:46)
• The main financial goal for Diversifiers (18:08)

Notable Quotes

• "We freelancers and consultants can get so fixated on winning the next project, staying ahead of bills, and achieving financial stability that we inadvertently become creative workaholics."
• "The last thing any freelancer should do, any consultant should do is blindly copy someone else."

Resources

• Listen to The 4 Stages of Freelancing Explained | Part 1
• Read the full post here
• Business Redesign Group Coaching Program
• $300K Flywheel for Freelancers & Consultants
• The Ladders of Wealth Creation: A Step-by-Step Roadmap to Building Wealth

This episode of Freelance Cake is brought to you by CrowdHealth

Healthcare in the US is complicated, confusing, and highly personal. Insurance premiums, deductibles, and copays can get really expensive, especially for freelancers and consultants who don’t have an employer paying for anything. Over the last 7 years, my family has saved $60,000+ in premiums, deductibles, and other out-of-pocket medical expenses that we would have paid with our previous insurance policy. Healthcare crowdfunding has been a game changer for us. If you live in the U.S. and you haven’t already explored what CrowdHealth has to offer, take the time to educate yourself. And if you decide you want to give them a try, go to www.joincrowdhealth.com. You can use promo code FREELANCECAKE during sign-up to save $99 per month for 3 months.

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!