As we wrap up our first incredible year of Breaking Solo, I wanted to pause and highlight something special — the four most-listened episodes of 2025.
These conversations stood out because they hit at the heart of what it means to build a business on your own terms: courage, clarity, reinvention, and the power of a single well-timed decision.
Whether you’re catching up or revisiting your favorites, these episodes deliver a dose of clarity, encouragement, and practical wisdom you can use right now as you build your own solopreneur journey.
Here are the Top 4 Breaking Solo Episodes of 2025 — and the biggest lesson from each:
🎧 Episode Highlight #1: Stephen Hart — Building Multiple Income Streams Before You Go Solo
Key Takeaway:
Stephen’s story is a masterclass in minimizing risk while stepping into entrepreneurship. He shared how diversifying income streams before leaving his corporate role gave him the safety, confidence, and momentum to hit four- and five-figure months within weeks of going full-time.
Why listeners loved it:
It’s honest, energizing, and full of practical examples of how to leverage your expertise to create offers people want — without burning out or starting from zero.
🎧 Episode Highlight #2: Jillian Anderson — Designing a Business & Life That Actually Fit
Key Takeaway:
Jillian reminded us that success doesn’t just come from business strategy — it comes from building a life that supports your energy, your family, and your long-term goals. Her gift is taking big visions and breaking them down into actionable, bite-sized benchmarks that make life and business feel doable.
Why listeners loved it:
She speaks directly to overwhelmed women balancing business, family, and personal wellbeing — and provides a roadmap for creating a life by design, not default.
🎧 Episode Highlight #3: Jonathan Sheeley — The Courage to Pivot and Start Again
Key Takeaway:
Jonathan’s career shift from higher education to solo marketing strategist is a powerful example of recognizing when something no longer fits — and making the leap anyway. His story reminds us that reinvention isn’t reckless. It’s sometimes the smartest (and fastest) way to build a career you actually enjoy.
Why listeners loved it:
It’s real, relatable, and a reminder that your skills are transferable — and your next chapter may be closer than you think.
🎧 Episode Highlight #4: Ryan Ware — Human Connection Still Wins in an AI-Driven World
Key Takeaway:
Even with the rise of AI, Ryan argues that nothing replaces human connection. His experience in change management shows that real transformation happens through relationships, trust, and watching how people respond — not through tools or tactics.
Why listeners loved it:
It’s a refreshing counterbalance to the AI buzz, and a reminder that technology is a tool — not the heart of your business.
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If you missed any of these episodes, now is the perfect time to dive in.
They’re packed with insights that will help you start stronger, think bigger, and grow confidently in 2026.
Thanks for listening, sharing, and being part of the Breaking Solo community.
More great conversations are on the way.
If you are a solopreneur or you were when you started your business, and you would like to be a guest on the podcast, here is the link to sign up.