Entrepreneur Honestly: Honest Tips for Freelance Entrepreneurs

17: Journey to Six Figures: The Messy Middle (pt.2)

Anastasia Marie

Today is Part 2 of our Six Figure Series, I sit down again with my business besties, Laura and Andrea, to get real about the grind of building a business as female founders.

Check out Part One of Journey to Six Figures: What's Blocking You? 

What We Cover in This Episode:

  • The truth about imposter syndrome and money blocks when scaling past your first glass ceiling
  • Laura’s journey into UGC (user-generated content) and why it’s actually easier to charge what you’re worth when you’re having fun
  • Andrea’s story of hitting burnout, taking a month off, and completely rebranding her design studio
  • My own breakthroughs around hiring a VA, raising prices, and finally feeling confident in sales (plus the emotional crash I had before I got there)
  • Why stability in your first year as an entrepreneur is something to celebrate just as much as hitting six figures
  • The role subconscious blocks play in business growth and how to rewire them


 If you’re a small business owner or female founder chasing six figures, this episode will make you feel less alone. We’re not just talking highlight reels—we’re pulling back the curtain on what it actually looks like to be in the mud of entrepreneurship while still holding the vision of freedom, stability, and growth.

Meet the Guests:


 → If you’re building your own six-figure dream, screenshot this episode and tag us—we’d love to cheer you on.
 → Don’t forget to subscribe to Entrepreneur, Honestly so you don’t miss the next update in our six-figure journey.
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Keypoints: small business owner, six figures, entrepreneur, female founder

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This podcast is for new freelancers, aspiring entrepreneurs, service-based businesses, and independent contractors wanting mindset shifts, work freedom and client attraction. They deal with burnout, client management, imposter syndrome, pricing, inconsistent income, self-doubt.