How to Run Your Biz Without Hating Your Boss

Episode 5: Listener Questions and Stories Volume 1

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In this episode of How to Run Your Biz Without Hating Your Boss, Michelle and Sara do something a little different: they open the mailbag.

If you’ve ever reread an email five times before hitting send, replayed an awkward conversation in the shower, or laid awake wondering whether you handled a business situation wrong — this one’s for you.

Drawing on years of experience helping hundreds of performing arts entrepreneurs thrive professionally without sacrificing their values, peace, or creative integrity, Michelle and Sara tackle real-world scenarios that keep coaches, teachers, and performing artists up at night.

No gimmicks. No “just follow my simple formula.” Just grounded, hard-won insight from people who refuse to hang out on business-coach island.

Key Topics:

  • Common business situations that trigger second-guessing and stress
  • How to tell the difference between a real misstep and normal business discomfort
  • Why spiraling over emails, boundaries, and conversations is so common for creatives
  • How to approach tricky situations with clarity, confidence, and integrity

    • Perfect for:

    • Creative entrepreneurs and accidental business owners
    • Business owners in the performing arts or service-based sectors
    • Anyone navigating people-pleasing, boundaries, or hard conversations in their business

      • If you’ve ever wished for a trusted sounding board when business gets messy, this episode delivers exactly that.

      🎧 Press play and let’s get into it.

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      Website: thespeakeasycooperative.com/speakeasy

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      Instagram: @thespeakeasycooperative

      Mentioned in this episode:

      Crucial Conversations: Tools for Talking When Stakes Are High

      View on Bookshop.org

      Difficult Conversations: How to Discuss What Matters Most

      View on Bookshop.org

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      How to Run Your Biz Without Hating Your BossBy Michelle Markwart Deveaux