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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Connect with us:

Website: thespeakeasycooperative.com/speakeasy Facebook: facebook.com/thespeakeasycooperative 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