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.

👉 Subscribe so you never miss an episode. 👉 Leave a review on Apple Podcasts or Spotify — it helps more creative entrepreneurs find us. 👉 Share this episode with a friend or colleague who might be struggling with scaling pressure.

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

Have you ever asked the question “Why the Hell Would I Need a Business Coach Anyway?” In this episode of How to Run Your Biz Without Hating Your Boss, Michelle and Sara tackle the question many creative entrepreneurs secretly ask but rarely say out loud.

Whether you’re coach-curious, coach-skeptical, or convinced you’re doing just fine on your own (…maybe), this episode is for you. With their signature mix of humor, honesty, and hard-earned expertise, Michelle and Sara break down what coaching actually is, who it helps, how to know if you’re ready, and why it’s one of the most transformational relationships a business owner can invest in.

-Why creative entrepreneurs often avoid coaching (and what they’re missing) -The difference between coaching, consulting, and just signing up for another course -What a great coach does — and doesn’t do -How coaching can protect your values, your peace, and your creative energy -Real talk about cost, timing, fit, and the “am I broken?” fear

Perfect for: creative entrepreneurs, business owners, and performing arts professionals who know they need support but (maybe) don’t want to admit it.

So, if you’ve ever stared into the mirror at the “boss” making all these decisions and wished you had some support, guidance, or just someone to help you stop self-sabotaging — grab your coffee, tea, or whatever helps you deal with your business-induced anxiety and settle in.

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

Joe Rohde (Wikipedia)

Ever feel like your boss never lets you take a break… even though you are the boss?

In this episode, Michelle and Sara dive into why creative entrepreneurs and self-employed folks are notoriously bad at resting — and what to do about it.

They explore the messy truth behind hustle culture, guilt-driven productivity, and the myth that rest is a reward instead of a right. Expect real talk, humor, and actionable “thinky-thinks” to help you stop running your business into the ground and start finding peace, presence, and grace for yourself.

Key Topics: - Why self-employed people are terrible at taking time off - How internalized “bad boss” habits drain creativity - Mindset shifts and strategies to reduce exhaustion - Practical ways to build rest into your work life - Learning to love your boss (you) again

Perfect for: creative entrepreneurs, coaches, and performing arts professionals who feel overworked, overwhelmed, and overdue for a break.

☕ Grab your coffee (or whatever helps you cope) — it’s time to talk about real rest.

Links you're gonna want: 7 Types of Rest — YouTube video with Saundra Dalton-Smith 7 Types of Rest PDF — by Dr. Sarah Ropp Book: Rest is Resistance: A Manifesto by Tricia Hersey

If you enjoyed today’s episode, here’s how you can support the show: 👉 Subscribe so you never miss an episode. 👉 Leave a review on Apple Podcasts or Spotify — it helps more creative entrepreneurs find us. 👉 Share this episode with a friend or colleague who might be struggling with scaling pressure.

Connect with us: Website: thespeakeasycooperative.com/speakeasy Facebook: facebook.com/thespeakeasycooperative Instagram: @thespeakeasycooperative