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Episode 3: I’ll Take a Break When I’m Dead
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
View all episodes
By Michelle Markwart DeveauxEver 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