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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Ever feel like you're working harder but not necessarily smarter? In this candid conversation, Jess and Cindy pull back the curtain on the simple but game-changing strategies they use to stay productive, focused, and sane while building six-figure consulting businesses.
From Cindy's "CEO weeks" that give her massive chunks of uninterrupted deep work time to Jess's 90-minute screen detox that flattened her afternoon energy crashes, this episode is packed with practical hacks you can implement immediately.
Whether you're struggling with boundaries around your time, looking for ways to generate content ideas effortlessly, or just need permission to throw money at problems (hello, summer childcare!), this episode will give you the permission slip to experiment with what actually works for your life and business.
Highlights:
- Stop living in meetings if you want to grow your business. Cindy's CEO weeks—alternating between meeting-heavy weeks and deep work weeks—has been a game-changer for actually getting needle-moving work done
- The first 90 minutes of your day set the tone for everything. Jess's screen detox (no screens, no caffeine before food) eliminated her afternoon energy crashes and helped with adrenal fatigue
- Change your environment to change your energy. Sometimes the simple act of getting out of your house and walking to a different workspace can make you feel human again
- Your best business ideas won't come at your desk. Jess generates weeks of content ideas during weighted vest walks—combining exercise, inspiration, and productivity in one efficient package
- Throw money at the problems you can solve with money. From hiring summer babysitters to getting salads delivered, sometimes the best productivity hack is just paying someone else to handle it
Ready to try CEO weeks? Start with just one protected week and see what happens.
Resources Mentioned:
- Brick: https://getbrick.app/?srsltid=AfmBOoo4tU7sTn04-E9A8rU8cxTkCwCBZoPF5OLMltu9ysX44DM3F_Jc
- Diary of a CEO: https://www.youtube.com/TheDiaryOfACEO
- IFC Conference: https://www.resource-alliance.org/event/ifc-2025/
Find Us Online: https://www.confessionswithjessandcindy.com
Connect with Cindy:
Cindy Wagman Coaching: cindywagman.com
Fractional Fundraising Network: fractionalfundraising.co/
LinkedIn: ca.linkedin.com/in/cindywagman
Connect with Jess:
Out In the Boons: outintheboons.me
140 episodes
