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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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In this episode of The Messy Middle Matters, Indra sits down with Juleen Mahabeer-Jackson to explore what it really feels like to be at a career crossroads. From packing up her life (and two cats!) to drive across the country, to rethinking what success looks like beyond job titles, Juleen shares her story of stepping outside her comfort zone and learning to trust herself. Together, Indra and Juleen unpack the tension between chasing external validation and building a life that feels authentic, sustainable, and joyful. They also reflect on the pressure of “picking your struggle,” filling your own cup, and how content creation can be both a tool for clarity and a leap of faith in itself. If you’ve ever wondered whether to keep climbing the ladder or carve your own path, this conversation is for you.
Useful Links:
- The Messy Middle Matters Merch: shop.themessymiddlematters.com
- The Messy Middle Matters Glossary: messymiddlematters.com/glossary
- Feedback for The Messy Middle Matters: messymiddlematters.com/feedback
- Juleen Mahabeer-Jackson on LinkedIn: https://www.linkedin.com/in/juleenbean/
- Indra Klavins on LinkedIn: https://www.linkedin.com/in/indrak/
34 episodes
