Working through awkwardness

What if the very thing keeping you from deep, meaningful friendships is the fear of being your true, imperfect self? 

This week Michael sits down with Jess Johnston for a chat about authenticity, friendship, and overcoming the fear of rejection. They dive into themes for her book, Perfect Is Boring (and It Tastes Like Kale): Finding Belonging and Purpose Without Changing Who You Are, which offers a refreshing take on embracing who you are while finding your place in the world. 

Together, they explore the ups and downs of adult friendships, including letting down your guard to create real bonds. Jess’s relatable stories and practical tips make it easy to see how consistency, courage, and even a little awkwardness can lead to meaningful relationships.

If you’ve ever felt like perfection gets in the way of connection, this conversation is perfect for you.

• Jess’ off-grid childhood that sparked her love for writing and how those experiences shaped her perspective on connection
• The tension between performance and authenticity in your friendships and the courage to be rea
• What are the profound differences between belonging and fitting in?
• What does it really mean to be authentic?
• Awkward moments forge deeper connections—why embracing imperfection matters in your relationships and life
• The surprising power of intentionality and courage in building your adult friendships
• Why the fear of rejection is key to building meaningful friendships

• Book: Perfect Is Boring (and It Tastes Like Kale): Finding Belonging and Purpose Without Changing Who You Are: https://bookshop.org/a/30734/9780593728246
• Instagram: https://www.instagram.com/jessmariejohnston/
• Facebook: https://www.facebook.com/jessjohnstonwonderoak/
• Website: https://wonderoak.com/

Jess Johnston lives in Southern California with her husband and four kids, who are the loves of her life. She is an Enneagram Seven and is enthusiastic about everything—but especially people, travel, and sauces. Jess’s writing makes you feel like you’re sitting cross-legged on her couch in your cozy pants while sharing hearts and drinking coffee. She is the co-author of the Wall Street Journal bestseller I’ll Be There (But I’ll Be Wearing Sweatpants) and has been a top contributor to publications such as HuffPost, Scary Mommy, and Motherly.

• 385. Oliver Burkeman on Embracing Your Limitations
• 360. The Laws of Connection with David Robson
• 374. Developing and Deepening Connections with Adam Dorsay
• 271. Cultivating Friendships in Adulthood Featuring Adam Dorsay

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