On the Road to Real Connection: Lessons from Kerouac & Life Outside the Hustle

What can a 1940s road trip teach us about living more freely today? A lot.

In this special episode of Kerouacs Cruising, Cara and James reflect on Jack Kerouac’s On the Road and how it parallels their own quest for a more connected, untamed life. From spontaneous travel and soul-deep conversations to the search for authenticity in a hyper-connected but emotionally distant world — they share what it means to truly live on your own terms.

Tune in to hear about:

• Why On the Road still resonates 75+ years later
• How traveling full-time helped them break free from the 9-to-5 mold
• The role of connection, spontaneity, and soul-searching in their journey
• Reflections on navigating culture, expectations, and personal growth
• Their next steps as authors in Together We Rise, coming June 24

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