Transform Your Approach to Change: Joe DeLoss on Wayfinding Through Life’s Defining Transitions

In this inspiring conversation, Joe DeLoss opens up about navigating life’s twists and turns, sharing his raw, personal journey through big changes and the lessons he’s learned along the way. Whether you’re facing a career shift, grappling with relationships, or just trying to figure out what’s next, this episode offers a relatable and refreshing take on the process of change. Here’s what we dive into:

• The Reality of Change: Joe unpacks the messy, paradoxical, and often beautiful journey of letting go and stepping into something new.
• Unlearning What No Longer Serves You: How to release old habits, identities, and societal definitions of success to rediscover what truly matters.
• Becoming a Wayfinder: Joe shares his approach to navigating uncertainty one small, intentional step at a time, and how you can start your own path forward.
• Why Nature Heals: The surprising way outdoor adventures helped Joe reconnect with himself and find clarity in chaos.
• Serving Through Your Struggles: How Joe’s challenges inspired him to create Baker Road, a space for men to find connection and purpose in nature.

This episode is like a campfire conversation between friends—real, vulnerable, and packed with wisdom for anyone ready to embrace growth and align with what truly matters in life.


Key Moments:

02:51 - Joe’s early relationship with change and the impact of identity shifts
06:48 - Reckoning with rock bottom: When personal pain meets external accountability
11:38 - Realigning purpose and identity: How to start the process of self-awareness
17:29 - The power of unlearning: Letting go of external validation to reconnect with inner values
22:42 - Defining personal success: From external KPIs to meaningful relationships
29:39 - Navigating life’s map: The wayfinding metaphor for embracing the journey
36:25 - Nature as a guide: Lessons from the wild and its transformative role in Joe’s work
43:09 - Creating Baker Road: Purpose-driven adventures for growth and connection
48:36 - Campfire wisdom: Letting go, finding peace, and embracing the abundance of change


About Joe:
Joe is a serial entrepreneur focused on building transformational experiences and businesses that improve the lives of everyone involved. Most recently, Joe exited Hot Chicken Takeover, a fast-casual restaurant chain he built in the Midwest. The business earned critical acclaim as a break-out brand in the segment and created nearly a thousand meaningful work opportunities in the region for people impacted by incarceration, homelessness, and addiction.

Since this acquisition, Joe’s continued his dedication to supportive employment, social entrepreneurship, and vulnerable leadership. And with eyes set on new ventures, Joe’s seizing any opportunity he can get to inspire other entrepreneurs and leaders to make sustainable impact integral to their organization’s future. He honors this pursuit as an advisor, investor, speaker, and occasionally, as a reluctant consultant. His newest project, Baker Road, is an adventure studio offering men and high impact leaders immersive opportunities to learn about themselves in wild, natural environments. 

Joe’s work been highlighted by The Today Show, Forbes, Harvard Business School, Politico, The Rachael Ray Show and many others. He and his family live on a farm in rural Ohio, keeping adventure close in their own backyard.

Connect with Joe:
LinkedIn: www.linkedin.com/in/joedeloss/
Baker Road: www.bakerroad.com/

Connect with Owl & Key:
Website: www.owlandkey.co