Guest

Ashley Jablow (Jab-lo, pronouns: she/her) is the founder of Wayfinders Collective and creator of Life Design School, a creative studio for people in career and life transition. A seasoned facilitator, speaker, coach, and design strategist, Ashley blends design thinking and innovation, emotional intelligence, and creative tools to spark clarity and action for teams and individuals navigating change. She's also the artist and author of 100 Days of Designing My Life, a guided journal series for reflection and reinvention, and the creator of "The Little Deck of Sweet Reflections", an intuitive card deck to inspire your creativity, connect with your inner wisdom, and reflect on who you are becoming.

Summary

In this conversation, Ashley reflects on the pivotal career transitions that shaped her work as a coach, facilitator, and innovation practitioner. She describes several moments of feeling "stuck," including graduating from business school without a job, working in prestigious roles at IDEO and the White House during the Barack Obama administration, and later being unexpectedly laid off from what she believed was her dream job. Rather than viewing those experiences as failures, Ashley explains how they became turning points that led her toward coaching and helping others navigate difficult transitions.

A central theme of the discussion is the relationship between reflection and action. Ashley argues that meaningful change requires both deep self-understanding and practical movement forward. Drawing from her background in coaching and design thinking, she describes how innovation, creativity, and human-centered leadership intersect. For her, reflection without action leads nowhere, while action without reflection risks solving the wrong problem.

The conversation also explores leadership development, trust, vulnerability, and the challenge leaders face in shifting from doing the work themselves to empowering others. Ashley emphasizes that the "people stuff" — culture, trust, communication, and values — must be addressed before productive organizational change can happen. She closes with an important reminder: when people feel stuck, creativity, play, and joy are not distractions but essential pathways to movement and renewal.

Ultimately, our conversation highlights the grit, interdependence, and adaptability required to survive in the historic West.

A key takeaway

Being stuck is not a dead end but often the beginning of transformation. Real progress comes from pairing honest self-reflection with concrete action, while staying grounded in humanity, trust, and joy.

References / Links

https://www.linkedin.com/in/ashleyjablow/

https://www.instagram.com/ashleyjablow/

The Power of Onlyness by Nilofer Merchant