29:38Reshma Nichani
A life you would choose for decades.
Reshma reconnects with her creativity and begins imagining work that feels meaningful on her own terms.
The Roadmap · Graduate conversations
Inside the CircleA fuller picture
of success.
What changes when your life starts to feel more like your own?
Meet Roadmap graduates in conversation with Jack. Candid stories about natural gifts, meaningful work, and the possibilities that open up beyond achievement.
Explore all 16 conversationsLatest conversation · Episode 16
A life you would choose for decades.
Reshma Nichani
Reshma reconnects with her creativity and begins imagining work that feels meaningful on her own terms.
Discover Reshma’s storyThe conversations
Find a story that speaks to you.
16 conversations to explore
29:38
11:55Rodrigo Herrera Aspra
Give ambition a direction that matters.
Rodrigo explores the difference between constant activity and work guided by a clear, personal vision.
23:05Allegra Poschmann
Find your North Star. Bring your gifts with you.
Allegra reflects on building businesses while staying connected to the creative gifts that make her work her own.
20:33David Riggs
See possibility where others see a mess.
After selling his agency, David finds a clearer connection between his natural gifts and the businesses he wants to help.
17:22Josh Williamson
Recognize the strength that was there all along.
Josh finds a new way to understand his work and contribution by recognizing his gift for optimization.
22:20Joel Hakala
Build for significance beyond the scoreboard.
Joel explores the connection between his natural gifts, customer experience, and a more meaningful definition of success.
19:16Zach Kosturos
Make room for a fuller kind of success.
Zach and Jack explore purpose, identity, and the restlessness that can remain after achievement.
19:27Juan Avilés
Turn understanding into forward movement.
Juan brings an athlete’s and investor’s perspective to the challenge of moving from analysis to action.
8:40Rodrigo Herrera
Meet a crossroads with greater clarity.
Rodrigo shares how coaching helped him find confidence and direction at a consequential turning point.
21:16Raghav Taparia
Discover who you are beyond the image.
Raghav reflects on stepping away from a successful career and examining identity, fear, and inner peace.
19:29Rob Fraser
Carry your competitive spirit into a new chapter.
Rob explores the transition from elite mountain bike racing to building a performance sock brand.
15:36Terry Moss
Build something that brings joy back into the day.
Terry connects teaching, creativity, and community through a business built around LEGO experiences.
21:44Anton Marano
Lead by making room for other people’s gifts.
Anton shares a perspective on personal growth, humility, and leadership inside a third-generation family business.
29:17Conor Kearney
Rediscover the creative part of your calling.
Conor explores the possibility that a thriving business and a long-standing creative passion can tell different parts of his story.
23:56Jean Moran
Let your contribution grow beyond a single role.
Jean reflects on leadership, family, community, and the freedom to live with greater authenticity.
14:03Jeff Durkee
Find meaning in the work you are here to do.
Jeff looks beyond the corporate ladder to the strengths, relationships, and contribution that make work fulfilling.
Real people. Individual experiences.
Each conversation reflects one person’s perspective. Explore the stories for insight and possibility; your own next chapter will be distinctly yours.
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