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Jillian Reilly: The 10 Permissions
Manage episode 516844663 series 3553749
The ground is shifting faster than our old rulebook can keep up, and pretending we can project-manage our way to certainty only makes us brittle. Today we sit down with author, activist, and leadership coach Jillian Reilley to unpack why lasting transformation starts with self-permission rather than big budgets, and how a life built on small, intentional experiments can outperform the grand five-year plan.
Jillian’s story begins in post-apartheid Africa, where hope and hardship lived side by side. Those years taught her a hard lesson: institutions can fund programs, but they can’t grant consent. Whether it’s international aid or a corporate change initiative, the real turning point happens in private—within families, teams, and the inner conversation we have with ourselves. That insight powers her new book, The Ten Permissions, a provocative set of invitations designed to help us navigate a fluid world: Go Astray to shed linear myths, Think Small to iterate like a pro, and Feel Your Way to move beyond over-analysis and into embodied action.
We dive into AI anxiety and name the uncomfortable truth: if your value is repeatable, a machine will eventually do it. The way forward isn’t fear; it’s accelerated human learning—curiosity, sense-making, creativity, and connection. Jillian shares practical rituals that keep you grounded under pressure, from walking and breathwork to micro-steps that silence the inner critic through momentum. We also talk about education’s urgent update, shifting from memorizing facts to practicing navigation skills so young people can thrive in ambiguity.
If you’ve felt “off-script” lately, this conversation will feel like both validation and a roadmap. You’ll leave with language for what you’re experiencing, permission to play a different game, and concrete ways to build a career and life that adapt as fast as the world does.
Resources from this episode:
Chapters
1. Welcome And Guest Introduction (00:00:00)
2. Purpose As A Feeling, Not A Label (00:02:35)
3. Arriving In Post-Apartheid Africa (00:09:15)
4. Aid, Disillusionment, And Humility (00:14:30)
5. Why Money Without Culture Change Fails (00:18:40)
6. The Ten Permissions: Origins And Aims (00:22:55)
7. Go Astray And Think Small Explained (00:28:20)
8. Agile Lives, Not Five-Year Plans (00:33:10)
9. AI Anxiety And Human Adaptation (00:36:50)
10. Preparing Young People For Flux (00:41:30)
11. Building Community Around Permission (00:46:00)
12. Meeting People Beyond Words (00:49:25)
13. Self-Coaching Across The Years (00:53:00)
14. Walking, Rituals, And Energy (00:56:05)
15. Imposter Syndrome And Action (01:00:10)
16. Drucker’s Wisdom And Closing Thanks (01:13:30)
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