Giving Yourself Permission: Jillian Reilly on trusting your gut and foregoing regret (pt 1)

Earlier this year, I interviewed Jillian Reilly, author of "The Ten Permissions: Redefining the Rules of Adulting for the 21st Century," about why people change (or don’t). And how “permission” and agency shape behavior more than resources, training, or workshops.She recounts leaving a prescribed path and law school plans to go to South Africa during the of apartheid, followed by two decades in international aid across Africa. During that time, she led an HIV/AIDS program in Zimbabwe, where she saw how cultural and safety constraints make “novel choices” dangerous. She describes disillusionment with the kind of change driven by funding incentives, moving into consulting, and later prioritizing motherhood despite career trade-offs. We explore the ideas of permission, conviction over certainty, experimentation, avoiding regret through intentional choice, and building “permission-rich” environments in villages and boardrooms alike.00:00 Why Permission Matters00:17 Meet Jillian Reilly01:59 Ten Permissions Explained04:53 Leaving the Midwest Script08:11 Aid Work Lessons10:03 Zimbabwe and Permission13:32 Agency and Modern Careers17:46 Moving to South Africa22:33 Conviction Over Certainty24:02 Feel Your Way Forward27:05 Transition to Consulting27:28 Aid Work Disillusionment29:39 Spending Versus Impact31:52 Leaving the Dream Job36:09 Consulting as Truth Teller36:55 Permission and Change41:12 Motherhood and Tradeoffs46:33 No Regrets Framework50:57 Returning Through Experiments53:22 Frontiers and Explorers Way55:50 Closing Reflections and Tease