The 10 Permissions - With Jillian Reilly

In this edition: In a world marked by continual uncertainty, we need a fresh paradigm to navigate adulthood with agency, courage, and creativity. Explore this podcast conversation with Jillian Reilly.

Sep 16, 2025

Here’s some news: I am now a podcast host, where my primary intention is to have nuanced conversations with people I admire - in the spirit of learning and exploration. My podcast is named “Uplifting Ideas” - ideas that inspire growth and change.

In the inaugural edition, I had the privilege of speaking with Jillian Reilly, author of a new book titled “Ten Permissions – Redefining the Rules of Adulting in the 21st Century”

Get the Book

Our education system conditions us deeply to follow a static and linear script of building a career and life from school to college, and degree to job. As someone who has built a non-linear career spanning teaching, technology, quality, consulting, sales, organizational leadership and solopreneurship, I found a lot of resonance in the book.

The problem with linear script is: we end up surrendering our agency and creativity to pursue different things, and pursue things differently. We rarely realize that we have freedom to design out days, and ultimately our lives.

Jillian says,

“If we’re going to drive our own growth and evolution, we’ve got to give ourselves permission to really make intentional choices, and make novel choices.”

In the book, Jillian invites us to shift from an “I am” mindset (fixed identity) to an “I can” mindset (fluid possibilities).

This doesn’t mean we abandon the structure, but if you want to create a unique path for ourselves, we have to loosen the grip of labels and identities that we carry along firmly.

We have to build a portfolio of skills, experiences, and passions that can be combined to create unique value as our life unfolds.

Jillian says,

“Stop trying to figure out what five years from now will look like. Come completely alive to your next best option.”

As a parent to a a teenager and young adult, I feel that the messages in the book will resonate deeply with younger generations, stepping into an unpredictable world: believe in your own authority, listen inward more than outward, and step into the world with curiosity.

The book is also an invitation for working professionals to think about possibilities and adjacencies that they can explore to build a portfolio of skills that not only keeps them relevant in the future, but also enables them to deliver unique value in their pursuits.

“Permission is not a meditation. It’s a green light to action.”

For anyone who feels boxed in by the convention, Gillian’s book is a wake up call. I loved Jillian’s suggestion of travelling light, designing the life, intentionally, and embrace the freedom of being a free agent in work and in life.

I left this conversation with a powerful reminder: we are diamonds with many facets, not coins with just two sides. Ten Permissions shows us how to reveal those facets and shine in ways we didn’t know we could.