Giving Yourself Permission to Live Differently – Insights from Jillian Reilly

In a world marked by continual uncertainty, we need a fresh paradigm to navigate adulthood with agency, courage, and creativity.

In the inaugural edition of my new podcast series “Uplifting Ideas”, 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”.

I had the opportunity to read the book and absorb insights on living and non-linear life. As I read the book, I found a lot of resonance with my own experiments of living a non-linear career path from teaching to technology to consulting, sales, organizational leadership, and being a solopreneur.

We are conditioned to live by a very static script of how to build careers from school to college to a job to promotions to retirement and so on. In the process, we often end up surrendering our agency and creativity to pursue different things and pursue things differently.  We rarely realise that we have the freedom to design our 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.”

Jillian’s own career has spanned international development, social change, and leadership consulting. Across these diverse journeys, she observed a truth – most of us are conditioned to wait for external permission before shaping our own lives.

“We seem perfectly willing to curate our coffee or our cars, but when it comes to designing our own lives, we often default to off-the-shelf choices.”

At the heart of Ten Permissions is the idea of embracing nonlinearity. Jillian invites us to shift from an “I am” mindset (fixed identity) to an “I can” mindset (fluid possibilities).

This doesn’t mean we abandoned 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.

My Conversation with Jillian Reilly

Sketchnote Summary of the Book

Get the Book

Ten Permissions by Jillian Reilly is available now. If you’ve ever felt trapped by the linear playbook of life, this book will help you reclaim your agency and author your own path.

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