Curated Questions: Conversations Celebrating the Power of Questions! The Permission Paradox & Why Questions Matter More Than Approval! | Jill Reilly #54
"The most fundamental relationship in any change process is the one that you have with yourself. It's the questions that you ask yourself first and foremost that are the game changers." - Jill Reilly
In this episode of Curated Questions, host Ken Woodward is in conversation with global citizen and author Jill Reilly to explore the power of questioning in navigating life’s complexities.
Jill shares her journey from the Midwest to South Africa, Zimbabwe, and beyond, reflecting on her experiences as an aid worker and the lessons that shaped her understanding of change and personal agency.
They discuss the importance of self-permission, processing grief, and the need to adapt amidst societal and technological upheaval. With insights from her new book The Ten Permissions: Redefining the Rules of Adulting in the 21st Century, Jill emphasizes the transformative potential of asking the right questions to unlock personal growth and resilience.
This Curated Questions episode can be found on all major platforms and at CuratedQuestions.com.
Keep questioning!
Episode Notes
00:00 Introduction: The Power of Self-Questioning
00:49 Milestone Celebration: 100,000 Downloads
03:13 Introduction to Jill Reilly
05:23 Jill's Journey to South Africa
07:37 Choosing a Different Path
09:30 The Concept of Permission
13:39 Exploring New Paths
18:23 Jill's Work in Zimbabwe
21:44 Engaging with Questions
29:05 Political Uncertainty and Fear
31:18 Grieving the Old Stories
32:05 Reimagining Our Future
35:36 Challenging Fixed Mental Models
37:16 Questioning Traditions and Conventions
38:54 Intentional Conversations Around Adaptation
40:07 The End of Predictable Progress
41:40 Exploring Personal Undoing
43:18 The White Savior Complex
45:49 The Importance of Self-Permission
47:04 Engaging with Yourself for Change
49:11 Navigating AI and Rapid Changes
55:56 No Need To Blow Up Your Life
59:09 The Value of Leisure Time
01:02:31 Professional Adaptation and Evolution
01:08:19 Right Now Question
01:12:27 Final Reflections and Takeaways
Resources Mentioned
Shame: Confessions of an Aid Worker in Africa by Jill Reilly
Vain Aid TED Talk by Jill Reilly
The 10 Permissions: Redefining The Rules of Adulting in The 21st Century by Jill Reilly
Ten Permissions website
Jill Reilly email: jill@tenpermissions.com
Questions Asked
When did you first understand the power of questions?
How is it that you chose to pursue going to South Africa?
Were we allowed to question it?
Were we allowed to create alternatives to it?
What else did you do?
What are the things that you could do?
Do we even feel allowed to have those conversations?
Am I defaulting to just take the next safest step, or am I allowing him and myself to consider that?
Isn't it a good opportunity to begin to explore a variety of options?
Are we preparing them for this evolving reality, or are we continuing to default to what worked in our day or what we've always done?
How did things go when you got to South Africa?
Who am I? How am I introducing myself? What am I about?
What do you think were some of the modality, spirit, and heart posture as you use questions to engage this new world for you?
Can you contract aids from a public toilet seat?
What are good questions to use when wrestling with political uncertainty, upheaval, and the like?
Am I gonna be the one to try and fill the void that's being created right now with something new, something better, or is our only option to try and patch together what once was and keep hobbling along?
Why haven't we done any more amendments? Why haven't we changed things?
How far can we go? What are we allowed to do?
Do we need to make changes?
Why would we choose the old version?
Isn't there a better way? Isn't there more? Isn't there different? Isn't there now?
Do I feel allowed to do the thing that I think I should or they say I should? Or does fear, intervene in my own sense of permission? Are there external authorities whose power over me is so great that I'm not willing to take a risk? or am I the thing that's in the way of me actually taking a risk to do something different?
What are the questions that you're asking?
How are you poking into your own assumptions?
How are you testing those? What questions are you intentionally using? And what is your practice for going after that?
And are you gonna be ready for that or are you gonna be blindsided?
Am I allowed? What's desirable? What's allowable?
What do you wanna do with it? What does it look like for you? How is it a vehicle for you to live and experience in ways that maybe you haven't fully lent into yet?
What is your Right Now Question?
How can, and how will my book and these permissions support people to navigate this age of AI?
What's possible in this time? What's allowable? We allow ourselves to imagine showing up to this moment differently, and what might that look like?
What situation in your life right now feels unfamiliar or uncomfortable where you could experiment with leading with questions instead of assumptions?
How might genuine curiosity change those interactions?
Where in your life are you waiting for approval when what you actually need is to give yourself permission?
What would change if you separated these two concepts this week?
How might you make space to process loss and grief that continue to weigh you down?
Can you identify three "shoulds" that are currently driving your decisions?
What would happen if you spent 10 minutes each day this week asking yourself what YOU actually want, without editing or judging the answers?