Unlocking The Ten Permissions for a Braver Life with Jillian Reilly

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Timestamps
00:00 Cold open & setup
06:48 The 23-Year Pivot: Cape Town or Bust
09:19 Listen First, Leap Second (Small Steps vs Someday)
12:40 Why Permission Beats Programs (Origin Story)
17:39 Permission #1: Be Willful (Want What You Want)
21:43 Approval Is Nice, Not Required
25:42 Failure Reframe: “I Am” → “I Can” (Try Small, Learn Fast)
31:44 Permission to Ask (Leaders Don’t Need All the Answers)
35:37 Admit & Commit: “I Don’t Know…Yet”
37:47 Permission to Think Small (Three Wins a Day)
39:01 Permission to Go Astray (Curvy Paths Build Readiness)

Jillian Reilly (00:03.074)
You know, whose choices weren’t, I’m afraid that, you know, my parents won’t accept me. It’s like, no, I’m afraid I’m going to be rejected by my community. There’s a calculation of, what am I supposed to want? What do you think I should want? Is it okay for me to want what I want? So, we learn early on to sort of calibrate our desires to be acceptable.

All of the uniqueness, all of the interests, all of the stuff that looks like it might take you, you know, off the safe and secure path gets squashed away and you become the thing that you think other people want.

Skot Waldron (00:41.976)
When I’m not hosting Unlocked, I’m speaking at events all over the world. I’m helping leaders and I’m helping teams communicate better. I’m helping them build trust faster and actually enjoy working together. I’ve spoken for companies like The Home Depot. I’ve spoken at national architectural firms. I’ve spoken for pharmaceutical company offsites. I’ve spoken at associations, you name it.

With 99% of attendees of all those events, over 1800 people have reviewed me at this point. 99% of them saying they got some value. That’s pretty awesome. Even the caterers have thanked me. And if they are thanking me and they’ve heard a lot of talks and they’re busy doing their jobs, that’s saying something. If you’re an event planner looking for a speaker who’s really easy to work with, trust me, I want to be the last thing you’re worried about on event day. I’m going to take care of you. And who actually delivers value for your audience that they are going to use on Monday morning when they return to the office, then let’s talk.

Skot Waldron (01:40.92)
Have you ever felt like people just were trying to fit you into some mold, telling you how to be or what you should be or what you ought to be, or maybe you put yourself in that mold, that little box of confinement. Yeah, I know. We’ve kind of all been there, whether it’s in a job role or whether it’s in life in some way. Maybe our partner feels, does trying to put us in this box that we don’t feel like we belong in or we’re trying to break out of, but yet we don’t fully have permission. That’s the key word y’all permission to do that or to be that or to whatever. And that is a problem. That’s a huge problem. And that’s why I’m so excited to talk to Jillian today about that very topic. She wrote a new book called The Ten Permissions. And we’re going to talk about that, but most of all, we’re going to hit on this idea of permission and why, you know, what, what do we fight against as leaders about giving permission and as a culture and as a society about giving permission. And she has some really thought-provoking ideas about things we should, you know, give permission for or take permission or give ourselves permission to do or to be. And some of these things make you think like, huh, wait, what should I really be giving myself permission to do that? Yes, you should. So, we’re going to talk about all of that today.

Jillian is a very accomplished person in the space and she has been doing this for a long time. And now she’s going to be talking to us from the lovely land of Cape Town. So, here we come.

All right, Jillian, welcome from lovely Cape Town. It’s good to talk to you.

Jillian Reilly (03:39.702)
It’s great to be here, Skot. Thank you so much for having me.

Skot Waldron (03:44.00)
Yeah, I didn’t want to wait. I didn’t want people to think I’m from Cape Town. No, you’re from Cape

Jillian Reilly (03:48.00)
I’m the one who gets to say I’m in Cape Town. Come on now. Yeah.

Skot Waldron (03:54.00)
I was trying to steal it. I wish I was there.

Jillian Reilly (03:57.806)
I know, I know. It’s really beautiful. I gotta say I’m very happy I made the choice to live here, but it’s also good to reconnect with somebody who’s from my hometown Atlanta.

Skot Waldron (04:10.00)
Yeah, you know, that’s how we roll here. We do; we do. And you did drop this little thing as like part of your story of like why you’re there. I don’t honestly know why you’re there, but now I want to ask because you had like got me intrigued. So, what brought you to Cape Town? And I know you’ve done some work in Africa with your previous organizations and whatnot. So, is that why or is it some other reason?

Jillian Reilly (04:36.206)
Well, no. I mean, I made the pretty radical decision at age 23 to come here. I was so yeah, I was at Northwestern University sort of set up to head out on a path to, you know, law school and be the success that my parents and everybody else wanted me to be. And I started to feel like I wanted to be a part of something that mattered.

I wanted to find a career that I felt had some sort of meaning and it had, trust me, I had no more than that. It was all very fuzzy, but it was just a feeling that there was something more out there. And luckily, I listened to that feeling. South Africa was poised in 1993 for its first democratic elections, which took place in 1994, which brought Nelson Mandela into power. Some of which now sounds like ancient history for some of your listeners, no doubt.

But I was sitting there in Chicago and I was like, I gotta get there for those elections. I wanna be a part of history. I want a front row seat. And I told my parents I’m going to South Africa. And you can only imagine, know, and Joe Riley in St. Louis, Missouri were kind of like, excuse me.

Yeah. Really disappointed and confused a lot of people at a very young age. And little did I know that that was going to set me up for a path that, you know, first took me to South Africa. I thought I was going to be here for six months. And then I do the election thing, go back home, get back on the path, you know. And I got here and I was just like, my gosh, there are amazing things going on here. So much opportunity for me as a young woman to kind of explore what I was capable of and I didn’t look back. And it started a career in change, if I can say that broadly, social change, organizational change. I sort of described my career as being present with people as they navigate really profound change. And yeah, I went to many, many places in the middle, but eventually came back to South Africa.

Skot Waldron (06:49.058)
That’s cool. I know there’s a lot of people out there going, I wish I could do that. You know, like I wish I had the guts to do that or the ability to do that or that whatever would you say to those people?

Jillian Reilly (07:05.00)
Listen. There’s nothing supernatural about me. I’m not Laura Croft. What I did that I think a lot of people don’t do was I listened deeply to my inner voice. There was a lot of noise around me that was pointing me in the direction that everybody else was taking. And I of was like, no, this is something that I’m not sure where it’s going to head, but I’m willing to act without certainty and willing to step into an unfamiliar space because I believe that there’s something that I’m going to learn there.

You know, I was young, I took a big leap. I think for anybody who feels like they’re longing for something else, it doesn’t always have to look like that. You know, it doesn’t have to be a parachuting into another place or another job or another anything. In fact, a lot of what I talk about is just then start to take small steps towards, you know, something that’s beyond your normal limits, beyond your normal life, a step out of your status quo and start to kind of nurture some of that in your life without feeling like you’ve got to blow it up.

Skot Waldron (08:13.00)
You got a fun new book coming out.

Jillian Reilly (08:17.74)
I do.

Skot Waldron (08:19.00)
And I’m excited to talk about it, because when you came to me and were like, hey, Skot, let’s talk about this thing. I was like, yes, because my purpose statement that sits on my wall right here, it says my purpose is to help people feel they have permission to be who they were designed to be.

Jillian Reilly (08:42.00)
No.

Skot Waldron (08:45.00)
Yes!

Jillian Reilly (08:46.00)
We didn’t talk about this before.

Skot Waldron (08:47.00)
Jillian, we have so many connections.

Jillian Reilly (08:49.00)
Are you serious? That’s amazing.

Skot Waldron (08:51.00)
That was the biggest thing for me is to… The injustice in the world for me was that I just didn’t feel like people had permission to be themselves. They didn’t have permission to… I don’t mean permission to be an a-hole. I mean, permission to be the introvert or permission to delay the process a little bit and maybe my brilliance comes out at the end of the process. And I don’t have to start my timeline milestone spreadsheet the day after the meeting because that’s just not how I work. But I need permission to work the way I need to work in order to deliver the product I need to deliver. And without giving each other permission, we just put each other in boxes that don’t let anybody feel the freedom that we should deserve. So anyway, I’m off my soapbox, but…

Jillian Reilly (10:02.00)
The fact that the title of your book, my book matches some of what’s on your purpose statement on your wall is super interesting. I mean, yes, yes, and yes. So let me tell you for me where what the origin of the book is about. So, it’s called The Ten Permissions. And, you know, part of what I say in the book is that I feel like I’ve spent my whole life with stock adults.

As you say, boxes that they don’t want to be in, in stories that they feel like they’re not allowed to get out of. And, you know, those people took all sorts of different shapes and sizes. But let me go back to my work in Africa, you know, in the development field and working with, the height of the HIV AIDS epidemic in Zimbabwe. And that was kind of when I realized we were trying to get people to change their stories, to change their behaviors, to do things that for us look completely common sense, but for them were big, big changes in their lives. And we were throwing everything at them, know, lots of money and lots of resources and facts and T-shirts and everything under the planet. And it wasn’t working. People still stayed in the box, despite the fact that from the outside, it was like, boy, it looks pretty dangerous in that box. Don’t you want to get out? No, because it’s the box I know. And it’s the one that I’ve been in my whole life and my parents were in and everybody else was in.

I actually remember kind of sitting down at some point and talking to a guy I was working with and being like, we can give people everything under the planet, but we can’t give them permission. We can’t. I can’t come into your life and say, Skot, you’re allowed to, you know, be the first in your family to do this or the last in your family to do this. I don’t have that power over you. And I think that was at a pretty young age, both super humbling.

Like, okay, I’m coming up against the limits of my own capacity to affect change in the world and in other people’s lives, but what an insight for me to realize that there was this agency, this sense of self and sense of will and power that for me is the green light. And what I can do, as you’re describing, is create the conditions, create the space in which other people can feel that it can feel that they won’t get in trouble, can feel that they’ve got more agency and more space, but they’ve got to make that decision at the end of the day. And, you know, it kind of cut through a lot of my work, which was I started to work a lot with sort of your relationship with yourself, your relationship with your story, your relationship with what you’re carrying along that tells you who you’re supposed to be and how you’re allowed to behave.

And the idea behind the book is that we’re living at a time where a lot of those stories are unraveling, where our identities have never been more fluid, for better or for worse. And that gives us the opportunity to make choices that maybe were unthinkable only a generation ago, but it also places an enormous burden on us to decide for ourselves what we’re going to allow ourselves to become.

And if we’re not accustomed to giving ourselves that permission, we’re going to be hesitant, drift, stuck. And so, the book is about developing that practice of engaging with your own sort of permission and beginning to step out of the box that you’re describing.

Skot Waldron (13:29.00)
That’s really cool. And I mean, I hear the heart in what you’re saying of your desire for these individuals. I think you’ve seen the pain and the struggle and you’re just like, ahh, it doesn’t have to be this way.

Jillian Reilly (13:48.00)
And you know, it doesn’t have to be that way. So, you know, what I say to a lot of people is, I’m not a life coach. I’ve spent 30 years with people who were in real danger, you know, whose choices weren’t, I’m afraid that, you know, my parents won’t accept me. It’s like, no, I’m afraid I’m going to be rejected by my community.

So, I understand what it’s like to fear change because you’re afraid for your own wellbeing. But for most of us, that is not the case. And for most of us, we’ve got so many choices and it’s kind of like, let’s make them, let’s make them. Let’s not act like we’ve got two choices when in fact we’ve got 20 or more. Like there’s never been a better time to be super intentional about the choices that we’re making in a world that again, for better or for worse, is allowing us to make choices that our parents might have never considered.

Skot Waldron (14:47.00)
When we’re talking about these permissions. So, I wanna dive into just the content. And so, we can get an idea of what permissions we’re talking about here. So, I’m gonna ask you like, which of The Ten Permissions do you feel society resists the most? And why do we push back so hard on that and against giving ourselves that freedom or that permission.

Jillian Reilly (15:19.00)
Yeah, I’m going to start with the first one because as much as they’re not sequential, the first one is, be willful. So, you know, I think human

Skot Waldron (15:29.814)
No, we’re not giving, we don’t give ourselves permission to be willful.

Jillian Reilly (15:33.00)
And we need to do that more than ever. That we are socialized to kind of outsource our wants and our will to our family, to our society, to our culture. We were raised from an early age to say, as they say, when you ask people, what do you want? It’s kind of like, there’s a calculation of what am I supposed to want? What do you think I should want? Is it okay for me to want what I want?

So, we learn early on to sort of calibrate our desires to be acceptable. And, you know, as we move into young adulthood, more and more of those desires get turned into a form that is, we see as being as monetizable, as commodifiable as ever. So, a lot of people, all of the uniqueness, all of the interests, all of the stuff that looks like it might take you, you know, off the safe and secure path gets squashed away, and you become the thing that you think other people want or the society wants you to be.

So, you know, most of the people that I’ve worked with, if you get to the core of why they’re in the box, it’s because either they don’t have a clue what they want because they’ve spent a lifetime following other people’s direction in that regard. They can’t articulate it. If they can articulate it, they have a very hard time acting on it because you know, we’re raised to feel like it’s kind of selfish, it’s greedy, it’s dangerous because it might take us to a place that, you know, other people don’t recognize. It might take us to South Africa.

So, you know, in these imperceptible ways, we become a version of what we think we’re supposed to be. And when it comes time to come to grips with what do I actually want in small ways and big ways, we’ve got no muscle for doing that. And we feel very awkward doing that. You know, I talk in the book about this kind of wrestling match between duty and desire and the simple fact that we feel like our desires are kind of dangerous, that they’re going to put us up against the world around us.

And, you know, the reality is right now in a world that requires so much agency to find your way through it. You’ve got to decide what you want because you’ve got thousands of choices about everything from your coffee to your career. And you’ve got to make them, and you can make them right. So, you know, you don’t have to default to yesterday’s choices, but you’ve got to be comfortable making choices that you want. And then over and over and over again, not once at the beginning of your professional career. And then you sort of sit in that for the rest of your life. But, you know, we’re in a period where people are going to have to and people are going to get to reinvent themselves pivot, move into new spaces to do that, you really have to kind of keep touching base with your own agency and with your own will. And that’s, you know, uncomfortable. That is not something that most of us feel, you know, comfortable doing. It feels a little edgy to be in that space. And I think that’s one of the biggest transitions that we are navigating now, and we are going to be asked to navigate ever more as a lot of our traditional roles get replaced and we are going to have to create new things or fill different kinds of spaces.

Skot Waldron (19:04.00)
And the comfort word is really important because, I mean, let’s talk about this for a second. I’m just throwing this out there. I haven’t fully thought this out yet. So, I mean, isn’t the reason we don’t give ourselves permission or other people permissions because it’s uncomfortable. Like from the root cause, like all the permissions that you have in your book, I’m not familiar with all of them, but isn’t just all of them just because of discomfort.

Jillian Reilly (19:34.306)
Yeah, fear of rejection, fear of failure. It’s fear. It’s, you know, I start off the book by saying, you know, you are imprinted with a story about who you’re supposed to be and what you’re allowed to do. We all are. We come into this world with that. And so much of it is implicit. You know, it’s not like somebody sits you down and says, Skot, you know, here are the rules. But you pick them up along the way, you know, you know, and so you’re always sort of feeling around and because so much of it is implicit and not written down, it can be this kind of like, oh, am I going to be okay? What’s going to happen? What are other people going to say?

So, you know, I think because we early on don’t and I describe it in the book as the permissions paradigm. You know, we raise young people to ask for permission to do the things they want to do, which is understandable and necessary. But we don’t necessarily prepare young adults to begin to give that to themselves to say, you know, I am allowed as a fully-fledged adult to authorize myself to make choices that I want. That does not mean that everybody’s going to applaud me or even approve of me. But once you realize, one of the game changers is realizing that approval is desirable but not a requirement. We kind of set it up as a requirement for action and we don’t step into the space as adults of sort of saying, you know, it’s okay. If some people don’t understand why I’m doing what I’m doing, if I’m prepared to back myself, which again, doesn’t mean you’ll succeed or that it will be easy, but that you are listening in and following your own best guidance.

You know, coming out of a 20th century where we were still, you know, fitting into hierarchical roles and rewarded for compliance and told to just stay on a path until we collected our golden watch. It’s sort of understandable that we haven’t behaved this way. We haven’t had to. We weren’t rewarded for it. And my point in the book is that we’re moving in ever more into periods where we’ve got to start to cultivate some of us, this and ourselves, because this world is going to require ever more of that.

Skot Waldron (21:46.522)
Yeah, I think that’s this whole idea is so big and it’s so built into our culture or in our psyche and who we are as humans and, that permission and the way we behave. Let’s tackle one because I want to hit on the failure one because I was, I’m, I was coaching, I was coaching someone at a company. And they came from this military backing raised by a military father where the mantra was failure is not an option. Failure is not an option. And from a military standpoint where somebody will die, it might not be an option. that, right? We have to this mindset that if somebody fails, somebody will die. In the corporate world, it’s more than likely not the case.

But that mantra that was built into him and growing up in that space, now he takes it into business of failure is not an option, which means that he can become pretty intense. He can direct a little too strongly. He can bulldoze situations when he thinks he’s right and other things. But, I’m trying to think about how do we reframe failure? Okay.

The moment when, where does the moment where failure stops becoming an identity like, I’m a failure to where it becomes information.

Jillian Reilly (23:23.00)
Yeah. So, one of the, I have two kind of related responses to this. And one is a big reframe that I think we have to start to play around within our own minds as we move forward. And I talk about it in the book from like an “I am” to an “I can” mentality. So, sort of this, you know, uncoupling our identities from our roles, in order to create a more fluid understanding of who we could become throughout the course of our lives. And for me, why that’s relevant with regards to your question is because what it does is free you up from the belief that your identity is this thing you need to protect, that it is somehow impacted by the experiments that you take and the ways in which you step into these spaces. The reason that we didn’t do that is because we thought every time we did that, you know, it would partially impact the status and the security of our identity. If I fail, then people will no longer respect me. But if I see myself as an evolving set of capabilities, you know, I can go out and do a number of different things and fluidly adapt along the way. And one of them is to experiment with new things and learn.

And I think the framing of failure as a process of learning something is one of the most important things that we need to sort of start to accept within our lives. The problem being that if you’ve never allowed yourself to do it, then those experiments are usually big ones, and the failures feel really high consequence. Which is why I think, my give yourself permission to experiment is to say, what if you allowed yourself to do it in smaller, low consequence ways where you tried new things and then found out whether or not you were quote unquote good at them, where you signed up for a course and you know, maybe you didn’t knock it out the park, but you, learn something along the way.

So, when you start to believe that your identity is fluid and evolving over the course of whatever experiences that you are gathering, it doesn’t feel so high stakes. Like I think the idea that failure is so high, a high stakes threat to your sense of value is one that you can, you know, kind of dismantle a little bit when you begin to see yourself in a state of constant becoming. And surely what you want to do is accelerate that. Like surely you want to accelerate your learning process. And the only way to do that is by saying, okay, like just as I was a kid, I’m going to fall off the bike. You know, I remember watching my son learn how to skateboard and falling off that stupid ramp thing a thousand times. Like, as young people, we absolutely know, especially if we’re going to do something big and interesting, we’re going to fall a thousand times.

So, if you embrace that becoming, then you want to fall. You want to kind of have those experiences that feel like uncomfortable learnings. But that takes you embracing the fact that you’re a work in progress all the time.

Skot Waldron (26:51.00)
We are. And if we don’t have, here’s where I’ll tie it back, because I think that’s all great. And I think that people, you know, fail forward mantras and all the kind of stuff that we want to talk about that through failure comes growth. I never learned to ride a bike unless I’ve fallen off a few times so I can know what works and what doesn’t work. That’s fine.

I don’t think that there are enough companies that give their people permission to fail. And therefore the people feel that this will damage my identity and my brand of who I am. So, if I fail equals this person will think I’m incompetent. They will think that I’m not good at my job. They will regret why they even hired me in the first place. I think, so I think first of all, I can give myself permission to fail all day, but if I don’t feel permission to fail because of the culture I’m in, like we don’t have a fail culture, then my permission to fail myself is gonna be hijacked. I don’t think it’s gonna matter.

Jillian Reilly (27:57.888)
Yeah, of course, 100%. I mean, one of the reasons that, you know, I’ve written the book is to not only engage with individuals but hopefully sort of contribute to a social conversation around these same themes, which is, you know, how are individuals allowed to behave within different types of institutions. And I do think that younger people are coming into workplaces with a different set of expectations, which is that they do prioritize learning, they do prioritize growth.

And in those situations, they will want to know that in the name of learning, in the name of trying something new, you know, we’re not talking about incompetence here. We’re not talking about, just didn’t do my job and therefore I failed. We’re talking about trying something that everybody buys into believing is, you know, a worthwhile stretch, a worthwhile exercise, which we cannot predict the outcome of.

And I think, you know, the idea that a lot of us have been raised to believe we only act when we know that there’s a predictable upside. Otherwise, why else would you do it? You know, that is such a straight jacket for you in actually stretching out a little bit and engaging with, you know, new parts of yourself and new capabilities. So, I do think companies in order to attract younger talent and some of the most interesting talent will need to create permission structures that allow for people to kind of stretch out and do some things that may or may not pay off, but there will be valuable learning along the way.

Skot Waldron (29:25.826)
What about the permission to ask? I think this is interesting in thinking about how we reward answers, but rarely do we reward questions. And I’ve also coached leaders that are hesitant to ask questions or hesitant to not have answers to other people’s questions, meaning they would have to go ask questions.

They have to put on a front that they have all the answers in a way because they’re leaders. They’re supposed to have all the answers, right? So, I don’t know, this whole culture of awarding answers and being impatient with questions, especially the, are we doing this question? Or can you tell me more about why we’re taking that approach? I mean, I’ve seen so many leaders like, oh, stop asking me questions, just do it. What do you think about the permission to ask?

Jillian Reilly (30:31.00)
I mean, I think in a complex world it’s everything. I mean, I would reward the people who were asking me questions because it was a sign of curiosity and a desire to understand better why we’re doing what we’re doing. I think the age of people nodding their heads and saying, yes, sir, yes, ma’am is over. And so, it’s time for you to let go of that idea that that’s again, what good behavior looks like.

If you associate questions with a degree of sort of impudence or difficulty, then I think you’re going to have a hard time moving forward because the reality is in a complex world where we can’t see five years in the future. We’re often moving quickly or making novel choices. Like we’ve got to do this differently. Okay, I need to understand why.

First of all, as a leader yourself, if you’re going to put the pressure on yourself to have all the answers, then again, you’re playing from a very old leadership playbook. I also work with a lot of those people who feel like they’re inadequate because they’re not Jack Welch, know, kind of guiding the troops through the grandness of, it’s like, no, that’s not what leadership looks like anymore.

It is a process of discovery. It is not sort of, you know, pointing that direction and everybody puts their head down and follow you. I think it’s gathering people around you and walking together and figuring it out along the way and giving people space to do that. So, your ability to ask good questions and to get the best out of your team is critical. You’re creating a culture in which people are allowed to ask, not just to pick things apart, but in the spirit of understanding and creating a common way forward is absolutely critical.

I think, you know, part of what I talk about in the book is that one of the biggest shifts we’re living with right now is needing to act without not knowing, you know, dealing with not knowing because so much of our previous sort of operating model was built out around knowing. We thought we knew, we thought we could predict, we thought we could work with certainty. We can’t. It can feel terrifying.

And but once you move to the other side of it, it’s like, okay, I need to potentially just shift my operating model to allow for more inquiry, as you’re describing, to allow for more adaptability, to let us learn together and accept the fact that nobody right now has a set of directions. And if any leader right now stood up in front of me and told me that they did, I would be skeptical. I would be far more impressed with somebody who admitted what they didn’t know and committed themselves to working through that and finding their way through it with intent and with curiosity.

Skot Waldron (33:18.536)
Admit and commit. We just made up a thing. Well, you made up the thing, but you made up the thing. That’s really smart. I mean, because, you know, there’s some, there’s some people out there would be like, if I ever heard a leader be like, yeah, I don’t know. Like, I think that’s one thing, but if they say, I don’t know, but I am committed to figuring that out. And by next week, next month, next quarter, I’m going to have answers for all of you.

I at least can be like, okay, so there’s some action being done, not just like left with wondering that they did. Like, I think there’s some real, there’s some action behind it.

Jillian Reilly (33:38.00)
There’s got to be action. I think you’ve got to be in a state of active learning. And I think that’s one of the things that leaders right now are finding so challenging is that their lived experience of leadership is one of active learning, like figuring things out a lot more than their mind tells them they should. Their mind tells them they should be operating in a sort of comfort of, you know, execution when a lot of it is more problem solving, more conflict, more this, more that.

And so, you know, sometimes the best you can do is just that I don’t know. I’m figuring it out. And quite honestly, I think a lot of people do respect that. I think people can see through, you know, the attempt to, you know, appear to know what you don’t. I think we’re all a little skeptical of leadership right now. And beyond that, we’re very cynical. People have to earn trust. And so to me, the best way to earn trust is by owning what you’re finding out and figuring out and doing that as well as you possibly can.

Skot Waldron (35:06.114)
And they are finding out with Gen Z that authenticity, I’ll say authenticity is a big deal for everybody, but for Gen Z, it’s a super big deal right now. So, paying attention, that’s really crucial. Okay, we’re going to do a couple of lightning questions. Ready?

What permission do you find yourself relearning over and over again?

Jillian Reilly (35:29.00)
I would say, think small. Where when I’m feeling overwhelmed that I just need to allow myself to take small steps forward to move through what might feel like overwhelm or confusion or panic that, you know, I’m not where I need to be. I sort of keep having to come into myself and say, it’s okay, just, you know, do three things that are going to get you forward and you’re okay for the day and do the same thing tomorrow.

So, I think it’s easy when you’re in a mode of trying to create something or when you’re in the mode of big change to kind of back up and get overwhelmed by the big picture of what you’re trying to do or where you’re trying to get. And so, to continually allow myself to just bring my locus of control inwards, take small steps, keep going, that’s been a lifesaver over the past few years for me.

Skot Waldron (36:24.00)
Permission to think small. Wow. Like people be like, wait, what? Because we see so many big posters on the wall, you know? Like, wow, that’s amazing. That’s a hard one. I can see that one. Okay.

Which permission do your clients resist the most?

Jillian Reilly (36:43.00)
Going astray. It’s my permission number two.

Skot Waldron (36:45.861)
Permission to go astray?

Jillian Reilly (36:47.00)
Yeah. You can see Skot, all of these permissions are sort of little cheeky prompts, provocative prompts to get people to think differently about, you know, what their path might look like, what their life might look like. You know, the idea that making a move, making a change, driving your own change is how you’re going to accelerate your growth and adaptability. It’s like you referenced it earlier, you we resist that, we’ve been conditioned to resist that. And my point is that we don’t have that luxury anymore.

Change is going to happen to us. What we need to do is to nurture our own change readiness by, you know, creating change in our lives. So, everybody is still very much in the default to the status quo. But to say, okay, what if you were to actually, you know, decide to dot dot dot, you know, take make a lateral move, take some time off, switch, you know, switch industries, this, that the other there’s the belief that the linear is still the safest is deeply imprinted in us. And I want people to start to engage with the fact that maybe by creating a sort of more curvy path, you’re actually building up a change readiness that’s gonna serve you at some point over the next decade or two.

Skot Waldron (38:12.002)
And which permission has surprised you the most with its impact?

Jillian Reilly (38:17.00)
That’s interesting. Travel light.

Skot Waldron (38:24.002)
Okay, like, like on a plane.

Jillian Reilly (38:25.00)
You could think of it that way. No, I think there’s a lot of people right now who are re-evaluating their relationship to what I describe in the book as linear accumulation, the idea that your timeline has to look like more, more, more, more, more until you reach a point where you are so that that box that you’ve talked about is actually a box of stuff around you. Because you can’t make any novel choices because you’ve got to protect the box of stuff. And I think there are a lot of people who, when they see this, they’re like, hmm.

And I say this like exhale of it’s not anti-accumulation. I got all this stuff too, but it’s intentionally deciding what works for you at different seasons of your life. And I will say this particularly to people in midlife who feel so hamstrung and so held in place, but it’s okay, you know, to make a decision to, you know, have a more liquid sort of approach to things. Like I know people now who downsize in midlife, which they feel like total failures because they’ve done that. But what they want to do is start a business. So, they’re going to free up some capital to go and do that. And that feels hugely risky to them.

So, anything that challenges that idea that your life should be a gradual accumulation of more stuff and status, when people feel allowed to do that, so many more options come into play. It’s like oh wow. So, you’re saying that, you know, and for younger people, it’s like, gosh, you know, they feel so much pressure to have certain things by certain points in their timeline. And it’s like, what if you were to throw that out? What would you do? What would you allow yourself to do?

So, I think, you know, a lot of what people feel shame about, and I use that word really intentionally, is that either they don’t have what they think they’re supposed to have by a certain time in their life or they don’t want it and they feel weird, or they don’t feel allowed, you know, as I talk about in the book is take only what you can carry. So, if you’re going through a part of your life where, you know, having all of that and doing all of that is too much and you want freedom to try something new, it’s okay to put some things down, regather, and then move forward. That is not a sign that you have failed at life.

I think in a weird way, that’s the most freeing one because yeah, we feel judged by what we have. And if we don’t have enough, then we don’t feel good enough. And that has, I’ve already heard from people that I’ve talked to and people who’ve reread the book, like, okay, that maybe is the one that creates the most space for me in my own mind to potentially do something different.

Skot Waldron (41:27.532)
That’s awesome. That’s awesome. So cool. Thank you for, thank you for writing this book. I mean, again, because it supports my purpose, but also because like people need that and they need like they need to hear you say things like permission to go astray and go wait, wait, what? Like, are you sure I have permission to do that?

Like, those questions should cause me to think. And when I do think that I should be thinking again, why am I thinking that way? What environment have I been brought up in or what thought process do I have that have conditioned me to believe I don’t have permission to do that? And there’s some thought work that definitely goes into that. So, thank you for this.

You have your books launching. If you’re listening to this before the book comes out. You can pre-order. You can. Yeah. And if you are listening afterwards, I’m sure you can get it anywhere books are sold, but you also have a different, you have a community you’re building. Like, tell us about that.

Jillian Reilly (42:36.00)
Yeah. You know, the book is for individuals, but I realize, you know, there’s so many of us going through things alone. know, everybody I know right now is, whether it’s my 17-year-old son or my 50-year-old husband is kind of looking at life and considering doing it different from what the default script is. And my point is we don’t have to do this alone. We’re all finding our way through a really significant moment in history. You know, a lot about how we’ve always assumed we are operated is changing. And it struck me that, you know, people are lonely, people feel isolated. We need spaces to kind of take some of this conversation and lift it up and normalize it and mainstream it. Because as you said earlier, I can give myself permission. But isn’t it great if we have spaces where we feel committed together, where we start to create spaces and companies and teams where it’s like, listen, it’s okay, we’re all figuring this out.

So, if they go to my website, tenpermissions.com, they can find out more about that. It’s, yeah, for now it’s a growing space where people who want to kind of figure out how to intentionally navigate their lives are coming together. And I’d love to grow that as a key part of building out this content over the coming years.

Skot Waldron (43:55.00)
Super cool. Thank you, Jillian, again for writing the book and doing the work you’re doing. Say hey to Cape Town. I’ll visit one day. Please do. The world is a beautiful place, and we should see as much of it as possible.

Jillian Reilly (44:11.00)
I couldn’t agree more.
Thank you, Skot. Thank you for what you’re doing. Honestly, I mean I love what you’ve got on your wall and I love that you’re out here creating conversations and spaces for people to engage with themselves and their stories in a really thoughtful way. So, I’m glad I got to contribute to that conversation.

Skot Waldron (44:35.832)
You know, there was something in there that was pretty profound to me, and I never really thought about it. And we didn’t really expand on it that much, but I don’t want it to slip by. It’s the idea that throughout life, children are taught to ask permission. We don’t generally want kids coming up to us demanding a bunch of stuff, okay? Like this entitlement culture or whatever.

We don’t want to breed people that just expect things and demand things and just tell us things. No, we want them to ask us things, ask us permission to do this, to go there, to have some friends over to eat that thing. And then we expect people to give themselves permission later in life. Or we find it hard, maybe it’s not that we expect it, maybe it’s just that we find it hard to do. As individuals give ourselves permission, we’re like, wait a second, I don’t need to ask for permission to do this thing. Or maybe that’s why it’s so hard for us to also, maybe when we get older and we start parenting and other things are happening, to give other people permission to just be or do the thing. And that’s so interesting to think about.

I love this kind of these, these punchy ideas. I was talking to somebody else yesterday about these ideas of like, do I have permission to think small? What? Can I please get that on a T-shirt? That is going to turn heads because it’s supposed to, because it’s different from the conventional thought patterns that we’re expected to have. And I want you all to rethink some of the things.

This is all thought work. All this is thought work and it’s so important. And I hope, I hope, I hope you took something from this episode that’s going to help you in your life just to give yourself just a little bit more permission.

If you want to find out more information about me or check out the show notes where there’s going to be more information and links to the things referenced in this episode, visit skotwaldron.com. And lastly, I’m asking for a little bit of love, just a little bit. So please take a moment, follow, rate the show. The algorithm is like that; it helps me get the word out. I really appreciate it.

Thank you. And until next time, stay Unlocked.