Varun Rajan 0:06

What if the reason that you're stuck isn't a lack of skill or opportunity, but permission? Permission that you haven't actually given yourself yet. My guest today is Gillian Riley. She's the author of the book, The Ten Permissions: Redefining the Rules of Adulting for the 21st Century, and someone who has spent the better part of three decades studying why people change, and more importantly, why they don't. Gillian's path to answering that question isn't a straight line. She grew up in the Midwest, walked away from law school at 21, and flew to South Africa at the tail end of apartheid. She spent the next two decades working across Africa, including running an HIV/AIDS program in Zimbabwe at the height of the epidemic. And what she saw there completely reframed her understanding of what it actually takes for a person to do something different. it's not resources, it's not training, and, definitely not a workshop. In this conversation, the first of two, we trace the arc of her career from international aid to consulting to motherhood, to author. And we get into what it means to go off-script when you can't really yet explain why. a lot of this really coincides with this theme I've been exploring of conviction over certainty. Certainty is an illusion that's really worth letting go of when you have an innate sense that you wanna pursue something. And, ultimately, we learn how a village in Zimbabwe and a boardroom in New York turn out to be less different than you might think. Welcome to the Push/Pull Podcast, where we explore career transitions and the future of work. I'm Varun Rajan. Let's get into it. We're here with Jillian Reilly, author and founder of The 10 Permissions. Thank you so much for being with us, Jillian.

Jillian Reilly 1:56

Oh, I'm thrilled to be here. Happy New Year.

Varun Rajan 1:58

New Year. would love to know, first and foremost, tell us a little bit about the 10 permissions. let's talk about the things that matter to you today in brief, and then we'll rewind a little bit and dive into your, career story.

Jillian Reilly 2:10

Great. Um, yeah, so I launched my book, the 10 Permissions, rewriting the Rules of Adulting for the 21st Century last year. Um, and as the title says, there's sort of 10. Invitations, if you will, to flip the script on what adult life is supposed to look like in a very fluid 21st century. I think we're all really still deeply conditioned with an old script about who we're allowed to be, how we're supposed to behave as adults, and it's really still framed around a kind of linear, predictable world where. You picked Elaine and you stated it. And I think we're living through the disillusion of that as people are having to be far more adaptive and creative in how we lead our lives. And each of the 10 permissions sort of invites readers to reframe what they think is possible and what they think is acceptable, um, to creating a life they want. And one that works for now, one that's fit for this world. Um, which I think for me, links to what matters to me right now, which is, you know, I'm a mom to two teenage boys. Um, I'm sitting watching them prepare to enter a world that doesn't have a playbook. And that doesn't play by the rules that it did when I was their age. So what matters to me is that we're actually really preparing and supporting people to thrive in this world. 'cause I think there's so much anxiety, burnout, loneliness, disconnect, and fear really. and I don't think we need to feel that way. I actually think there's tremendous possibility right now. But if we're working from an old script. All of this feels really scary. If we allow ourselves to embrace a different way of operating, then all of a sudden possibility opens up. So yeah, I wanna support people to, kind of reboot their operating system for this moment. And in doing so, find a degree of clarity and courage about who they're allowed to be for this world.

Varun Rajan 4:18

I love that. Obviously, I read the book and I went through it, and I have a bunch of questions for you. but I would love to know, I know obviously that book is in addition to being your take on how to approach the worlds that we're coming into and we are in today. A lot of this is also, I think, informed by your. Story and the things and the wisdom that you've collected along the way as well. would love to dive into, how your story has helped shape your worldview. if I were to ask you, where you would start the story of your career, where would you start?

Jillian Reilly 4:53

well, I guess I would start it, at the place where I sort of gave myself permission to step off the path that was laid out for me as a young woman in the Midwest. In the 1980s where you know it was go to college, get a good degree, get a good job, find a nice husband, and at some point I started to become very interested in the world. I started to feel like I wanted to make an impact on it and create meaning in it and South Africa. So it was the sort of late eighties, early nineties, South Africa was going through its transition from apartheid to democracy, which I know is ancient history for a lot of your listeners. it was going through this really profound transition and if we talk about scripts and if we talk about rewriting things, you know, it was trying to rewrite its script and I wanted to be there and I wanted to feel, like I could be a part of something bigger than myself. I still remember going home and telling my parents who thought I was gonna go to law school, that instead I was gonna go to South Africa. that did not go down well. but you might remember, one of the things I talk about in the book is that when other people don't recognize you is when you're starting to get to know yourself. So. I set off on a path to work in the world of international development, international aid. I had no idea how it was gonna unfold, but that first trip to South Africa, which was only supposed to be for six months or so, really sparked something in me. I was like, I'm not going back to the Midwest. I got a job with an American nonprofit that was providing, um. Sort of human resource support and organizational support to local charities. And they took me in and really allowed me to learn on the go. So a lot of what I learned about human change, about making change, about why we do or don't was born in that period. So yeah, as you say, I have a, I have a deep, connection to helping individuals and organizations navigate profound change. Um, I ended up working all across Africa, eventually coming back to Zimbabwe where I headed up an hiv aids program at the height of the AIDS epidemic there. So I got real wide and deep exposure to individuals and collectives trying to find their way through really profound disruption, and that's what we're facing right now. I mean, we are, we are living through something pretty profound in terms of its, you know, mass impact on our understanding of what life is supposed to look like. And it's hugely disorienting and it's really scary. And, you know, at the same time, it calls upon us to start to adapt the way that we work. And so, yeah, I had. I worked in that world for a couple of decades and learned a lot. It taught me a lot, and the seeds of the theme of permission are really there,

Varun Rajan 8:11

I would love to know, a little bit more specifically, you mentioned, working with organizations and individuals and really talking about that kind of like change management and being the person to be agent of that change. I'm curious, when you were doing the aid work, was it with one organization? Was it multiple organizations over time? did you make it, the decisions to join the organizations that you did? What were the things that you learned along the way?

Jillian Reilly 8:41

So I stayed with the same organization until the point that I became a consultant. long story short, you know, the, uh, experience in Zimbabwe was. Hugely humbling I was in my twenties and really deep into some very heavy, wicked problems, social challenges. You know, I was in Mozambique after the end of a civil war. I was in, uh, you know, Namibia as it again, sort of. Found his way post-colonial. So these were a lot of very challenging situations and I think I was, I was learning a lot about my own limitations. So, I went in there bright-eyed and thinking I could change the world because I was this white, well to do, well educated woman from America. And, uh, I experienced a necessary humbling. Which is, we can't roar into people's lives or roar into other countries. Very relevant conversation for today. And think that we can play Savior or think that we can play change maker. and people have deep and rich cultures, traditions, their own stories that they are, that have shaped who they are. And so, in the case of for instance, hiv aids, we were in Zimbabwe in the midst of this massive epidemic. We had all the money in the world and we were throwing it at that problem saying, come now, don't you understand if you just, we had these ABCs, which was abstained, be faithful, where condoms, it was really straightforward, right? That's all you gotta do is those three simple things. But of course it's not simple and we just lived through. An epidemic, and we know that humans behave illogically and, and in varying ways to what we perceive or not as a threat. So,

Varun Rajan 10:40

probably all sorts of like social and cultural incentives and customs that kind of

Jillian Reilly 10:45

I

Varun Rajan 10:45

way that like you come in not understanding or Right.

Jillian Reilly 10:49

totally, and you know, it, it took me. Observing that the degree of nuance, the degree of complexity, the reality that our advice was so actually superficial in the face of what people calculated as their own sense of place within that society and their own sense of purpose. And one of the things that emerged for that for me was the theme of permission. And you know, I said to my boss at the time, we can give people all sorts of things. We can give them training, we can give them facts. In that case, we could give them condoms, we could give them money. T-shirts. We can't give them permission. So in other words, my presence to you saying, you know, it, you can, you should wear condoms. That's really what you should do. Do I feel allowed individually to be the first person in my. In the relationship to raise that? Or does that put that relationship under threat? You know, if I, there was a tradition of, um, what they call bride price, which is that families exchange, resources for a woman to enter into a family and, and long story. But it puts women very much at risk because once that exchange has happened. It takes a lot for a woman to want to break it. there's huge cultural taboos around, breaching that. So we found that, that was one of the risk factors as in the context of aids. But were you gonna be the one to break that tradition? Were you gonna be the first, were you gonna be the last? Did you feel allowed to make what I call novel choices? The unfamiliar, the unpredictable, the unconventional. Do you feel allowed to do that? And for most people, the answer's no. but when you're going through these periods of rapid social change, you have to make novel choices. You have to be the first in your family, the last in your family, because the traditional choices that you always turn to maybe don't work for that moment. So that's why for me, this theme of permission of self permission, which is my willingness and ability to kind of override my own default to what I think I'm supposed to do, is absolutely critical. 'cause it's actually the centerpiece of becoming more responsive and more flexible and more willing to do what's required to thrive in a moment of. Really deep and profound change.

Varun Rajan 13:33

Yeah, it sounds, it sounds to me like permission here. almost synonymous a little bit with and this is a word that comes up a lot in your book, is agency, right? Is like having that

Jillian Reilly 13:44

Yeah.

Varun Rajan 13:45

And it sounds like in this moment with this example that you're talking about it. Didn't sound like the people that you were working with, had that agency,

Jillian Reilly 13:55

No.

Varun Rajan 13:55

they,

Jillian Reilly 13:55

They did.

Varun Rajan 13:56

didn't have, they, they couldn't necessarily just give themselves permission because

Jillian Reilly 14:01

No,

Varun Rajan 14:01

what we see, I think today as like social consequences are like, what are my friends and family going to say? Whereas for them, the social consequences might actually have. More real material impact to their lives, and,

Jillian Reilly 14:14

did.

Varun Rajan 14:15

Yeah.

Jillian Reilly 14:15

did. Yeah. it did. it took me seeing women coming back to us. Who'd been beaten

Varun Rajan 14:23

wow.

Jillian Reilly 14:23

because they raised the issue of condoms with their husband, which then led the husband to say, what's going on? You know, are you unfaithful? So one of the things I talk about in the book is that I have been present with people for whom a novel choice is a deeply dangerous one. in very hierarchical. Companies, for instance, in very traditional societies and any place where the container is so tight that your personal safety rides on you, maintaining the status quo, then you don't have agency. You do the calculation in your head and you sort of decide, listen, I'm better off, sticking with the way it's always been the reality in the. Western World, and that's a huge generalization, but is it, it's much looser than that. And what's happened, as I describe in the book, is the great unraveling is that over the last several decades, it's gotten looser and looser and looser so that, individual choice has become ever more, the norm. Whether that's as consumers, which we love, we get to curate almost everything. we get to have things when we want them. We get to have them just the way we want them, and that is a source of great power for us. But, you know, it's one thing to cur curate your coffee. It's another thing to curate your career. but that's what we're being called upon to do is not pick an off the shelf. I'm gonna be a, an accountant and that's what I'm gonna do for the rest of my life. It's, I'm gonna have to. Develop this, something that might be unique to me, that's a reflection of me that might take turns, that look nothing like my father or my sister. My path will probably look different to other people's. And historically that was a problem, right? You were rogue, you were weird. What's she doing? I experienced that. I'm the only one in my family who did what I did and I got a lot of like sideways looks for it. But increasingly our paths are gonna look different now, degrees of difference, whether the difference is in what we do or how often we do different things. but it's unlikely to be a, you know, cut and paste, find a big job for a big company, and hold onto it for as long as you can because the companies aren't rewarding loyalty and hard work the way they once used to. So. We are being forced to, allowed to create different ways of moving forward. And that is challenging for us because just like the women from those, you know, Zimbabwean villages who were never brought up to do that, to challenge their husbands. We were never brought up to think that. We could have lives that were unique and varied and ever evolving. That was risky. And that was, that was for only a small number of people who might have been artists or very elite, but actually all of us are going to, to greater or lesser degrees, be called upon to create that.

Varun Rajan 17:46

You came into social work and left behind this alternate path of being a lawyer, I would love to know, obviously what came next and the decisions after the social work. But I am curious, before we get to you, understanding the people that you're working with on the ground to needing that permission and that agency to act on the advice and guidance that you're giving them and resources that you're giving them. You also had to give yourself permission to go off the beaten path. And so I'm curious what that decision was like and obviously, Obviously, one of the things I'm always curious about are the push and pull factors that you and the trade-offs that you weighed, when choosing to, go to South Africa at first, instead of going to law school.

Jillian Reilly 18:32

Yeah, I've thought about that a lot because. You know, I can't, I don't have a simple answer for why at age 21 I did something that most people considered completely off limits. I think what I can say is that I grew up in a, um, not very happy household. I watched two people who had just about everything. I mean, they'd lived the middle class dream of that boomer time. You know, my father worked his way up from the. Not the factory floor, but the warehouse floor of a, scientific supplies company to being a vp. We had everything. Um, my mother was the traditional housewife who suddenly had enough money to get her hair done and get her nails done, and, and they were miserable. and I remember looking at that in my own, however, I made sense of that at age 16, 17, 18, and kind of going.

Varun Rajan 19:28

Right.

Jillian Reilly 19:29

There must be something more than this. So the push I would say was, uh, this is not an ideal for me. This is not something that I will consider. the golden ring that I'm reaching for, particularly as a woman, um, because, you know, my generation of women was also among the first to move fully through higher education and out into employment. My mother was sent home when she was pregnant from her clerical job. so we were the first generation that was really truly like, yeah, of course. go get the degree, get the job. and so I maybe took that farther than others would be, which is, yeah, I'm gonna go, I'm gonna go as far as I can and, um, start to. Go beyond the boundaries of what my upbringing had told me was desirable. So I was pushed in that sense. I think I was pulled by, I went to Northwestern University. There was a super strong history program there in African studies program and I was a part of both of those. And there were some really great teachers lecturers who really stimulated my own sense of curiosity about the world. So I just couldn't imagine not at that moment taking a chance to go out and see it. I happened to have a professor who was gonna be in South Africa after I graduated with his family, and he said, if you can get yourself there, you can stay with us. So there was a bit of a safe landing place. I wasn't completely, you know, going out into the great unknown, but, yeah, I think, it was rough. I mean I, my family really did not get it and did not appreciate it could not make sense of it. It was also a very different world. I mean, 1993 was, pre-internet, pre social media, pre phones, pre everything. South Africa was far away and very foreign. Africa was the dark continent. You know, I'm sure there was a degree of both worry. And concern that I was, throwing away what looked to be a, a very promising life and career for something that just made no sense to them. And I wasn't particularly good at that point of making it make sense for them. So yeah, I listened in really hard and, dealt with the discomfort of family members who didn't approve. And one of the things I say in the book is that you learn that approval is desirable but not required. Um, I didn't need their money. I was earning everything on my own. You know, if you don't need somebody else's material support for something, then you actually can deal with them not approving of what you're doing. it might not feel warm and fuzzy, but also you learn to kind of have a pretty strong compass.

Varun Rajan 22:35

Yeah, and this, I also find it really interesting that. you followed what I think was a really strong internal sense of mission and adventure, even though you couldn't quite articulate it to the people that were demanding answers of you. and I'm curious, how important is it? To be able to articulate that for yourself versus having that innate sense of, maybe I can't explain it just yet, but I'm going to take that chance anyway. it actually reminds me of a, I have a note on this. One of the things that you mentioned in the book. Was that we can't, the quote is we can't wait for certainty in order to act. And I find myself wanting to articulate everything and putting it into words before I can have confidence in whether it's the right decision to make.

Jillian Reilly 23:25

Yeah.

Varun Rajan 23:26

what you're saying there is that don't wait for that to be perfect. but before making that sense. So I'm curious if. If that comes from as early as your early twenties when you made that call. I am I'm curious also about the flip side of that, which is, A, is that, do you feel like that's a, that's an accurate description of what you were going through at the time, and does it map to that quote from the book? and then second is, I'd be curious about any examples that you have of where waiting for certainty, however you might define that, Stopped you from having what might have been a better outcome.

Jillian Reilly 24:02

Yeah, I mean it absolutely tracks with that time. it was a feeling and I think, one of my permissions is feel your way. And I think we too often dismiss feeling as an. Unreliable guide. we wanna layer on a degree of cognition and intellect to it to make it feel palatable and acceptable. But actually our feelings are, as we know in so many situations, actually the strongest guide. And I truly believe that for some of the things that are most meaningful for you and most uniquely yours, you won't have words. And if you wait for words or you try and manufacture words, you're possibly diluting the uniqueness or the interest in it because you've already made it familiar, right? By making something familiar, you make it something that already exists and therefore, maybe it doesn't. maybe it in my world, somebody who, went off to. Who was driven by curiosity, meaning a desire to contribute. Nobody else in my family did that. They didn't recognize it. And I tried a little bit to be like, it'll be great for my cv. but they could see through that.

Varun Rajan 25:19

Right.

Jillian Reilly 25:21

so yeah, I really want to, especially now encourage and especially young people to say, you won't have the pitch. And if you try and pitch it and wait for the positive reaction to that to be your only guide, that is good to go. You will either wait too long, you will make it a dulled down version of what it is, and you will undermine your own confidence and trust in yourself, which is probably the most important thing. Now, I'm not saying that you at your house on something that's a fuzzy feeling. for me, there was risk involved. But, nothing that couldn't be reversed. Nothing that couldn't be undone. I could always turn around. I could always, one obviously has to calibrate the degree of, actual risk to the extent to which you want to feel. And I wouldn't even call it certainty because I think certainty is an absolute and complete illusion. I certainty about. Certainty about what all you can be certain of is that you feel at that moment, this is a really high quality decision. Like I'm backing it, it's gonna teach me something. My risk is relatively low, the upside is super high, and you know that's the kind of calibration that I would go through, and I'm banking on the quality of the choice rather than the certainty of the outcome.

Varun Rajan 26:49

Yeah.

Jillian Reilly 26:50

Because I have no idea what any choice is gonna lead to. All I can do is say, okay, I'm backing this because I know it will open up something new for me. And from that position, I'll, you know, go from there.

Varun Rajan 27:03

Yeah. that makes a lot of sense. So te tell me a little bit, let's bring it back up to where we were before. in your aid work, you obviously wrap that up eventually and then move into, consulting. and I think it's around this time that you write your first book as well.

Jillian Reilly 27:21

Yeah. Yeah, it was.

Varun Rajan 27:23

a little bit about that. and yeah, let's let's leave it there. and I'll dive in with more questions.

Jillian Reilly 27:29

Yeah, I mean, I, so I left all of that. I wasn't even 30 yet. Like I just reached a point where I was sort of like, I am, I'm sitting here in Zimbabwe. I had this huge job, far bigger than I was actually on paper qualified for. we were moving huge amounts of money. I had lots of responsibility and I was looking around kind of going, this is not having the impact that I think it should have. the organization was called pact, PACT. They were funded by the now defunct, U-S-A-I-D. they received money from the US government, as I said, to strengthen local NGOs. The, the phrase, the kind of jargon was capacity building. So the idea was. We are not coming to directly deliver aid. We are here to work through local organizations to strengthen their ability to give them funds, to try and, you know, build up that civil society component in these countries where, they were a huge, player in the development world. so I had, when I was still based in South Africa. They sent me to Zimbabwe to write a proposal for an hiv aids program because at that time, Zimbabwe had the highest AIDS infection rate in the world, and the NGO non-profit community in Zimbabwe was under huge pressure to alleviate the problem, correct the problem. I wrote the proposal for that project and then they said to me, do you want to go and run it? And I was 27 and I was sort of like, yeah, sure. 'cause I thought I could do just about anything. So they sent me off. I was the youngest director in the whole organization. I arrived and everybody was a little bit like, who are you? I was much younger than most of the other directors, so yeah, I had about five people, local people working for me. We had a budget of roughly five or $6 million and we were delivering support to local agencies. Um, but people were just pushing so much money into the AIDS epidemic that we were also getting a lot of money and being expected to spend it. I mean, that's part of how that. World works is that you gotta spend the money. 'cause if you don't spend it, then you don't get more. So it's also quite difficult to spend millions of dollars in a very small African country. So you end up spending it on things that aren't entirely necessary. Now I wouldn't, I saw no corruption. I saw no mismanagement. I did see a very heavy emphasis on kind of process, like we ran hundreds of workshops. we did a lot of stuff that was sort of very process oriented and when I started to ask questions about, okay, do we know if all of this stuff that we're doing is actually having a tangible impact on the ground? I was sort of told to just be quiet and keep spending money. So that was where my own disillusionment with this world of. What I later described in the book and in my TED talk is sort of supply side change work where you've got so much money and you just have to spend it. and it, and change is, it's long. It takes a very long time. It doesn't work in short timeframes where you can go, Hey, look, A plus B equals C. it's a very complicated process and we were under a lot of pressure just to sort of. Perform.

Varun Rajan 31:17

sounds as an employee of this organization, you didn't really have the agency or permission to report back what the actual results were on the ground. Like how are you able to

Jillian Reilly 31:31

Yeah.

Varun Rajan 31:32

of change for the communities that you're

Jillian Reilly 31:35

Yeah.

Varun Rajan 31:35

If the organization that is supposed to serve those communities is unwilling or unable to like. Take the feedback that you're giving them because their incentives are essentially to make sure that the funding levels do not subside, one way or

Jillian Reilly 31:50

Totally. Yeah. Now it's, and it's in my first book and it's actually in some content that was cut out of this book, which was, looking back, could I have taken more risks? Could I have given myself permission to push harder, to scream louder, to say more probably. But again, I'm this 27-year-old woman, um, in a system that's dominated by older men and older people from all over the world. I didn't feel using my own language aloud. now I wasn't in danger. I could've probably, again, using my logic done more, but I was trying to play the game and trying to succeed by its terms I felt sufficiently compromised. to leave, like I was really on a track to either get another job similar to that in a bigger country with a bigger budget, or to go back to Washington and become part of the headquarters staff. I mean, that was the, if we're talking about paths, that was the path that most people in that world were taking. Like, I had my dream job and I had it earlier than most people, and I sat there and was like. No thanks. we need to, this needs to be far more fine tuned, far more nuanced if we want to make the impact that we say we want to make. And the truth is, it's too blunt of an instrument to do that kind of work. Like there's just too much money that you're trying to throw at things. So I sort of realized that that was not. Again, what good looked like for me. And so I left and that was when I started to do freelance consulting to other NGOs, to corporates around some of the things that I'd been working on there around change management, around leadership development, team building really to pay my bills and to kind of figure out what the hell I was gonna do next, because I really didn't know I. As I said, I had my dream job and I left it. And then I was kinda like, well, if I want to, if I'm serious about making meaning and doing something of value in this world, what is that gonna look like? And it took me a very long time to try different things and arrive at different conclusions around that. But yeah, it's uh, it's uh, a very strange thing to think that you can. incentivize people to depart from who they've always been and how they've always behaved with money. It doesn't work.

Varun Rajan 34:40

The go ahead.

Jillian Reilly 34:41

or, no, I was gonna say, or with facts or with logic. It doesn't work.

Varun Rajan 34:45

and this is so interesting because there's the change for the communities that you're trying to enact and running into obstacles. There's the change within your own organization that you are unable or unwilling one way or another, right? because I think. all been there and there's something to be said about like youth and ambition and career trajectory, it's not just youth. I think a lot of us, like a lot of people get stuck in, I can't do this. I have my marching orders, like at a job and you could always take the chance and get fired, but you gotta take that chance or you leave. and I've definitely been there, obviously in far less, I think. far less impactful, circumstances, but I think organizations, function, similarly across different categories. And so what I'm curious about is, what, when you. When you moved from your obvious, you had a push, a series of push factors here where you're like, the work that I'm doing here isn't impactful and I can't make the kind of change that I want to. and it sounds like you were looking for your next pull while you were doing some consulting to pay the bills. did you find as more of a free agent when you were consulting that you had some freedom and flexibility and agency to be a little bit more forthright and honest about changes that. The organizations that you were consulting for could implement, in ways that you

Jillian Reilly 36:06

Yeah.

Varun Rajan 36:06

to do at your, full-time job before.

Jillian Reilly 36:09

Yeah, absolutely. Sure. You know, you can be a truth teller, you can be a, one of my colleagues used to call it a stone thrower. You know, you can come in and kind of say the things that nobody else can say, and sometimes that's actually what you get hired to do. at the same time, you often end up getting instrumentalized in change processes that. Again, back to this issue of permission, and I'll weave it through here too, which is, you know, going to, I was suddenly, now I was working with major headquarters of large multinational nonprofits in New York City, and the dynamics that play out under a tree in a village are not that different from what plays out in a boardroom. And one of the things that I talk about is the unspoken question that hovered around all of those things is, am I allowed. You know, we're always kind of looking for cues to tell us. If I say what I want, really wanna say, if I do what I really wanna do, if I present that idea, if I share that opinion, if I, is there gonna be blowback, is there gonna be, is, will it be welcomed? Will I be rewarded for it? So there's this constant calibration that we're all making sense of at all times that. Mostly is unspoken, unwritten. You know, a lot of the work I'm doing now with the 10 permissions with teams is around those internal and external cues that the more explicit we get about what are the rules, what are we allowed to do, what are we allowed to be? How are we creating environments that are permission rich in terms of people bringing their best? You know, so much of that stuff we just take for granted, or as leaders, we don't attend to. I was doing this work in the nineties when there was just in early two thousands when, consulting was still new-ish and people were still betting big on firms and individuals coming in and solving problems for them. And, you know, a lot of times there was a, a stated desire for change, but as we've all lived through the actual reality of. What it's gonna take to shift behaviors is deeper and more complex than what anybody truly had an appetite for. So I think as with all of these things, and again, it, it left me even in that phase kind of going, whew, do I honestly think that I can orchestrate change as an outsider? what are the limitations of that role? Whether full-time or as a free agent and it just, gave me more data in that respect. I learned a lot, again, being thrown into so many different situations and yes, at times I could, be a little bit more, if you will, authentic towards the end of that work in that period that I was doing, as I got more bold, if you will, you know, you certainly get pushback. Some companies don't want the person who's gonna come in and say, this is what I'm hearing, this is what I'm seeing, this is what I'm perceiving. They want somebody who will just act on their own, perceptions. But it was all unbelievably rich learning for me about this concept of why and how we change or don't as individuals and as collectives, even when we. Know we should, or even when we know we might want to, but we actually need to go through a process of allowing ourselves to override what's always been in order to create something new. And again, that's for me where explicit permission is like a turnkey to a wider range of behavioral options.

Varun Rajan 40:05

Yeah. is there, so from the kind of. Change consulting that you were doing with nonprofits, did that evolve, into working with what were the sizes of organizations that you were working with? Did you move on to working with firms and companies? I heard you say, I'm trying to just understand the, like the process of your, just the timeline of your career and kind of what the, what would you say the next kind of big pivot was?

Jillian Reilly 40:34

becoming a mother? yeah, I, so mainly, I would say 80% of my work was with large nonprofits. Washington based, DC based, Geneva based. So a lot of also UN organizations. that was just the natural progression for me. And then thrown in. There were a handful of mostly not, corporates that would had either I'd been directed to from the nonprofit field or were had links to that ecosystem. I wrote my first book in that time. I was really feeling around for what do I think I can do that's actually gonna have integrity? And I was feeling really burnt out by it all and 35 years old and going, okay, I think if I'm gonna have a family, it probably should be now. And when I did have my first son, I realized that, one, I needed a break. Two, if I was gonna have a child, I was gonna be, I wanted to be as present as I could for him. And the nature of my work had involved so much travel and so much moving around the world that it was gonna prove very difficult for me to have that stability. So I stepped back and, immersed myself in the mothering role, which was. As challenging as anything else that I'd done. but I also did my TED talk. During that time, I started to eventually play around with starting other little communities of like-minded people. I started a small group called Troublemakers, because I think if I look back on my time in that world, the regret that I had was. My unwillingness, my to make trouble, my feeling that I wasn't allowed to be as difficult as I probably should been. And, the more empathetic, generous part of myself towards that young woman was that nothing in my world had prepared me to be anything but the good a student. The, if I was asked to do something, I was gonna do it well.

Varun Rajan 42:45

and or yeah, consultant and.

Jillian Reilly 42:49

I didn't feel allowed to do it. But the truth is, if we're gonna make change, then we need to make trouble. And I knew that from my own life, which was if I was gonna walk off on a path that felt right for me, I needed to deal with some trouble in my life, which was uncomfortable and contentious, but I could handle it. It was okay in my personal sphere, I think in my professional sphere, I didn't feel. Quite as confident, doing that. So yeah, I played around with a whole bunch of different things in the process of raising my two kids. continued to do kind of light consulting work and kept really, thinking about the theme of what, what could I offer to enable and support change. That might feel like the word I kept coming back to was integrity. You know, that wasn't me coming in and trying to, layer certainty onto very complex situations or pretend that I was pulling strings, but rather something that felt like a, a generous contribution to a conversation around what does it take? For us to do the things and be the people that we want and need to be at different times as the world changes. I think I felt at some point very early on, after having Luke, my older son, that there probably would be nothing more important that I would leave in this world. Than my children. And then if I were to have regrets, the ones that would sting the most would relate to them. So I was going to err on the side of making decisions in relation to them that I felt very, very comfortable with in terms of, and that's different for everybody. And so it's not dogma around what that looks like, but for me. I sacrificed a lot in my career and, I'm dealing with that now. That's very real. you know, I, I was raising my kids at the time of, social media coming online as a key network builder. So I, when I felt like I was ready to press, go on a more intentional career building phase in my life, I did so with like zero network. I don't have the big kind of institutional networks behind me that help to leverage things and telegraph things quickly. Um, and I, at the time, because of when it was all unfolding, probably didn't do as much as I could to just start building my profile and keep that alive at that time. we took the decision, my husband, south African. we took the decision to move from London back to South Africa because we wanted the kids to be close to one set of grandparents. And, you know, I've thought many, many times about how my physical location definitely shaped for better or for worse, how my career from that stage developed. I was physically far away geographically. Isolated from some of the people who would've in organizations that would've been natural clients for me. Um, I was aware of that and kind of comfortable with it, and I still am. I'm also clear-eyed that it now, I got a lot of there, there's no catching up. I will never catch up. But that, it's positioned me right now in a place where I don't have as much to reach for as if I had continued to build my career, during that period. And kind of back to the theme of the book, for me, intentional choice is the antidote to regret. if I back my choice and it doesn't turn out the way that I wanted it to, or it has long-term consequences that I realize I've got to deal with. Um. The feeling that I have will be, won't be regret. It will be, perhaps an awareness that I had other choices. There might be some sort of, huh, maybe I could have done it differently. But regret is a very specific, and I talk in the book about avoid regret because you can't change that. And that sits with you and it stings you. And for me it's very often a product of choices that we didn't want to make but made anyway. And, as long as I want that choice, and I, and then I find out that there are obviously a variety of consequences related to that choice. In my case, it was gonna put me on a back foot career-wise, but it was gonna mean that I, I have no regrets about the time that I spent raising my kids and piecing together. I did a lot of local work. I tried to kind of keep. Little things going to bringing, keep income coming in. But one of the reasons we moved back here was because it was almost impossible for us to live in London on one income. it was just too hard. So at least here we could kind of make it work. and both my husband and I have had, career implications from that. But we still look at each other today and say, no regrets. I was there, I saw a lot. I, yeah, for me, that made sense. That's not a choice that everybody has. Everybody has different sets of circumstances, but, yeah, it's, it's meant that as a now, 54-year-old woman trying to orchestrate a sort of third chapter, new chapter, um, I got a lot of building to do. I don't have a strong foundation to build it on because there's a big hole in the middle of about 15 years where I was not actively growing my network or building my public profile. but okay, I can live with this. it just means I need to be a little bit more, inventive right now. But, um. That would, that probably is what comes to mind for me in terms of my own values, I would say, and who my kids know me to be. I do think the whole, you know, you will walk that and you will be that person, and you don't have to, I didn't feel I had to be evangelical about it with my kids because, no. Who their mom was and you know, what she stood for. and I think sometimes we need to lower the pressure on ourselves as parents to, inculcate a certain worldview or set of values that is best shared through the actions that you take. And if you remain true to yourself, they will see that. They will understand that. Um, and it's interesting now being a mother of two young men. uh, they're their own people as well. And that's the other thing is you're not creating little, it's not a project. It's a little human who's gonna turn into a big human and he will have his own opinions, um, about the world. So, yeah, I, for me, the biggest, premium I would place is on your own personal integrity. And that'll do all the work. And, so many other things will sort of fall into place from there.

Varun Rajan 50:24

when did you start pivoting back into kind of career stuff again, your kids are, getting older and coming into their own and also are a huge inspiration for the work that you're doing today. And for the book, as well. tell me a little

Jillian Reilly 50:38

Yeah.

Varun Rajan 50:39

like. And entering the kind of like professional world. it's not, it sounds like you never really left necessarily, but I'm curious about making that maybe like a bigger focus in your life and having it take up more space and time, and how that's led into where you are today with the book, what you're seeing in the world, et cetera.

Jillian Reilly 50:57

I gave myself permission to experiment. which as you know, is one of the permissions. And I think one of the things particularly, moms, and all, but all of us, you know, we treat everything as a binary. I need a job. I'm at, I'm stay at home, or I'm at work, I'm this, I'm that. I think sometimes we need to allow ourselves to try some things and figure out how they work, if they work what we want. I ran a lot of experiments, you know, as they sort of moved out of their small kids into sort of medium-sized kids, from little ones to tweens and whatnot around, as I said, sort of creating communities. I was taking on consulting work

Varun Rajan 51:40

All throughout

Jillian Reilly 51:40

all along. I kept kind of thinking that I wanted to make my own thing. I didn't wanna just be a gun for hire. I didn't wanna work for somebody. I wanted an offer. And I went in to put an offer out into the world and then have that attract people to me, be attracted to me so that I, I was never gonna work for somebody else again. I mean, I think I'm virtually unemployable at this stage and was for a very long time. So it was not a case of working for somebody else, it was a case of what do I wanna create and what does that look like? And gosh, that's been a very long journey from, creating communities. I. I, and I would say this is sort of as they moved into their early teen years trying evermore to, yeah, offer experiences. I had a very strong feeling that I'd learned what didn't work in the realm of change, which was. You know, shoving people in a room and talking to them and having them sit and absorb cognitively. I was, I was very driven by this idea of creating experiential learning, helping people move into spaces, physical and otherwise, that helped them engage with this idea of, how far am I willing. To go in my life, can I cross those boundaries? So I think the red thread throughout everything that I was trying to do was that issue of how do you help people go beyond the known and familiar to do the things that they want to do, but feel afraid of to, as I said, be the first, be the last. and that took a variety of forms. Right before COVID, I had started, something that I called first. It was called Ante Carra, which means frontier in Sanskrit. And my tagline was, kind of Find your Frontiers, which was, yeah, get to those places where you're like, am I allowed to be here? This is scary, but this is where I need to be if I'm gonna go and do the things that I want to do or have to do. And then I pivoted that into what I call the Explorer's way. Which again, theme of moving beyond what we've always been and where, what we've always known into kind of new spaces. And I was offering, um, immersive experiences here in Africa that we're using the bush, using the physical landscape as a learning ecosystem for Yeah. What does it feel like to be in spaces that are. It's unfamiliar, even scary. so I kept playing around with this idea of the, the real catalyst for people to kind of move beyond what they've always been or known or done into. And the real theme here, and I think we can stop here for now 'cause it's the link up to permission, is I became more and more interested in people's relationship with themselves. Because we are pretty much, 80% of the time the thing that's stopping us. we can blame a variety of other factors, but in fact, we're, we are our own green light, we are our own red light. And until you start to engage with yourself switching those lights on and off for yourself, you're not gonna be growing and changing in the way or at the rate that you need to. So. Yeah, that was kind of where all of this work took me, which is we actually need to work on and with ourselves much more than we've ever felt we had to.

Varun Rajan 55:25

Awesome. Thank you so much. Yeah.

Jillian Reilly 55:28

Awesome. Thank you.

Varun Rajan 55:30

I really appreciate it. I,

Jillian Reilly 55:31

I.

Varun Rajan 55:32

this is the super, honestly, like I'm learning so much from this as well because I'm in a very, like transitory part of my life where I'm also experimenting a lot. And your book has been really helpful to me. I'm really excited to dive into it in our next conversation. That's part one with Jillian Reilly. There was a lot that stuck out to me about this conversation, but one of the things in particular was this idea of avoiding regret at all costs. Always index on the quality of your choices rather than what resulted from them, Because you could make a good choice that leads to bad outcomes, but as long as you made that choice in good faith making a bet that you fully stood behind, even if you haven't quite articulated it perfectly to yourself or those around you, that is integrity, and that should give you the confidence to move forward and continue to make those bold bets and choices in your own life. and that's fundamentally different from making a choice when you felt pressured into it or feeling like it was the thing that you should be doing. Which gets me to the second thing that I really took away, which is that most of the time, we are the thing that are stopping ourselves, not our circumstances, not what other people think. It's, it's us, and the real work is learning to recognize when you're the one running the red light on yourself. In part two, we go deeper into the book, the specific permissions, how Gillian applies this framework to life and career, uh, how it might work with teams and organizations, and what it actually looks like to rebuild your career from the ground up. "The Ten Permissions" is linked in the show notes. Please check it out. Uh, I found that it was an incredibly thoughtful book, and it really resonated with me. So if this conversation landed for you, I would genuinely love to hear how. Uh, you can reach me at Varun, V-A-R-U-N, @pushpullpodcast.com, or slide into my DMs, uh, if you're seeing this, uh, on your socials. Uh, thank you very much, and I'll see you next week