Varun Rajan 0:06

There's a phrase that comes up constantly when organizations are trying to transform, and it's called change management. And Jillian Riley thinks that that framing is the problem. In this second conversation with Jillian, the author of The Ten Permissions, we go deeper into what real organizational change actually requires. Not programs, not events, not consultants parachuting in with answers. The real answer is capacity, capacity for change. The ongoing ability for a team to keep adapting as the world keeps moving, and if you can't build that, she argues, you're not really changing anything. You're performing change. We also get into what happens when automation removes every role that can do it the same way every day, what a permission-rich culture actually looks like in practice, and why optimism isn't naive, it's a prerequisite for agency. And we also talk about how to think about your career less as a ladder and more like a portfolio. Welcome to the Push/Pull Podcast. I'm Varun Rajan. Part two with Jillian Riley starts now. Okay, we're back with Jillian Riley, author and founder of, the 10 Permissions. You found organizations that were willing to change where you could come in as a consultant to make that change? Because sometimes it's easier to do as a, as like an outside person coming in to really just be honest. And then there are other times where consultants are hired to just make the bad decisions or something like that. And I think what it comes down to is, you know what, I guess what differentiates those two? and do you do that kind of assessment of the leadership or the teams that you're like going to be held accountable to before coming in to do that work?

Jillian Reilly 2:03

Yeah. Whew. Big question. in an ideal world, I think yes, there is a degree of pre-work that goes into just understanding what the existing dynamics are among a group of people, a team, I think with the nature of the world right now, that's becoming less and less viable. A lot of teams don't wanna devote time and money to that kind of assessment. but yeah, I generally don't prefer to parachute in, if you will. having said that, as you rightly say, I'm increasingly seeing my role as that. Very much of a catalyst and a guide as opposed to a source of answers. because I think it's very hard to have answers for people when you are not part of their lived reality. I think, increasingly over the years as I worked more and more, I felt like my job was to help. Create the conditions for people to have the conversations that they wanted and needed to have more than anything. it wasn't about me magically pulling, answers or ideas out of the air. It was. To what extent could I create a space or an experience for people to feel, to use my language, perhaps a little more permitted to explore the things that were on their minds. And of course, depending upon the culture of that team and its background and its conditions that is more or less difficult depending upon what it is that they are contending with. sometimes there are issues that are what I would describe as Growth oriented, generative, Hey, let's figure out, how to grow. Which, is not something rooted in pain or conflict or challenge. and I think in those situations, your job is to just. Generate the best ideas and make sure people feel comfortable sharing those, which is not easy. 'cause most of us self-edit quite a lot. if you're dealing with something interpersonal where people, where there's conflict, where there's a history of mistrust or any sort of dynamics where people feel as though they haven't been heard, they haven't been seen, I think then of course you have to tread a lot more carefully on. A degree of, I wouldn't say repair because I don't think that's possible within a single experience or consultation, but beginning to surface the ways in which people can adjust and adapt themselves to start rebuilding the kinds of relationships that they want and need. So to me, it's very context specific. in terms of the shared history of the people that I'm working with. And then it's also very issue specific in terms of what's on their mind, what's on their agenda that they need to deal with. And I would, adjust my approach accordingly. and always mostly try to listen and ask questions and as I said, create the conditions for people to have the best possible conversations they can have at that moment.

Varun Rajan 5:19

on that same note about, just how different organizations can be, in terms of what it is that they need to work on, what phase of their kind of life as a, as an organization is, what phase they're at. I'm curious about where change efforts might fail, when I think one of the things you touched on was when the incentives, reward activity and optics over outcomes. what differentiates an organization that has a real appetite for change versus a performative appetite for change.

Jillian Reilly 6:03

If I said permission, would that, would you roll your eyes? I think it's, I'm gonna, I'm gonna keep drinking my. Kool-Aid, how much do people feel allowed to ask questions? Really ask questions, ask hard questions, to disagree. Like in most places, that's really dangerous. to run small experiments, to have big ideas. Are they really coming with the full scope of their individual contributions or are they always massaging what they say or do to fit a sort of sanitized version of change that is normally a version of the status quo? So that would be my definition of performative is there's a stated desire for something to shift, but actually there isn't an appetite to really embrace. All that would require, right? Because it will require you to behave differently. And a lot of people don't actually wanna do that work of changing the way they, converse with each other, changing the way they meet, or, approaching whatever aspect of their work differently. So I think, in the environments when I work with teams that I'm trying to help them. Create for themselves because they will create it for themselves, not me. there's a space in which people feel allowed and to use your word, incentivized to really bring it and work on this and dream and try and yes, fail. And that's what change evolves. We all know that from our own lives. It's rarely the pretty before and after. It's messy. It can cause confusion and it can cause conflict. It probably should. Otherwise you're probably not changing very much. a lot of teams find those things threatening. So I think that's part of my message to leaders and teams is that you've gotta get really explicit about what you're prepared to allow. In order for this to happen and then keep practicing that. it's not a poster that you put on the wall. It's a routine practice of saying, it's okay. don't worry. we're fighting here today. we have totally different opinions on x. I respect you, you respect me. Let's use this as creative fire instead of, character assassination. Those things. I think it's incumbent upon leaders within the team to nurture that. And that takes work. And I think the primary job of a leader right now is to create those conditions. Because if you've done that, a lot of other things take care of themselves, right? you get growth, you get innovation, you get good conversations, so I think in a very fluid environment where there's a huge premium. On your capability to keep adapting and changing to the fluid circumstances, creating the conditions for people to do that is really key. And that's not an event, that's not a, we are running a change, program that is an, a capacity that gets, tested and honed and strengthened over time. yeah.

Varun Rajan 9:23

Yeah. No, that, that makes a lot of sense. It's an ongoing commitment, right? It's not, it's not a single intervention. it's an intervention that's supposed to, change the trajectory of, of how an organization approaches things like its conflicts and culture overall. is that a fair way to,

Jillian Reilly 9:40

Yeah, I think, if I can say when I started to do this work in the, I'm about to date myself, but in the nineties it was an event. the way I see it is, status quo, blip on the screen. You try something new, you then, whereas now it's just much smaller iterative and adaptive loops that allow you to keep adjusting as opposed to. Correcting or changing on an intermittent basis. And what that means is that your job is to build change capacity within your team, not to execute change programs. That's a very different thing, right? Because most of the time it was seen as, I have to take my team through this. I shepherd them through this change. And then we return to our business as usual mindset once that change is quote unquote complete. And what we're dealing with now is a change is never complete. It's never a cool, we did that. Now you will have a sense of closure and you will have a sort of, waves of perhaps urgency or focus around specific things. You can't necessarily say, okay, cool, that's done. Now let's just go back to, day-to-day implementation. So I honestly think that's one of the biggest mindset adjustments that leaders and teams are grappling with right now, which is we've gone from a world where it's kind of implement the plan, do the thing, do it every day, do it anything that's, do it every day in exactly the same way, is. About to get outsourced if it hasn't been already.

Varun Rajan 11:25

Right.

Jillian Reilly 11:26

if you can do it the exact same way every day, then something else can do it,

Varun Rajan 11:30

Yeah. That's what automation is,

Jillian Reilly 11:32

That is what automation is,

Varun Rajan 11:34

Yeah.

Jillian Reilly 11:35

so you know what, especially for humans right now to say, wow, okay. My job is not to be a corporate cog because corporate cogs. Are close to obsolete. And this is very challenging because every single generation before us was raised to be a cog, whether in a factory or a corporate or a school or wherever. And now it's okay, no. Those things will be automated. They should be automated given the existing technology. So what is it that I as human bring to this endeavor? And if that isn't a degree of upper level thinking of innovation, of a willingness to look at things critically and tinker and change, then you are gonna struggle to find your relevance. And this is where, I'm quite concerned about future generations and current generations and their readiness for this new and emerging reality. But it's. It's what we're facing and I think we need to acknowledge it sooner rather than later.

Varun Rajan 12:48

so glad that you brought it, brought it back to, from the kind of like organization level to the individual level because

Jillian Reilly 12:54

Yeah.

Varun Rajan 12:55

definitely what I wanted to dive into next. But before really getting into it, I want to set the backdrop, I'm sure of, how we're all thinking about this when it comes to, knowledge work more broadly. I, one of the things that you defined in the book. this kind of like dual definition for what we're experiencing right now, which I think you gave it two names, right? There's the unraveling, as well as Renaissance. And if you wouldn't mind going into it and just, talk a little bit about the forces that you see, what's actually breaking, what's being born. You touched on this a little bit just now, but. it, it would be nice, I think to just wrap, wrap it up in a package, that we can unpack for, digging in a little bit further on permission at the individual level.

Jillian Reilly 13:36

Yeah, I think we're all acutely aware, particularly at this moment of what I call the unraveling, which is, the sort of loosening of ways of living, ways of working, ways of being that have shaped our understanding of how the world works. For several generations, the containers that held us and told us what to expect, what was normal, what was likely to happen. No longer are delivering on that promise for better or for worse. And I would say that, anybody who's an adult right now will have experienced that from, the late nineties, early, late 20th century, early 21st century, when things started to become. More highly curated, more on demand. the desires of the individuals started to drive, certainly from the standpoint of consumption. how we understood how things worked. We also had, more liberalizing social norms. our roles in society came under question and appeared much more, up for definition. Than they previously had. as I talk about in the book, it's everything from nine to five as a concept that shaped our understanding of what a workday looked like, or Monday to Friday as the container that told us when to work. which we all know now is largely a joke, and yet still. Shapes, it's still alive. We still use it. So you know, we're in this phase where these things are no longer truly in place, but they still shape our sort of general beliefs around how things are supposed to be to creating your own pronouns. Two, looking at institutions and how we would expect them to behave and what we think they're supposed to do for us, which was a kind of. Social contract. That was, what I describe in the book as an if then world where I feel fairly confident that if I do this, then this will happen. If I get a, a degree in accounting, then I will likely find a job and my strategy will be to install myself in a large corporate and begin to work my way up that hierarchy That was. Sort of the unspoken default life navigation strategy, right? and I worked within that fixed container and felt that the odds were pretty high, that if I did that, then I would be rewarded with security and status. And we all know that these things now are unraveling. So the expectations, the promises. The kinds of guarantees that we felt we were given, no longer hold. And some of that's wonderful. Some of it probably makes us feel like we've got a whole lot more choices than we used to have, which we do on every single front. We have more choices about everything from, and as I say in the book, from, a coffee to a career. And I think we feel like very empowered consumers who can stand there and say, I want my double shot extra hot. almond milk, no foam cappuccino, and go, ah, isn't it a wonderful world when my grandparents were, getting, filter coffee decaf or with milk. So all those options make us feel hugely empowered. And I think what we're feeling now is that we're moving into the rest of our life where we similarly have to say, oh my gosh, I've got choices. I don't have one choice about how to, find my way forward. I've got. Hundreds of them and I don't know anymore which ones are good ones. there are no guarantees anymore. I don't, let's take the example of going to college, that was a given only probably a decade ago. If somebody asked whether it was worth it to go to college, you'd probably say, what are you talking about? That is. The absolutely necessary hoop that you have to jump through. now it's a for grabs, having children, getting married, all the things that were a standard part of an adult's life are now your choice. So the pressure on the individual to make choices in every single realm of their lives and to rely on their own agency and discretion to make those choices is massive. And nobody can tell you whether it's the right choice. You have to decide for yourself. And so that can feel like, oh my God, I don't know what to do. I'm exhausted. I'm exhausted from scrolling through Netflix trying to figure out what to watch instead of having it programmed for me. Now I've gotta figure out whether I'm supposed to go to college and that's a good choice. I don't know. so that can feel very overwhelming and loose and everything is just up for grabs. The Renaissance is. All the space and all the options that exist within there for you to make those choices. But you've gotta be prepared to make them. And then you've gotta rely very heavily on yourself and back yourself and say, I'm not going to college. I don't want to, or I wanna go, I'm gonna go and get my law degree. And I love, I feel passionate about this. I wanna, but you have to back yourself in those decisions and. Know why you're making them not just sleepwalk through a life of what I call ready made choices, because not only are they not there anymore, but the remnants of the ones that are still there are I don't know if they're gonna serve you the way that they serve your father or your mother. So the unraveling becomes a renaissance when you're prepared to make your choices and back yourself and go for a bit of a ride. Because it is not gonna be A plus B equal C. And that's the world that we're in right now. And I think there are a whole lot of people who are staring at it going, oh my goodness, I don't know what to do. because they weren't prepared, they weren't conditioned, they weren't raised to make all these choices. But that's what we, as I like to say, that's what we've got to do. That's what we get to do. my mother didn't have those choices. I'm acutely aware that at age 53, I'm, on a podcast and she was sitting at home during the New York Times crossword and slowly disappearing. 'cause that's what 50-year-old women did.

Varun Rajan 20:22

Yeah.

Jillian Reilly 20:23

I have options and I have choices, but I need to make them We're living longer, we've got more that we can do. But if we remain programmed for a world that no longer exists, we're gonna walk blinking through this one going, oh my gosh, will somebody tell me what to do? Somebody show me the way.

Varun Rajan 20:45

I love that. And I love the distinction between kind of, the approach to the unraveling versus the approach to the Renaissance, right? one where there's the kind of like unbundling of the promise and the security, and like the flip side of that is obviously the opportunity and the choice and. I really like the distinction of what we've got to do versus what we get to do.

Jillian Reilly 21:07

Yeah.

Varun Rajan 21:08

really, I think that really puts that into perspective. on, on that note, and this is something that I remember you actually opened the book with. you were talking about the importance of being optimistic over being cynical.

Jillian Reilly 21:18

Yeah.

Varun Rajan 21:19

given the trajectory of where things are going with AI and the gig economy and all of these things, I've seen so many. Cynical and dystopian takes. There's a lot that I think there is to be skeptical, and weary of. but your take I think, really resonated with me as a kind of perennial optimist. Why is it important? And I think more crucially, why is it useful to be optimistic

Jillian Reilly 21:47

Yeah.

Varun Rajan 21:48

How do you know when optimism bleeds into willful ignorance? How can you stay optimistic while avoiding, ignoring warnings?

Jillian Reilly 22:02

Yeah. as I said in the book, I think

Varun Rajan 22:04

I.

Jillian Reilly 22:05

agency is born of optimism. Our best creations are. our greatest sense of power is born out of optimism. And I think that's one of the things that sort of fueled humanity, for generations was a belief in self, a belief in possibility when, and I think one of the phenomenon that social media has been responsible for is the kind of baking in, of cynicism and. catastrophe, catastrophization, into a collective psyche where any, anything other than that feels naive. but listen, I don't have the luxury of not being optimistic, and I've got two teenagers and I refuse on their behalf. To believe that I'm sending them out into a broken world where the best that they can do is hobble along and hope to, garner some modicum of security for themselves. They have to. Look out at this big, beautiful, chaotic world and see that within the space of everything that is breaking is the word you used just a few minutes ago, is all sorts of space to make new things, but you won't make new things if you're hooked on an old story. And if you're waiting for somebody to come to you with a new script, with a new formula for, just do this and you'll be fine. There are no more scripts. Not right now. What every if. If somebody's coming to you right now and claiming they've got the formula for security in this moment, then I think they're selling you snake oil because we don't know, and we have to exist in this period of heightened uncertainty for a while. It makes us deeply uncomfortable, and I think a lot of times that spills out at least digitally as cynicism because it's a form of self protection. And it's a way of bonding with each other. in reality we've got to, within this suspended we don't know what's happening. We don't know what's coming. We don't know what's possible to believe that within this space there's room like never before to make new things. And that. I say that with an absolute straight face. I'm not ignoring warnings. I can see what's happening right now. And again, I think, I don't mean to sound like Pollyanna, but I'm looking at my kids and I have to believe that they will move into space and begin if they own their own agency to find new ways. I can't say that I can see them right now. maybe it's a portfolio career that's the label that we're, which is fine. I think in this time people try and create new alternatives and give them names to make us feel better, but the truth is that,

Varun Rajan 25:03

have, yeah, we still have this need to like, categorize things and put names on things to

Jillian Reilly 25:07

yeah.

Varun Rajan 25:08

of structure to orient ourselves and give ourselves some guardrails even when we're going towards something new and, innovative, right?

Jillian Reilly 25:16

Totally. And that's fine. That's what we do. I don't think we know what that looks like in real life, in real time, but some people are at the front end of trying to work that out, and I think that's great. I think it's highly possible to heed warning signals and maintain optimism. In fact, I would say that I would want to. That I wanna be clear-eyed. I don't want to be starry-eyed. and I believe that there can be clear-eyed optimism right now. It's very hard. I would say switching off media is a critical part of that because you'll get told that it's broken. And I feel like that is part of, I wouldn't say some concerted effort. I don't wanna sound conspiratorial. But that reduces our sense of what is possible and our sense of power, and we need to protect our power. and that comes through lots of real time, real life engagement. Lots of, Time spent together, and so that's another conversation. But I do think optimism is born for me in real life. In the real world. It's very hard to find it digitally right now.

Varun Rajan 26:31

Yeah. and also it reminds me of one of the things, from our earlier conversation when you talked about intentional choice being the antidote to regret. I think that also is like just intentional action being in the real world, right? like connecting with people right in front of you is it is like the opposite of. The kind of passive consumption of all of the negativity that gets amplified about the things that are happening all around the world. And I'm not saying that those things aren't necessarily important, but if we are accepting those things without taking any sort of like intentional action, then we're putting ourselves in a place just to be cynical and not actually taking action towards building that better world and lives for ourselves.

Jillian Reilly 27:14

Absolutely.

Varun Rajan 27:15

I.

Jillian Reilly 27:15

I was just thinking as you were saying it, when I was, many years ago, there was a phrase that gained currency, which was like, think global, act local. Maybe that's still in the,

Varun Rajan 27:27

Yeah.

Jillian Reilly 27:28

we are also consumed with things that are largely out of our sphere of power or influence. So returning the locus of control to self. To community, to family, to spaces where we can begin to create the conditions that we need and want, is really important. And yeah, I think tuning some of that out coming into intentional choice to be with and among other people within our world is every time I do it, I walk away feeling. A hundred pounds lighter because I'm like, okay. I know it's all happening, but I have people here who I can connect with who remind me of who I am and where I live, and what's possible within this space.

Varun Rajan 28:20

Yeah. let's pivot a little bit to some of the practical advice that you have for folks. one of the things that really stuck out with me was. When thinking about, planning for a life and a career, you good design, being something that's preferable to renovation, right? having to excavate and renovate over time. amazing analogies and metaphors throughout, as I understand it, it's, it's better to plan for career flexibility, than it is to err on the side of. Establishing too much structure because you may find that path too rigid. and I'm curious, A, is that, an accurate, read and then b, what are some practical ways that you've seen this work in your own life and with others?

Jillian Reilly 29:08

Yeah, I think that's a very good read, and I think that. Comes from a career spent, meeting people in that renovation stage where they made all, they made, I'm gonna go back to my off the shelf choices. They did all the right things. They stayed on a certain path, they reach a point where it's no longer desirable, viable. They have no lived experience in designing anything intentionally. they outsourced all of their decisions to. Their family, their community, their society, a story that was never theirs. And then at age 40 they go, I don't like this. I think I want something else. But they have no lived experience in creating something that they want. So how are they gonna start at that point? So the message was to start, from an early age, entertaining. Let's start with what do I want as a source of good design? If from the beginning. That voice is ignored completely. It's very likely that you will, it'll come back sometime later. if you suppress your desire to do something, be something, explore something completely, then it'll emerge at some point and you'll go, oh, I wish I'd spent more time learning about that, or exploring that, or just doing something with that. So I think. this is not to say that you know your career or your life is in total pursuit of that interest, but I would say that in this world right now, we need to think beyond the thing that pays us in the first instance in creating multiple paths forward. if it's something that is a area of expertise, a field or something that you're like, I'm not sure that can be my, that, that might not pay me in the short term, but there's something in it and I wanna know more about it, then find a way to keep cultivating that because there's something there and I think you should go towards it. So allowing yourself. To entertain your wants is, for me, a big part of design and accepting that at this moment when, and I would say as you alluded to, the second part right now of good design would be a degree of diversity and adaptability. So don't get caught into a singular linear mindset because that you are going to be required to, or you're going to want to. move and pivot. And so I would, from the beginning have a multitude of things that I was interested in, have, kind of concurrent streams that I was entertaining to greater or lesser degrees at different times. And whether that was sources of income and or sources of interest and potential growth. I will use the portfolio thing because I think it is a good word for us. To because we can make sense of it. just as you have a portfolio of investments or a portfolio, you're, you are starting to look at the range of resources, interests, and capabilities that you are gonna cultivate throughout a lifetime of an adaptive career. And being very intentional about, Nurturing those things to allow for different outcomes I think is really important. So I would, sit down and really map out a range of capabilities, I'll just use that word generally that is going to allow me to apply those things in different situations. And one of the things I talk about in the book is separating. I can and I am. so for me, good design at this stage would be to approach it with an I can mindset. So I can do a number of different things I can possibly, and there I would do an audit of my capabilities and I'd keep growing them intentionally. So I'll go back to the accountant example. I would say I can do accounts as opposed to I am an accountant. Because I am an accountant is a fixed identity that I then go around looking for, roles that only fit. That saying I can do accounts means that I can apply that knowledge in a variety of different situations. good design is, and I say it in the book, is some combination of beauty and that for me is. Something that's desirable, something that's appliable, something that's adaptable and is fit for purpose. And that in this world means that it's gotta be something that allows you to continue to go out into the world and find different situations where you are going to be able to apply your talents and knowledge and capabilities to different situations. People are calling it a company of one mindset. I talk about free agency. So I think you need to design a company of one, like this is me, I am Jillian, Inc. And I can do these things for you. If it's me, I'm gonna say, I can write. I'm great with speaking. I'm a great reader of people. Now, those are agnostic. Those are, industry agnostic skills. So that's a, a core set of things that I'm gonna apply, in different industries. I might then layer on top of that some industry specific interests or capabilities, and then I'll use that portfolio to continue to Grow and adapt to the situation that's evolving around me. Let me pause there and see if that has made sense.

Varun Rajan 35:11

that actually ma it, it makes a lot of sense. One of the questions that I had that I feel like you've teed up really perfectly for me here, is this idea of building temporary things that you talk about also in the book. you touch on the idea of trying to emulate a DJ while, pursuing new productive efforts, you and I do feel that it fits what you're talking about in terms of building that flexibility and then for making room for that. Joy,

Jillian Reilly 35:36

Yeah.

Varun Rajan 35:37

which I

Jillian Reilly 35:38

Yeah. Yeah.

Varun Rajan 35:38

and maybe you could touch on that specifically, that idea very specifically about, why focus on prioritizing building something transient or impermanent. what does that, afford you?

Jillian Reilly 35:52

Oh, a durability and a flexibility and an opportunity for shifting. Relevance. I think the DJ example is a great one, which is why I used it. a great example in the sense of. Of, the way that role has evolved profoundly over the last 10 to 20 years from, knitting together songs to making music out of old things, and sometimes with new stuff, weaving it together. that is a person who is reading a room, reading an event, reading a something. their way through it. They're showing up. They know how to do something. Everybody knows you're a dj, this is what you can do. But I don't know what you're gonna do tonight. I don't know. You know exactly what's on the cards and you might not either. It's gonna be different every single time, and that's part of the beauty of it. Like you're not there to play the exact same set every time. Otherwise, nobody would hire you, right? They'd put music on, they'd download a playlist to put it on. So a perfect example of, an automated service versus a very human service. And this opportunity, this requirement for very human services. Is where the Renaissance sits because as you say, there's joy and beauty in those. It is not repetition and sustained application. It's an ability to show up to something, figure it out, adapt what you know how to do to that setting and gain a, develop a degree of currency for your ability to do that.

Varun Rajan 37:31

Yeah.

Jillian Reilly 37:31

And that, is completely counterintuitive to what a career looked like previously. I think I've heard various people say probably one of the closest things that we can imagine is. The film industry, the entertainment industry, which works very much on this basis of project based. people show up, they create something together, they move on. They know how to do something. They have to do it differently each time, each new project. we do have templates for how to do this, but the nature of this fluid world is that the more that you are able to build things that have a specific. That meet a specific and possibly temporal need, right? It might not be there in six months time, the more relevant you can remain. for me, part of this, I have to share this anecdote because it was when I had such a big aha moment. the United States hosted the Cricket World Cup, I think a year or two ago. I can't remember when it was, but living in South Africa. Big cricket fans here, so we were following it. I'm from the US and so I saw them playing in stadiums where I was like, where is this? What is this? Because I was thinking, I know most of the stadiums like, what is this? They were all temporary stadiums and I thought, oh my gosh. So now stadiums are even temporary. of course they are. You put them up for an event, you take them down for an event. Now people don't want to invest in building a whole new stadium, but they're very happy for something that can be put together, taken down and put up again. So that for me was like, oh, of course.

Varun Rajan 39:17

Yeah.

Jillian Reilly 39:18

is what we're moving into. I can meet this need right now. In a very specific way, and then I can go and do that again somewhere else. Now, if you can start to think about what you know, how to do, what you like to do, what you want to do, in that way, you start to really shift into a posture and a way of navigating that's much more relevant for today than. I do this, I build this, the same way over and over again every single time.

Varun Rajan 39:53

Yeah. it also does feel like it ties back a little bit to the management within organizations. a little bit in

Jillian Reilly 40:01

Yeah.

Varun Rajan 40:02

One of the things that you had pointed out when I was asking you about it just earlier in our conversation now, was that you weren't just implementing like a single point of change and then expecting all of your problems to be solved. You were trying to enable and empower the capacity for constant change in decision making, like amongst your team, which is what I think your. Pointing to with this DJ analogy, right? Like you are trying to find ways to identify, how to read the vibe, read the room, generate something that fits that, whether you're solving a problem or creating a moment or an experience, and then being able to have that. the generative reps basically,

Jillian Reilly 40:44

Yeah.

Varun Rajan 40:45

of doing that is the way that you're like building that skillset. And it can be different every time. It's not like structured rigid. I learn a skillset that I'm going to apply in the same way over and over for the rest of my life. That has like very little variance. one of the things that I saw in terms of the kind of structure of your book, at the end of speaking about each of the permissions, you, you ended every chapter with. A section that said, you already know this, and talked about how it was like inherent and intuitive in a lot of ways. why emphasize this idea to the reader that we have the permissions within us and we already know some of this stuff? I'd love to, that, that really resonated with me, so to hear your, hear you talk about that a little bit.

Jillian Reilly 41:32

Yeah, because I have worked on change and helping people change and grow for a long time, and I think a, in many ways. as I moved through that career, I started to bristle at the idea that I, that there was a gap in an individual that needed to be filled. That it was a, there was a skill that they needed to learn. There was something absent from them that if they could only learn that they would, everything would be okay. in this case, I think it's more of an unlearning. It's. It's, you actually can do all of these things as children, we do them as young, it gets conditioned out of us to be exploratory, adaptive and creative. We are, as humans, very capable of doing it. The simple realities. We have been conditioned for a set of circumstances that would make us. good workers, frankly, I don't mean to sound like I'm, but it's true. We were conditioned to fit within systems. In this moment, those systems are crumbling around us and so it's really important to remember that you don't have to become some new superhuman version of you to do these things. You just have to allow yourself to experience yourself afresh. Maybe you once were even more of when you were 10, 11, 12, 13, 14, 15, even younger than that, or older than that. But, the answers are within you and the green light is within you. It isn't to look around and say, but I need to now learn this or do this, and then I will suddenly feel more capable. It's. And in many ways I think I obviously deliver that as an empowering message. I think for a lot of people it'll be disappointing 'cause they wanna believe that there's somebody out there that's gonna come and give them some magic key that will turn on this ability. And it's no. This is about you. You know how to do this. You've gotta negotiate with yourself and yourself only to start. Now, there might be some other people out there that you need to negotiate with, but the truth is, as adults, we don't have that many people who are actually standing in our way. They're not really, we like to pretend that they are, but they're not. They might disapprove, they might ask questions, but they're not really gatekeepers. Learning to sit in conversation with self and remind yourself of what you already know and what you already can do is a really important starting point for me with this.

Varun Rajan 44:19

Yeah. the negotiation with self is. really important. and that understanding that you're really the only person in your way if there is someone in your way, I think is really salient today.

Jillian Reilly 44:31

Oh. So much and again, I think part of what I despair in the dialogue of looking out at the world and pointing to everything that's wrong is that it's very easy to locate the problem outside of you. there's a hundred different culprits on any given day for what a mess this is. But there's only one person who's gonna shift your relationship to that mess, and that's you. And so you've got to come into self and engage with again, what do you feel allowed to do? what do you not and why? and that's an ongoing conversation.

Varun Rajan 45:12

One, one more thing that I want to make sure that I dig into with you. in the book, there seems to be a kind of flip side to every prayer mission that can still get you stuck, right? and I think like that's something that you warn against through throughout the book, wor against throughout the book.

Jillian Reilly 45:30

Yep.

Varun Rajan 45:30

can you speak to the difference between, giving yourself permission and, A concept of either letting yourself off too easy or going too far. for example, in the permission to experiment chapter, you encourage the reader to take small bets and learn from them without the expectation that every set, every. Without the expectation that every experiment or test will be successful. but then you also warn against dopamine chasing. And as someone, this is very personal to me, as someone that is prone to starting way more projects than I finish, how do I know which is which before I jump in?

Jillian Reilly 46:08

I don't think you can though, before you jump in. I think what you can do is have a healthy enough conversation with yourself. To pause, take stock of what you've learned in the past, and then with great, gentle care and kindness say is remember what you know, Jill, you love to, to get into things like what have you learned from in the past that will inform this choice? So I can relate to this too. I'm actually in the process of breaking that and it's coming from deep within me of a no, I can't keep doing this. I cannot keep. pursuing new things because they might be interesting, going down a road because I wanna see what's possible. That's not the season of life that I'm in right now. I literally can't afford to do that. I could up until the book and then it was like, no. This is it. You're now in a different season of your life. So I think there's that, which is. Respecting and understanding where am I right now and what do I need right now in life to help me continue to grow and move down whatever path I'm on. Last year, it was fine. I actually felt fine to put out a bunch of feelers, start a bunch of different things, and then as I moved into this year, I was like viscerally, like no. It is dissipating my energy. It's limiting my ability to actually focus on things that I want to really grow. so I would still, for me, the mandate, the opportunity to experiment now just gets shifted in a slightly different way. So it's not experiment. It's okay, this is where my focus is, how within this focus. Can I experiment in order to grow my capability to do this? So my experiments are more focused rather than diverse, and they are really in service of a very specific aim. so that's the other thing. There are different kinds of experimentation. some is testing a bunch of different things. Some is running an experiment within a certain field that is a particular. You. I don't find sales all that easy. not an easy and natural thing for me to do, but this is my year of doing it, so I'm gonna have to run a lot of experiments within that space to figure out how I can learn to do it well. so that's what my focus for experimentation is this year. And that's come from learning and observation and just being really honest with myself without being judgmental. I'm sorry, you can't afford to run around and try and start five different little projects right now. You don't have the energy or the time and you financially can't afford it either. So stop doing that and just put this energy into this space.

Varun Rajan 49:17

I think a lot of it comes down to your intuition, question of you already know this.

Jillian Reilly 49:22

absolutely.

Varun Rajan 49:23

yourself permission, you can be negotiating with yourself, and then making sure you understand when you're standing in your own way, from all of the cultural societal expectations. Like no one's actually like physically stopping you from doing what you wanna do, but at the same time, like you're also the person that. Should be placing those constraints on yourself. and you tend to know when that is and following your gut. Because it doesn't sound like, and the other thing you pointed out with making sure that you're being kind to yourself and understanding your tendencies and learning over time. When you talk about the shift that you made this year, it wasn't something that was about, oh no, I did this again. Oh no, I like went into this thing. Or there's no kind of like self flagellation or guilt. It's just okay, hey, I'm entering a new season. I realize my tendencies and it's going this way, and now I need to like. Sharpen my focus onto maybe one new skill set I'm experimenting with because I need to do this right now. And also just gonna own my focus on this particular project because this is what has legs and is important to me right now. And, it's that because you've built that capacity for change. and for pivoting when you need to.

Jillian Reilly 50:30

Totally.

Varun Rajan 50:30

yeah.

Jillian Reilly 50:31

No self-flagellation is ever required. It really isn't. all it is, as you say, an intuitive stock taking of, is this serving me in this moment? I've had some of my happiest times and my most fruitful discoveries by experimenting with all sorts of different things. It's just not for me right now. yeah, I think listening in is key.

Varun Rajan 50:52

I love it. Jillian, thank you so much. I think that's all I have for you, but I've learned so much from these conversations and even the conversations that we didn't record, and there's. many connections that I'm making about the themes in your book and also how it's connecting to me and my life and my career choices right now. And, I'm really excited to share this conversation with folks. And, I know a lot of people will be getting a lot out of, out of your book, the

Jillian Reilly 51:18

Awesome.

Varun Rajan 51:19

as I did for

Jillian Reilly 51:19

Oh, thank you. I've so enjoyed it and you ask great questions and I love your curiosity and your intention in asking them, so thank you. It's been a total pleasure.

Varun Rajan 51:32

Wonderful.

Jillian Reilly 51:33

Okay.

Varun Rajan 51:33

much.

Jillian Reilly 51:34

Thank you.

Varun Rajan 51:42

And that's it for my conversation with Jillian Riley. Over the course of these two conversations, I think one thing in particular stays with me as I talk to people about how they're trying to transform their organizations. Your job as a leader, if you have been entrusted with a transformation process or mandate, is not to execute a change program, it's to build change capacity. The former is a project that you complete and everybody gets to pat each other on the back for doing it, but the other is a lot more serious and lasting. It is a muscle that you develop, and it's there when the next disruption arrives and the one after that. The book is The Ten Permissions by Jillian Riley. I've linked it in the show notes. And if you know someone that is stuck in the performance of change without any of the substance, send this one their way. Uh, it might be helpful. we have a ton of awesome guests still coming up this season. Uh, friends of mine that are really navigating what the future of work means for them and what's actually important to them in their lives, uh, as well as founders that are building in the space, actively using AI and thinking about what AI actually means and changes when it comes to hiring and talent. So look forward to it then. Join us again next week.