TLDR;
Many leaders find themselves at a crossroads today.
Because they understand that the traditional “command and control” style of leadership is no longer working across the nuanced human dynamics of today’s workplace.
So if you’re here looking to explore this concern or need help navigating change, you’ve come to the right place.
Hello, this is Michael Hunter from Uncommon Teams. With me, I have Jillian Reilly, founder, author of The Ten Permissions, and a visionary who’s spent decades at the forefront of social and organizational change.
Together, we explore how to build a new adult operating system—so you can stand resilient on the volatile ground of the modern workspace.
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Things you’ll learn from this conversation:
- How to transform workplace confusion into clarity by understanding the “new rules” of engagement.
- The surprising power of boundaries and why being direct about expectations creates profound psychological safety.
- How to move beyond “fake permission” to truly empower yourself and your team.
- Strategies for leading in constant change
- Practical steps to lead with humanity: Learn how small shifts can create significant impact and a culture of true fit.
Tune in now to gain the insights and practical tools to lead your team with greater connection, psychological safety, and authentic impact.
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Meet the Speakers
Jillian Reilly
Author | Founder | Keynote Speaker | Leadership Facilitator | Re-invention Mentor for anyone ready to ditch outdated rules and design a life that fits now
From the front-lines of the HIV/AIDS crisis to executive coaching in London, Jillian has guided people and organizations through uncertainty and change. She is also the author of book like Shame: Confessions of an Aid Worker in Africa and The Ten Permissions, a bold framework for personal and social reinvention. Her work empowers individuals and institutions to unlearn outdated scripts, give themselves permission to thrive with clarity, courage, and creativity.
Michael Hunter
Founder @Uncommon Change | Interlocutor / Curious Host @UncommonLeadership Interview Series | Author | Change & Innovation Partner
Michael Hunter partners with top tech leadership teams across six continents to create extraordinary cultures. With 35 years of experience at companies like Microsoft, Salesforce, and Tableau, he helps leaders sustain meaningful change. Michael believes that only by integrating mind, heart, body, spirit, and intuition can leaders truly navigate change safely and build a lasting legacy of impact + human-centered leadership.
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Presented By: UncommonChange
Transcript:
Michael Hunter
Whether you want more innovation, more easily, you’re feeling burnt out or overwhelmed, or you simply know that something isn’t quite the way you know it can be. You are not alone. I hear the same from leaders every day. On Uncommon Leadership, we explore aligning personal fulfillment with business success, creating authentic teams, and cultivating the resilience, adaptability, and ease necessary to move beyond simply surviving today’s challenges into thriving. I’m Michael Hunter with Uncommon Teams, and today we’ll uncover fresh insights into what it means to lead today. And joining me is Jillian Reilly. Jillian is a founder, writer, keynote speaker, and consultant.
Having spent her 30-year career working in social, organizational, and individual change across Africa, Asia, and Central Europe, Jillian focuses on helping people unlock their ability to navigate change and accelerate growth and learning. Jillian’s upcoming book, ‘The 10 Permissions’, guides readers in permitting themselves to design lives that fully leverage the possibilities of our disruptive world, offering 10 direct ways to turn stuck-in-the-past work and life strategies on their head. Welcome, Jillian.
Jillian Reilly
Thanks, Michael. It’s great to be here.
Michael
I have been looking forward to this conversation since we talked a few weeks ago.
Jillian
Yeah, me too. I love what you’re doing, so I’m excited that I get to be a part of it.
Michael
You and I kind of read the same book only in very different ways.
Jillian
Okay. Yeah, it’s interesting ’cause I think they’re different entry points to the same subjects, right?
Michael
Yeah, absolutely. When did you first recognize that integrating your whole selves and bringing that into everything we do might be a valuable approach?
Jillian
Oh gosh. I guess it would be at a very young age because I started to do work in social change and individual personal change. Early on I came from, I went from the United States, from the Midwest of America, to here to South Africa where I still am, and sort of got thrown into the deep end of doing community-based change, and I think I realized early on that the more that I brought of myself and the more that I, you know, was willing to share of myself, as not just a professional but a human, the better connection I made with people, the richer the conversations were, you know, we sort of moved beyond the transactional into something that felt like it had a better chance of making a difference and making meaning. So I think as somebody who has spent my life going into people’s lives at vulnerable moments, at challenging moments at, you know, very rich moments, I definitely have found that the more, that I was willing to share with myself and the more that I was willing to be real about my own journey, the better, I don’t wanna say the outcome, but certainly the better the connection.
Michael
What has most helped you maintain those connections as you’ve grown and changed over from when you first started this through now?
Jillian
Yeah, that’s a great question because I have to be honest, I stepped away for a while, when I decided to have my first child, I thought, okay, I think I’m gonna use this as a very intentional break from the kind of, at that point, I’d left Africa and I was working as a consultant, and I felt like things were getting a little bit rote.
Like I knew how to land somewhere or show up with any team or sit down with any leader. And I think I felt like I had slipped into a little bit of an autopilot mode. And it was time for me to step back, and having a child was a good way to do that. And then when I decided to step back into this work, honestly, I think having the child had done me a world of good because in many ways it had introduced me to parts of myself that I hadn’t really accessed very much before. You know, there was a playfulness there, there was a forgiveness there. So in some ways, I was more open than I’d ever been. And if I just, you know, I said to myself, if I’m gonna keep doing this work, then I’ve gotta keep accessing all sorts of different parts the minute that I feel like I’m just consultant for hire.
You know, bringing out a sort of standard playbook. I’m out. So I think there’s just a degree of real intentionality, and trying to really be in whatever room you’re in, whatever conversation you’re in. But it’s a practice. It’s just a practice of intentionality, I think.
Michael
Many of the leaders I talk with. Come to me in part because they have trouble integrating their work selves alongside everything else.
Jillian
Yeah.
Michael
Either they feel or they’ve been told they can’t bring all their everything else into the workplace, or they want to do this, they’re perfectly free to do it, and they just don’t know how, or it feels weird or uncommon.
Jillian
Sure.
Michael
What helps you do that integration?
Jillian
I will say, to use my own language, I think women have, in some ways, more permission socially to do that. I think we are allowed to tap a wider range of emotions and experiences, and it feels more natural for us to go there, if you will. On the other hand, I think, are a lot of our personal lives and our lives as mothers and other things are a little bit off limits in many ways. I think the more that you kind of approach things from a very human level and an understanding that each one of us is coming into this space as a human, you know, I think in the workplace a lot of our formal roles have unraveled a little bit, and that creates a bit of confusion.
You know, it’s not the formal, stiff, sort of very positional interactions that it was 20 years ago or 30 years ago. Now people are sort of trying to figure out what’s allowed and what isn’t allowed. So, you know, one of the things I do with workplaces and with leaders is to help them create more intentional cultures around helping people to understand what’s allowed now.
Like, you know, am I allowed to talk about my family, to talk about my emotions, to talk about my issues? And I think I try to just have very direct questions that just, or conversations, if you will, that just directly get there. Sort of, you know, are we allowed to go there? is this relevant for this conversation?
I think the more explicit that you are and the more intentional you are about, you know, setting expectations and boundaries within conversations and relationships, you know, you take out the guesswork, you take out that fearful kind of, oh my gosh, you know, have I overshared, you know, there’s space now for us to do this.
I think everybody’s accepted the fact that we are all, you know, complex creatures. So I would encourage people just to take it head-on and, as I said, to be as explicit and intentional about creating shared boundaries and expectations.
Michael
Are the shared boundaries and expectations, is that the primary tool you use that helps people who haven’t felt safe or comfortable or allowed talking about whatever the untalkable things are to bring those in?
Jillian
Yeah, I mean, we all carry the state fear that, you know, we’re going to be rejected, we’re going to be judged, we’re going to get into trouble.
You know, one of the things I talk about in my book is that we’re raised in cultures of permission where we seek permission, particularly to share things or to do things that potentially feel outside the norm. Right? May I do? May I speak? May I? And what we haven’t done, and what we don’t do is to really prepare adults to give themselves permission and then to work with each other to create a shared understanding of what permission is.
And I think when workplaces were very formal, when, you know, we did sort of operate in a far more fixed environments, it didn’t feel quite as relevant now. I think that lack of safety also comes from a lack of clarity. You know, Brene Brown has this great line, which is clarity is kindness. When we’re clear about our shared understanding, as you’ve just said, boundaries and expectations, then we’re operating at least from a place of, awareness and knowing and, you know, it might be that we’re out of alignment in terms of what we think is allowed or should be allowed, but at least then we can discuss it and I can make a decision about whether the explicit sort of permissions are in line with what I need and want. I think in many ways it’s the ambiguity, the, you know, lack of intentional dialogue, and clarity around, you know, who, who are we allowed to be in this space?
That creates that feeling of lack of safety.
Michael
If I’m a leader who wants to create more of this clarity around boundaries, expectations, and I’m not sure how to get started, and I care about my team, so I wanna do this in a way that works for them and isn’t just me forcing everyone to now be clear and have the boundaries and expectations that I might feel are right.
How can I start that conversation, and how do I ensure that it goes well?
Jillian
Yeah. Well, I don’t think you’re ever gonna be sure that a conversation’s gonna go well, right? But what is, well, I mean, as long as you can surface some of what you wanted to surface, I personally would say that by asking the question, you’ve achieved something.
Because what you’ve then done is. If I’m gonna use my language again, you know, create permission for things to be voiced that perhaps previously people weren’t sure that they could be. So, you know, I would again be as open as I felt comfortable coming, and I would do it individually to start with. I don’t think that getting people around a whole table and expecting them to have hugely revelatory conversations is particularly helpful as a starting point.
I think having one-to-one spaces where people feel more comfortable, where you also can say, Hey, look, you know, and you know, max out your sense of, honesty and openness around your intentions, because I think that’s what is often, you know, on people’s minds, why is he doing this? Why is she raising this?
Is there something else going on? Will this be used against me? What’s gonna happen here? So I think it’s kind of being clear, not just about the purpose of the conversation, but the intent behind it. You know, I’m coming here because I wanna know this for this reason. You know, I think it’s incredibly helpful to people when you share your own potentially lack of certainty or clarity or confusion around things like own the fact that you’re also not necessarily clear of, you know, how this is all gonna unfold, but you feel it needs to open. And I think ask questions, you know, I think people want to feel heard, they want to feel connected, and I think oftentimes leaders feel like they have to come with answers and come with, you know, directives.
And I think more and more leading with questions, leading with curiosity, leading with receptivity is just a signal to everybody else that it’s okay. You know, I’m genuinely interested, not, I’m collecting data.
Michael
So that initial one-on-one conversation, we might open it something like, I am trying to give myself more permission to talk about things that I haven’t felt we could talk about. Right. And want you also to feel that you have permission to talk with me about everything. Anything that’s on your mind, and especially, anything you may have felt you can’t talk to me or others about. And my only expectation here is that we’re able to have a more authentic and complete conversation than maybe we’ve been able to have in the past.
Jillian
Yeah.
Michael
How do you feel when I say this?
Jillian
Yeah. Absolutely. I mean, you know, one of the reasons that I began to kind of work with this theme of permission is because it’s very visceral.
Everybody knows immediately, not only what it means, but what it feels like. It’s an integral part of most of our coming-of-age processes in one way or another. And so we both know what it feels like to be permitted, to feel free and relaxed and safe and at ease. We also know what it feels like to not.
And so I think one of the interesting things is by using that word, it shifts conversations a little bit in which people kind of go, oh, okay, wow. Alright. He’s talking about, you know, feeling safe and at ease. Do I feel that? Do I not feel that? I mean, again, I think you could start it that way.
You could start with a question, you know, I’m curious whether how much you feel permitted to share your feelings and thoughts, and ideas, and how you don’t. But I find that conversations around themes or permission kind of open relatively quickly because people start to access a lot of their own sort of experiences with it.
And, they can work with it, right? They can work with it quite easily. So I think it’s a great conversation starter.
Michael
For people who are listening to say, yeah, this is all great. But when my boss tells me I have permission to do things, he/she/they really mean I have permission to do things the way they want, not to ask questions or do things the way that I want. How do you suggest those people turn the not-a-real-permission permission into authentic permission?
Jillian
Yeah. Well, it isn’t, if they’re not really allowed, is it? It’s a directive, sort of masquerading as something else. You know, one of the other rules, one of the other words that I use is rules, which is another way into this conversation, which is, you know, let’s talk about what the rules are here.
Which is the same thing, right? What am I allowed to do? What am I not allowed to do? But it’s also an interesting one because you get people kind of going, oh wait, are there rules? Yeah, there are, most of which are implicit, right? I mean, very few workplaces with adults have written down rules as to how you’re supposed to behave or not, but sometimes an entry point into this is just for everybody to get clear about and sometimes it’s easier around specific things, you know, meetings, the Monday morning meeting or the weekly debrief or the quarterly performance review. You know, what are the rules? And you can break it down even further. What are the rules in terms of what we’re allowed to say, you know, da, da, da?
And by getting again, super clear, about what those are on every front, you can then kind of hold them to it where you said this, or you can push them a little bit in terms of, well, you know, I thought one of the rules was that we were supposed to be able to, you know, give open feedback to each other, but I did that and you then penalized me.
So, you know, the more things are explicit, the easier they are to work with. The more everything stays implicit, the more fuzziness it creates. So, you know, I do a lot of work with teams around making implicit ways of operating explicit in order to allow for us to hold each other accountable, if you will.
If somebody doesn’t wanna be held accountable, and if somebody wants to use their positional authority to break whatever rules you claim you set together, then they will do that. And then that’s up to you to decide, you know, whether that’s an environment that you feel you can stay in, but at least you know, if they’ve been put out there, it makes it easier for you to, you know, keep returning to them as a shared, again, back to boundaries and expectations.
Michael
I like this reframe of permissions as rules. Even if, even when I feel I have no permission, I always can, at least for myself, list out all the rules I believe are in play. I don’t need anyone else’s permission to do that.
Jillian
Right.
Michael
And I don’t need to go confront or talk with anyone about those rules. I can, now that I’ve made them visible to myself, I can test my understanding against what reality is actually happening, and adjust those to what I think, and then I have the ability to notice those discontinuities between what I think the rules are and when they shouldn’t be broken. Then I can use that as a conversation, like you said, for the way we did things with this, from everything I’ve seen in this case that didn’t happen, and I’m wondering, is my understanding wrong? And then we can start to kind of softly begin some of these conversations to bring that up more explicitly with our manager peers, other people around that are involved in the group.
Jillian
Yeah, I mean, I think a lot of what I’m talking about when I work with themes of permission is about making our implicit sort of ways of operating and behaving either as individuals or with each other. If we’re talking about a team context, you know, raising it to the level of the conscious and explicit so that we begin to see whether or not our defaults, you know, are serving us, whether they ever have, whether they still are.
For me, those implicit rules are a key part of that. You know, I would also, kind of, I look at sort of what the autopilot behaviors are, you know, the ways of doing things that just become, feel like they’re ingrained, even if they’re not. But yeah, I think it’s an incredibly important exercise now, particularly now with the whole five generations in the workplace.
Norms of work unraveling, only promising to do further. You know, I think it’s one of the key roles of a leader right now is to hold culture. And I put this under the rubric of culture in terms of how we operate together. I think being explicit and intentional about culture is, for me, would be right at the top of any leader’s set of responsibilities because in the absence of it, there’s so much room for conflict, for delay and, you know, hesitancy and all sorts of things that just are going to slow you down and frustrate you. So, yeah, I think for me, I run whole things that are like rewriting the rules, which start with, okay, well, what are the rules?
So to me it’s a really important exercise in creating a shared understanding of how we’re supposed to operate together.
Michael
These are all ways where you help teams build cultures where they feel safe and empowered to bring their unique talents into everything that they do. I describe culture as how we lift each other up and how we stay out of each other’s way.
Jillian
Okay. I love that.
Michael
That’s everything that we’ve been, that’s everything that we’ve been talking about today.
Jillian
Yeah, very much so. I love that.
Michael
And you’ve gotten into this a little bit, what is the business value of doing all this work, creating these cultures?
Jillian
I mean, I have, I just, you know, was there in terms of, I mean, if you want a bottom line sort of productivity and efficiency to me is, you know, key in terms of to use your language, staying out of each other’s way.
I think we’re in a point now where we cannot expect to be on autopilot a lot. You know, we can’t always expect the way we’ve always done it to be the way that we need to keep doing it. So there’s a premium, I think now on sort of, you know, low level adaptation and innovation and problem solving and pivoting and adapting.
Which is all contested ground, right? I don’t know. I’m figuring it out. A lot of us right now are in kind of figure-it-out mode with a lot of things, and in that space, it’s very easy to get into each other’s way. It’s very easy to pull each other down. It’s very easy to have a sort of, I don’t know. Am I allowed to do this?
Am I not? Do I need approval for that? So, you know, if you’re all just sort of, you know, on an assembly line churning things out in your own little bubble, it’s, you know, one thing. But if you’re all in that kind of figure-it-out mode, in creative mode, in a space where, you know, there’s a lot of room for error, there’s a lot of room for confusion, misunderstanding, then this kind of explicitness will serve you in terms not only of your efficiency and productivity, but your morale, you know, your general ability to kind of keep getting better and keep learning. So, gosh, I mean, this is not a feel-good thing at all. It might’ve been, it might’ve felt that way, and I think 20 years ago, when we still felt like we were operating in fairly sort of predictable territory, this felt like, oh, wouldn’t it be nice if we liked each other more or whatever.
We talked more. I think now it’s about working as an adaptive team, and that requires really good communication, really clear expectations, and, as you’ve just said, not getting in each other’s way.
Michael
And it strikes me that the more we can make explicit, then the more we can understand what is actually changing, what we are actually still have to figure out, and what might be staying the same or changing much more slowly that we hadn’t realized. Which for people who are not super comfortable with change, gives them a much more solid foundation than they might have believed they had.
And for people who are excited by change, then that gives them yet more visibility into how much change we’re getting to experience and explore and play with. And for everyone in the middle, it helps them on both of those sides.
Jillian
Yeah. It brings them clarity, that they have a clear picture of that. But yeah, a hundred percent.
And you know what’s so interesting is that what I often find is the two groups you mentioned on either side, you know, super excited for change and very reluctant to change. It’s almost like, you know, these parts of the Venn diagram come a little bit closer together when you do this kind of thing, where you realize that, actually, maybe we’re not as far apart as we thought we were in terms of our expectations or understanding of our current reality. I think particularly when you talk about sort of norms and expectations, you know, often our perception of each other is skewed in terms of, you know, a lot of these generational issues where we think we’re polar opposites and actually we’re not.
There’s a lot of common ground. There are ways in which those who are very change ready can then be of more service and support to those who are, you know, change reluctant. And so, you know what I often, it’s an immense, incredibly connective experience to create these, this more explicit set of rules, expectations, and boundaries because you know, I think nine times out of 10, you realize that you’ve got much more keeping you together than pushing you apart.
Michael
I agree. And the more we understand what that is and how we prefer to work, and the more we understand how we can help each other.
Jillian
Yeah.
Michael
Someone who is super spontaneous and doesn’t wanna have a schedule for anything and rules for anything. There’s a whole lot of things that has to be done on a schedule and have to be done by rules.
And knowing that I am not that and I have these other people on my team who are that, then I can work with them to let them take that stuff. They would probably love to do, off my plate, and I can take any of the super changey, spontaneous spontaneity, requiring work that they maybe aren’t so excited about doing.
I can take that off their plate, and suddenly we’re all much more able to work in the way that we work best and do the kind of work that we love, while also everything is still getting done, probably much more effectively than it was before.
Jillian
Yeah, absolutely. And, you know, when you put it that way, it’s common sense, right?
Like, why wouldn’t you do that? Why don’t we do that? Why wouldn’t you, why don’t you, why wouldn’t you? I mean, it’s like we, we all understand that we bring different styles and preferences and proclivities and ways of working and you know, I think the reality is that now we need all that more because we’re not, you know, working in these very constrained environments. So some of the qualities and some of the ways that maybe used to get sort of left on the edges because they weren’t deemed fit for a workplace, you know, where we were squashed a little bit more into conforming to roles. You know, we are now maybe a little bit more allowed to bring a little bit more of our specific way.
Why not optimize that? Why not take advantage of it? Why not invite people, to both own their preferences and how they work best and to own, you know, maybe their unique contributions? I, kind of talk about it in the book as sort of, you know, finding a fit as opposed to making people fit in. And so that does not make for a free for all.
It doesn’t say that you can do and be anything you wanna be, but it does mean, as you’ve just described, how do we take who’s here, who’s in the room, and the way, excuse me, that they, like to work and work best and figure out how to work with them. I think more teams are moving in that direction, but I also think we are in under a lot of pressure.
The workplace is as stressful and is bound to be more so as people navigate the implications of AI, as I think an insecurity around that seeps into people, I think it’s gonna be really important to just, you know, continue to have these types of conversations.
Michael
The thought that just struck me is that we see this in other parts of our life in ways that. Often, we feel we have more permission to deal with. For example, when we are looking for a new home or buying a new car or bicycle or lawnmower, or dishwasher, it tends to be much more approved by friends, family, society, spouses, and colleagues to get the thing that fits us exactly. And it has exactly the features we want and doesn’t have what we don’t want. You want to live in the depths of downtown, and I want to live out in rural nothingness, or I want the super fancy, all the gadgets, dishwasher, and you want one that turns on and off and gets things cleaned.
We think that’s it. Right, right. And yet, when we come into the workplace, it’s so often we’re all supposed to be this interchangeable, fungible half set. Right. Right. That can be arranged at will, which, it doesn’t really make sense.
Jillian
Yeah. There’s a guy named Daniel Priestley. I don’t know if you know who he is.
He is an Australian kind of cultural commentator, futurist, but he made a comment that I found very interesting, which is that, you know, from the industrial revolution to, you know, sort of the knowledge economy and the corporate world of the late 20th century, the reality is that we have been groomed to be component labor.
We fit parts, you know, it’s not the same as being the part of a car, but it’s part of a big machine. And the mindset of that was exactly as you described. There was a pre-made role, and you filled it. And I think for, you know, the boomer generation of, I think about my father’s generation and mother’s generation, that was the mindset they took to it.
There was a role that they were filling, and that role preceded them. And we interacted with each other via those roles. So you sort of, your personality yourself was well behind the, you know, whatever sales director or marketing manager, whatever it was. And that has been to me, if in my book I talk about unraveling, that to me has been one of the key unraveling, you know, is the kind of unraveling of the role.
As the container of your identity and the idea that it preceded you. And I mean, it just is carrying on a pace now and all the better, which I think is what you are implying, that why would we just be widgets in a large corporate machine? I think we’re seeing Gen-Z now, kind of very clearly, not wanting to be that.
I think it’s the source of a lot of resentment amongst those people who came into the workplace with that set of expectations. You know, back in my day, we just put our heads down and did our work, and nobody cared. And I got the job done, sort of, mindset. But I think we are, you know, clawing our way out of that sort of component labor mindset to be something that is more of an individual, more of a creative and a creator, bringing a unique set of offerings to a situation, and there’s so much, you know, clumsy negotiation now around, okay, what does that look like? And which is what we’re talking about. How much is, am I allowed to bring, you know, what’s out of bounds? And that’s why I think as we are moving through all of this, you know, we’ve gotta deal with it. We’ve gotta talk about it because we will have different expectations at this stage.
It is very blurry. So I think there’s a deep desire among people, to bring a fuller expression of themselves and their talents and their contributions. And I think there are still people who find that very threatening, who would like somebody to just sit down and do their job kind of thing.
Michael
Absolutely. It’s becoming even more critical, too, that we can raise the level of abstraction that we understand of what our job is, what our role is, what the work that we do is. Yeah. For a long time, it was fine to be someone who wrote code or did accounting or was a salesperson, and that’s not enough now because those are the roles that AI is quickly taking over.
Jillian
Yeah.
Michael
Those were never actually the output that anyone cared about. Even if that was what people believed, it was the output they cared about or what they believed that they were creating. It was always something higher up. And I’m starting to believe that the bigger thing that each of us is always trying to do, whether we’re writing code or talking to customers to convince them that the product we buy is better than anyone except we make is better than anyone else’s. Or we’re keeping the books to help everyone have the money to be able to do all everything else.
What we are fundamentally doing is solving problems. Solving problems that help our business continue being a going concern to help our teammates work better that we’re finding better, more effective, more efficient, more fun, more playful, more exciting ways to lift each other up and stay out of each other’s way.
Jillian
Yeah, I think that’s true.
Michael
And that is a puzzle that will never be solved.
Jillian
No, but I think what’s happening right now is this acceleration of what you’ve just described, that you know, that idea of problem-solving as the kind of unit of engagement. You know, what am I doing here? If routine functions and routine elements of operating are about to be, you know, handled by machines, then the human contribution will, I think, even more starkly be around, among other things.
That idea that I’m here to do something with a clear defined output, and so, that’s a very different mindset, isn’t it, that you enter into an engagement around, and, you know, I really do think, I talk in my book about this idea of free agency that I think we are going to see ourselves as more, as less of, you know, a job or a role and potentially operate like free agents, solving problems in different places.
For a time being, for a long while. You know, I’m not saying it would entirely be gig-based per se, but I do think that, you know, something that is more focused around a specific, you know, project task challenge will likely shape our understanding of what we’re doing more. And I think there’s great potential in that.
Because I think it might help us to tap into a little bit more of our value, add a little more easily.
Michael
I agree. One of the reasons I’ve always loved technology, one of the promises of ever-increasing more capable technology for me is that it allows each of us to take more control and have more steps available in the way that we’re solving problems.
Jillian
Yep.
Michael
There used to be, the way I could solve problems is I could talk with someone.
And I could talk with them on the phone where I was stuck to a wired thing on the wall, or I could go meet them in person, and that was pretty much it. I could send them a letter if I wanted a very async conversation. Now we can have live Zoom meetings where we can be face-to-face and almost as good as being in person without having all the travel involved.
Jillian
Yeah
Michael
We can talk with AI and have a conversation to build an application that’s exactly customized to the thing I need for the next five minutes, and then maybe I throw it away. Or, people who never would’ve considered being computer programmers can now have these conversations with AI and build applications that are exactly what they need, exactly what their clients need.
Jillian
Right.
Michael
And it’s so much more ability to solve the problem we’re working on right now with precision and clarity, like we’ve been saying throughout the conversation today.
Jillian
Yeah, and I think, you know, I’m in this weird position where I absolutely understand the perceived threat of it and the real threat of it.
You know, I get it. That it is forcing a very profound reckoning with our relationship to work, with our relationship to labor, and, you know, human labor and what its value add is. And I don’t think we are as societies engaging with the implications of it to the extent that we could and probably should.
As a solopreneur, whatever I wanna call myself, I am, I feel liberated and empowered like never before. As you’ve just described, I created my own website. I’ve built an app to go along with my book. I feel like it has changed my life. Given me a set of capabilities that were unthinkable six months ago.
So, you know, it’s complex the ways in which it’s going to free us to create, and force us to redefine what it is that we’re here for. And I think, you know, for a lot of us, it’s going to help us, as you know, everybody’s saying sort of 10x what we can do, and I think we are facing a lot of people who are going to be having very profound identity crises as a result.
Michael
So much change, uncertainty, and overwhelm on the way and already here.
Jillian
Already here.
Michael
How do you help people find their way through all, how do you help people find their way through all of that?
Jillian
One step at a time. I think, you know, obviously, that’s the theme of the book is we’ve got to find our way through this period of ever-accelerating uncertainty and overwhelm and change as you’ve just described. And you know, when I started writing the book, AI wasn’t even on our minds the way it is now. So I kind of smiled to myself that I wrote, I started it during COVID, which was, of course, I think the first global, you know, “Hi! We’re about to blow up your sense of, you know, seamless normalcy that has shaped your understanding of how you operate for a very long time.” And now it’s like all bets are off. I think, you know, one of the things that I talk about now is how I think, like individual change management, personal change management needs to now be considered like a 21st-century skillset, capability, whatever you wanna call it. So many of the things that we’ve done at an organizational level, I think now we need to kind of shrink them down into our own lives, where we are going to have to sort of oil the ability to surf change as a routine part of our lives, not as a periodic disruption. And that’s very different to how we’ve been raised and trained. I think it is a profound coming into self. We do not have, you know, I describe it as finding your way versus following the way. So there were very clearly paved paths and people telling us where to go, and now we have to rely more on ourselves.
So I think we have to start cultivating a relationship with ourselves that’s very different than any of our parents did, where we are far more, you know, looking inwards before we look outwards. Listening to and validating some of our own desires and opinions because we are our own guides. There are no trusted guides anymore.
There’s millions of them. There’s none of them. It’s on us to decide this, and the communities that we choose to create where we can, you know, consult and support each other. But I think, you know, there’s so much opportunity in terms of relationship to self and personal agency, which I do believe is now, I think, education needs to shift quite fundamentally, to really harnessing individual agency in a way that it never has. So, you know, I think it’s come a lot of work on self, and it doesn’t have to be big. It’s a practice. You know, I’m sort of thinking in terms of like the fitness industry these days in terms of that capability, that muscle, that tone, if you will, to be able to do these things. It’s like you’ve got choice muscles and you need to work them and keep, you know, keep them strong. So I think we’ve all got work to do on ourselves.
Michael
We do. And one of the lovely things about this work in particular is that, as you said, it doesn’t have to be a lot. Even a tiny bit more ability makes everything all so much easier and makes it so much easier to get the next tiny bit and the next tiny bit, the next tiny bit. So it’s not that we have to walk into the choice gym and start lifting 2000 pounds, we can start half an ounce, and that’s gonna make a world of difference.
Jillian
You know? So, when somebody buys the book, they’ll get a QR code to a getting-started workbook, and it’s about managing your days, and it particularly directs you to your weekends. And I think that I’m gonna call it ‘Weekend Your Choice Gym’, since you just used that, and I like that, because you’ve got a thousand choices to make over a weekend, and many of us never make any.
We just sort of sleepwalk through them, and yet they’re wonderful places for us to start to get super intentional about how we’re operating. And for me, that’s what we’re talking about here. So as you say, you know, I tell people, go for the low-consequence, high-pleasure choices first, and I know it’s gonna feel frivolous, and I know you won’t care, but trust me, one little ounce of you becoming more intentional about your everyday, “What do I wanna eat? What do I want on my pizza? You know, do I get the same thing every day because I’m on autopilot? Why don’t I start, like making myself try new things, experience new things?” All of those things are the foundational muscles of choice, of curiosity, of receptivity, of a willingness to kind of show up to a different situation and navigate it.
And that’s what I think we’re being called upon to do now, and that, you know, we can start to build that capacity within our existing lives. In all sorts of pleasurable ways. So, you know, I think this mental model of whenever we’re talking about personal growth or human growth, it’s big and it’s heavy and it’s problematic and it’s about fixing something.
It’s like, no, it’s not. I don’t want you to fix any problems. This is not about that. This is about you tapping into your ability to, you know, design your days, make intentional choices. And as you’ve just said, it’s amazing what happens when you just start doing that in small ways. The compounding of it is far greater than you imagined before you start doing it.
Michael
It really is. For people who would like to talk to Jillian to get your help in compounding their experiences, what’s the best way for them to connect with you?
Jillian
My website has pretty much all the information about what I’m currently offering. I guess there’s a, you know, as a first offer, there’s obviously the book, which is the Foundational Ideas.
There will be, and there is currently a download on my website, but the book is the basic ideas, along with the workbook that I just mentioned. One of the other things that I’m building very intentionally right now is community. You know, the book is important, but it’s for an individual, and I think part of the challenge that we have right now is that we’re heaped with responsibility and pressure to figure all of this out on our own. And it feels hard, and yet we’re all doing it side by side in our own little silos. So, you know, it was important to me in creating the book to set out to create a community to go along with it. Where, you know, a million individual permission slips become social permission, where I realize that I’m not the only leader.
Who goes into work and feels like, I don’t know what I’m doing. I’m supposed to have all the answers. Instead, all I have is questions. You know, when I realized that I’m not the only 40-year-old facing a layoff who doesn’t know what to do and is scared to death of what AI is gonna do to my career, like, we need to make these things public.
We need to have these conversations, not, you know, in shame, but as a reality of living in an unbelievably. Volatile world. So go check out my website, you know, pick up the book, join the community, start to kind of play around with what some of this might look like in your own life.
Michael
Thank you. And we’ll have links for all that in the show notes. What would you like to leave our audience with today, Jillian?
Jillian
Gosh, we’ve touched on so many important things. I think, you know, part of what we kind of got to here around, I mean, there’s a couple of things. I think we touched on some important things, which is, you know, two things that I think we underestimate, which is what happens when you make the implicit explicit and how much easier it is to kind of address things in your life.
And then I think the ways in which super small incremental changes compound and kind of begin to give you a sense of space and capability that you didn’t know you had. Because I think a lot of people right now are laboring under a lot of what feels like big, heavy decisions. Big heavy stuff they’ve gotta deal with in their lives.
And I guess I would love for them to know that, you know, it’s okay. We’re all in the same place. We’re all trying to figure this out. You’re not alone. I know so many people who feel inadequate, like they’re not a good enough leader, ’cause they aren’t as decisive and visionary as they think they should be.
They feel like they’re muddling along. And I guess I want people to know that I think that’s part of being alive right now. I don’t know a lot of people who have everything figured out and feel totally solid. So, you know, just to know it’s okay, we’re all in the same place and we’re all figuring it out.
And I think the more that we give ourselves permission to do it with intention and boldness and clarity, and the more that we give ourselves permission to do it together, the easier it will start to feel.
Michael
And on top of all of that, the more we give ourselves permission to realize all the ways we believe are failing.
Jillian
Oh yeah. I mean, you know, I talk about people right now, and I think this is particularly important for leaders who are trapped between yesterday’s expectations in today’s realities, ’cause I think a lot of us are still carrying around this kind of inspirational Jack Welch style like leader in our head. And that’s what good looks like. And we feel like a failure because we’re not, you know, standing up. You know, as I said, most of the leaders I know right now are really struggling to get by, and they feel like failures. And I think that’s one of the reasons that I think the permission to rewrite the leadership script.
The leadership story to be more of a figuring it out, finding your way, as I describe it, sort of more explorer, less executive. You know, you’re heading into new territory. There’s no way that you’re gonna be like, cool, let’s go. You know, we’re all on, you know, cruising forward together. Like, and that feeling of failure I think creates, it limits your ability.
To actually respond to all of this in your most real, creative, thoughtful way because you’re hiding in some ways. So, yeah, I think we need to be, we need to feel permitted not to hide, all the ways in which this moment and the these realities are challenging us.
Michael
Thank you, Jillian, for wonderful conversations today.
Jillian
Oh, thank you. Just as I said when we started, I love what you’re doing, so I’m so pleased that I could, yeah, explore more of our shared interests.
Michael
Myself as well. And thank you, audience, for joining us today, Jillian. And I would love to know, how are you giving yourselves permission to do more tiny experiments and be less bound by rules? We would love to hear.
Jillian
Absolutely.
Michael
Thanks, and have a great day.