The Transcript for the Podcast
Setting the scene
What’s the human contribution? What is human value? While very uncomfortable and while very confusing at this moment and deeply destabilizing, might over time be an incredibly beneficial and meaningful conversation for humanity more broadly.
JANE
I’m with Jillian Reilly today. She wrote The 10 Permissions with the intriguing subtitle, Redefining the Rules of Adulting in the 21st Century. That title caught my interest over a year ago, and we had a good conversation about it then. This time, we talked about navigating the fluid world we live in and the role of AI in that fluidity. We need to engage in the impact of this, what it makes possible, what it makes desirable, and what it makes acceptable. These are the conversations that we need to be having right now.
So Jillian, the thing that is really stand out about you is you talk about permission. Permissions, I should say, with an S. In our first conversation, you talked about it in the context of what you called adulting. And today we’re going to talk about it in a different context, in the context of AI. What’s the difference for you in those two contexts and why have you changed?
The lens of AI in a fluid world
I wouldn’t say that they’ve changed. I think it’s just another lens through which to have a similar conversation about we’re adapting to an increasingly fluid world where a lot of our old default understandings of how things worked, of how we navigated our professional lives, our personal lives, those defaults are no longer holding. And I think what’s funny for me is that when I started to write the book in 2020, AI was not a prominent part of the conversation.
And I even smiled to myself that having published my book last September, even then, we weren’t having this very public conversation and analysis and scrutiny around the role of AI. And in many ways, my book now to me feels a bit like an artifact because I don’t know if I’d ever write the book in the same way, but it is a generational driver of change. It is forcing us to reckon with so many elements of our understanding of human value, of human contribution, of human work. And those are fundamental pillars of our identity.
So for me, the broadest framing around adulting includes an understanding of what our adult professional value is, what our human identities are. And I think this is forcing some very uncomfortable conversations around those things, and it’s driving adaptation even quicker than I personally could have imagined it in 2020.
The value of permissions in an AI context
So Jillian, can you talk to me a little bit about what moved you to the AI… Not moved you to the AI era because we’re all in it, but to position your thinking about permissions in an AI context. What triggered that?
JILLIAN
Well, being alive in this moment, being present to conversations about a generational technology and a generational innovation that is forcing, for better or for worse, a reckoning around human intelligence, human value, human labor. So when I wrote the book or started to write the book in 2020, it certainly wasn’t on my agenda and it wasn’t part of public mainstream conversation the way that it is now. And I sort of smiled to myself that even when I published the book last year in September, we were not as preoccupied as we are now with its impact, with its role in our daily lives. So its full force is starting to be reckoned with. And it felt to me like if my framing was around navigating a fluid world, to not contend with the role of AI in that fluidity would be a little bit tone-deaf to this moment.
And I think that we need to have these conversations, either acceptance, resistance without engagement with the impact of this, what it makes possible, what it makes desirable, what it makes acceptable. I think these are the conversations that we need to be having right now to arrive at conclusions for ourselves as individuals, for our teams of what do we want to create with this? What do we want to do with this?
JANE
How do you see the concept of permissions in the AI era?
AI facilitates creative, intuitive, empathetic, deeply human capabilities
In my best moments, in my most optimistic moments, I think it is going to force us to allow ourselves to permit ourselves to access a series of creative, intuitive, empathetic, deeply human capabilities that previously were not considered valuable or relevant. If it is doing some of the repetitive machine-like labor, it’s going to free us in many ways to engage with our own humanity in ways that were never considered necessary before.
So I think I might come under a lot of heat for saying this, but I think in many ways, it’s going to create an architecture permission within ourselves as individuals, within schools, within companies to begin to engage with, okay, what’s the human contribution? What is human value? And that for me, while very uncomfortable and while very confusing at this moment and deeply destabilizing, might over time be an incredibly beneficial and meaningful conversation for humanity more broadly.
JANE
That’s interesting, to engage with our humanity more and to engage in general with humanity. Because for a lot of people, AI is the opposite of humanity.
Is AI the opposite of humanity?
Well, it is certainly forcing us to look at the types of capabilities that we believe should be protected and honored and recognized as singularly valuable in a human capacity versus easily replicable by a machine. And I think that’s some of what’s coming up right now all over the place with people spotting it in writing and spotting it in particular creative ventures. Its ability to mimic certain human capabilities is forcing us to then say, okay, what is it about us that we want to honor and preserve and lean into and own, if you will?
And that, I think if I look at my children and the conversations around human labor and the philosophers now have higher employment rates than the coders, those are very interesting little indicators of this evolution that we are experiencing in real time. So if, and I do think more about my two teenage sons perhaps in this conversation than even myself, if for them it’s going to create a necessity to consider lines of inquiry and employment and value creation that even a decade ago were off the table, then that’s very interesting. It’s not to say it’s not going to come with difficulty or confusion or anxiety or even suffering, but it is an interesting moment for us to look at ourselves and consider who we allow ourselves to become in an age where a lot of our most machine-like capabilities are very easily copied by something else.
Do teenagers see AI differently from us?
Do you think that teenagers, and I don’t mean yours in particular because that’s too personal a question, but you must be in contact with a lot of teenagers because of your teenagers. Is there a big difference in the way they see AI and the way we see it?
JILLIAN
Without being able to speak super broadly, I think like most things, they do not engage with it as a threat. They engage with it as a resource, even as a partner, and it’s not taking from them. I think for a lot of us who did locate our value in certain capabilities and roles and responsibilities and tasks that could now be done by AI, it is a clear and obvious threat. Whereas now they’re still young. I think the younger teens aren’t necessarily contending with it as a threat to their entry level employment. I think they’re saying, “Okay, this is now going to be a real resource for me. How do I use it?”
Now obviously their first instinct at their age is what can it do for me? How does it shortcut some of the things that I don’t want to do? But I think at the same time, they have the room and the space to explore it and discover its dimensions in ways that as a 40 or a 50-year-old, you need to make it practical and monetizable and figure out its role in your professional career with a greater sense of urgency. So I think they have a little bit more room to sandbox with it than we do. And so they will probably discover its fullest promise, if you will, and capability perhaps more naturally and intuitively than we will.
JANE
That’s interesting. I have a son who’s considerably older than yours, and he works in the film industry and works on videos and films and editing. And there are lots and lots of AI tools that are, I’m not talking about making content or making videos with AI, but tools that facilitate his editing process. And he’s very much into keeping up to date with what’s going on because all of his work is done with humans. But there are just a lot of tools now that are enabling him to do some things faster and some things better than he could be for different ways of editing and combining things.
We need to be willful – my first permission
Yeah. I want to come back to my 10 Permissions. The first one is be willful. What do you want? What you want to create? How do we approach this willfully of what does this allow me to make? What does this allow me to build? And I think recognizing that not everybody will treat it as a building partner in its fullest sense, but with a mindset, if you approach it with that mindset, where does that take you that you couldn’t get to before? And then to bookend that with my 10th permission, which is make believe, I know as an entrepreneur myself, it has made me believe that I can create things that I couldn’t create a year ago.
So I think for the independent creator, for the builder, for the freelance person, it’s an unbelievable resource and partner that you didn’t have before. I think if you’re sitting within a system that’s being destabilized by it, then obviously it is a much bigger source of anxiety than it is potentially a source of promise. But I think what we will all be forced to do to greater or lesser degrees in the coming years is have to contend with what do I want to make of this and what do I believe I can make with it?
JANE
That’s interesting. A lot of what people talk about online or in other meetings that I’ve been in are very concerned about AI taking over things. And I don’t know technically exactly what they mean, but I think people normally can control how they use AI. Do you think so?
JILLIAN
Yeah. I think this is a moment for us to remind ourselves of our human agency. I think, and I always come back to my first permission, be willful, because I think it’s so easy in times of deep flux to retreat into, if not full victim mode, at least the sense that you are being acted upon rather than being an actor. And I think in many ways, this whole conversation has come at us as a, here’s this train that’s coming towards you and what are you going to do about it? And our own sense of agency has been flattened within that conversation to, it is this force that will impact us.
And as you said, I think it’s important for us to, in whatever ways we can, engage with how we are going to use it for our own ends, how we can contribute to broader conversations about how it gets used. And I think it’s super important that we don’t see ourselves as subject to it, even if that might be our lived experience of it on some days of, oh my God, it’s taking over customer relations or something. I’m so sick of seeing it. How we continue to assert our own willfulness in the face of it, I think is super important. And it’s a great moment for us to keep reckoning with our own power as creators and actors in this discussion.
Experiment is another permission we need to give to ourselves
Can you think of another one of your permissions out of the 10, or maybe a couple that you think are especially relevant to our discussion about AI?
JILLIAN
Yeah. Well, I can think of all of them.
JANE
Maybe the… All of them. Yes.
JILLIAN
But let’s go to an obvious one to start with, which is experiment. And I think it is through the act of experimentation that we exercise that agency. I think it’s easy to sit back and again, feel as though for many people, I don’t understand it. It’s bigger than me. It’s happening too fast, it’s taking over. And I think the self-permission to play around with it in whatever way makes the most sense to you on your own, even if it’s just for 15 minutes a day, to start to understand what it can do for you is really critical. And then if we cascade that up to collectives, teams, whatever, how do we play around with what it can do for us?
Another permission is to look for trouble
I think maybe an unlikely one is look for trouble. Because I think as with so many of these conversations right now, the ways in which we’re engaging with it publicly are so commercial as opposed to the broad social implications around some key wicked problems that we’re dealing with, be they social, medical, inequity. Not that I’m coming at this with those answers, but what if we were to collectively individually decide that this could potentially, if not provide wholesale answers, at least help us to engage with some things that have previously appeared intractable? What if we began to see it as a tool to deal with some of our biggest problems? Because right now, the public narrative has shaped completely towards it is cutting out entire layers of organizations and replacing human labor.
Okay, that’s one lens. What if there’s another lens which is, huh, is this a liberator? Is this a problem solver? If only to allow ourselves to see it that way for a period so that we can still play around with what it makes possible. I think the danger is as ever, the single story and the way that, that limits our understanding of what we can do and who we’re allowed to be in this moment as we figure out the implications of this.
The No Harm successful experiment in Brazil
It reminds me of a conversation I had, I don’t know, maybe six, eight months ago with a guy in Brazil. And he’s famous for what they call the no harm idea. And he and his sister, who was a medical clinic expert, she talked to him about how difficult it was in their case, in their country, in many places in Brazil where people find it hard to get the right information about a particular medication, a particular illness, that what medication is good, what potential dangers might it have, or what does a person really need?
And they together set up this, I don’t know how it works obviously, but a thing that makes it very easy now for the doctors, the hospital workers, the drug store people, the clinicians to be confident about what they’re prescribing, what they’re prescribing and why. And it spread very fast through Brazil, and it was AI-based. I mean, not AI-based, AI played a major role in how they built it.
JILLIAN
Yeah. I think it’s unfortunate the timing of this, because it’s coming into our lives at full force at a point when I think people are tired, fearful, feel hugely disempowered to affect some other broader changes that are taking place. So this is not hitting at a moment when humanity is feeling in its fullest flow, is it? So it’s easy to experience it as yet another imposition from a series of actors who exist beyond my control. And I think that routine engagement with it as something that is within my control, within my purview is critically important.
AI felt as a flow that can overcome humanity
And that is not to be unnecessarily bullish about it or naive about it. It’s to say if we surrender in this moment to a narrative that puts it beyond our control, then it will be. If we continue to engage with it as humans seeking answers to problems, as humans wanting to create things that don’t exist yet, then what can it make possible for us whether we’re sitting in Brazil or South Africa or France? So will it enable a degree of creativity in the broadest sense? I don’t know. We’ll have to wait and see.
JANE
It probably will. I wrote an article, it’s about the gig mindset. And you’re familiar, I think, with my work in that area.
JILLIAN
Absolutely. Yeah. It influenced me deeply.
JANE
How did it influence you before I go on with what I was going to say?
The Gig Mindset is essential for people who want to advance in AI because the human element today is the weakest
Well, I think you were well ahead of your time in terms of understanding what I described in my book as the unraveling, the unraveling of these kind of fixed mindsets and ways of seeing ourselves in the world that fixed our identities to singular roles and singular ways of creating value in the world. And I think that what you were pointing to is what we are living through right now.
JANE
Oh, that’s interesting that you say that. In my article, I wrote about how the gig mindset is essential for organizations that want to advance in AI. And I connected it to the different aspects of gig mindset behaviors that I have identified in my book and how those behaviors are the very behaviors… They probably relate a lot to your permissions, actually. I’ve never related them to the permissions, but I think they do. They’ll fit in somehow. Yeah. And that’s necessary if we’re going to explore AI in a way that makes sense.
And my whole thing was triggered by two articles, one in MIT Sloan Management and the other, I forget where it was, where they talked about the problem with AI. It was going along and things were happening, but the human element was the weak side. It was the weak aspect of what was happening today. It was the human side, not the technical side. And then in my article, I developed how the human dimension of the gig mindsetter has those characteristics that are needed, like the permissions, I think. We could probably take the permissions and make a little table where this permission works this way in terms of understanding and using AI, and this permission works this way. Does that make sense to you?
Today’s modern corporate is antithetical to making the most of this moment in time
It is. And in fact, that’s a lot of what I am offering at the moment through what I’m describing as Permission Labs in that I would say I arrive at a similar conclusion that the way that organizations are wired, the DNA of an organization of today’s modern corporate is antithetical to making the most of this moment. Those corporates were created to execute in predictable times on fixed plans. They were not created to be as responsive and adaptive and as this moment requires, that there are specific behaviors and ways of seeing and being that are very much baked into the provisions.
And yes, I think they link up very much with your gig mindset around, again, the willfulness to ask questions, to challenge orthodoxy, to let go of what’s no longer working in favor of something that perhaps was unthinkable even a year ago to experiment, to create all the things we’ve already talked about here in a far more adaptive and responsive way than the monolith that is the modern corporate.
AI is not a technology top-down rollout
And so I think what we’re seeing right now already is corporates taking this, treating it like a technology rollout that’s top-down and one size fits all in many cases, and we’re already hearing the depressing statistics around that. So yeah, I think the permissions that we have to give ourselves individually and collectively to meet this moment and allow it to open us up to what’s possible rather than what’s cheapest or what’s quickest or what’s easiest is really critical. And I think those companies, those leaders who can see that that’s what’s required right now are going to be the ones who will take this forward in a way that is truly transformational. The rest will probably just gut a lot of what was valuable within their organizations and then deal with whatever the positive or negative effects of that might be.
JANE
I’ve read about organizations that got rid of a lot of people because they implemented AI in different areas. And a few months later, guess what? It wasn’t working like they thought it was going to work. And so some of them are trying to get their people back. Some of the people want to come back and some don’t. I find that very interesting. Serves them right, if you know what I mean.
We need a series of moving experiments; principles, permissions, boundaries
Well, I think there’s a certain hubris in assuming that this is a moment for large scale action in the face of something that is as fast-moving and developing as this is. If I were sitting atop something, I would, and I didn’t read your article about the gig mindset, so I don’t know what you’re saying, but I’m guessing there’s an element of I would treat this as more a series of moving experiments that can be scaled up or down as needed. I would be in learning mode. My goal would be to learn as quickly as possible. Yes, for sure where this might be able to create efficiencies within our system. But I think that’s just the floor. I think there’s another whole mindset and a whole area of inquiry around what does this make possible? What can we make now? What can we do now that we couldn’t make before?
And I think within that, I’ve worked with some people who are having competitions within their company for who can come up with new ideas, giving teams permission to experiment and play around with new things without it having to become a wholesale policy. I personally would even challenge the logic of we need a policy. Do you? Do you need a one-size-fits-all policy? Or do you need a set of principles, a set of permissions, some boundaries, and a period of time in which you allow yourselves to discover what’s possible and what’s desirable? And that is not to say that you remain in sort of experiment mode forever, but I think the rush to cement the policy and roll it out is a very 20th century approach to something that actually would benefit from a very different posture towards it.
Horizontality gives impetus and freedom
Yeah, I think one thing, the way you’re talking, I can even see with your hand movement, you’re moving your hands like this across in a horizontal way. And that’s one of the things I’ve always described in the gig mindset approach is that it works across the organization, not top-down, and not bottom up. There is some bottom-up and there is some top-down, of course, but it’s not totally that. And the whole idea of horizontality gives a lot of impetus and freedom for people to do things differently based on where they are on the horizontal dimension of the organization.
JILLIAN
Yeah. And I guess I feel like, as I said, that’s where you were pointing to phenomena and that unraveling. The top-down is very much a… it’s from a different time. And I think right now for us to contend with the reality that organizations are evolving to not necessarily look like the military or factories or industries where a lot of our previous mental models for work were borrowed from. And I think now what we’re moving into is something that’s more of a, as I described in an article that I wrote, a little bit of an atelier to go along with your industry, a little bit of something, and here I’ll point to my permission to travel light. Is there a lightness that you could find to allowing yourself to try things and make things and do things that doesn’t have to come with the kind of industrial area baggage of, okay, now it has to become a finished product that gets rolled out across the entirety of the place? And again, I’m assuming that’s some of what you point to in the gig mindset.
JANE
Yeah. I just wonder. I’ve worked with organizations now for how many years, but it’s very different to be able to think and write and create ideas that I can do freely as I wish, which is very nice. I was just cleaning up a bunch of hard disks I have, and I’m going through a lot of old client presentations, workshops, all that for the last 20 years. And some of this stuff that came out of them, it’s just really, really interesting. It’s given me a lot of triggers about things I can write about without the company name, of course, but a lot of ideas that at the time just didn’t take off really and didn’t work for different reasons. And I think some of those ideas now would be a great success.
Unravelling is an opportunity that creates space for ideas
Yeah. Yeah. Well, you’ve been ahead of your time for quite a while. I think one of the opportunities of this moment is, and this was, again, part of the larger conceptual framing of the book, was that this unraveling that we’re experiencing, which is deeply disconcerting in ways that we all experience many times a day, equally as creating space for ideas that maybe at a certain point felt unnecessary, irrelevant, even dangerous to suddenly find some oxygen, find some space. So again, that’s where I really want us to keep allowing ourselves to tap into our thinking, our critical thinking, our creative generation, because that is what we can bring to this moment to shape what’s possible and not feel like we are being shaped by it.
JANE
Do you think that’s something that adults, I mean old adults can do or do you think we really need the younger generation to push that?
JILLIAN
No, I think it can be a wonderful coming together at this moment. I love the idea of you going through your old files and finding ideas that could only have come from decades of experience and marrying those with the fresh minds of young people who are very alive and present to the possibilities of this moment and saying, “Okay, what can we do? What can we do together?” I think we are coming out of, I sense a coming out of an era of this generational strife and being pitted against each other to say, “What do you bring that I don’t?” And I find myself in that space in my own work kind of saying, “Cool. I know that I’ve been doing change work for 30 something years and it’s taught me a lot, but I cannot reclaim the fresh lenses of a young person. So tell me what you’re seeing in this moment and how do we bring those together to create value?”
JANE
You said you were doing some, what did you call it? A hub? A workshop?
JILLIAN
Labs, Permission Labs. Yeah.
Permission Labs to engage with the possibility of this unique moment
Labs. Yeah. Permission Labs. How does that work?
JILLIAN
I’m trying to help teams engage with, unlock some of their boldest thinking in this moment, ala this conversation. So how do we allow ourselves to move beyond the cheaper, faster lens that I think a lot of teams are approaching this with? How do we allow ourselves to engage with the possibility of this moment? It does take permission because as we’ve described, we’re not necessarily wired for that. And I called them labs because I was very deliberate about this is not sitting down with Post-it notes and generating ideas. I use play, I use movement, I use creativity to try and sort of hack a little bit into some of the stuff that maybe we’ve historically kept off the table, like you and the ideas that you’re unearthing.
What can we unearth in this moment that’s going to allow us to look back on it and say, yes. Because this moment isn’t coming again. Soon enough, everybody’s using the same technology. We’re all playing around with things. The individuals, the leaders, the teams that can really seize this to say, okay, we’ve got time here to play and create, I think will put themselves ahead in ways that we can’t even measure right now versus those who are just trying to slap a policy together and say they’ve ticked the box.
So I’m really looking for the creative thinkers, the ones who are sensing that there’s time right now that won’t be here in two years for us to still kind of play around with this because it’s still coming into its fullest expression within our work and within our lives. So yeah, it’s a creative space to give ourselves permission to unlock our best thinking and our boldest ideas in a moment that I think is really calling out for them.
JANE
Who comes to your labs? Are they within a single organization?
JILLIAN
So far, yes. Although that is not the sole model. I would love to gather individuals within a certain industry or who share an interest in something that hasn’t happened yet, but it is on my mind because Jane, remember I come also from the social change background. I come from the world of wicked problems. And part of some of the invitations that I’ve been putting out is to say, “Hey, if we are all working in the field of whatever it might be, can we come together to really look at the transformative capability that this is offering us? What we can create together?” It hasn’t happened yet. Maybe you bring your gig mindset and I bring my permissions and we help people to do that. But yeah, that’s something I’m very interested in doing.
JANE
Is there one or two things you would say to someone who wants to advance in this AI era and who wants to understand your permissions and do something about them? How would they go about that?
Help people be willful and develop their agency, and also go astray to find new things in life and work
Yeah. Well, again, I tend to come back to my first two time and time again. And the first one is the message I’ve been putting out here, which is be willful. What do I want? What do I want to create? What do I want to do? What do I want to make? What kind of value? That question, don’t ask it once and then think you’ve got to arrive at a [inaudible 00:33 :30] answer. Keep asking it. I find myself doing that. And it heightens my own sense of agency. And I think in a world of agentic AI, we need to have ever more agentic humans who will bring new value to the world in ways that wasn’t possible five years ago.
And I think the second piece of that, and my second permission, which I want them to think about, is go astray. Doing this involves you doing things you haven’t done before. And many of us don’t allow ourselves to do that. We stop ourselves before we even get started. We go, “Oh no, I can’t do that.” And yet that is a critical thing. I’ve said, “Oh, I can’t make a website.” Well, I’ve made a website. I’ve made an app.
So it’s going to feel awkward. You’re going to feel weird. You’re probably going to have a conversation with yourself around, “Oh, but I don’t know how to do this.” It’s okay. Keep practicing the art of being willful and going astray. And even if you just practice those two permissions over and over again in little micro ways throughout the course of your work, your life, your path, then observe what its making possible for you.
JANE
That’s great. That’s a good tone on which to end our conversation.
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