Define Success for Yourself: Why the Old Rules No Longer Work

Episode Transcript

Julianna Yau Yorgan:

Hello, and welcome to the Daring to Succeed podcast.

I’m your host, Julianna Yau Yorgan. And today I am so excited to be joined by Jillian Reilly, who 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’s focus is on helping people unlock their ability to navigate change and accelerate growth and learning.

Welcome to the podcast, Jillian.

Jillian Reilly:

Thanks, Jillian. I’m thrilled to be here.

Julianna Yau Yorgan:

Yeah, I’m so excited to be talking to you today about defining success on your own terms. I thought we’d just kind of dive right in because there’s so much you shared in your book and talk a little bit about your perspective on sort of the modern day prescribed ideas of success and why it’s such a challenge for us to try and find a way to define success for ourselves in a way that’s meaningful.

Jillian Reilly:

Absolutely. Yeah, I mean, I think, weirdly enough, I feel like we’re living in a really exciting time in terms of the unraveling of the sort of default definitions of success.

I feel like everywhere I look, people are starting to have conversations, to share their choices that are kind of challenging, you know, the standard.

Basically, it’s about money and status. Simply put, you know, I think when I was growing up, it was basically get a good job and good meant in an industry that was perceived as, you know, white collar, blue chip, where there would be ample jobs, where the salary would be good.

And, you know, all of that’s understandable. None of that is not desirable. But I think, as we all know, we are moving into a place where that very, you know, standard, linear story of moving through a corporate success story is either, you know, not desirable.

So I think that’s what we’re seeing a lot of people kind of going, no thanks, particularly Gen Z, but also

So on the edge of this AI revolution, I think it isn’t going to be feasible either. So I think what we’re being presented with is an invitation to really engage with, you know, fresh thought around what does good look like and what does success feel like for me?

And maybe, just maybe, there’ll be far more varied answers to that question.

Julianna Yau Yorgan:

Yeah, I love your perspective on that because I was actually just having a conversation with someone else who was talking about how a lot of men are struggling right now with having achieved that success measure that they’ve been told all their lives that they need to chase, you know, the money, the status, the titles, all the physical things, and they’re still not happy.

Jillian Reilly:

Right. Well, I think that was the unspoken trade-off was that you, in many ways, traded satisfaction, personal satisfaction for success.

That your sense of meaning, that your sense of contribution, or that your ongoing growth and continued satisfaction was a nice to do, not a must do.

Like, if you happen to get the two together, amazing. But, you know, the midlife crisis is a function of a lot of people reaching that certain point of saying, wait a second, I have played the game, I have worn the suit, I have slotted myself into a ready-made role, and often into a story and a path that I sort of inherited, or at the very least sort of, you know, was outsourced to me.

And now I’m waking up to the fact that maybe there’s more. But the problem is, by that point, you don’t have any lived experience of what it would feel like for you to go out and create something and drive your own path.

So, you know, I think the problem is not only that at that stage you’re, you know, a little bit burdened.

It’s responsibility and expectation, but you also don’t have the, what I would call the muscle to really start to redirect towards something that would feel more satisfying to you because you’ve never done that your whole life.

So, yeah, I think part of what I’m trying to achieve with my book is the suggestion that maybe we need to more consciously build that muscle in younger people because we’re moving into a phase where we won’t even have the luxury of sort of slipping on a suit and sleepwalking.

We’re going to be much more required to actively drive our own path. So, you know, I think it’s going to be an interesting time for us as humans to adapt to a very different professional marketplace than what existed for previous generations.

Julianna Yau Yorgan:

Yeah, and I love the idea of building and flexing that muscle to allow ourselves to go in that direction because I think for so many people, it’s, it’s really scary to step out of that prescribing.

Path where, you know, we’re kind of told, if you do all these things, this is the payoff. This is exactly what you’ll get if you do these things.

And most of the time we do get that payoff. But as you alluded to, we’re starting to see that unravel where the loyalty, the hours that we put into our jobs, we’re not getting that in return anymore.

And I think that’s kind of that fissure that you’ve been touching on.

Jillian Reilly:

Yeah, totally. The reward structure shifted. It was basically hard work, loyalty, compliance. And, you know, for our parents, for my parents, it was basically just that for the entirety of your life.

You know, we were risk averse and change averse because that was perceived as insecure. And, you know, for my parents, it largely paid off.

And I think with every successive generation, it’s sort of like, wait a second, I can work as hard as I want and be incredibly loyal.

And when the layoffs come. That doesn’t matter. Nobody’s taking stock of that. So, you know, kind of that social contract that shaped so much of our decision making is, to use my language, unraveled.

And within that space is, you know, I think deep insecurity, anxiety, because that’s how we made decisions. It was if then.

And as I describe it, there were kind of requirements and guarantees. So if you go to college, you’ll get a decent job.

I mean, that started unraveling a long time ago. But now it’s quite, you know, it’s staring everybody in the face that there are no requirements and there are no guarantees, which means the pressure on individuals to make choices is huge.

And, you know, we’re not raised really to make choices that align with ourselves. We’re raised to look around and ask other people what the best choices are.

So, yeah, I think it’s, I think we’re at an interesting point in terms of the way that we need to operate in order to.

To gain the same security and the same benefits that maybe our parents did.

Julianna Yau Yorgan:

Yeah, and in your book, The Ten Permissions, you talk a lot about the concept of difference between a destination mindset and a direction mindset, which I think is so valuable in this discussion.

Can you walk us through a little bit about what that means, like the difference between the two?

Jillian Reilly:

Yeah, I mean, it’s sort of, if I can relate it to real life, it’s sort of like, you know exactly, you think you know exactly where you’re going, and, you know, you know how to get there.

So it was, you know, down the four-lane highway to a place you’d been a thousand times, and that was sort of the old school, like, yeah, I know where I’m going.

I just know I need to follow the signs and follow the course. And so, you know, in that way, you kind of switch off, you put your car on cruise control, and you just go.

You don’t have A lot of decisions to make. You don’t have to be that conscious and aware of your environment.

You don’t have to learn anything. You just have to press go. And in that scenario, if I think about how you pack for that, well, you can take as much as you want because you don’t have to be agile and adaptive.

You just have to get there. And then you unpack and then you stay there. So that mindset of I’m just going there.

I can take as much as I want and I just have to keep going is very, very different from, you know, the finding your way of, you know, I’m heading in this direction.

I don’t necessarily know what the destination is. I haven’t been there before or I can’t see it yet. And so in that, you know, naturally, you’d have a very different posture, wouldn’t it?

You’d be far more awake and alert. You’d want to travel light, which is one of my permissions. You know, your whole way of moving through the world would be very, very different.

And so, you know, the need to learn, the need to pivot, the need to constantly be sort of making sure that you’re heading in the right place is a super different way of operating.

And I think that that’s what we’re seeing ourselves having to move into. It’s, you know, taking the gas guzzler to the same family holiday destination to kind of setting out into the world.

And for a lot of people, that’s going to strike fear deep in their hearts. I think it opens up tremendous possibility for us to discover what we’re capable of and what’s possible when we set out into the world ready to learn and grow and adapt.

Julianna Yau Yorgan:

Yeah. And I mean, it’s so understandable when we’ve been told for so long, this is the path, this is what to do, that when you just set off and go without a specific destination, without even maybe a map, that it can be terrifying and in your brain.

I you also talk about making small bets, which is something I’ve got a similar concept I do with my clients where it’s taking little steps, small actions that kind of accumulate.

But I’d love to hear more from you on why you put it that way in terms of making small bets for your life.

Jillian Reilly:

Yeah, because I think in the previous model, you made sort of three, you know, your degree, your job, your partner, you know, I’m going to bet that this is going to work out for me and it’s going to pay off.

Now, you, first of all, are going to make so many more decisions and bets on yourself. So, you know, one of the things that paralyzes people is they, when there were only three, it was like, I better get this right.

Because if I don’t get it right, my life’s a disaster. And it was to some extent. Whereas now, where, you know, as you’re describing your work with your clients, you’re probably working in…

Shorter time frames, you’re preparing for more change. You want to perhaps have lower risk, more frequent experiments that you’re undertaking where you say, I’m going to try this, you know, I’m going to, and, you know, by bet, it’s, you know, what do I think the payoff is going to be?

And yes, that might involve some investment on your part, either, you know, in a range of different resources. But, you know, if it’s small, and it doesn’t put you at super high risk, but the potential for reward is that it teaches you something new, it exposes you to something different, it opens up something new in your life, then you can kind of keep moving forward.

So you’re not paralyzed by that, I have to get it right. If I don’t get this right, I’m on the wrong path, which I think is what led many of us to being so afraid, to, okay, I’m going to accept the fact that I’m going to make a lot, I’m going to try a bunch of different things.

Some of them are going to pay off, some of them won’t. But if they’re small, then, you know, I’m

And a lot of this Ten Permissions is about allowing ourselves to operate with a way that allows us more scope for growth and adaptation and creativity as opposed to narrowing us into a way of operating that feels super linear and high stakes because you’ve got to hold on to the status quo at all costs or else you’re booted out into kind of insecurity.

And this is a completely different way of operating.

Julianna Yau Yorgan:

Yeah, and as you were speaking, it reminded me of something that I really love from your book, which you wrote, which is, success is as much about what you know as how you keep finding your way through the unknowns and being ready to leap into the unrevealed.

Some of your best decisions will be leaps of faith, incalculable risks. And I think, like, I’m getting goosebumps just reading that again because it’s so profound.

And it’s, I think for a lot of us, kind of looking and making that leap is such a big thing.

And I guess my next question for you is, why did you kind of wrap all of these concepts and all of this advice into the idea of giving yourself permission?

Jillian Reilly:

Right. Because you won’t feel allowed to go into the unknown. There’ll be so much wiring in you that will say, what if, you know, what if I fail?

What if it doesn’t work? What if I look like a fool? And the negotiation that you have to do as an adult is mostly with yourself.

There’ll be maybe people around you, whether that’s your family or your community, who might have something to say about it.

But at the end of the day, that decision to step into something new and different is yours and yours alone.

And I think that that’s something that You know, can either feel hugely liberating or very daunting. But the idea of permission is self-authorization.

I’m not waiting for somebody to tell me that it’s okay. I thoroughly accept that other people’s approval and opinions are important to weigh in.

It’s not that you’re some complete rogue who’s off ignoring everybody and everything around you. You take those into account.

But the bottom line is it’s you. And I think having been with so many people through so many change processes, which are in essence stepping into the unknown, right?

It’s something I’ve never done before. It’s operating in a way I never have before. It’s a conversation that I’m not used to having with somebody.

That sort of, okay, I’m going to do it. That, all right, I don’t know what’s going to happen here.

But I’m going to give it a try and, you know, bet on the fact that by doing it, I’m going to, you know.

Create something that will be better than my status quo. The only person who’s going to choose to do that is you.

And so that permission is something that, you know, for me, after decades of working and change, I kind of came down to me as outsider could do so many things.

I could show you all the reasons it made sense. I could train you and all the tools that would help you do it.

But, you know, you work in a similar field. And ultimately, what I’m hoping to do with this is sort of open up a deeper and richer conversation with self.

Because that self-awareness and that self sort of exploration around what’s at stake for me here is the difference between people who, you know, are prepared to move into uncertainty and discomfort and the people who wait on the edges of it going, I can’t because I’m too afraid.

So, yeah, I see it as a deepening. In a richening, a richer conversation with self.

Julianna Yau Yorgan:

Yeah, I love that concept of self-permission because I think you really nailed it there with we’re always looking to the external for that right decision.

Like even when I think about past decisions I’ve made, one of the big ones was which university to go to.

And I remember taking the advice of one of my high school teachers who I had so much respect for and I thought he was just a really smart individual.

And within the first two days on campus before class even started, I realized I had made the wrong decision.

And it took me an entire year to get back to the university that I had chosen for myself in the first place and didn’t trust for myself that that was right because what do I know?

I’m just a kid. know? Right?

Jillian Reilly:

And I think that’s one of them. Biggest imperatives right now in, broadly speaking, education or preparing young people for this world.

You’ll remember one of the things I talk about in the book is that we raise children to be permission seekers, but we don’t prepare young adults to give themselves permission.

Now, in the old world of the linear path and the sort of limited options, it didn’t feel like it was as big of an issue.

It certainly led to a lot of satisfied people, but it didn’t lead to the same degree of what I think we’re seeing right now, which is overwhelmed, anxiety, because the number of choices is much greater, because the number of voices in people’s heads just counts, you know.

So it’s not only the people around you, it’s the people online, it’s the influencers, it’s this and that. So you are bombarded with opinions and data, and if you have no access to your own internal voice.

Then you’re just going to, you know, suffocate under the weight of other people’s ideas. It is no longer possible to outsource your agency to everybody around you and expect that you’re going to be able to navigate this quickly changing world as efficiently and happily as you could.

So what I would say using your example is, of course, we want to ask other people. Of course, you know, there’s nothing wrong with gauging other people’s opinion.

But rather than starting there, why don’t you first check in with yourself? What do I feel? What do I really want?

And allow yourself to just answer that question without that, but, but, but, but what will everybody else think voice coming in?

You know, allow yourself that unfiltered access to what I really want. And then, you know, check it with other people, see what they say.

And if anything comes out as factually new data. Yeah. Yeah. Yeah. That will shift your understanding of what the decision points are, fine.

If it’s a bunch of other people’s opinions and they’re not really operating on data, then you come back to self and say, well, okay.

And I have to tell you that when I do talks with young people and we talk about this, one of the biggest things they come up to me and say is, thank you so much for acknowledging the fact that I, my voice is valid even when I’m 15 or 16.

Like, I am the authority in me. And that’s not ego. That’s not entitlement. That’s the human existence. And the more that we nurture that voice in individuals, which we’re so afraid of because we think it’s going to lead to somebody who’s demanding or rebellious, but the more that we kind of give people permission to listen in first and trust, gosh, I think we’d all be far better contributors.

Julianna Yau Yorgan:

to the world. Yeah, and as you were explaining that, I actually realized that I’ve been teaching that method to my clients in a business context, where like leaders trying to make good decisions, it’s the same kind of process.

start from what you think is right, and then you reach out to all the people that you think you need to get all your data points and your opinions and reassess.

And I’m almost embarrassed that it never occurred to me that that same process can be applied to like anything in life.

Jillian Reilly:

Yeah. Well, I mean, I don’t think you should be embarrassed. None of us was raised to listen in. And I think that a lot of the way that I describe what the Ten Permissions is seeking to give people a framework for understanding is sort of finding your way versus finding

Following the way. You know, the idea that there was a way, and if I followed it, I’d be safe and successful.

Okay, that’s fallen by the wayside for better or for worse. So whether you like it or not, it’s time to find your way.

Guess what? You’re really well equipped to do that. Nobody has encouraged you to do it. Nobody has necessarily sat you down and say, hey, you’re actually like amazingly well equipped.

If you give yourself permission to listen in, to, you know, do some of other things I talk about in the book.

So I don’t think any of us has really been intentionally prepared to find our way. And so I see a wonderful opportunity for that now.

And the opportunity is that hopefully it leads to more and more people who have better access to what it is they want, what it is they think they can contribute.

And yeah, with that as a starting point, I think we’ve got a better chance of creating more of what we want to see.

Julianna Yau Yorgan:

Yeah, and as we start to wrap up, I’m reminded by another quote that you had in your book, and I think this is a really good time to drop it in, because for anyone who’s listening, who’s kind of encouraged by hearing all of this and ready to do something, the quote is, most people imagine having to blow up their existing lives to design a more desirable one.

And that’s something I hear a lot with people who, like, they look at some of the crazy things I’ve done, like, just quit corporate entirely and move halfway around the world.

Not everyone needs to do that to start making those changes in their lives. What would you suggest for them to kind of think about as that first step towards giving themselves those permissions and diving into this big new world?

Jillian Reilly:

Yeah, well, with the book, for anybody who buys the book, they’ll get a QR code to download it. Sort of Getting Started Workbook.

And it was really important for me to have that because, you know, this book is necessarily ideas, you know, and it exists up here.

And what I wanted was to quickly help people translate in just the way that you’ve described sort of, okay, these are great ideas, but what do I do tomorrow?

And the focus of the book is on starting with where you are and working with your life as it is, because I think most of us have so much more scope in our existing lives to begin to explore our own sense of agency.

And for me, that’s like the starting point is that I can, I am allowed to make choices that reflect my own desires.

And that sounds so stupidly small, but actually it’s the kernel of everything. And, you know, I say it, people want to like change their job, but they can’t figure out what they want on their pizza.

And it’s like, you’ve got to start to listen in. So that listening in that. Learning to listen can start really small, and it can start with stuff that’s low stakes.

So I would encourage people to start really sharpening their agency and their decision-making and cultivating that inner voice within the scope of their existing lives.

And then let that start to unfold ever more into some of the more high-stakes decisions that exist in their lives.

But, you know, as I’ve said in the book, you know, it’s like you can’t do a high jump from standing still.

You can’t suddenly be like, boom, I’m now going to go out and do something. And guess what? You’re going to get to that other side and be the same old person you were before.

So I would much rather you build up the muscle and the ability to make super intentional choices and then get to the ones that really matter to you than to just make one big choice.

And then land on the other side kind of going, okay, now what? Um… So, yeah, I think there’s so much room to start small.

Start on a weekend. Forget about your job. Deal with the rest of your life. You know, we’re so obsessed with our work and our professional lives, but there’s huge scope within our off time to kind of start to engage with self and story in a much more intentional way.

Julianna Yau Yorgan:

Oh, that’s so amazing. I am ready to do it myself.

Jillian Reilly:

Awesome.

Julianna Yau Yorgan:

Yes. So for those of those listeners out there who want to hear more from you, connect with you, find your book, how can they do that?

Jillian Reilly:

Connect with me on social media platforms, of course. I’m very active on LinkedIn primarily, so please find me there.

My website, 10permissions.com. And the book is available already on pre-order. It’ll be released on September 16th on Amazon in the U.S.

It’ll be in bookstores then as well. But please go ahead and pre-order it. I’ll send you the link for that.

And yeah, and reach out. I’m super excited to kind of be in conversation with people as they use some of this in their own lives and explore what permission might feel like for them.

Julianna Yau Yorgan:

Yeah, absolutely. I’ll be sure to put all those links in the show notes so people can find you.

Jillian Reilly:

And I can definitely attest to how easy it is to talk to you.

Julianna Yau Yorgan:

So I encourage you to reach out to Jillian if you have anything you want to talk to her about on this topic.

Jillian Reilly:

Wonderful. Thank you so much.

Julianna Yau Yorgan:

Yeah. Thanks, everyone, for listening. And I’ll see you next time.