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- [00:04]
A
Fulfillment and purpose, they're verbs, they're processes, they're not fixed things. So it's not something that you can lose or have. Fulfillment to me is alignment. It doesn't mean perfect, squeaky clean, like nothing is bothering me. Fulfillment comes from a sense of being who you truly are and living fully in your life and having a life that is yours in all its messiness. So how do we begin? There are three core shifts that we really need to make in order to shift from destinational living to directional living. The first one is switching from external approval to inner alignment. We really want to be insourcing our decision making as opposed to outsourcing it. Fulfillment is not one size fits all.
- [00:59]
B
Welcome to the work for humans podcast. This is Dart Lindsley. Megan Hellerer. Welcome to work for Humans.
- [01:08]
A
Thank you so much. I'm so happy to be here. Dart.
- [01:10]
B
So I don't have very many people on the show who speak on sort of the career side of the equation on the part of the equation where people figuring out what great work is for themselves so that they can even create it. But I did have Bill Burnett on the show who wrote Designing your life and he gave a lot of really great examples. But I do think that it's super important if we believe that great work is a co creative act. It's something that companies help to create in partnership with people at work. That that co creative act needs to be understood from both sides and that in fact it's a capability that you might want your company to have, which is the capability of people at work to decide what they want. And so that's where we want to go with your book directional living, where you've dived so deeply into how career can go wrong when we focus too much on destinations and how we can set it right. So I'm going to start with the under fulfilled overachiever. It has an acronym. How do you say it?
- [02:20]
A
I say oofo, but I actually usually just say the whole thing. I did it more for like a writing purpose. So I would just say under fulfilled overachiever.
- [02:28]
B
What is that and how did that manifest in your life?
- [02:31]
A
This is the perfect place to start because that's also where it started for me. I consider myself to be the original under fulfilled overachiever and someone who checked all the boxes, did all of the right things, achieved everything I set out to, had this great on paper life that did not feel great inside. And I had done really well in high school and I was like president and captain of everything and I went to Stanford undergrad and I graduated with a 3, 9. And I started working at Google immediately and dutifully climbed the ladder, even though I didn't even really have an interest in tech, but I was in Silicon Valley, so it was like, all right, I guess this is what I should do. And was secretly miserable and deeply ashamed of how miserable I was, because I felt like, how could someone who has this dream job be so miserable? There must be something wrong with me. And also how could I be so competent in so many areas and well trained in so many areas and cannot for the life of me figure out how to figure out what I want to do with my life? And for years I was asking this question, and it was a constant question of should I stay and should I go? Without any real action or sense of even how to make sense of that question. And until I finally quit with no plan, which was very out of character for me simply because I really couldn't do it anymore. I was deeply depressed. I was having almost daily panic attacks. I literally had to schedule time in my calendar to have a breakdown in the shower every morning and set my alarm accordingly. And I left with no plan. And when I went to try to figure out who could help me to make sense of this and to figure out what I really wanted to do, and I believe deeply there must be something that I can do that has impact and contribution that matters and doesn't make me want to die every day. And nobody seemed to have a good blueprint for that. You know, this was back in 2014, so coaching wasn't the thing that it is today, but there was coaching and it was like executive coaching. So people who were like, helping you climb the ladder faster. And then there were coaches who were like, super woo. And there are people who tell you to lean in, and then there are people who tell you to lean all the way out. What we would now consider trad wife type of things. Right? And there wasn't like the middle way, the third way that I was looking for that felt like it had to exist. How do you achieve? How do you have ambition and fulfillment at the same time? And that was the question I set out to answer for myself at first and then for others.
- [05:13]
B
You said it very fast and very lightly in a way that didn't express how bad it was as it's expressed in the book. You mentioned in the book that you've thought about doing creative writing at one point. You're a really good writer and a part of what you do as a really good writer is you make it in the book very visual and very alive. And it starts with you. And this is a quote. I was a place nobody ever wants to be. On the floor of a public bathroom, in the middle of a panic attack, in the middle of a meeting that you'd had to leave. And this had become a way of life for you in the perfect Job. Let's talk a little bit about the perfect job. What did perfect look like for you? And we're going to talk about your clients too, along the way. But for you, what were the boxes that were checked in your life that should have meant that you should not be on the floor of a bathroom?
- [06:21]
A
I think the first one was impressive. It was like a hot company that really felt still, but especially at that time, like Elite. So it was something that was. Seemed admirable and it also seemed important on some level, like it felt and probably again still does. But there was literally only one office, only Mountain View existed when I started working at Google. So, you know, it had just unfortunately just IPO'd. So I missed that boat. But it was new and it was nascent and it was innovative and exciting, or it should have been. It should have felt those ways. And I think also there was a real path for growth. You know, it seemed like there was a clear trajectory and it was something that I could climb sustainably. But then there were a couple of other pieces that I don't know if I would have identified as much at that time, but stability and security, this sense of, of course you could get let go, but this company wasn't going to go under and that this was going to be a real resume builder, like this was getting me somewhere. And then the security of it, the paycheck, the 401k, and then of course the benefits and all of those pieces of it, it came with this. And it's interesting to think about it from the flip side, of course, of where you more commonly sit, of what they were selling me, because they definitely were selling me something which was this whole package of this dream perfect job, which felt more like golden handcuffs in the end. But it was a pretty package.
- [07:56]
B
Quite a few companies are good at building the box that work comes in, but not the work itself. And so a lot of that box is snacks, Climbing gym, primary colors, really nice architecture. I personally think that Google is a very tough place to go into right out of college like you did, because you don't have any perspective beyond that environment. Everybody else is telling you it's great. A classic Path for a lot of these top companies is Stanford or Harvard, then consulting for five years and then right into a company like Google or a Facebook or an Apple. You just went straight in right outta Stanford. Even less perspective, I think that's really hazardous.
- [08:45]
A
I could go either way. On the one hand, you're right. One of the hardest things about it was that when I would articulate to people, I don't know if this is for me, I don't know if this is it. People would say you are insane. You do not know how good you have it. Nothing is gonna compare to this. Never leave, never let this go. And again, without anything to compare it to, I didn't have a choice really other than to listen to it, you know. And it felt like this precious thing that I could never let go of at risk of ruining my life. On the other hand, I will say I got an incredible business education. Basically like getting paid to get a business education that has served me so well and there are many things that it had going for it too. And so on the one hand I'm not sure I would advise someone if they asked me if they should do something like that right out of school. On the other hand, I got to get my hands dirty really early and learn a lot. And there is something valuable about that too.
- [09:44]
B
This is one of the core questions I'm going to explore throughout this conversation which is some of what made you unhappy. And really reading it, it feels like you could have died. It felt really, really bad. Some of what made you unhappy may have come from the environment. But a lot of what made you unhappy you brought with you. What did you bring with you and what do people in general bring with them that puts them in that situation?
- [10:10]
A
Yeah, I want to be really clear that I don't think this was Google's fault. I have coached people into Google. There are some people where that is what's aligned for them. That's what's fulfilling. That is what in my language is directionally right. And it is a great opportunity for whatever it is that they are setting out for. And same for other sort of equivalent big tech or other industries. This isn't like an anti Google campaign. They didn't do anything. To me it was a co creative toxicity. Right. Where perhaps they had a part in it. And if they approach things in the way that you talk about it, maybe we would have had a different situation. But I think the things that I brought into it were one this outsourcing of my decision making. So I did not have an Understanding of what I now call my inner navigation system. I did not know what I wanted and I did not know how to navigate my life accordingly. And because I didn't know what I wanted and I didn't know that I was allowed to know what I wanted, especially when it came to work, it felt like something that was very top down, like somebody assigns me something and I do that job. I don't get to participate in co creating my work or saying I love doing this work. I don't like doing this as much. Are there more opportunities like this? That never occurred to me to participate in that way except for whatever was going to be the most visible, the most marketable, the next promotion, whatever those things are. So my one on ones didn't look like, you know, I'm really psyched about this, I'd love to have more opportunities to practice that or I'm really curious about this, like is there any way? And that at least when I was there, I think there could have been more opportunities for that to have that conversation if I had been able to be more self directed in that way. My conversations more looked like what do I need to do to impress the powers that be so that I can get the promotion that you guys say that I need? And what happened was that I eventually realized that I didn't want the life of anyone more senior than me. And so I tried a lot of things. I switched offices, I switched teams, I went from emerging products to business development to partnerships. I really tried to tweak it in a way that might make it work. And I don't think there was anything for me that would have worked there. But that isn't necessarily the case for anyone. And I think now I have much more capability of sort of playing this game of warmer, colder and saying, well this is closer to what I want to be doing and paying more attention to my inner landscape as I'm evolving, even as my own boss. You know you mentioned for before we started talking, even if you're in your own company, there's the employer and the employee, right? And I'm both of those things and I still have to pay attention to what is it that I want. Where am I feeling stagnant, where am I feeling energy and how do I create a role for myself, create a business that allows me to evolve in that way. And I really thought that I in the world was more like a static fixed thing and the goal was to achieve as much certainty within that as possible.
- [13:24]
B
That's fascinating. That's a very interesting Insight, which is seeing yourself as a fixed thing, seeing the world as a maze created by others that you navigate using the opinions of others. Can you describe the moment in the grocery store with the Kleenex? So this is after you'd quit. You know, you'd walked away from the job everybody thought was amazing except you. You're in the grocery store and you had a problem with a Kleenex box.
- [13:55]
A
Yeah. And this is a true story. Yes. I'd left, and I was in this process of who am I? Without this title, without someone to report to, without everything every day fully baked for me. And, you know, I was in the drugstore and I was trying to pick out a box of Kleenex. And, you know, there's all these different designs. And I realized in that moment, I was paralyzed, trying to decide which design on the Kleenex box I wanted. And I realized that I knew what my very fashionable friend would get. I knew, like, what would be most aesthetically pleasing to this other person. I knew what, you know, if I had this sort of vibe, then I would go for that box. But I did not know what I wanted. I had no sense of my own responses to things in the world. I had so dismissed and suppressed any sense of my own preferences, my own sense of self, that I could not make this decision about the Kleenex box. And of course, who cares what the Kleenex box is? But it was realizing in that moment just how far away I was from my own instincts or my own ability to feel into what was true for me.
- [15:17]
B
What was the not that experiment?
- [15:20]
A
What I did from there was I knew that I was going to get scared with no income and no one supporting me and probably take the next job that was offered to me. Somebody would be like, oh, come be the CMO of this random app. And I'd be like, yes, okay, I'll go do that. And I knew I would end up in the exact same place. So in order to protect against that with myself, I made a commitment to myself that I would not do any interviews, I wouldn't update my resume. I would not look for a job in traditional sense in any way, shape or form for at least six months. And during that time, I didn't know what I did want. Example being the Kleenex box. But I had more of a sense of what I didn't want. And I find that that's true frequently of people I work with who don't have this sense of what they do want. A lot of times it's easier to feel into what we don't want and what we want to move away from. And so, you know, I put it in this container of an experiment which felt a lot safer and gave me a lot more permission to explore and be in the not knowing. And I went about it in a way of just moving away from things that I did not want in hopes that that would start to steer me towards something that I did want.
- [16:34]
B
We're going to start talking about living in the destinational world. It's the world of all the shoulds of how other people see us. Where in your experience, for your clients and for yourself, do the shoulds come from? Who teaches us this? Where is this acquired? And then where we're going to go with the conversation is we're going to say, how do we get beyond the shoulds and into other things? So let's start with what's the destinational world?
- [17:04]
A
What I discovered when I started getting really curious about why there were so many of us under fulfilled overachievers, when I realized that it wasn't just me, I started sharing my story more and more. So many people were like raising their hand. Me too, me too. I would quit if I knew what else to do. And I really like, how did we get here? How did so many of us find ourselves in this position where we have all of the achievement and none of the fulfillment that seems like such a loss, not only for us as individuals, but us as a society, as a culture? And what is so broken here systemically that that's happening? And what I started to notice was that the thing that every person who was an under fulfilled overachiever is getting wrong is this destinational thinking. And it's so pervasive in our culture. And the idea here is that it's outcomes focused and outcomes based. So we think about what do I want the end result to be or what do I want to be when I'm 65? And then try to reverse engineer your path to get there and then just brute force your way to it and ignore any information along the way that might tell you that that is not the right path, because that is a distraction to your clear, linear, secure, certain up into the right path. However, what many of us learn the hard way, obviously myself, is that even when you arrive at that destination, it often doesn't feel like what you thought it would. Because when we're choosing these future destinations, we can't actually know if that is what we want. And then the second part, which I think is becoming increasingly obvious, evident and important salient is that it assumes a certain level of certainty that you can pick some future destination and feel like it's likely too certain that you are going to end up at that destination that just doesn't exist anymore in the realm of career. Maybe that was possible in like the 1950s when it was like a lot of people started a company and they worked at that one company for the rest of their life. That isn't the norm anymore. And it's not even really possible. There are no safe jobs anymore. Ten years ago, 15 years ago, being an engineer, like a computer science engineer, was the safest thing you could think of. Everyone thought you would always have work. And now so many people's jobs are being eliminated as a result of AI. And we've seen this happen in so many different industries. And I think there's a blessing in that. There is something for us all to learn from. The opportunity to see that it wasn't ever really that certain in the first place. The certainty was always an illusion. And in the absence of that certainty to depend on, what do we look to instead? And I think that is where that leads us into the directional world or the other way of operating, as in contrast to destinational living into directional living.
- [20:00]
B
There's something really interesting in there, which is that success is the only way to find out what success can't give you. I'm sure that there are a lot of people who set the five year plan and they go toward it and they can't get there. And they think that they're not happy because they're not there. But just the fact that you were able to get there was the proof that it wasn't where you wanted to be. It reminds me of pushing on a door, having the door open and falling into a pit. You think if I just get through that door. Right. If I just get through that door. And one of the things I say sometimes is that when you're designing a house, you don't design how people are going to live in the doorways. You design how they're going to live in the room. You design a room that's good for living in. And yet when we set these destinations, I want to pass through that doorway over there. We're designing all about our lives around the doorways, not the rooms.
- [20:53]
A
Yeah, exactly. The milestones. Right?
- [20:55]
B
The milestones, yeah. Which frankly are in a data model in workday that is essentially saying there's a box over there for you that you're gonna like better. It's not a thing in the world.
- [21:07]
A
Yeah. Yeah. And I do think a couple things. I think I knew this on some level. On a smaller scale, I don't think that everyone has to reach the highest level of success in whatever they're doing in order to understand this. Like, I would get an A on something and then not care about it or feel nothing in response to that. Right. Or work really hard in a class and do well in the class and then be like that. I felt nothing that did not feel rewarding to me, that wasn't fulfilling if it wasn't a class that I was inherently interested in and in for the learning and the experience. And so I don't think it's like you have to get to the pinnacle of your career in order to understand this lesson, but I do think it's true that you do need to have some experience of that and how it doesn't work. And I also wonder that if we weren't so focused, you know, I have a toddler and I think about a lot teaching her decision making as she gets older and how to think about these things. And I wonder. And I'll. I'll have to see how it goes. I'll have to come back and let you know. Or she will. But if she wasn't focused on outcomes at all and she was truly focusing only on basically playing a game of warmer and colder in her life, if success could be truly defined differently for her, meaning the success was based on how good and fulfilling the. And when I say good, I don't necessarily mean like relaxing on a beach good, but how fulfilling, how meaningful, how purposeful the experience of the thing felt. You know, I can say that doing something like writing a book, the process of it, while torturous at times, certainly that felt rewarding. In the process, it really wasn't just about the publishing of the book and having it out in the world, although of course, that was a part of it and a stage of it, too.
- [23:05]
B
You described directional living because we're going to get into directional living now. The focus is on moving iteratively in our own personal right direction without needing to know the precise destination. And so you mentioned in just several sentences, going to school, getting A's, and then your daughter. And how might you create some more directional living in her life? Is there something that our education is leaving out or hyping up that primes us to be destinational?
- [23:40]
A
Yes, definitely. So I think it's worth going back to what makes destinational living so seductive in the first place? Because if people were just Telling us to live that way, but there wasn't anything in it for us, it wouldn't be so pervasive. And the reason that destinational living is so seductive is that it feels safer. We feel safer when we think we know exactly where we're going and we know all of the steps to get there. It creates this sense of certainty, of security that we don't necessarily feel like we have if we don't have a clear destination. It requires, and I do think this is the most essential skill of the 21st century. It requires a tolerance for uncertainty and being in the not knowing. And that for humans in general is uncomfortable. It triggers, it activates our fear self, right? Our fear self likes certainty. Anything new or uncertain is going to feel scary to our nervous system, right? Even if it actually isn't scary. So it requires increasing our tolerance for that certainty and some sort of training and setting up that skill. So I think that's why we fall for this trap, why we fall into this trap, why it's so compelling, even if you know that it doesn't really work or doesn't really help, in combination with the fact that we don't have that skill. So I think there's two reasons why all of our systems are set up this way. And this kind of touches on a question you asked earlier, like where do the shoulds come from? I think they come from a societal level or systemic level. And we're sort of conditioned in this way because it's helpful for the powers that be to maintain the status quo. People who are invested in the status quo can say, here are the five paths you can take. And they sell it to us by saying, these are the things that will make you secure and happy. So just pick one of these five paths. Then you're going to have this great life, and that is great. If you want everyone in society except for you to be lemmings and not challenge your power and all of that stuff, right? So we could get into all sorts like that. But it is, I mean, I think that's some of where it comes from. Like people, very powerful people are not consciously right, but like invested in keeping, maintaining the status quo. So that's one part of it. And then I think people who are closer to us, right? You think about asking, what do you wanna be when you grow up? Parents fall into this trap also. Not because they're trying to cut us off at the knees or make us feel stuck or depart from our own authenticity and sense of self, but because they want safety for us. It feels great not only for you to have a safe path, but for your kid to have a safe path, right? Like, oh, you're gonna be a doctor. That feels great to me. Maybe for optics reasons, but mostly I feel like I know that you're going to be okay and taken care of and because again, we could get into systemic things like we don't live in a culture, at least here in the US that has safety nets. And so those things become even more important. Could also talk about the ways in which doing things like offering health insurance through your job makes it even more imperative that we stay in these roles and have a job even when that's not actually serving us, or I would argue serving culture. So in terms of where that comes from and why these things show up, and I think our schools definitely were missing the skill of tolerating uncertainty. Some of that I think is perhaps important. And again, I'll talk to you in 10, 20 years when I've gone through this personally in terms of raising a child. But our schools are set up in a way that it's like you do this and then you do this and you graduate and. And it's very focused on milestones and test taking and all of these sort of quantifiable things that it's like you pass or you don't pass. And I think there's good reason for that. I'm not an educator, so I can't necessarily speak to that. But I do think one of the costs of that, and maybe the hidden costs that I think is worth thinking through is this becomes ingrained in us, this sort of linear, performative, milestone based way of thinking where there isn't a lot of choice and we don't have a lot of opportunity to again sit in that uncertainty. And of course there's developmentally appropriate levels of uncertainty to experience, but I think that's where that comes from. From a few different angles.
- [28:19]
B
It's laying out a very interesting landscape. And it relates to some. At least three episodes from past shows. One of them was William Hurst came on the show, he's a political scientist and he talked about how governments strive to make the population legible to them. And in their desire to make it legible, they simplify it. And when they develop simple mental models of how it works, and when those simple mental models don't fit reality, they force people into the model. And so introducing the idea of legibility, which is if you're running something and it extends into the schools, which is that a school wants to have tests because we're trying to understand if we're trying to make this incredibly complex thing of education legible, to see if we're making progress. But then the tests themselves oversimplify the world and miss a bunch, but it, it forms the scaffolding for directional living. We also had Margaret Heffernan on recently who spoke about how the artistic mind deals with uncertainty. And it's not by grasping for certainty and legibility, it's like experiencing that illegibility. So anyway, it really ties a lot of things together, what you're saying, and how does one begin to recover? And so I spent the first 10 years of my career in the literary arts. And one of the things that I've always said is really great about a creative writing degree is that it teaches you how to start from a blank page. So I have nothing in front of me. How do I move forward in that situation? And my answer to that was my parents were scientists. And so I grew up in a very logical world and in a very data driven world. And so the big breakthrough for me as a writer was realizing that I needed to rely on the bedrock of opinion. And that whole sentence didn't make any sense when I was growing up. The idea that opinion could be a bedrock, that that's the more fundamental thing than data, than all these other things. And so a lot of what you describe in your book is how to start establishing an understanding of that terrain. So how does somebody even start down the path toward identifying a direction?
- [30:57]
A
I want to touch on something you said a second ago, and then I'll come back to the how do you even start questioning? I think what you're touching on with Margaret Heffernan and creativity is so important and fundamental to this conversation because building a life is a creative act. There are many synergies with writing or any other creativity. Like, what is creativity? It is building something from scratch, building something that has never been made before. And that creativity, innovation, entrepreneurship, even whatever kind of creativity you're talking about, cannot exist in the destinational world when we're focused on outcomes. And speaking of writing, one of the best explanations I've come across for directional living is From a writer, E.L. doctorow, the novelist, and he was talking about writing a novel. But I think it applies here, and I think it very much applies to building a life and a career. It's like driving a car at night. You can only see as far as the headlights in front of you, but you can make the whole trip that way. And that is something that I come back to over and over again, and I think is a great analogy for this. And so I listened to your Margaret Heffernan episode, and she was talking about how it was a surprise to her to find out that many novelists don't actually know the whole plot of the book before they start writing it. And it's the same point here. Not only do you not know, but you can't know. And you can have a hypothesis. There's sort of the scientific method for life is another way I talk about it. You can have a hypothesis of where you're going. I think I might want to be a novelist or a writer, or I think I might want to be the CEO of a company, or I think this might be the plot of my novel. I think I might want to start a podcast. But you then have to test that hypothesis through mini experiments. Basically, where the goal in the scientific method is not to prove yourself right, it's not to get to that destination that you set out. That is simply the thing that provides the structure to allow you to, like, move forward without overwhelm. And so talking about the sort of hidden costs of destination living, like, for an individual, it's fulfillment, right? And it can be extremely painful to live in that world as it was for me, this existential suffering, truly, to live that out of alignment with yourself. But the other costs, individually and collectively, are creativity, innovation, authenticity. And we're missing so much of that, because that can't come when we're on these preset, predetermined destinational paths.
- [33:45]
B
Hey, everybody. Work for Humans has launched an invite only community. And if you're listening to this right now, you are invited. It's a place where listeners can meet each other and guests, discuss episodes, suggest new guests share tips, and just generally find kinship with other people who are building better businesses by building better work. Come join us. Help us kindle the conversation. Go to elevenfold.com community that's eleven fold.com community. Thanks for being a listener and I very much look forward to sharing ideas with you there. Reading the book, there was one thing I constantly hesitated around, which is the idea of fulfillment. And a part of the reason why I hesitated is it sounds like another destination to me. Like, I need a big purpose. I need something that fulfills me, and if I don't have it, I'm a failure. There's this risk there. And so it crosses my mind that lowering expectations might be very healthy.
- [34:59]
A
Yes, I agree. It's a subtlety that you're talking about where I don't say, like, Find your purpose. Right? Cause I think that has become very destinational, where we think it's this one thing that we have to find and then we know it for our whole life and then we have to live into it. And that's not the vibe here. Right? Lowering the stakes into tiny experiments and launching and iterating is absolutely how we go about this. And I'll speak to. How do you even start? But again, I think there's a difference between this is my hypothesis, this is my best guess of where I'm heading, and this is the thing that I must achieve or it's a failure, and fulfillment and purpose. They're verbs, they're processes, they're not fixed things. So it's not something that you can lose or have. Fulfillment to me is alignment. And that can mean living in all of the messiness of your fullest humanity. Right? It doesn't mean perfect, squeaky clean, like nothing is bothering me. Fulfillment to me comes from a sense of being who you truly are and living fully in your life and inhabiting your life and having a life that is yours in all its messiness, in all the confusion. It's not like a squeaky clean, perfectionist piece of this. So how do we begin? There are three core shifts that we really need to make in order to shift from destinational living to directional living. The first one is switching from external approval to inner alignment. So this is all the things that we were talking about with the sense of warmer, colder, not being driven by the shoulds or optics or outcomes, like all of these things that would be external drivers. We really want to be insourcing our decision making as opposed to outsourcing it. So that's the first crucial shift because fulfillment, and I'm used that word as a bucket word, but fulfillment is not one size fits all. It's not like you can say this is what will be fulfilling for everyone. There's only what will be fulfilling for you. Right now. It's bespoke. It's unique to you and no one else. And so the only way that you can find that, the only way that you can live into that is, is by insourcing your trajectory, by insourcing your decision making.
- [37:23]
B
It's such a practice. In other words, you had insourced very few decisions leading up to the challenges at work. And I don't even know how to talk about that thing because you have to gain access to it. And a lot of the way you describe gaining access to it is just trying things and see how they feel. That's what you mean. Describe warm or colder. Because even that needs a description, I think.
- [37:52]
A
Yes, no, no, no, 100%. This was exactly the question that I found myself asking myself and then realizing how many other people struggled with it too. Because people would say things to me like trust your gut or what's your intuition? And I had no idea what the hell they were talking about. And I was like, if I knew what that was, I would be doing it. Why do you keep telling me this and what is this thing? And the way that I started to understand it was that it's simply playing a game of warmer, colder. You don't have to know the ultimate right answer or the thing that you're going to do forever and you're not trying to find the best thing. It's relative and it's just warmer or colder and then it's calibrating your sort of inner navigation system accordingly and then it does become a practice. So the way that I suggest people stay start is to think of a decision that you've made that you know is or was really aligned for you or some situation in your life. For some people this will be their partner or their spouse or having children or it could be a job that you were like, this was at that time the best thing for me. Or maybe it was choosing the school you went to. Whatever it is, I feel like most people, they have some touch point that you're like, this was right, this was very me, quote unquote, whatever that means to you, this was aligned. If you can't think of something like that, it can be just somebody who you feel like has your best interest, you trust completely, you love and adore and knows, loves and adore you. Or this could be a pet. But the point is you then want to try that on in your mind's eye and feel into your body, not your brain, right? This is not rational, intelligent decision making. This is feeling into your body what that feels like when you try that on in your mind. So for me, the analogy here is coaching, right? Leaving Google and becoming a coach. When I think about coaching, I feel the shorthand I use for it is light and right, but I feel relaxed, I feel calm, I feel freedom, I feel expansive, my shoulders drop, it feels warmer and it's something I want to move towards. It compels me. On the flip side, we want to think of what is a colder example. For me this is Google, right? Working at Google, think about how that feels in your body. So similarly think of a decision, you know, in Hindsight was not a good one for you. So a classic one would be an X. It could be a job, it could be a place you lived, or, you know, it could be a small decision that you made, an outfit that you now know looked terrible on you or something like that, or you actually really didn't like from there. You want to feel how that feels. So when I think about if somebody came to me and said, you have to go back to work at Google, I feel extremely stressed out and anxious. I start speaking quickly, like my stomach hurts. I just feel stressed out. And I call this hard and heavy. It is a sense of contraction, right? It feels like stuckness. So hard and heavy or colder. So I suggest everyone really tries on those two things. And then you have the sort of axis of warmer and colder of Google or coaching and Google for me and toggle back and forth in your mind between those two things to like feel the contrast. And that is sort of the most basic and place to start. And I come back to this when I feel stuck. And again, it's not, does this feel like the most extraordinary experience of my life or does this feel like the worst, most torturous, traumatic thing that happened to me? It's does this feel more like coaching or more like Google and using that as the basis for your decision making? And I suggest that people experiment with it in small stakes decisions to start. So things like the Kleenex box, right, Go into a store and try to figure out what designs feel warmer or colder, what outfit you're gonna wear today, what you're gonna eat. Like, are you actually eating what you wanna eat for dinner? Are you eating what you think you should? What podcast or book or TV show? Just try using this. And the thing is, is that the mechanism, this tool works as effectively deciding what to wear for the day and deciding what job to accept or if you should move across the country. It works equally well for smaller and bigger decisions once you have used this muscle. So again, it's like anything, like going to the gym, you really have to practice it. And that is where I begin with this sort of warmer, colder analogy. But I think it takes the preciousness out of it or like the sort of grandiosity that can sometimes feel like, oh, my intuition, what does that sound like? Or it just brings it down to like a more practical, grounded place that feels more accessible to most people, I've found.
- [42:34]
B
I like that a lot. I like a couple of different things about it, which is that first of all, your descriptions of it are not logical. Hard, heavy or light, Easy. I've borrowed the language of Christopher Alexander, which is, does something make you feel whole and alive, or does it make you dull and dead? And it's interesting because dull and dead doesn't have to be existential crisis, but it can last forever. And so you may not get pushed out of dull and dead the same way you would from hard and heavy. And I also liked how you framed it as you can imagine past decisions, but for future decisions, try it out, test it. Because the truth is imaginary things we don't know until you try it.
- [43:24]
A
That's the whole point of why destinational living actually doesn't work and doesn't serve us, because we're guessing we're committing to something in advance that we don't even know that we want. And then we're sort of dedicating our lives, or at least some portion of our resources and our energy, to something that we don't even know that we want when there is a way to feel into it. And you touched on one of the other shifts that we need to make, which is moving from fixed plans to iterative experiments. And that's how we shift also from this five year plan, ten year plan, to how do I get more information about this? So if someone came to me and said, you know, I think I might want to start a podcast, I would say, great. That doesn't mean you need to, like, quit your job, buy all the equipment, and invest in somebody to do your branding and all this stuff. It's like, go have one conversation, talk to someone who's been on a podcast, or, like, read a book or watch a YouTube video on, like, how someone got started and see how that feels. Right? Give yourself some information to respond to, because you may discover after a few minutes of watching a video of somebody talking about how they got started in podcasting, that you're like, actually, this does not sound interesting to me at all. And then you've saved yourself a whole lot of time and energy, but it was still valuable because it may steer you in a different direction. I think whenever there's curiosity there, there's some piece of information in it. It might just not be what you thought. So maybe you discover, oh, you know what, it's not podcasting. It's actually, maybe I want to have my own, like, YouTube series or something, you know, and you discover, I don't want to do the interviewing, It's, I want to have like a sitcom. There's this iterative approach, and this goes back to what you said earlier of taking the pressure off, because anytime there's pressure around something, we are going to freeze, we're going to clam up. And that's not the place that we make our truest, most authentic, expansive decisions from. It's not where creativity comes. And so the lower the stakes you can make it, the better it is for me with coaching, even though I didn't have this language at the time, it was like, all right, I'll go take a intro to coaching class. And I did that. And then I didn't go back for like three months. That was also because I thought it was so fun that it occurred to me that it could not possibly be a way to make a living because work couldn't feel that good. But it was a step. And then I went back, you know, three, three months later, six months later, I can't remember how long it was, but I went back to the next section of the course and was like, okay, I'll try to coach one client and see how it is. And at no point did I commit in advance to spending the rest of my life coaching. And this works on all, again, all sorts of scales. So the way I talk about it is your job is only to move the plot forward any amount. So take an action, any action. It doesn't matter what it is. Just anything you can think of to get a little more information is going to move you forward.
- [46:21]
B
Two things popped for me there. One is the number of times as a manager I have been asked by someone on my team, what do I need to do to get to that destination over there, to that promotion to that? And really in my heart the answer was it's unknown, honestly. And so it's this idea that managers are often put into a position to predict an impossibly predictable future. And one of the things that I recommend, managers asking is what's the in the moment experience of work that you want to have? And what is the work right around us that is in that direction, that has that texture? I say that the in the moment texture of the work. And frequently that steers people away from those destinations because they say, I like to solve little Rubik's Cube math problems. And you say, well, do you think directing would actually satisfy that need for you? And they say, no, actually, I don't think being a director. So that's one thing is that. In other words, I can imagine that this is going to be a real challenge in the co design of work. And I know it is because I've experienced it, which is that you want to co design work. And there's two responses to that. One is I don't know what I want in the moment. The second is I know what I do want is to get over there. And the third thing is I think you have the knowledge about how to get me over there. In other words, I'm waiting for your approval for me to get over there. So anyway, it's this, this is a super important skill in that co creation.
- [48:06]
A
It's a chicken or an egg problem, right. Because if both of you are ingrained in the destinational thinking, right, you're sort of like co conspiring in continuing that. And it's hard. It is definitely hard for an employee, for example, if they were living directionally, to come into a destinational system and try to operate that way, right. It won't necessarily make sense to, to their managers or to their peers. But I do think, and I have found that if someone, and it's exactly what you're talking about, like what's the in the moment experience that you want? And focus on that. And I can't guarantee it, but typically you don't care as much about the promotion one because you are enjoying and fulfilled by your work. And then counterintuitively you tend to be have more impact, make more contribution because you're more engaged in your work and you're doing the things that you're uniquely well suited to do, that you end up getting the promotion and doing it in a way that actually felt good to you. Maybe it takes a little longer, you know, I don't know. But it usually tends to be a win win. But I think if someone is committed to the destination, it's tough. Yeah. Certainly as a manager who would want to co create to say, I don't know, but I think if I were in that situation, obviously committed to directional living, I would be like, let's try and experiment, you know. And again, I think using that language of experiment, like let's try and experiment this quarter and I want you to focus on what you are experiencing in each part. You know, I sometimes talk about a calendar audit, right. And I don't necessarily do this in the context of like talking to your manager, but look at everything that you do at work and try them on in this warmer, colder way and find out what feels warmer and what feels colder and colder things. Do whatever you can to get rid of them, right? And sometimes it's easy things. And again, that's not to say that your whole career is going to be made of this. But I think you had an example of this in your article where it was like somebody, the colder thing could be that this meeting was in a time zone such that I was missing my kids breakfast every day. Right? I have people who are like, I hate this freaking 8am Monday morning meeting or I hate having 8am meetings every day. If everything was moved down 2 hours, I would be so much happier and more productive. And so sometimes it is things like that that you can have a conversation with. But I think looking through your calendar and trying to get clear on what you do enjoy and what you'd like to lean into and what you wouldn't. And as a manager I think I would suggest I would like try that experiment and see what I'm able to get more from my team and how I'm able to sort of reorganize around that. And so I think it can be led by the manager.
- [50:47]
B
And at Google we had bungees, which were two month rotations. You could bungee into another organization and you could just try it out and then theoretically you could bungee back into your original role. It didn't always work that way because sometimes, you know, you bungee too long and your role gets filled somehow. But this was something that I did with my team members and oftentimes they'd bungee off into that other organization and they'd come back sort of wide eyed and just crisped. Like whatever was over there was really bad. Like a sample, like they went over, they came back, they said no, no, no, not that it wasn't a completely risk free way to do it, but it is an example of how you can operationalize experimenting.
- [51:33]
A
You know, I often suggest, and obviously this isn't possible in every situation and harder big companies, but especially for people who I know who are thinking, who are either doing like fractional thinking about going to a smaller startup is to do trial periods, you know, especially if you're going to be on a really small team, like do you guys collaborate well? Do you get along? Does this feel like the right thing? And that tends to benefit everyone because they, the company isn't committing in advance to something that might not work and you aren't committing to something that might not work. And so you both get to sort of collaboratively figure out is this a good fit. You know, it's sort of like an extended interview type of thing. And I really wish there was a way to do that more easily and frequently. But again, that also introduces uncertainty. And so a lot of people don't want to Try, you know, they don't want to try a job for a little while because then they might end up having to, like, job hunt again. Or they're worried that, you know, the company will say, no, actually, we don't want to hire you. Like, people want that security. But I do think we'd all benefit from that.
- [52:35]
B
What do you think about hedging your bets? And so I had Matt Higgins on the show, who wrote the book Burn the Boats. And his thing was, I can't be successful at things if I don't give them 110%. That means 110% of my finances, 110% of my time. And in order for me to do that, I have to make going back impossible. My first line when in that interview was, I read the title of the book and I was like, don't burn the boats. That sounds terrible. But he ended up convincing me that in some cases that was true. So are there any techniques for testing possible futures without burning the boats?
- [53:18]
A
I'm not sure, given how stubborn I am and how sort of, I don't know, lost or deep I was in destination living, if there was a way for me to make this shift without quitting with no plan.
- [53:32]
B
Classic example of burning the boats. Actually, you absolutely did it.
- [53:36]
A
Yes. And I think it was really important that I did that. However plausibly I could have taken a year, gotten myself together, gone back and, like, I don't know, interviewed a big tech again or done something else, like, and that was an important thing to be able to tell myself I wasn't like, I'm free because I'm never gonna go back there. It was like, tech is always gonna be there. And certainly that wasn't on, like, day one, but, like, after a few months, helping me myself to be able to explore coaching and remind myself, tech is going to be there. Yes. Maybe I'll be, like, set back a couple of years from where I was on my trajectory or whatever it is, but it's going to be there. I still have valuable experience to offer in that world if I need it. So I do think in some cases, I'm sure there are some cases that that's necessary and even helpful. And part of why I want to do this work is that people don't have to sort of, like, hit rock bottom. They don't have to burn the boats in the same way that I had to, that they can do it in a more sane, slower way that you don't have to, like, burn it all down every few months, because that's risky and it can also cause harm. Again, I haven't listened to that particular episode, but I'm thinking of burning it all down often means losing relationships and like doing, you know, so there's costs to that too. Right. And maybe you need to do it anyway. Right. I'm not saying never, but I guess I wouldn't suggest that you want to do that like many times over in your life, every time you need to make a decision.
- [55:00]
B
I always hold up Gauguin in my mind. He left his wife and daughter and went to Tahiti or the Marquesas Islands to paint and he abandoned them. And I often think, well, there's somebody who managed to get away from the shoulds. And I also think, what a dick. There must be some hard decisions about what one does for oneself and what one does for one's family.
- [55:26]
A
Yes. So one thing I think about with alignment, right? So making these decisions, making your aligned decision is I don't think that alignment exists in a vacuum. So I believe that if you're making aligned decisions for you, it's what's best for everyone around you. So I don't know. Because you can't tell from the outside. Like you can't diagnose if somebody is making an aligned decision for them, if they're making an authentic true self decision or if it's a should. Right. I don't know if I don't know. In some world, Gauguin thought that that was like the preferable thing to do or something like that. Like maybe he thought that was the should. I don't know. But let's assume if that was aligned for him to do that, that was best. There's a case to be made. Again, I don't know all the details, but that that was actually best for his wife and daughter to have a life without him. You could argue that you leaving your job because it's not aligned for you anymore is like selfish. A lot of people come to me and say, I feel selfish to leave my team, to abandon my team. And they're, you know, all the. What they're going to have to go through in the change. I'm like, I think of it as donating your job, what is good for you, leaving. If this is truly not aligned for you, it is better for you to leave and donate that job to someone who, like that is exactly what they're meant to do. And for your team members to benefit from having someone in that role who really wants to be doing that role and is fully engaged and wants to be doing that, like, it's not necessarily a bad thing for them. Same thing with, like breaking up with someone. You know, it's sort of like, oh, it's so selfish of me to leave this relationship. You know, I hear people say that all the time and it's like, if it is not aligned for you to be in this relationship, if you don't want to be in that relationship, it is not good for the other person for you to stay in it in the short term, that might feel easier or better, but they deserve to be in a relationship with someone who wants to be in a relationship with them. Right. So my experience has been that what is aligned for you has a more full, holistic picture. It's not always like the most money or like the most success at the expense of everything else. Unless that's what's truly aligned for you. I do think that there can be a balance. This was like a big question for me in terms of a book tour. I had an infant and it was like, do I want to take her with me? Like, that seems really hard. Do I want to travel without her at that age? Like, all of these questions in another period it would have been and like, what is aligned for me is to go on a book tour. And when I really sat with it, I realized that like what felt the line for me was to do more of like a virtual tour. Right. Like a lot of podcasts and that sort of thing and like maybe some local events and not to like spend the time that I could have been with her in those early years planning and spending my own money, planning like a book party in LA or whatever it is. Right. That did not feel aligned for me. So there's a trade off there, right? Certainly. I'm sure you could argue there were missed opportunities, all of those sorts of things. And yet I was clear that that was the aligned right decision for me and my family. And not in a way that I feel like resentful of my daughter. And I don't think that's the right thing that everyone should do at all. I know many people who've made different decisions that felt aligned for them. But I do think it factors like when you can really hold the complexities and the contradictions and the fullness of yourself. Like, it's not just a one thing. It isn't just about like the most visibility or the most time with my child. There's certainly like a balance and there are trade offs and I still find that, you know, there may be a grief involved, like that kind of sucks that I didn't have a book tour. Right. Part of me is like, I'd like to experience that. So I had to like grieve that. And there was freedom still. It felt free and expansive for me to like make that choice. And if I'm meant to have a book tour, I will have it at another time with another book, if there is one. And so that's an example of it doesn't always feel easy. And yet I felt completely clear I wasn't confused about it when I really sat with it, even though there was a major trade off in the decision.
- [59:32]
B
That's one of the things we say about the research we've done about what people want from work. And it's that when you actually ask people all the things that they want out of work, many of the things that they want are essentially mutually exclusive. There are some features on some products. When we talk about work as a product where the features are antagonistic, you can't get them in the same product. You know, you can't get a four season tent that can handle a blizzard and weighs one pound. Those two feature sets don't exist together. And so I think that the way that you navigated that was you felt in your heart. Here are these two potential products that I could subscribe to. And one of them feels worse to me. Warmer. Colder. And I'm sure that there were books who said you should do a book tour and you were like, dad, I'm not going to listen to that. Should.
- [60:26]
A
Yep.
- [60:27]
B
So I ask a few questions at the end of every show and one of them is, what do you, Megan, hire your work to do for you?
- [60:35]
A
I think I'd be remiss if I didn't say fulfillment.
- [60:39]
B
Fulfillment. Yeah. And I'll know it when I feel it. Right. I can't tell you what your fulfillment is. I know it when I see it.
- [60:47]
A
Yeah. And it's not like I package my work and I go coach people and say, do what I did. Right. It's not have my life. I don't expect anyone else to want my life. And that's why it's, you know, that's why now it's fulfilling and aligned for me. And I don't even expect myself to want the life that I have currently in five years. And I didn't want the life I have now exactly as it is five years ago. It has evolved. So I think for me it is fulfillment. And for me that means to use the words you used earlier, whole and alive. It's wholeness. There's like a self expression. It's a sense of being who I fully am. It's such a joy. And I mean that's the other. It's joy and delight. It reminds my work, reminds me of who I am. Postpartum is a good example or times when I like have felt, I don't know, struggling with other things or off like coming back to my work. Not as an escape in the way that it used to, where I'm like making myself so busy that I'm not paying attention to something. It reorients me now I can almost feel, always find. It gives me energy, it gives me life. It's life giving for me. I don't think all work for everyone has to be that. And not all elements of my work are like that at all times. But to me it's like an opportunity to live my fullest life and be as like on purpose and in my integrity and whole as I can. It's offered me a richer experience of my life and the world and humanity. Frankly.
- [62:22]
B
What is different about that answer than many of the answers we've gotten is that it's expressed as feeling as opposed to features or surfaces that I like to interact with. And what's interesting about it is that anybody could pick that up and say, I'm going to use my sense of self to navigate my way in the world. I'll know when I'm there. And the path to there is curiosity and experimentation. And so there's a method. We're going to test things. We're going to hill climb. Maybe hill climb's not the right word. I like warmer, colder. Hill climb sounds like achievement. This is not a hill climbing, you know, but so what does your work cost you?
- [63:07]
A
You know, I guess what it would cost feels has a negative connotation and I'm not sure that it has one. I invest, I invest. I guess it costs me time, it costs me energy. And these are all things that I like. Eyes wide open. Willingly invest in this. I mean, you could say, for example, like it cost me time with my daughter, right? But I feel like I'm able to have all of the time with my daughter that feels like aligned for us and for our family. Like I don't. Doesn't feel like a big deal. I spent a lot of time like iterating on it, I think especially the book process, I guess I would say. And again, this, I. I don't know if I'm just like Pollyanna Ish over here, but it's it still feels like a positive thing, but, you know, there's some, like, wound activation, like, healing stuff, sort of, you know, especially with book coming out, invisibility and vulnerability and all of those sorts of things. Like, there's sort of inner struggles that I'm confronted with as a result of my work. And so it costs me my. I guess you could say cost me my peace. And I think ultimately I want my work to do that, just like I want my relationships to do that. And I think ultimately it's peace giving because the more I heal those things, the more peaceful my life will be as a whole. So I didn't really answer your question.
- [64:38]
B
You did. You absolutely did. You totally did. I'll reflect back on what I heard. You have the opportunity to design your own life because you're a founder. You made a choice, for instance, not to go on a book tour, which if you had done that, you would have said, it cost me time with my daughter. And so because you were able to have enough flexibility to design your work, you didn't say that. And it's also true that you used a very specific word, which is investment. And when people are subscribing, I'm going to use some jargon here from the experience, design, world transformation design. When you are subscribing to a transformation offering, the measure of the quality of that offering is you say it is time well invested. And so you're making investments. This is a price, it's a cost. But you recognize that it's not just throwing it into the ocean. It's something that you're tilling to grow the next garden. So it made perfect sense to me. It made perfect sense. I didn't think you dodged it at all.
- [65:47]
A
Genuinely wasn't trying to dodge it. I was just like, wow. I really, truly my truest. I was like, maybe there's gotta be something here. My truest answer is this doesn't feel. I mean, I guess technically it's a cost, but this does. I don't feel. I don't feel that. I don't experience it that way anymore.
- [66:05]
B
Yep.
- [66:06]
A
And I will also say I, like, very consciously design my work, like, down to, like, the schedules when I have meetings, when I schedule what? And I change it up as things change, when they don't feel right. I'm like, this is not working anymore. Like, my daughter's not sleeping through the night. We no longer have morning meetings. Right. Like, I want to be able to show up as my best self. So that's a lot more flexibility than A lot of people have, but I really do iterate a lot on the life design part.
- [66:31]
B
Well, and it's a great example, which is that a part of creating an organization that can, on an ongoing basis, design work is to create the flexibility to respond to design signals. And so you have that. And in fact a lot of founders say that a lot of founders have come on the show and felt that way. So this is exactly the conversation I wanted to have.
- [66:57]
A
Oh, I'm so glad.
- [66:58]
B
Which is what are the muscles? I want to say the muscles of directional living, but sometimes they're the opposite of tensing up. So I don't want to say muscles but like what are the capabilities of directional living? Because that's fundamental to the kind of iterative design that is going to make great work. So it's really wonderful conversation. Where can people learn more about you and where can people learn more about your book?
- [67:26]
A
My website is my name meganhellerer.com and on Instagram eaganhellerer, which is H E
- [67:33]
B
L L E R E R. Yes, double E R. Yeah, but in double L. Well, great. Thank you very much for taking the time to talk to me.
- [67:44]
A
Thank you so much. Dart,
- [67:47]
B
thanks for joining me for another episode of Work for Humans. If you enjoyed this episode, please give us a five star rating. Wherever you listen to podcasts and share the show with one person you think would get value from it, believe it or not, this really helps us grow the show and reach more people who want to build the kind of work that be people really want. As always, thank you to my producer Jason Ames at 9th Path Audio for his insights into content and his high standard for quality. Final note, the opinions shared here are my own and not the views of Google or Cisco Systems. Thanks again for listening. See you next time.