Directional Living for Aligned Fulfillment
Episode 510 | Host: Emilie Aries | Guest: Megan Hellerer
What would happen if you stopped driving toward a career destination and focused instead on figuring out the best direction for you?
Most of us are seeking a fulfilling career and life. Some of us have managed to cultivate these very circumstances, but for most of us, these elusive signs of “success” are hard to come by.
Today’s guest spent a long time as a self-proclaimed “underfulfilled overachiever”, and this led her to forge a unique path, eventually becoming a coach for others like her and writing Directional Living: A Transformational Guide to Fulfillment in Work and Life, which came out last fall. I was so pleased to sit down with Megan Hellerer to talk about the difference between destinational and directional living and why there’s a better way to find joy than pursuing your “purpose,” whatever that is!
The American Dream has changed
For decades, American adolescents have been told that if we just make the right moves—work hard, get a degree, find a job—we’ll be happy. A well-paying position with an upward trajectory is the best (or only) way to gain stability and success in life.
It’s only recently that the fading American dream has become more glaring and thus more widely discussed. In particular, we millennials who checked all the boxes are still finding ourselves on the fast track to burnout, unfulfilled and spinning our wheels. Some of the reasons for this fallout are fairly clear: back when the American Dream was popular, we didn’t have the technology to work 24/7, we weren’t inescapably bombarded by communications, and most of us could afford to buy a house after a few years’ hard work. Today, the landscape has changed.
Why success ≠ fulfillment
Megan highlights one big problem with the American Dream: the assumption that we will discover fulfillment by finding success. Too often, success is defined objectively. It’s prestige, income, the things that supposedly stem from choosing the “right” degree and the “right” career trajectory. From her research and experience, though, Megan knows that’s way too specific. “Successful career choices” don’t fit into a box. Your successful job is the one that aligns with you.
Seek a direction instead of a destination
In Directional Living, Megan urges us to stop setting our sights on a destination and start focusing instead on a direction. She describes it as a sailor and a lighthouse. The sailor isn’t headed to the lighthouse—it’s a beacon showing them the general position of the shore. You might also think of it as following your own warmer vs. colder compass. You make the choices that move you in the direction of what feels aligned.
When we live destinationally, we select a place we want to end up and then reverse engineer a roadmap and follow it to a T (or become distraught if we fail to do so). Unfortunately, too often, the destination we choose is based on what our parents want for us, or what the TV shows we watch celebrate, or what the books we read tell us we should do.
Too often, it becomes distressingly clear that we don’t actually want that destination, but we’ve spent so long ignoring the direction we want that we don’t know how to do anything but head blindly to the pin on the map. As a result, we just speed toward the potentially unfulfilling destination. Megan encourages us to instead seek out the “warmer” decisions we actually want—the ones that take us in the right direction.
The practical side of seeking alignment
Megan endorses learning how to listen to your inner thermostat and getting into the practice of making those decisions, even small ones like what to have for dinner, that keep you trending in the right direction. I love this, but I was also curious about the practical realities of directional living. For instance, I have a friend who decided to make a big career change to launch a product he knew he was passionate about. A year later, the new business was floundering, and he ultimately had to make another decision: to return to a corporate job in order to support his family, or risk losing his family entirely. This is a pretty familiar trajectory, so how does it fit into Megan’s philosophy?
Megan’s response is comfortingly straightforward: in my friend’s case, it sounds like he was following directional living both when he left his job to pursue that passion (the aligned choice for him at the time) and when he returned to an employed position (also the aligned choice for him at the time). Directional living doesn’t mean abandoning all hope of making good money or supporting your family. If those are important components in your life, they will be factored into your directional decision-making—the choice won’t feel “warmer” unless it supports those requirements, too. Ultimately, finding the path that combines all your needs is what will bring you fulfillment.
So, how are you already acting on or planning to incorporate directional living? Have you taken a different route or wholeheartedly embraced the path over the destination? I’d love to hear your thoughts on Megan’s book and process, so hop over to our Courage Community on Facebook or join us in our group on LinkedIn to weigh in!
Related links from today’s episode:
Buy “Directional Living: A Transformational Guide to Fulfillment in Work and Life” by Megan Hellerer
Learn more about Megan’s coaching
Connect with Megan on Instagram
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[INTRO MUSIC IN]
EMILIE: Hey and welcome to the Bossed Up podcast, episode 510. I'm your host, Emilie Aries, the Founder and CEO of Bossed Up. And today we are talking all about clarifying your career's direction.
[INTRO MUSIC ENDS]
Particularly for those who might identify as underfulfilled overachievers. That's who today's guest, Megan Hellerer has written an entire book for her new book, Directional Living: A Transformational Guide to Fulfillment in Work and Life. Just dropped this past fall and is all about her unique framework that comes from her innovative premise that a fulfilling, purpose filled career in life are built by cultivating your inner sense of direction, not pursuing a fixed destination.
To give you a little background on Megan, she graduated top of her class from Stanford, worked at Google as an executive for eight years, had a wonderful boyfriend, perfect apartment, and amazing wardrobe. It was all literally perfect on paper. But despite all this, she was deeply unhappy and felt like a fraud. She quit her job without a plan and eventually founded the company Unfulfilled Overachievers, where she spent the last decade learning, training and coaching. She helps folks who feel like they've done everything right for their careers. So you picked a career destination, got the grades, made the five year plan, checked all the boxes, worked really hard, climbed the ladder, and now you're miserable. Every career milestone has just made you feel emptier. You finally arrived at your destination only to find that you're stuck, burnt out, and wondering what the heck am I doing with my life? If that sounds like you, today's guest is here to break things down and get you back on track and heading in the right direction once again. Megan, welcome to the Bossed Up podcast.
MEGAN: I'm so happy to be here. Thank you for having me.
EMILIE: My pleasure. It seems like we've got a lot in common and so do our listeners here. So for all of my fellow millennials who've gone through a quarter life, or at this point, a midlife crisis, let's be real. I feel like your book Directional Living really speaks directly to what getting Bossed Up is all about. So first, take us back to the beginning, what inspired you to write this book?
MEGAN: Yeah, I wrote this book to be what I needed and couldn't find when I needed it most. I was the OG, what I call, underfulfilled overachiever. So someone who checked all the boxes, did all of the right things, climbed the ladder, achieved everything I had set out to do, and still found myself really unfulfilled, unhappy, and in my case, depressed and having almost daily panic attacks. And for me, that looked like, you know, going to Stanford the day after I graduated, starting at Google, working there for eight years and again climbing the ladder, doing all the things, getting the promotions and, you know, the awards and whatever, but was, you know, secretly really unhappy and was so ashamed of that, that I couldn't, you know, I was so competent in so many other areas of my life and I couldn't figure out what I wanted to do with my life. And how could I be so privileged and have such an amazing job, you know, this dream job, the best company to work for and be so unhappy. And I really thought something was wrong with me.
And eventually this led to me quitting my job with no plan, basically because I didn't feel like I had any other choice. It was really killing me and my mental health and eventually my actual physical health really was suffering. And when I quit my job with no plan, my only objective was to figure out how to do this whole career thing basically without wanting to die, but at least without hating my life. With this hypothesis that maybe there actually is work that could be fulfilling. What would that, you know, is that like an urban myth or what, you know, what could that actually look like?
And in that process, I started, you know, looking around for help and I went to therapy and I went to meditation retreats and, you know, this was back in 2013, 2014, coaching wasn't quite as big of a thing as it is now. And it really felt like nobody was speaking to this specific problem. You know, there were coaches who were super WOO, which I love, but was not what I needed in that moment. Like I really needed like spreadsheets and get s*** done. I had no income, I needed to get employed. And therapy, which was also wonderful, but, you know, is a longer, deeper process and not really the actionable insights that I needed, or executive coaching, which was really about like climbing the ladder faster or how to be more successful in the positions you were in, which also wasn't what I wanted to do. I couldn't find a place that had, you know, sort of a blueprint for how to figure out, what the f*** I want to do with my life.
And so I started kind of putting together my own DIY program of, you know, listening and reading and talking to people and running experiments essentially on myself, just trying to figure this whole thing out. The more I started sharing my story with people, I realized just how many of us there were and that this was really more of an epidemic than an isolated me, you know, data set of N plus one situation. And so I started to, eventually I found myself taking a coaching class and this was simply in my broader exploration and effort to coach myself essentially. And I loved it. And I was like, this is it, this is the language, this is what I've been looking for.
And I promptly didn't go back for any more because I thought this is too much fun, this feels too good. This is not what work is. So this can't be a sustainable way to earn an income because work is not fun. Work is not supposed to be fulfilling or aligned, which is vocabulary I wouldn't have used at that time, but that's what it was, was the alignment. And eventually I, you know, not doing anything else, went back and finished my certification. And to be certified you had to do 100 hours of paid coaching. Now mind you, I had no intention of becoming a coach. I was skeptical of the whole thing. I really thought it was going to help me when I went back to managing teams and my corporate job, that was going to come as soon as I finished Eat, Pray, Loving and figured out how to like manage my stress better or do whatever I needed to do in order to go back into this world and more successfully.
And through that hundred hours of paid coaching. You know, I just sent an email to a few friends being like, anyone knows anyone who wants to be my guinea pig. And people responded and I coached them and I, my life changed, their lives changed. They started coming back for more and wanting more sessions and referring people. And before I'd even finished my certification, my coaching certification, I had basically a full roster of clients. And I realized that all of the people I was working with are what I've now come to call, underfulfilled overachievers. So people who were like me, in really similar positions. And it was clear to me that this population, we really needed solutions. And I tried to figure out, you know, I started thinking about, how did we get here? What caused this? And what is, is there a methodology or a program that we can embark upon that's sort of replicatable that we can all do and we can teach to prevent this from happening to all of us?
EMILIE: Yeah, I mean, being an underfulfilled overachiever seems so common these days, and yet I wonder if it is really just like a sliver of the population. You are talking to a specific kind of person who is underfulfilled and yet has been overachieving their whole life. What kind of person tends to find themselves in your chair, so to speak, and how do they get there?
MEGAN: So yes, I think underfulfilled overachievers are a certain part of the population, but they are a lot bigger than I think most of us realize, or at least most of us realize back in 2014. More and more people, I'm grateful, are talking about this, and they're more. You know, it's become more hustle, you know, the hustle culture. And all of those ideas have started to become more and more part of the conversation, and I'm so grateful for exposing that. But I think it is, we've gotten there by a few reasons.
The first one is, and I think it is particular to millennials in a few different ways, because we were sold this vision that if we did the right things and we checked the right boxes and we made the right decisions, then we would be happy. And I think in, you know, the 80s and 90s and, you know, early 2000s, when we were growing up, this message was plausible because there were things that you could do, or it seemed that there were things you could do that would offer some level of certainty and success and stability. Things weren't moving at the pace that they're moving right now, given the technical, you know, revolution that we're in. People weren't working 24/7, and so it was easier.
And industries weren't being, like, eliminated. You know, you could say before, oh, be a journalist, right? That was, like, a pretty safe thing you could do that would be respected and pretty much guaranteed. There would be some journalism jobs, and if you went to journalism school, then you could. But now journalism has completely changed, and, you know, not so many jobs exist, even engineering now. You know, that was the thing for a while, learn to code. That's the safe thing to do. And now AI comes along, and so many people who are in those roles are needing to either to reinvent themselves.
EMILIE: I do think there's an interesting distinction that you're calling attention to for me, which is, you know, this American Dream, like, you can be successful through, you know, following the rules, getting your education. That used to be a lot more sound. The premise of the American Dream equals stability and financial ability to, you know, to provide for your family on a single income, let's say, or to afford a home in your lifetime. Those things used to be more attainable. But fulfillment through your career feels really different, right? It's like, what do you actually mean by fulfillment? Because I think the millennials were sold this idea of our identities being wrapped up in our careers in a very explicit way, right?
MEGAN: Yeah. That success equals fulfillment. And I think that's the core lie of the underfulfilled overachiever is that if you're successful, you will be fulfilled, you will be happy, slash you will be fulfilled. And so we focused all on the success, right? If I can just be successful. And often that has to do with prestige or income or whatever those things are, but that was what we focused on. And the way we thought we would get success is by doing the right things, making the right decisions, having the right jobs, the right colleges, whatever those things are, right? So I think that is the central lie that success equals fulfillment.
And in fact, what I've learned through, you know, working with underfulfilled overachievers for the past 10 plus years and my own experience, what actually leads to fulfillment is alignment. So this doesn't mean don't be successful or don't be ambitious, but not all success is created equal. So one person could be a professor, and that would be considered by a lot of people to be successful, a tenured professor at a prestigious university. And for some people, that would be miserable and so unfulfilling. And for someone else, that would be extremely fulfilling. So what we're looking for is the alignment piece. And I think that is the thing that we have missed out on is that we have thought that success fits it neatly into a box. And so we've just sort of like. And you mentioned earlier, my book is called Directional Living, which is what I propose as the new paradigm for fulfillment and success that is success that is actually fulfilling.
EMILIE: Yeah, I think I read somewhere in your book, actually there's nowhere quite as lonely as the top of the wrong career ladder, right? This idea that success can look like success, but on whose terms? According to whose values, right? And so you could be striving your entire life, checking all the boxes, doing all the right things for your parents or for your entire race and gender, right? To become a boundary breaker, to pursue what you committed to in the first grade. You know what I mean? Like, what version of you and what values are you really aligning as you, as you say, with what direction you're headed in? And that's a, I think that ladder metaphor was a really breakthrough moment for me to say. Yeah, you know, you can be quote unquote successful, which, to be clear, is already hard enough in today's world, you know, economically. But even if you are quote unquote successful, you can still be miserable if it's not your definition of success. Is that what I'm hearing you say?
MEGAN: Yeah, I think when most people say they want to be successful, what they really mean is they want to feel successful. It's not that they want some objective version of success. They want to feel successful. And feeling successful is fulfillment. So what we're really looking for when we say we want to be successful is that we want to be fulfilled.
EMILIE: And that's different than checking the box. That's different than arriving at some kind of destination, as you talk about, right? So when you write directional living as opposed to destinational living, help us understand what that distinction is all about.
MEGAN: Yeah. And just to go back for one second, that was the moment that on the ladder, like the being at the top of the ladder and having it be this lonely moment. That was the thing, one of the things, the really culminating moment for me that made me realize I needed to leave. Obviously I wasn't like the CEO of Google, so I wasn't like the top of the ladder, but, you know, I was, what happened was that I got the promotion that I had been working my a** off for like six months, a year, however long, and, like, had been arguing for and advocating for, and I got this promotion and I felt nothing. And I thought that was the thing that it was. I was going to feel fulfilled when I get this, like, there was this certain level that was like, really hard to get to, and if I got to that level, then I was going to feel fulfilled and I was going to feel satisfied, and I felt nothing.
And so in that moment, I was like, who am I doing this for? And I didn't have an answer for that. It wasn't for me. I don't even know if it was for my, like, my parents didn't care what level I was of the corp, you know, it wasn't. I couldn't figure out who it was for. And that was, you know, it was still quite a while actually before I was able to actually leave. But that was a very defining moment for me as well, of recognizing that.
EMILIE: I think so many people can relate to that. I've, i've long called that merit badge chasing. When it feels like you're just collecting achievements and waiting for them to transform the way you feel about yourself and then nothing happens. Or that, that little high that you get is pretty fleeting, right? The world of psychology is very clear on those milestones don't necessarily lead to lasting happiness and fulfillment.
And so you propose an alternative vision as opposed to destinational achievement or destinational living. Your entire framework kind of flips that paradigm on its head. What do you mean by directional living? And how is it different than destinational?
MEGAN: Yeah, so let's start with the old way of doing things, which is the destinational living side of things. So I have noticed that in my research and my observations that underfulfilled overachievers, the thing we all have in common is that we've been living destinationally and this is how we've been taught to live, which is you pick a destination, you reverse engineer it to figure out exactly how you get to that destination, and you follow that to a T.
Now the problem with that is that the way we typically pick a destination is by what other people think we should do. What we've inherited, what we've seen around us, it doesn't usually have anything to do with what we actually want. And this is partially because we cannot predict the future. We need to be allowed to evolve, we need to be allowed to grow and change. Oftentimes what we want when we're 21 is not what we want when we're 40. And a lot of us have not let ourselves adjust the direction that we're going in because we're so set on, I will achieve what I set out to achieve. And we fixate on this destination. And the problem is that when we get to that destination, it doesn't usually feel like we thought it would when we get there. And we've now spent all this time getting to that destination to realize it's not actually what we wanted. And then we don't know what we actually want when we get there because we've spent so long suppressing and ignoring what it is that we actually want.
EMILIE: Yeah.
MEGAN: And so instead what we want to do is live directionally. And what this means is that instead of figuring out where we want to end up, we only figure out what direction we want to be heading in. And if we allow ourselves to focus on the direction. And is this directionally right? In this framework, we can constantly be launching and iterating and tweaking as we go, as we get more information about ourselves and about the world. And this allows us to respond and react to what is actually happening in the world and learning more about ourselves and allowing ourselves to grow and evolve as we go.
The other thing is that directional living has to be in sourced. When we're living directionally, we can't say, you know, it's not about what I should do or what someone else thinks I should do. We have to be asking what is directionally right for me right now. And this is like the biggest anti anxiety because you do not need to know where you're going. You only need to know the single next step. And the best way I know actually to articulate this is this quote from E.L. Doctorow that is in my book. But he's talking about writing a novel. But I believe it is really well suited to navigating a career or navigating life, which is. It's like driving in 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 really the crux of it. We only need to know where the headlights in front of us are showing us to go. We don't need to know where the end destination is.
EMILIE: So is it safe to assume then that you're anti what is your five year plan? [LAUGHTER] Right? It's shorter term that we're focusing on to head in the right direction. Is that what I'm hearing?
MEGAN: Yes, definitely. We need to get rid of our five year plan, our ten year plan, whatever it is. But that doesn't mean we don't have any sense of vision of where we're heading. We just don't want to get attached to it and the plan and getting there. It has to be something we hold loosely and I call it the big direction instead of your destination. So it's a lighthouse, right? Like if you have a lighthouse and you're navigating, you don't. Your plan is not to hit the lighthouse, it's to head in that direction. So it's useful as a beacon as long as we know that that is very movable and we can change our mind at any moment and we're not actually going to end up in that place. Its only purpose is to serve as a direction.
EMILIE: Yeah, I love that. And when you say insourced as opposed to outsourced, right? What does that process look like for someone who's having a total career crisis, who's arrived at midlife, right? Let's say as many of my listeners are. And it feels like all of our values have changed. Everything I want out of my career that I thought was true no longer feels aligned with where I'm at right now. And it feels like I don't want to throw the baby out with the bath water, but it feels like everything I've worked so hard for no longer is in alignment with my new direction. How do I go about clarifying what it is that I want in that moment? When you feel like you have no idea what direction you want to be heading in, all you know is that this one doesn't feel right anymore.
MEGAN: So I think there's two related answers to that. The first one is, take an action, any action, in your right direction. So whatever that looks like, this is the smallest, most tolerable, actionable step that you can take. And trust that if you keep taking directionally right actions, you're going to end up in the right direction. So eventually things will probably coalesce around a big direction, meaning you'll have a sense of where you're going. But in the beginning, it's okay if you're flying blind.
So just asking, what is directionally right for me? Meaning, what am I curious about? I often say, forget about finding your purpose, which has become a destination, right? This one thing that I'm meant to do for the rest of my life, that is my purpose and my passion and is so stressful because then you just sit there trying to think in your head about what is the purpose. There's so much pressure. Most people when they ask themselves that, they just spiral out and kind of blow a fuse and can't answer that question. So what am I curious about? And so, it's recovering the sense of curiosity that is the thing that's going to lead you in the right direction. And those curiosity and joy are actually the best, best proxies for purpose.
So step one is, where are you curious and what brings you joy? Now, this could be listening to certain podcasts, it could be reading certain books, but just like paying attention to what the patterns are. It could be in your current job, looking at what are the parts of my job that feel the best to me and how can I do more of them versus less of them in the short term, that doesn't mean you're going to stay there forever, but really doing the work of like kind of a life spring cleaning or a life inventory, where you're like, what is directionally right and what is directionally wrong. Another way I talk about this is warmer and colder. And again, it's so simple because we tend to make it so complicated. But what is warmer and what is colder?
So the second part of this is that sometimes, and this was the case for me, to know what is warmer and colder, to know what is directionally right can in and of itself be so hard. Because if you've spent your whole life ignoring your curiosity, thinking that it's a distraction, ignoring your joy, like I did in coaching class, because that also feels like a distraction and kind of suppressing any sort of insourcing you might do, it's very hard to know what that voice says, so we need to recalibrate that and recover that sense of what is warmer and what is colder.
EMILIE: Yeah, I mean, I think that's very common for women in particular, because we grew up in a society that basically teaches women to detach ourselves from our own sense of joy and pleasure and, you know, to push through, hustle hard, put everyone else's needs before our own. We get really good at suppressing our own needs for the safety of our families or ourselves or what have you. And so, what I'm hearing you say is that, you know, if you don't use it, you're going to lose it, that sense of what it is that you want, yeah?
MEGAN: Totally. And you can recover it. So it's not your fault that you lost it, but you will need to do some work to find it. And so, again, I think it is a matter, you know, this is going from a framework of what should I do with my life? To what do I want to do with my life? I don't just ask that question, like, go figure out what you want to do, because again, that feels so overwhelming and so big. And if you aren't used to asking what you want to do, that feels like, if I knew, I always felt like if I knew what I wanted to do, I would be freaking be doing it already. Like, that question doesn't help me.
And so I talk about it in terms of, you know, we all have this inner navigation system, and we want to recover that sense of the inner navigation system and start following that. And so keeping it really simple, warmer and colder. And start moving through your life, making as many small decisions as you can, figuring out what is warmer and colder. So what are you having for dinner? Are you having a salad because you think you should, or that's because your body really wants that? Are you going to yoga because you think you should? Or that's truly the form of exercise that feels the best to you. Are you wearing business casual, because that is what you think you should, or that's truly what feels comfortable to you? Or experimenting in that regard in these small places. And that is how we start to come back to ourselves and understand what is my warmer, my directionally right, and my colder, my directionally wrong. And once we get in practice with doing that again, it doesn't have to be hard or complicated. We can start doing this in the lives that we're actually living. We can start to make bigger decisions about what is warmer and what is colder, like leaving your job or whatever the thing is, if that is what needs to happen.
EMILIE: So I want to ask about the practical realities of this because I just had coffee with a friend and mentor of mine who for the past two years basically took a pivot in his career with two teenage daughters at home to pursue a startup. And, and you know, he got some funding, they got some early traction, but they were basically in competition with ChatGPT and I think it's all very obvious how that went, right? Like ChatGPT is just dominating this market when it comes to AI and this person's startup was destined to be beat out basically by ChatGPT. During that same time. He went a year and a half without bringing home a paycheck after being a very high earner for his family with again two teenage kiddos at home. And when he put it to me bluntly over coffee when we were catching up last week, he said, my wife was really sick of me not earning an income so I had to decide between saving my marriage and continuing to pursue my startup.
And I just thought in that moment, like, that is putting things in sharp relief for folks. Like, there are financial needs to be met in our day to day lives. So when he's pursuing this passion, this energy, the thing that makes him feel excited and yet it's not tolerable. You know, a year and a half is much longer than most of us could even go without bringing home a paycheck for our families. I just wonder how you balance that directional pursuit of what lights you up with the day to day realities of finances and privilege.
MEGAN: Definitely. So money is a very real thing and this is not a just like, do what you love and the money will follow, at all. What I believe is directionally right and aligned for you is holistic. So it's not like these things have to be or are at odds. If you, in my mind, if you're really, you know, grounded in your life and making decisions with the full picture of who you are in your life, what is going to feel aligned for you might be again, I don't know this person, but as an example, it might be like, I can't take a year and a half because I can't support my family right now. So is it a nights and weekends thing, you know? Or can he work somewhere else part time while he's doing this? Like again, I don't know. Or is there a set amount of time where you say to your family and your wife, I can do, I'm going to do this for one year. And if it's not successful at the end of one year or we don't have indicators that it's going to be, we will come up with a new plan and then everyone's expectations are clear.
I don't think you have to choose between these things. I will also say that what is aligned for you is what you are uniquely well suited to do in the world. And what I believe is what we're looking for. And when you're doing what you're uniquely well suited to do in the world, you tend to make more money doing it because you're adding more value, because you're adding more unique value. Again, in the systems that we live in, that does not work perfectly all the time. But there are studies that are showing that when you are, feel purposeful and aligned in your work, your net worth tends to be higher.
So another thing I would think about with your friend is, okay, so he has to decide between his startup and his wife in this scenario. And he decides, I'm assuming he decided to save his marriage.
EMILIE: Yes, he did. Good assumption. Yes. He got a day job in city government as a result, yes.
MEGAN: Interesting. So, but, so I don't, you know, there could be so many ways that that pans out, but maybe he's like, okay, this is the end of my startup, but you know, this experience that I had doing, you know, ChatGPT, something is lending me to be able to be able to go get hired for this other thing that pays like double what I was doing before or whatever the thing is, right? So sometimes it's like not linear where you're not making these like incremental steps up. And I'm not saying that everyone can or should do this, but sometimes we take a year off to invest in doing a startup or whatever it is when we come back, if we come back into, you know, the market and to look to be hired as like, a W2 employee, we actually, that was skill building. That is adding more value. That can actually add more value and maybe not fully cancel out the not having a paycheck for a year and a half, but can add to it.
EMILIE: Totally. And I think he and I both agree that we're not at the end of our experiment that is our career, right. You really talk about this experimental iterative process in your book, which I completely align with and love. And we're just in the middle of figuring it out. You know what I mean?
MEGAN: Yeah. You know, that was a phase and it was like, okay, now I have to come to a decision and that, you know, that happens sometimes you take a. You take a W2 job and you're like, this is. I'm getting paid a lot, but I'm, my mental health is deteriorating to such an extent that now my marriage is at risk, right? Like my relationship. So there's so many ways this plays out and that, you know, there's a juncture where it's like, oh, it was in my, the way I see it is for him, it was no longer directionally right for him, and it was time to make a different decision.
When you're making decisions that are that stark or that extreme, the question I always ask with that is like, is this something I can't not do? And I don't know if he felt, you know, how he felt about that. And again, thinking about his holistic life and career, that isn't over, the conversation I would have with, and again, his wife is free to have whatever feelings and needs she has too, right? But if I, it was my partner, let's say, you know, and somebody comes and says, I don't think I can be fulfilled and happy if I don't give this a try. I don't know if it's gonna work. But, like, can you help me give this a try? And this is, this with the ChatGPT situation, like, a lot of things, you know, another scenario would be like, I really want to try this in my lifetime. Maybe it doesn't have to be until my, 10 years from now when my kids are out of the house, and then I might have a little bit more financial flexibility. With AI stuff. Like, it was probably a now or never moment. Like, if I don't jump in here right now, the ship has sailed.
EMILIE: I mean, to your point, a year and a half ago, that direction was right for him and his family, and now it's not. You know what I mean? So.
MEGAN: Nobody did anything wrong, you know, and his wife was on board for that long, and then it was like, we have different needs as a family, so it's just not directionally right for him anymore. I don't see that as like a failure or a mistake. It's just part of the evolution. And I don't, again, I don't know if he regrets it, but very few people regret trying things. They usually forget not trying.
EMILIE: Yes, I think that's a good point. I remember speaking to someone at a Bossed Up event years ago who really, her whole inner narrative was, I tried this thing and it failed. And so I had to go back to corporate or what have you, and I remember saying to her, maybe you're not at the end of your story, right? That language you used earlier, maybe you're in the middle of your story. And that just, just absolutely shifted something in her. It's like, I want to really get into this experimental process because to me, if we can apply that iterative design process to our careers and lives, we'd all be better for it. So what is that part of your book all about?
MEGAN: Yeah, so this is a key part of why switching from destinational thinking to directional thinking is helpful. Because if that person you were just talking about was thinking directionally, she wouldn't have felt like anything failed, because she's still going, right? It's still an experiment. Your friend did it. Uh, you know, your friend who did the ChatGPT competitor startup, also was just in the middle of an experiment. Like, we're allowed to evolve. There was no destination. There is no there, there. So all of these things are successful if you tried something and you learned, and that's really what directional living allows you to do.
Another way to conceive of it is, it's the scientific method. But for life or for your career, where you have a hypothesis and then you're testing and learning, the goal is not to prove yourself right, it's to find out the truth. It's to get closer to the truth. It's to move the plot forward. And so in both cases, they tried something and they went back to corporate like, you know, the person who tried something went back to corporate. That was a test. She learned something from it, and maybe she will leave corporate again or she won't. And your friend tried, you know, with the startup tried something, and that was a testing and learning experience. And both in terms of skill set, in terms of what he wants, all of these different things. And now the experiment is continuing, you know.
So the phases that I talk about are really, the first thing is to recognize that this is what's going on. Like, I'm an underfulfilled overachiever or, and I would say not all people who live destinationally, because I would say that's our whole culture, are underfulfilled overachievers. Some they live destinationally, but somehow it doesn't, like, existentially plague them in the way that it does for a lot of us millennials, or, you know, the people, myself and the people I'm talking to, some people are just like, I don't like this. But when we see what destination, directional living is, and to move away from that.
The second piece is to figure out that alignment, right? So like, knowing what it is, how to discover what it is you want, what is warmer and colder for you? So your friend to know this ChatGPT competitor startup is directionally right for me. And oh, now it's not directionally right for me anymore. It was warmer and now something else. Now going into, you know, public service or government work is directionally right for. For me. So once we figured out how to do that and we can sort of trust our instincts on this, and we're coming from a place of making our own decisions, then we want to like, try to get rid of all the stuff that isn't warmer, is that's not aligned for us and do kind of like a clearing phase. But once that is set up and you have some spac
e in your life, then we're figuring out what is that hypothesis? What is that big direction? And really the point of that is again, is not to get it right. It's just to have a sense of where you're going, of your big direction, right? Imagine taking a road trip and you're like heading to the west coast. You don't need to know exactly where you're going in this scenario. Just you're heading in the west, towards the west coast from the east coast, let's say where I am. And then once we have our big directions, like, how do we move towards that direction? What is the quality and the sense of our movement? And that's where the iterate phase comes in. And the iterate phase is basically take an action, any action, and our job is only to move the plot forward. So any step that feels warmer is a great one.
EMILIE: Yeah, absolutely. What would you say to the person who is really afraid and paralyzed because they know this next step they're thinking about taking isn't perfect yet?
MEGAN: Again, this is where the experimental philosophy is so, and like, directional experimental philosophy is so good for perfectionists, like myself, where you don't have to get it perfect because it's an experiment and not only do you not have to, but you cannot. And so if we can let go of the fact that there is a perfect destination and we can say, I don't know, I can't know, and not yet. Not only do you not have to know, but you cannot know.
There is like, there's this myth of certainty or like, objective right way of doing things that we get really stuck in. And your job is not to figure out what that right step is, that right destination is, or know if it's perfect or not, you know it's not going to be perfect, but everything, pretty much everything is changeable. So you will be able to change it. As soon as you make the decision you make, you make the warmest decision and then you know you're going to be making decisions and tweaks from there.
EMILIE: I remember when I first started Bossed Up, there were voices in my life who were skeptical as to what I was doing because I was walking away from a very stable job in political campaigning to launch Bossed Up, this women's leadership development and career services company. And one person put it quite bluntly to my father, actually, you know, what makes Emilie feel like she is even remotely qualified to do this? [LAUGHTER] I remember when I received that news secondhand, I was like, nothing, nothing makes me feel like I can definitely do this. I have no idea if I can do this, but I'm not willing, to your point, I can't not do it. I'm not willing to not find out. I need to find out. And so I'm going to give it a shot and see if it works. And here we are 12 years later.
But what's interesting is that, seeing how the company, this experiment, right? Has evolved to meet my differing needs over the years was really challenging, honestly. Because when there were decision points, Megan, along the past 13 years where I had to make some fork in the road choices of how do I want to set us up in 2020, for instance, when I had an entire year of in person trainings booked that then got all canceled in one week, you know, how do I want to evolve the company to provide online services in a whole new way? And 2023, when the backlash against DEI really made our existence questionable and I had to really pull back on the business in a big way, how do I want to continue to exist in this world? Do I even continue Bossed Up, right?
And now today I've kind of pivoted back into a full time role in house doing leadership development and made Bossed Up a side hustle after being full time for over a decade. And it's like once I let go of that feeling that there is a right way for me to lead this company, there is a right way for this company to look. I could ask myself what is right for me right now and how do I design my career to match that, but it does feel like there's this future you projected and then the future that you're actually orienting yourself toward and when there's a big gap between those two that can create a lot of feelings.
MEGAN: Yeah. So I think what you're getting at is, and this is another myth I think that we have about aligned careers, or aligned life, or fulfilling life. And I do say take the path of most ease, right? But it doesn't mean that it's always going to be easy or feel good. Meaning you can have something that is the directionally right decision for you and you know that wholeheartedly. And yet it still requires you to do something that it still requires you to give up on something or give up something, or lose something.
So I think what you're talking about is there's a lot of grief involved and that is often a part of evolving, right? We don't really evolve without having to let things go. There's like a skin shedding that has to happen. And I don't think we get out of that just because it's aligned for us. And so I think it sounds like that's what happened for you, is that, and you know, often there's like an ego thing involved too. That's like, I thought it was this and it was, you know, whatever the story is that we had, and we have to like untangle the story. But like we oftentimes that sometimes not oftentimes, sometimes it's so clear.
But let's say you have to, you know, again, going back to your friend with the startup that probably had a lot of grief involved, he could know this is the right decision. And it sucks to put a year and a half into something that you're so passionate about and work so hard on and then have to let it go. It sucks to work for 10 years on something and then be like, wow, this is not what I thought it was going to look like. If you need to leave a job that you've worked hard on or, you know, leave a relationship, or even leave a city, you know, there's so many times where it's like, I know this is my directionally right and yet this feels really sad and hard.
And we were talking about motherhood a little bit before we got on this. Like, that's a classic time where you can be like, this was absolutely what I wanted for myself. And there's grief in the things I had to say goodbye to in order to be in this phase of my life. So I think that's a big misconception, is that fulfillment always looks and feels good or alignment always looks and feels good. And I don't think that is, that's not the right question.
EMILIE: Yeah, I think that's such a good point. You know, I could talk with you all day, but we're gonna have to leave it shortly, not at that. But I think you're underscoring the fact that fulfillment is a little different than happiness, isn't it? And you can have grief, you can mourn the life you've given up to become a mom, to become a boss, to become an entrepreneur, to become a leader at work, and still be happy you took those risks. But, you know, the path with no risk involved is not going to have any highs or lows, right?
MEGAN: Well, and that's actually, you know, I know we need to wrap up, but that's actually a really important point because I think that is also a myth that there is a life that has no risk and no uncertainty. And I think 2020, especially, kind of destroyed that and took down the veil of certainty for us that we, and again, going back to the very beginning, this idea that there are destinations that we can reliably predict where we're going and that can keep us safe and secure when there never has been, we could sort of believe it before, but what directional living really is, at it’s core is a process for living and making aligned decisions, fulfilling decisions in a world of uncertainty without pretending that that isn't a thing.
And I think that is, you know, so many people say, oh, I'm risk averse and I'm like, well get you, like risk is part of this. The best, the most secure thing you can do now is actually not fixate on a destination or what you think is secure, but to know that you are making the most aligned decisions for you and that when something comes, that you come into a fork in the road moment, you trust your inner navigation system enough to be able to make the next directionally right decision for you. And you can feel disappointed, but that's different than feel like you're falling apart because the destination you thought you wanted no longer exists or doesn't feel like you thought it would or isn't available to you.
EMILIE: Absolutely. That's amazing. Where can our listeners learn more about you, get their hands on a copy of your book and dig into this even more further with you?
MEGAN: Yeah. Either on my website, MeganHellerer.com or Instagram at @meganhellerer. And there's links to, you know, all my stuff, my book and everything else there. And podcasts and articles and anything else you would be interested in finding out.
EMILIE: Well, congratulations on this achievement. That is the book itself, because I know how long, how much of a labor of love writing a book is. You know, as moms, I can still call it a book baby and say like, yeah, that book took even more time, frankly, to cook up than my child.
MEGAN: That's a whole other conversation of the parallels of the baby and the book. But maybe we'll have that conversation another time.
EMILIE: I love it. Megan, thanks so much for being here. I really appreciate it.
MEGAN: Thank you, Emilie. Such a joy.
EMILIE: For everything Megan and I just touched on head to bossedub.org/episode510 that's bossedub.org/episode510. There you'll also find a fully written out transcript and blog post that summarizes the key points we discussed in today's conversation, along with links to related resources and other Bossed Up podcast episodes that you might want to listen to next.
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And in the meantime, I want to hear from you. Let's keep the conversation going as always in the Bossed Up Courage Community on Facebook or in the Bossed Up Group on LinkedIn. And in the meantime, let's keep bossin’ in pursuit of our purpose, and together let's lift as we climb.
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