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Ex Google Executive, Megan Hellerer, on Living a Fulfilled Life

 

 

Welcome to Strategy Skills episode 491, an interview with the author Directional Living: A Transformational Guide to Fulfillment in Work and Life, Megan Hellerer.

In this episode, Megan shares her experience as an executive at Google and how she realized the misalignment in her career path, which led to physical and mental health issues. She also discusses how she navigated through it by listening to her inner voice and experimenting with new paths. Additionally, Megan explains how she built her coaching practice, how to find clients that are a good fit for you, the common issues clients face, and how to help them solve those issues.

Megan Hellerer is a career coach and the founder of Coaching for Underfulfilled Overachievers. She has led hundreds of women, including Representative Alexandria Ocasio-Cortez, to transform their lives by transforming their careers. After checking all the traditional boxes of success—graduating at the top of her class from Stanford University and spending eight years as a Google executive—and still deeply unhappy, she quit her great-on-paper job with no plan. Now her mission is to provide others with the support and guidance that she needed when she herself was struggling. Megan has been featured in New York, Vogue, The Wall Street Journal, CNBC, and The Times. She lives with her husband and daughter in the Hudson Valley, New York.

Get Megan’s book here: 
Directional Living: A Transformational Guide to Fulfillment in Work and Life


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Episode Transcript:

Kris Safarova 00:45
Welcome to the strategy skills podcast. I’m your host, Kris Safarova, I’m the CEO of strategytraining.com and our podcast sponsor today is strategytraining.com if you want to strengthen your strategy skills, you can get the overall approach used and well managed strategy studies. It’s a free download, and you can get [email protected] forward slash overall approach. And you can also get McKinsey and BCG winning resume, which is a resume that got offers from both firms. So if you’re currently updating your resume, you can get [email protected] forward slash resume PDF. And today we have with us, Megan Haller. Megan graduated at the top of your class from Stanford and spent eight years as a Google executive, and now she’s a career coach and the founder of coaching for under fulfilled over achievers. Megan has been featured in New York Magazine and the Wall Street Journal and many other places. Welcome Megan.

Megan Hellerer 01:41
So happy to be here. Thank you for having me.

Kris Safarova 01:43
Megan. So let’s just start from discussing your career a little bit before we go into your current, very important work you are doing. Maybe you could take us through that journey a little bit that led you to your current work.

Megan Hellerer 01:55
Absolutely. So you mentioned already that I work with people I call under fulfilled overachievers, and that’s because I was the original under fulfilled overachiever. That describes me perfectly. I was, you know, took taking all the AP classes and getting straight A’s in high school, and went to Stanford undergrad, and then went right into working at Google, and was sort of just doing all the things, checking all the boxes. And I realized at some point when I was at Google, is this all there is. What am I even doing this for? And I was really unhappy and felt disconnected from myself, my life, my work, and from there, I was really starting to also have physical and mental health ramifications. You know, I was really depressed and I was having panic attacks, and that was not characteristic of me. You know, throughout my life, this was this was new, and as a result of that, I decided eventually to quit my job with no plan. And I say I decided, but it was more like I didn’t really have a choice. Internally, it got to a point where it felt like the only option was to leave, and then I started looking for answers how to do this differently. What was I doing wrong? What could I do better moving forward? How can I do this whole career and work thing in a way that isn’t going to lead me down such a path of misery. There had to be a way. I really believed that there was, and when I looked around for answers, I was surprised to pretty much only find other people reflecting back to me a similar message of this is just the way things are, or a job is just the job, try not caring so much about it, or this is just what adulting is. And that was too hard for me to stomach and not acceptable to me. And so I decided to start to try to come up with my own way of figuring out how to navigate things differently. And through that process, I ended up kind of stumbling into a coaching class, which I was very skeptical about, and definitely did not intend for it to become my career. But I found something there that felt so aligned for me and just really connected to it. And through that work, started coaching other people, really just for a cup of coffee at first only in order to get certified as a requirement. And found that their lives started changing. And I loved the work, and my life started changing, and I realized that was what was the most powerful part of the coaching was actually the stuff that was coming out of my own experiences and my own life and my own search for how to help us under fulfilled overachievers recover from under fulfilled overachieving and find fulfillment finally, and from there, you know, the rest is sort of history, and we end up where we get to writing a book today.

Kris Safarova 04:58
Megan, just to take a step back. Thank you so much for sharing this. Could you share with us what was it like to be a Google executive for some of our listeners who are considering it as an option, and a little bit more about why it felt that it wasn’t the right path for you?Megan Hellerer 05:14
Yeah. So I’ll caveat with a couple so in terms of what it felt like to be a Google executive, I’ll caveat with the fact that this with the fact that this was over 10 years ago now, and so it was a very different company when I started working there in 2006 unfortunately, it was post IPO, but we only still had a Mountain View office. So there wasn’t even a New York office. There weren’t any of the global offices, a completely different size company and completely different experience than it would be today. And the other thing I want to say about it is that I certainly do not feel that the issue was Google. The issue was that Google wasn’t aligned. For me, I have coached people into Google. I work with people who for whom Google or tech in general, is extremely aligned, and it is their most fulfilling work, and there’s something bigger. So this isn’t a anti Google or anti big tech or even anti corporate stance that I have at all. It’s about finding what is aligned for you, and that was not aligned for me. But I mean, there are many things I can also understand what attracted me to it, and I think there’s a blessing and a curse in this for many under fulfilled, overachievers, myself included, I am just curious, and I’m interested in learning new things and having new experiences in general. And I think that’s one of the things that kept me there for so long, which is there’s was a steep learning curve, just of and there was always exciting new things going on. And I was always working on what they called, at the time, the emerging platforms team, so these new products that we were sort of incubating, and it felt like working at a startup within a larger company, right? So you didn’t have quite the same risk factor. And I learned a ton, you know, people say, and I think this is true, it’s almost like getting paid to get an MBA, I got an amazing experience being there that I think helps me to do the work that I do today, in terms of the knowledge that I have, and able ability to coach other people, and also in terms of running my own business. So there are many wonderful things that came out of that time, and I still think some of the most brilliant, creative, intelligent, inspiring people that I know and have met in my life, I met there. So there’s many wonderful things about it, and many people do thrive there. I think what was not what I how I knew it wasn’t a line for me, there are a couple of things that really stand out, I think. And on some level, I knew on day one that this was not the exact right fit, but I didn’t know that I was supposed to listen to that voice. I thought that that voice was a distraction. I labeled it as fear or something that was just like getting in the way of my ambition, right, or my goals or my dreams. And so I ignored that feeling as as something that was, yeah, a distraction or a hurdle that I needed to get over, as opposed to valuable information about myself and my work and my life and the where my purpose could be found. And so I think that’s one of the first things that I say to people, is that voice is not a distraction. That is important information that we want to integrate. Another moment that really stands out to me was, at some point I had been working, my goal was to get this promotion. You know, there had been like two years, and there was this one promotion I really wanted to get. It was like this hard level to get to, and I’d been really focused on getting this promotion. That was the thing that, like, kept me going and inspired me, and kept me working long hours and all of those things, and I got the promotion, and I felt nothing. In fact, I may have even felt more empty, and when I looked ahead at like, what is it? What do I now get? Like, what do I get now that I got this promotion, and the answer was nothing, really, like, it didn’t really mean more responsibility. I mean maybe a bit of a pay raise, which, of course, is not nothing, but it wasn’t. It just meant more work. And when I looked ahead, also at the people who were, you know, the next level above me, let alone five levels above me, I didn’t see anything that I wanted. I couldn’t see anything that I wanted to strive for next. And if I wasn’t striving for a promotion, then what was I striving for? And it was this real moment where I was like, What am I doing this for? Or who am I doing this for? Because it wasn’t for me. Clearly, it wasn’t for myself. It wasn’t from this internal sense of drive or desire or impact. Um. And I think having that reaching one and this, I hear this from many people who come to see me like reaching this pinnacle moment, and it not feeling like what you thought it was going to feel like, and is a real sort of can be a mirror, can be a good reflection of where things might be off. And I guess the last story I’ll share is, and this was sort of one of the last ones, is having an actual breakdown at work, you know, in the bathroom, on the bathroom floor, having to leave a team meeting, and throwing up and being physically ill and like seeing myself in the mirror and just not even recognizing myself and feeling so far away from, you know, the vibrant, aliveness part of myself that I knew and that I loved, and not really knowing where that had gone, or how I’d gotten so far away from that. And so I think those, those two moments in particular, stand out, but when I reflect back even further of why I didn’t pick up on it sooner. I think the biggest one was that I initially thought it was a distraction. It was something I thought I was not supposed to take seriously.

Kris Safarova 11:10
Thank you so much for sharing this so that first day and your voice inside telling you this is not the right fit. And of course, Google is a great company. They do great, important things for the world, but I understand what you’re talking about. After MBA, I went into banking, and first day, in my gut, I knew this is not the right place, and I couldn’t imagine spending few years there. I couldn’t imagine even spending another day there. I know I can’t force myself to do anything. I have the bill, and I did Same to you. I stayed for a long time and experienced similarity that we did, and there are many of us like that around who, not early on in our careers, don’t listen to our voice. So could you share with our listeners what that voice feels like, to help them hear it earlier?

Megan Hellerer 11:53
Yeah, and I’m curious first, what eventually, and maybe your listeners know this already, but what eventually led you to leave.

Kris Safarova 12:01
So, eventually I left and went back to consulting. And I love consulting. I’m very happy there, but I still felt that I was not doing my life’s work. And I had that voice very prominently talking to me from inside, kind of you’re not doing your life’s work, and it just feeling that you have in your gut, and it was getting louder and louder and louder that feeling, if you can say that about feeling. And then eventually I got sick, similar to you, my body broke down, and I knew and it was also in the bathroom. I was looking in the mirror, same as you was looking in the mirror in the morning, and I realized that I need to go to emergency room urgently, and I didn’t hear if I will live or die. And that moment of looking yourself in the eyes and knowing that you are not doing the work you’re supposed to do here.

Megan Hellerer 12:44
Yeah, it’s amazing how similar the story is. And I hear such a similar story over and over and over again. You’d be shocked by how many of us there are, or maybe you wouldn’t be shocked once you start, once you know that this exists, you start to hear it more and more and what you’re describing. And I will come back to the question of how, what does that voice feel like? What you’re describing is what I call the fulfillment ache. And it’s the pain, the suffering, that an existential sort of chafing that develops in the gap between who you actually are, as you spoke about your life’s work, or alignment, fulfillment, wholeness, whatever you want to call those things, and how you’re actually showing up in the world. And the larger that gap gets, the further away you get from yourself, the more painful it becomes. And so that is also something that I think people when once they have a name for it and they’re like, oh, that’s what I’ve been feeling. It can it’s very powerful to realize that there’s something you can call it. So how do you recognize that earlier, before it starts turning into a breakdown in the it’s always in the bathroom. For some reason, I feel like we should do some research on why that is. But so there’s an exercise I do with clients to try to figure out what your own internal navigation system feels and sounds like and internal navigation system is what I call, you know, intuition, or gut, or whatever you know, inner voice, inner knowing, whatever you want to call it. I like using that analogy, because it feels like it’s sort of like proactive and actionable in a way, like it’s telling you how to navigate. And the the reality is that it feels and sounds a little bit different for everyone. And so there isn’t one way that it sounds or one way that it looks. And so it is about getting to know how yours sounds and feels. And but that’s a key difference, is that it is not in your thinking brain. It is a sensing, a feeling, a knowing, if you and it’s not verbal, so if you are justifying or explaining, or there are a lot of words coming along that, oh, I should stay in consulting because of this and this and this and the resume and this, and when I get to this, then it will be like this. Or whatever those things are, that is 100% not your inner knowing, not your internal navigation system. So it’s non verbal, and this is one of the things that we’ve been taught to ignore, right? That sensing in favor of this idea that our logical thinking mind is superior, but actually that’s where our fear and anxiety lives. And that doesn’t mean our brains aren’t useful for anything, but there’s an expression that they’re they’re a good servant, they’re not a good master, right? We want to be using this knowing to direct our minds where to go, and so I often describe this as the like the child game of childhood, Game of warmer and colder. So you want to start to get a sense of what feels warmer, closer to your authentic self, or your most aligned self, your most fulfilled self, and what feels colder. For many people, warmer feels relaxed. It feels like freedom. It feels like light. And right is an expression that often resonates with people where there’s just like a lightness that comes along with it. Versus colder often feels tight, more contractive, versus warmer feels expansive. It feels like possibility. Colder feels um, off, tighter. You know, people can feel it in their throat or their stomach or their chest, you know, they’ll be clenching a lot of things. It can feel hard and heavy, right, like a burden almost. And it’s sort of just a feeling of not self or dis ease. Those are the sorts of feelings you will start to come across. And figuring out, a great way to do this is to think of something that you know is warmer for you or so maybe that’s a person who you trust completely, or a time in your life, a place a decision you made, a pet, whatever it is, something that you know definitively is aligned for you, you trust, and That’s sort of a core feeling or belief for you, and feel what that feels like to Matt, think of that person or that thing, and then do the opposite for colder, what is a decision you made that was not aligned for you that or person you didn’t trust, and think and see what that feels like to think about spending time with that person or being in that place again, for me, an easy one is Google versus coaching, right? If I ever feel like I’m scrambled or I can’t orient myself around what my own warmer colder is, that’s a really easy way to get right back there. Does this feel more like Google, or does this feel more like coaching? And with that comparison of warmer or colder, it’s can always sort of snap me back into it. So I would recommend doing something along those lines to have a shorthand for your listeners, too.

Kris Safarova 17:47
I loved what you wrote. You said, when you look in the mirror having that panic attack before Google social event, you wrote, my eyes were hollow and empty and raccoonish, you’re in serious trouble. I said to the haunted reflection in the mirror, you’re not okay. Look at you. You are dying. And that is the experience that I think many people are going through. And I could feel that it does feel like you’re dying. It feels that your body is breaking out. Your earliest at this is that basically leads to disease. It leads to serious issues with your body, because your body, at some point starts screaming at you and saying, No, I’m not going to live like that anymore. You have to listen to your voice. I’m glad that we are speaking about this, because I hope that we can help someone listening avoid that moment in the bathroom.

Megan Hellerer 18:34
I feel that way so strongly, and that was a big part of writing the book for people to realize like you’re not alone, and also that it doesn’t, you don’t have to get to that point.

Kris Safarova 18:46
Let’s talk about your note that experiment after you left Google.

Megan Hellerer 18:50
Absolutely. So I sort of briefly touched on this earlier, but when I left Google, you know, I thought that when I finally did it, you know, I’d been toying with this for so long that I was going to feel like blissfully free and phoenix rising up from the ashes and totally exuberant. And in reality, there it, I think I say in the book, it sucked in new ways. It was very difficult. And I was depressed in another way, because there was this sort of ego death that had to happen. I had no idea who I was or how to describe myself, how to think about myself, not to mention the uncertainty and the fear and all of these other pieces that were going on. And so again, in an effort to figure out what was next, and I was truly ready to give up anything with the optics of high powered income anything. I did not care. I was like, I’ve seen what that looks like, and that does not fulfill me. I don’t care if this looks good on the outside anymore. I really was ready to do whatever I needed to do to be fulfilled, but I still didn’t have an answer for what that was. It wasn’t like I. Had some secret dream that I didn’t, you know, believe in myself I could do I had no idea, because I’d been so disconnected for so long. I didn’t know where to start. I didn’t even know how to spend one day without a to do list and being accountable to someone, because it had been so long since I’d had a day where I truly didn’t have anywhere to be or anything to be doing or catching up on or whatever it was. And so I just so I gave myself, and this was one of the best decisions that I made through this whole process. I knew I was gonna be scared, and I would probably take the next job that was offered to me, and because I didn’t have any income, and then I would end up on the bathroom floor again in two years having the same crisis. And so I committed to myself that for six months I would not apply for any jobs, not update my resume, not interview, not accept any jobs. I sold a bunch of Google stock in order to do that, which was, you know, not necessarily advisable, but it was so important for me to be able to give myself a runway where I could try to figure this out, and from there, I knew what I didn’t want. And so again, I didn’t have the vocabulary that I do now that I’ve come up with for this reason, but this warmer or colder idea, I was basically doing research by playing a game of warmer, colder, and so I was just doing as many experiments as I could, and getting closer as warmer, moving warmer every day and moving away from the colder. So the not this experiment was just not doing the things that I knew did not lead me to fulfillment and trying to find more that did, even if it was one degree closer every day. And one of those things, many things were colder, but one of those things ended up being a coaching class so that, but giving myself, making it an experiment, I think, was so crucial to not for such a like linear thinker and someone who was so used to like having goals and achieving them at all costs, creating it like a little bit more spaciousness around this, for that experimentation, for that trial and error, for that iteration, was so important for me.

Kris Safarova 22:13
And what was very commendable is you gave yourself six months and even at three months mark, you still didn’t know what you wanted to do. So people need to give themselves enough time, especially after a very long period of time when we don’t listen to what we want to do. What makes us happy, what what actually gives us energy when we do that work. Tell us a little more about how you were able to motivate yourself not to give up during those six months and continue searching.

Megan Hellerer 22:42
Yeah, I was trying to think what, like, what was the motivation factor? And I think it was, I there’s a phrase that comes from, like, 12 step recovery groups. And I do think this is a sort of a sort of recovery, right, recovering from what I call destination living, or recovering from this under, fulfilled, overachieverness, which is the gift of desperation, and that’s the phrase that they use to describe the motivation of having been in so much pain and suffering so much and I think that’s a good analogy for what was motivating for me, which was I just could not go back to feeling that way, and even, and I was willing to do anything in order to do that. And so even though I had no idea what I was going to be doing next, I was starting to feel glimmers of myself each and every day. And I think that was what motivated me, even having one speck of like, Oh, this feels warmer. This feels more like me. Was the encouragement I needed to keep going forward and but I think mostly it was just that I was desperate not to find myself in that much pain anymore, and almost like a will to live like it really didn’t feel like it was, it wasn’t some enlightened vision that I had. It was, I can’t go back. There has to be another way.

Kris Safarova 24:11
Remember that moment when you decided coaching is what I want to do with my life.

Megan Hellerer 24:16
There wasn’t a moment where I said coaching is what I want to do with my life, per se, and I think that is part of the whole point of this is that I still don’t know if I would say that coaching is the point of my life. I do think that, you know, the goal my life’s work is, you know, to help under fulfilled, overachievers find fulfillment. But that could look so many different ways. I love coaching. I don’t see myself giving it up anytime soon, but I didn’t necessarily know that a book was part of that. You know, I’ve done online courses like speaking. There are so many different iterations of how this could look, and I have no you know, I don’t think that I know how this is going to continue to evolve and that now that feels exciting to me. Um. Um, but I think again, I had learned from that experiment. And I said, I again, I was very skeptical. I had a full roster of clients by the time I came out of certification, which was enough to make me say, Okay, I’m going to give this a try. And again, I said, six months. And I said, I’m going to give it six months. I feel like I can’t not do this. I’m gonna give it six months and see if this feels like a viable path, simply a viable path, both in terms of purpose and fulfillment, but also in terms of income, right? I really didn’t know if this was a way that I could support myself at that point. I didn’t know a lot of coaches who were doing it in that way. And so again, I gave myself six months, and I made another very important decision I think then, which was, but I’m going to give it six months to do it in the most aligned way possible. Meaning, I’m not going to just take any client just because I’m scared. I don’t want this to be fear driven or fear based. I’m not going to just take any client, even a client who I, you know, don’t think is aligned for me, or I don’t think is the right fit, or I don’t think I can help, because that is not going to give me the information I need to know if this is sustainable for me and if this is aligned for me. So I again, was really clear of I’m going to do this in a way that feels in the most aligned, fulfilling way possible, and I’m going to see how I feel about it in six months, and if this feels viable and sustainable, and fortunately, it did, and at that point, I committed to, yeah, I’m going to give this a go for the foreseeable future. You know, I’m going to make this my full time work, and I’m going to give this everything I have. But it was never like a this is my life purpose conversation that I had with myself. And I think that’s really important, because one of the things that people tend to do is turn purpose into a destination. So then they’re like, Okay, and a great example of somebody being like, I’m going to go work at a non profit. Work at a nonprofit, and that is going to be the thing that fulfills me. And they go work at the nonprofit, and it feels it looks purposeful on paper, but they’re really just enacting the same thing they did in corporate in a nonprofit, right? So we need to be able to have a purpose that’s evolving. It’s not static and fixed. So I don’t think I often say, Forget your purpose and follow your curiosity. It’s counterintuitive, but that is the best way that our curiosity is the best proxy we have for purpose, and so I continue to live in that way, feeling very on purpose. I don’t feel scattered and lost and confused about what my work in the world is, but I hesitate to, and I really don’t think about it in this way, of like, putting, you know, a stamp on it, putting my foot down. Of like, this is my this is my work. I reserve a lot of room for it to evolve.

Kris Safarova 28:00
Makes a lot of sense. Yes, it was more about you decided to focus on at that time and see how it goes, follow your curiosity, your interest, and see how it goes. So at that moment when you decided I will try being a coach full time, how did you figure out the services you will offer the pricing?

Megan Hellerer 28:19
Yeah, so that is another thing that I think we need to let evolve. But there are a few things that I thought about then the first thing I did, and I would recommend to everyone, is have a bunch of conversations. So I just talked to a lot of other coaches about what the services they were offering, what kind of packages they offered, what kind of rates they offered, and modeled it based on that and but I did some experimenting to figure out what worked for me. You know, even things like, am I do I coach weekly? Do I coach biweekly? Am I willing to do one off sessions, or do I only do longer term engagements? And even at that time, when I very first started coaching, I had a sense of who my ideal client was, or who I was sort of specializing in or focusing on, but I didn’t have the name under fulfilled overachievers yet, and so some of that had to come through the doing through that, having the conversations, through the coaching and realizing who was attracted to working with Me and who I was most inspired by, and who I felt like I was the best fit for. And by doing that again, that same, warmer, colder, with clients, with packages, with all of those things, and launching and iterating, as they say in tech, right? I think we need to be launching and iterating in all of life. And so it was going through that process with a lot of input from other people who were already doing it and had more experience than me and then, but trusting what was feeling warmer and aligned for me in particular, knowing, you know, having some basis of what other people were doing, and then getting clearer and clearer about who it was that I wanted to serve, who. I wanted to focus on, and my personal offerings and methodology eventually came from that as well.

Kris Safarova 30:07
What did you find most effective after experimenting in terms of the format of the program?

Megan Hellerer 30:12
So I think that a six month minimum is for a coaching package is unless it’s someone who I’ve worked with for a long time. You know, sometimes people will come back for single session refreshes. But if you’re really looking to do kind of like a life transformation, or really go in depth, I think anything shorter than six months, you’re not really going to see the process through. You’re not going to get the results that you want to get. And even if, and, you know, I have a lot of clients, especially the type of clients I work with, who are like, well, what if we meet, like, twice a week? Can we speed it up? If I do it faster? And I think the answer is, unfortunately, no. I mean, yeah, there are ways maybe that would make it go faster. Um, but the, you know, there’s sort of the world has to catch up with you, right? There’s only, like, so many conversations you can have in a week. And you know, it takes time to do some of this reflection, have some conversations, get more information back, try some new things, get some information back. So I think six months minimum, and then weekly or biweekly. I think either one is depend. It really depends on the person in the situation, and also how much time and capacity one has, I would guess, I would say my most favorite way to work is the first three months weekly, and then, if it makes sense, move to every other week from there for, you know, the next three months. I guess that would be my favorite way to work. And I have some clients who I’ve worked with for eight years and seen through multiple career transitions, you know, different companies, and then founding companies, and so it doesn’t, you know, the work doesn’t stop at some point. Some people just need to, sort of, really want to learn a new approach and a new way of looking at things, and then take that off on their own. But even for those people, it’s there’s no there there. It’s not like you get to you make this one job switch, and then you’re done for life. And I think we want that so badly. But if that is what you’re leaving working with me believing, then we’ve missed something in translation, right? It’s an ongoing process, so, but I think, I guess I would say that is my most favorite way to work is six months, the first three months weekly, and then the second three months every other week.

Kris Safarova 32:25
And what did you find works best in terms of duration of the call with the client? Yeah,

Megan Hellerer 32:31
so I did a lot of experimenting with this too, and I really like 75 minutes, especially if you’re meeting bi weekly, but I think that, but all of my calls are now 75 minutes, I think 50 minutes like a therapy session or even an hour. I always find myself feeling like I’m cutting off the call early, or we’re like in the middle of a thought, or we’re, I don’t know, getting to the end of a juicing and so I really was experimenting with, what is, if we didn’t put a timer on it, what is the time of the call that would sort of like, naturally feel like an ending point and 75 minutes, like, you know, sometimes it’s a few minutes before, but that is what doesn’t feel rushed and feels like it gives you enough time both of you to, like, sink into the call and, you know, really get below the like, catching up and whatever, you know, like the top level stuff, and get to a deeper level, and then sort of move through a process, a thought, a whole theme, or multiple and and be feel complete in a way that doesn’t feel rushed. So that’s the time that I like. And I also will say, one of the things that I love about coaching versus therapy, or at least most therapy in the way I coach, is that it’s not just in session that’s obviously a big part of it, but I’m in touch with my clients via multiple ways in between sessions, I’m, you know, sort of like a 24/7, obviously, I’m not a 911 call, but there’s so much that happens in between sessions, especially when you’re doing these sort of, like intensive six month things or and when you’re really ready and willing, that I want to be able to capture those moments as learning moments like you just had an interview, or you just had an idea, or you just had a conversation, I want to be there to process that with you, or at least make a note of it. And then so I usually have a pretty good sense of already what is going on and what has gone on in between sessions before we get to the call. And then I do have an official, I shouldn’t say official, but like, a check in process, a pre session. We call pre session reflections, that people go through, you know, a day or two before, and some of it is just like, you know, wins, struggles, that kind of thing. But there are deeper questions to like, what’s feeling really raw or vulnerable right now? What’s something that you. Haven’t wanted to admit to yourself or to me those sorts of questions that make sure that I have a really we can, sort of like get really to the core of what, what we need to talk about when we get in session and make the most of that time.

Kris Safarova 35:15
Megan, and when you work with clients over this at least six months period, what the most typical issues you focus on.

Megan Hellerer 35:22
So given that I work with under fulfilled overachievers, and for under fulfilled overachievers, most of the time, they’re coming to me with feeling unfulfilled in work, I say I’m a career coach, because that is usually, if you imagine, like personal development work, as a house. Everyone has some door that they’re going to get in to that house. So for some people, it might be relationships or romance or divorce or something like that. For someone else, it might be health. There are other doors you can walk through. For the clients that I work with, it’s usually career. That’s the thing that feels painful, that’s the thing that’s chafing, that’s the thing that makes them say, I need to ask for help here. I need to do something differently. So that’s usually the door we’re walking through. But it’s never just career. So we’re always looking at life holistically, and whatever showing up at work is showing up in other areas of your life, and vice versa. So people are coming to me, I mean, mostly saying I feel unfulfilled in work, or my work doesn’t feel aligned. And that can come anywhere from I don’t I just like, I just, I have a sense that this isn’t really what I want to be doing, and I’m not sure what to do next. So kind of like a little bit of again disease, like around the edges to I’m having a breakdown, and I don’t think I can show up to this job one more day. What do I do? And anywhere along that spectrum, but it’s typically something is off with my career, I feel unfulfilled. I don’t want to do this the rest of my life. What do I do?

Kris Safarova 37:05
Megan. And when you work with clients, what the usual places where clients get stuck? So they work with you through this six months process. Are there usual places where clients get stuck?

Megan Hellerer 37:16
Yeah, so, oh, there are multiple. I think one is, you sort of mentioned already when we were talking about, you know, the six months, which is, people want it to go faster than it can go. And so there is, like, a patience that has to come with this, and a trust that has to come with this. And I get it. I wish it could go faster too, but we really need to, like, I try to remind you, we’re playing the long game here. We’re not just finding you another job. If you just wanted to go find another job, you would go to a headhunter or a recruiter. You wouldn’t hire me. Or if that’s what you want, don’t hire me. This is like a deeper excavation of work that we’re doing and work that once you’ve done, once it’s ongoing, but it’s sort of like cleaning out your whole closet or something like that, right? If you stay on top of it after that, you never have to deal with, like a huge overhaul or your basement or something like that, right? And so, but this is like a real mindset shift, and the beginning part is going to, it’s sort of like a slowdown to speed up. This is going to that we’re playing the long game. This is going to help you for the rest of your life. You know, I think another place that people get stuck is the making the shift from what I from the old way, the traditional way of doing things that I call destinational thinking, to what I encourage people to shift to, which is directional thinking or directional living. So moving from this linear, outcome oriented approach, where we’re like climbing the ladder, we pick a destination, we reverse engineer it, and we, you know, put on blinders, and we blind ambition, like brute force our way to the top, without paying any attention to how it’s going, or the inputs or the process, or how it feels along the way, or any of those things to this directional living which is focusing on the our inner sense of direction and moving iteratively in the right direction, even if we don’t know exactly where we’re going. And this is a major shift to make, because it is exactly the opposite of what we’ve been taught our whole lives, and it requires getting becoming more tolerant of uncertainty, and that’s the thing, that’s why we like, why it’s so alluring to live in this destination, a way where we’re like, I this is what I’m going to do. This is what I’m going to be doing when I’m 65 and this is exactly how I’m going to get there, because it gives us this sense of safety and security, of like I know what’s exactly what’s going to happen. But the thing is, that’s actually always been a myth. I think, if anything you know, covid has taught us that, that there actually isn’t all the certainty that we think there’s going to be, and the acceleration of technology and jobs and industry. And how much things are changing. It’s hard, it’s hard to believe that you’re going to be in a job, you know, at the same company for 40 some odd years, right? So that that’s sort of disintegrating, but we haven’t figured out what to replace it with. And so I think where people get stuck is they want again, and we touched on this a little bit, which is, they want to figure out their life purpose, and they want to know it, and they want to figure it out once and for all, and then they want to never have to think about it again, and that is never how it’s going to work. So they want that destination. They want that security, and that can get very frustrating. So people stop. They’re like, they just stop. They decide, okay, this is as far as I’m gonna go. This is my purpose. I’m sticking to it. And they end up relapsing in the sense that they end up in the same place again, even if it worked for a little while. What worked five years ago may not work five years from now. So that’s another big place that people get stuck. And similar to that, another reason that destinational Living doesn’t work is that it requires us to be able to predict the future, basically. And obviously, we can’t do that. And so people we kind of suffer from a lack of imagination. Just because you can’t see it or think about or figure out what it’s going to be doesn’t mean it can’t happen. And so people think, let’s say they have an idea. You know, I want to start a company, but they can’t see exactly the path of how to get to starting that company. They shut down the whole idea. So instead of thinking like, Okay, I’m just going to have a couple conversations, or I’m going to drop a business plan, or I’m gonna buy a domain name, or whatever, like, whatever the small step is to keep exploring, they think, Well, I don’t have enough money to do that, or I’ve never started a business, or whatever the thing is. And they shut down the whole idea, and they stop right there. And I think that’s another place that people get really stuck. If they can’t see exactly the path forward, they don’t engage, and that’s one of the key shifts that we really need to make in order to create anything new, is to be in that uncertainty, and most people are wanting to even a life is creating something new, right the way you’re designing your life, and so bringing back that creativity, it’s a completely different experience than the way we’ve been taught to manage our career, which is very risk averse, but I would argue that it’s way riskier to spend to continue to invest in doing work and living a life that you don’t love living than it is to sit with the uncertainty that comes with building a life that you do,

Kris Safarova 42:42
Megan and in working with so many clients over so many years, have you observed specific qualities mindset of clients that get the biggest results and that are most enjoyable clients for you to work with?

Megan Hellerer 42:54
Yeah. So I think I love this question, and I love when clients ask me this question, when they come to me in the beginning, like, what do you know? What is going to set me up for success? How do I approach this in a way that’s going to get me the results that I most desire? So I would say the first two are willingness and open mindedness, and we can control that to some extent, and I have a pretty good gage of it now. And so if I’m talking to someone who I don’t think is willing yet, I will say that. I will say, I think you should come back in six months, or I think you should really reflect on that like I want you to when you’re going to invest in this. I want you to really be ready. And so it’s this, it’s there’s like a Geno se quad to it, like a readiness, but it’s really a willingness to try doing something differently, and again, realizing it’s going to be scary, and you’re not in it alone, and I’m holding your hand, and we’re gonna get, you know, we’re gonna get through this, and this isn’t that doesn’t mean follow me blindly, right? I be skeptical. Challenge it. Don’t take my word for it. Like try it and see how it works for you. You know, I don’t claim to know everything, and things land differently with different people, but we can figure out a way through that. But I think it’s really the willingness to try something new, and the open mindedness if you’re stuck in how you’ve been doing things you can’t change. And so if you’re going to come and invest in this, and make the financial investment, the time investment, all of these things, all of the resources that come with this, the emotional investment, I really ask clients like, are you really ready for this? Do you really want this? And you know, you can always go back to the old way that you were doing things before. Can always go back to consulting. You can always go back to banking. You know, in your case, you I could always, you know, within reason, I’m, you know, could go back to tech or go back to corporate if I if I needed to or wanted to. And again, it’s not just those things. It’s whatever those things represented in my life. For me, you can always go back to those things. But I would say, you know, the open mindedness, willingness and curiosity. Curiosity, right? I think that’s a big one, especially curiosity about self. And then I think this is sort of tied with it, but, or tied into that also, but not having a fixed mindset. You know, there’s the book by Carol Dweck, growth mindset and directional living is very much like a growth mindset for your life. And I think that goes into flexibility, adaptability, curiosity, all of these things. It’s kind of different angles of the same, you know, the same cube, the same box. But I think having, yeah, this to believe that you can change, that the world changes, and not only that you can change, but that you are changing, right? You don’t have to do anything to try to change. You are changing. You are evolving. That is the whole point of this. And so to sort of embrace that and lean into that with curiosity, I think those are the sort of qualities that I think go a long way. And I guess the last one I would say is a sense of humor always helps. Again, that’s, I wouldn’t say that’s a requirement for success, but I think in life in general, especially when you’re doing hard things, and you know, deep work, again, that this is serious, deep work. This isn’t to say that it’s, you know, all light hearted, but it’s joyful, right? The point of this isn’t is to be happy, to be joyful, to be engaged in our life. And so we want the process of doing this to feel joyful as well. And because it’s very hard to get an end result that’s joyful and feels fun and inspiring if you’re miserable the whole time that you’re doing it. So I really try to bring that sort of lighthearted joy. Sense of humor like this is deep, hard work, but it’s also fun, worthwhile and enlivening work at the same time.

Kris Safarova 46:58
In this last few minutes that we have together, can you talk to us about the concept of big direction?

Megan Hellerer 47:05
Yeah, so big direction is what I call my term for purpose, and the reason I have another word for it is what I alluded to earlier, is that many of us, the way that we think about purpose, has become destinational, right? It becomes this goal that we think we’re gonna reach, and we’re gonna cross a finish line, and then you’re gonna have your purpose, and it’s something that you can like, wear like a badge of honor, you can carry around, and you’re done. And so I found that the connotation, or the way that it’s become used, has stopped serving us, or at least the clients that I work with. And so I realized we needed to come up with new terminology. And so big direction is the directional living version of purpose, which means we are moving. You know, there’s one of the best analogies for what it is to live directionally. Is this quote by El doctoro, and he says it’s like he’s talking about writing, but I think it applies to life, too. He says that 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 the whole thing here, right? Is that we don’t need to know exactly where we’re going. We only need to see where our headlights are showing us, and that is enough. And headlights, in this case, is your curiosity, your interests, your joy, those your desires, all of those things that we figure out what those things are. But if we take this car analogy a little further, we also this isn’t about wandering, right? If, like, if we’re taking a road trip, we’re not like driving around in circles. You know, this isn’t aimless. We do want to have a sense of not only do we want to have but we can have a sense of where we’re going. So we want to have enough structure that we know, like I’m heading to the west coast, but we don’t need to know I’m heading to this address in Los Angeles. We just need to have enough of a structure and enough of a direction, and even that can change, right? We’re not attached to it. We’re not clinging to it, but and then we can decide from there, like, what is getting me again, warmer, closer to that big direction, or further away? And you know, an example of this is working with Alexandria Ocasio Cortez. You know, our big direction for her was public service. It wasn’t run for congress or be president or some other thing. There are many iterations of what public service could have looked like for her, but that is her and continues to be her big direction. And so we’re really looking for this like something bigger, something that’s kind of like an umbrella, a loose umbrella term of where you’re heading in your life. And for me, again, it’s something to do with like helping under fulfilled, overachievers find fulfillment. And that, again, can look very many different ways. We could probably even broaden my big direction to something bigger. That’s like, you know, we. Is the meaning of life? Or how do we how does one live a good life? Like those are the kinds of questions, like life philosophy that I’m you know, that I’m asking and thinking about, and I can imagine so many different ways that that plays out. And I don’t need to know what those things are, but I know what my big direction is. Alexander AOC knows what her big direction is. I imagine you have a sense of what your big direction is, even if you don’t know the specifics of every single step and how that exactly is going to play out. And so it’s giving us enough of a sense of where we’re going and kind of looking for purpose patterns, like, what are the patterns in our life that we can sort of say, oh, it’s not even thinking about it to, like, figure it out and decide on it. It’s looking at what already exists in your life and letting it like eMERGE, allowing your big direction to emerge. Like, where is it that I’m heading in the broadest of terms? And so that’s what we’re looking for. And then from there, we just say, okay, is this what’s the next directionally, right step from here again, where are those headlights showing me? And I that’s all I need to know that I’m heading in the right direction. And it’s like the best anti anxiety around seriously, like you don’t need to know, you can’t know, and you don’t need to know, you just need to have a sense of your direction. And I think when we if you can really lean into that, there’s so much more space for creativity and inspiration and originality, and it just feels much more fulfilling and joyful and easeful.

Kris Safarova 51:39
Yes, and not only we don’t need to know, we cannot know. No one can know, because everything can change. We have free will. We’re constantly making decisions, and the decisions and all the other elements around in our world influence where we will end up. But I agree with you. I always think of it in terms of going up backstairs and you only see a first step. You have this flashlight and you can only see first step. You just step on it, then you see the next one, the next one. And sometimes you get someone, you realize, you know what, I actually need to go back and go this way because I went in the wrong direction. But yes, you just need to keep…

Megan Hellerer 52:13
Yeah. That’s a perfect analogy. But the thing is, with directional living, it allows for that, right? It doesn’t see that as a problem. It doesn’t see the fact that you can only see the next step, or you might have to go down and go up a different way or take a detour. None of that is a problem as long as you continue to move, as long as it’s directionally right, and sometimes directionally right is going backwards right or reverse and going a different way. In destinational Living, when we’re thinking in this linear way, anything, all of that would be a failure, right? And it doesn’t allow for those changes. Like everything changes in an instant, the whole world shuts down, or you get laid off, or you get sick, or someone you know, any of these things that can happen, bad or good, that can alter everything. And there are so many small ways that that happens too. But in directional living, it allows for all of that and incorporates it into it. And so you don’t feel like all of those things are a failure, or you’re doing something wrong when you can’t see the next step or you need to, you know, go back a little bit it all of that. It sees that as part of it. And I think that is one of the places that it gives the most spaciousness and easefulness too, because that’s the reality of life, right? Destinational thinking, actually, we’re trying to, like, fit a square peg into a round hole with that one.

Kris Safarova 53:32
Megan, thank you so much for the work you’re doing. Thank you for how honest you are in your book about your experiences that led you to the work you’re doing. Now, I think it can help a lot of people avoid this kind of experience. Where can our listeners learn more about you by your book? Anything you want to share?

Megan Hellerer 53:47
Yeah. So my website is my name, so meganheller.com, m, e g, a, n, H, E L, L, E r, E r.com, and there’s links to buy my book there and to learn more about what is destinational living. And there’s a quiz on, are you an under, fulfilled overachiever, to see if this is something, how this is showing up in your life, and many other things there and then on Instagram. It’s also my name at Megan Heller, and I share a lot of resources there as well. And I hope many of you get to experience this book. I can’t wait for you to read it.

Kris Safarova 54:23
Our guest today, again has been Megan hallera. Check out her book. It’s called directional living. And our podcast sponsor today is strategytraining.com. If you want to strengthen your strategy skills, you can get the overall approach used and well managed strategy studies. It’s a one page we created for us a gift, and you can get [email protected] forward slash overall approach. And you can get another gift if you’re currently updating your resume, and that is a McKinsey nbcgb in resume, which is a resume that got offers from both firms. And you can get [email protected] forward slash resume. PDF. Thank you so much for tuning in, and I look forward to connect with you. It all next time. Thanks for listening to this episode of the strategy skills podcast. Stay up to date on all of our latest training by signing up for our email updates on firmsconsulting.com we look forward to helping you develop your strategy, critical thinking, decision making and communication skills next time here on the strategy skills, podcast, music.

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