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Success Exchange

Megan Hellerer Can Change Your Life

Feeling wobbly about your career? An underfulfilled overachiever? Revisit our interview with the former Google executive who helped transform the future of US Congresswoman Alexandria Ocasio-Cortez


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Dear Reader, have you ever thought to yourself: “What The Fuck Am I Doing With My Life?” My guess is, probably. At some point. Maybe you’re even thinking it right now. Which is where Megan Hellerer comes in: hailed as an ‘anti-career’ career coach for “under-fulfilled overachievers”, she is a professional fairy godmother on a quest to empower millennials to find their unique path, set goals and, ultimately, thrive. The New Yorker’s unique approach is directional rather than destination-led (in other words: scrap the 10-year-plan, burn it, good riddance). One of her most notable clients is Alexandria Ocasio-Cortez - the youngest woman to serve in the United States Congress, TIME magazine cover star and arguably one of the most influential people of 2019, if not the decade - whom she first met four years ago at a live workshop (more on that later). “Your guidance, help, and support was pivotal, in a time when I felt very lost,” reads Ocasio-Cortez’s glowing testimonial. “You helped me reframe a lot of my thinking and were part of a series of events that culminated in the big adventure of a Congressional run … and win! I opened a door I didn’t even know existed.”

image | via instagram @time

“Your guidance, help, and support was pivotal, in a time when I felt very lost” - ALEXANDRIA OCASIO-CORTEZ 

Speaking with Megan over the phone - from her home office in Greenwich Village, which looks out onto Washington Square Park - her buoyant energy is completely infectious. “I think a lot of people in previous generations have tolerated careers,” she says. “The thing is, they were able to do that better than we can, because they weren’t always on.” Enter: Generation Burnout, a large portion of society craving change before they’ve hit their thirties. A big part of Megan’s coaching philosophy is helping her clients find their “inner GPS,” rather than pursue (to paraphrase one Love Island-er) what looks good on paper. Importantly, she practices what she preaches, after leaving a six-figure salary job at Google with no back-up plan.

“I had what they call the gift of desperation,” she laughs. “I was at a breaking point. All the methodology I use came from my own experience, but I didn’t have these words ahead of time. I simply started experimenting. In tech companies we call it launch and iterate - it’s a similar thing. [Future me] looked like so many different things: starting a meditation practice, doing a lot of reading, journaling [and] taking all sorts of classes. Really, I grabbed onto anything that sparked my interest. We need to reclaim that sense of playfulness - play is creativity, it’s deeply relevant.” Fulfilment in your career, she says, is when it can look like “both success and joy - but have to start with the joy part.” Through a confluence of events, Megan found a career coaching school in New York, and hasn’t looked back since. “I became what I needed and couldn’t find.” Here, we’ve picked Megan’s brain on a range of topics, from the art of playing a game of “warmer/colder” in every aspect of our lives and the myth of impostor syndrome to how to silence your “fear self.”



Most of us feel like we have to know that destination or passion. Like, define it in one sentence, have your mission statement or whatever the hell it is before you can begin moving forward. And I think that does such a disservice to us, because there’s so little credit in terms of what we know about ourselves and how responsive we can be. It also assumes that the world is, and humans are, static; that we can anticipate what the world is going to look like in ten years, and we know what all the opportunities are going to be in that time. It doesn’t allow for the opportunity to grow, to change your mind, to learn. All of these things that are part of what it means to be fulfilled. My biggest pet peeve is to say you’re either a ‘starving artist’ or a ‘rich sell out’ – I believe strongly that the more you are doing what you are uniquely well suited to do in the world you will have more impact and contribution, which adds more value, which means more compensation.


What differentiates me from traditional ideas of career, is using your intellect to define your career. In reality, what I’m trying to do is shift out of that intellectual place - because so often we drive our careers through a place of fear, of protection. That is not where you have the new, disruptive, creative, entrepreneurial ideas. That’s not where fulfilment comes from. Traditionally, we have said “it’s not about how you feel,” we’ve been told to do the hard thing. All of that means looking externally for information. Part of finding your inner compass, is a sense of unlearning and recovering your alignment. People said to me when I left Google, “just follow your gut!” when I was really lost and I was like, “If I knew what that was I would have done it already!” [laughs]. We’ve been suppressing this feeling for so long so we need to learn how to cure that. To do this, I would start off simply by asking yourself on a daily basis - what do I actually want to eat right now? Or, what do I actually want to wear right now? Is it because I really love this thing – [or] to use the words of Marie Kondo, because it sparks joy? Or, am I doing it because I think this is something I should wear in this position? Start small is one way, and to think about this idea of warmer or colder, to try different things on and to think about different decisions in this way.


Alexandria Ocasio-Cortez’s story started from a much humbler and more uncertain place. It wasn’t like, “I’m going to run for congress and change the world” - it was about understanding a lot of the things she had internalised and inherited these myths about herself before figuring out what felt directionally right. I first met her about a year into my practice, in 2016, at one of my first live group workshops. She is an amazing example of the directional approach, which is my unique coaching style. It’s the complete opposite of the traditional approach, destinational style - which is, “I’m going to be a partner in a law firm by the time I’m 30 and I’m just going to put my head down and do it.” You are following the course, blindly. Alexandria [felt] “there’s some bigger impact or contribution that I want to make.” I didn’t know what it was at the time. But her feeling was, as well as everyone else in the room, that we’ve been taught that you have to figure out what the destination is. In other words, she had to decide, I want to be a politician before she could make any moves. The reality is exactly the opposite - it’s saying to yourself, “I don’t know what these things will be, but I’m going to take an action and let go of the result.” Enjoying things, just because. For Alexandria, it was going to Flint - a city whose water had been poisoned by lead - and visiting protesters at the Standing Rock Reservation and there she met the people who encouraged and supported her in running for congress. Remember, that when me and her started talking it was before the 2016 US election. Meaning we all thought that Hillary Clinton was going to win - none of us could have predicted the result. And that’s what I mean when I say the world is not static. It’s more important to take just one step towards your curiosity.


Impostor syndrome has become this widespread thing where people just accept it as something that happens when you’re an ambitious person and I find that to be completely false. That doesn’t mean you’re not going to encounter fear (and, in fact, that saboteur voice is going to get louder the closer you get to doing something that you really care about, because it wants to protect you from failure and humiliation) but, if you are doing something that is uniquely suited for you, you don’t feel like an imposter, because you aren’t one. Take me at Google. I felt like an impostor the entire time I was there - the reality was I was an imposter. I was living a great life, but it wasn’t my life. It was a great job, but it wasn’t my job. I was performing this other self. There’s a difference between imposter syndrome and feeling some fear.


I have an acronym called a HAYWALT (How Are You Walking Around Like That), and this is something I work with my clients and on my course. The genesis of this story is that, essentially a friend of mine had really bad headaches and she was putting off going to the doctor because she was so busy and eventually got used to the fact that she had headaches and took Advil (Ibuprofen) - because we as humans adapt to anything until it gets so bad. Eventually she went to the doctor and he said “how are you walking around like that?” and she had this incredibly bad sinus infection. When she told me that story I laughed, because I thought we do that in so many areas of our lives - we start to lower the bar and think “well, I guess this is just what work should feel like?” and eventually you don’t even realise you’re in pain anymore. I think that’s one of the things about social media, first identifying accounts in this way, as a HAYWALT, anything that does not make you feel not excited, not awesome, not light and right. That that applies to anything: your job, social media, specific accounts, your family and friends, what you’re eating to what workouts you’re doing.


Instagram can be a tool for recovering our curiosity – you don’t need to eat, pray, love around the world. For me, it’s a powerful, educational tool. I have to think why am I there (Instagram)? For me, it’s about being of service, so as long as I am coming from a place of service [and] sharing content, this is my offering. I feel good about myself. I want everyone to have these skills - if it’s from me, awesome, if someone else, also awesome. I ask people what is the thing that you go down the rabbit hole on Instagram? Not the thing that makes you feel crappy about yourself, whether it’s body shaming or feeling smaller as a result of…that I’m not interested in – but rather, who are the expanders? Who sparks joy? If you can start curating your feed to be those things, that’s actually a really compelling thing. Ask yourself, “do I find myself looking at home decor all the time?” You want to pay attention to this, for practice. Maybe it would be something as simple as becoming an interior decorator, but maybe it’s something different – for example, learning you have a real passion for woodwork and colours, going into real estate or perhaps studying art history. It causes a lily pad approach - we don’t know where it’s going to lead.


You should dress in a way that is aligned for you - we should never self-abandon for the sake of someone else. Meaning, you want the impression and the perception to be aligned with your true authentic personhood. We know what that is - not by what it sounds like, but what it feels like. I think it’s OK to fake it until you make it in some capacities, if it feels directionally right. For example, if you want to be a lawyer in a law firm and you find trying on a suit makes you want to throw up every day and it doesn’t feel right for you, that says something very important. Or someone might move to a new city and discover that everyone has a pixie haircut and that’s the ‘cool’ thing to do and you don’t know if that’s you, so you might try it to fit in and discover it’s not you. Sometimes we need to try things on, literally and figuratively, to know if it’s warmer or colder. To me, the important part of ‘dressing for success’ is to see it as an experiment and give yourself permission to change and to learn from it. Am I someone who wears a jumpsuit? Of course, that’s not an existential question, but it goes back to where to you begin. You begin by asking yourself these low-consequence questions to really feel into what you want and once that happens, you can do the exact same thing about whether or not to leave your job and it won’t feel any different.


I thought there was some virtue in being too busy or too stressed out. This is not healthy, but aside from that it’s actually not productive. What we need to say to ourselves is that is not to your professional advantage - and that is not where creativity comes from, that being new ideas. What is actually selfish is not taking responsibility for your own happiness and fulfilment. Because if you’re not doing it, someone else has to.

A lot of people say, “Oh I can’t quit my job because what will my team do? They rely on me.” That’s a valid fear. But if that is a job that you are not uniquely suited for then you are not doing anyone on your team any favours, so I say donate your job - for someone else out there it is their dream job. We have different rules for relationships and the stories we tell about love and marriage versus our work. You would never say “yes, you should stay with this person you are not in love with because you are so loyal to them.” Yes, it is hard to break up and it is going to be hurtful, but in the long term that is so much better for both parties involved. Donate the person into the world so they can find their most aligned partner — it’s the same idea here. No-one says when you’re 20-years-old, figure out who it is you want to marry and put on blinders based on what it says on paper. We are all about that match and finding our soulmate, so why don’t we have the same idea in career? I think we can learn from both sides of things. And understand that you never stop growing.

For more information on Megan's online coaching courses and private practice head to her website here.

Images | courtesy of Megan Hellerer

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