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Alexandria Ocasio-Cortez’s Career Coach on How to Find Your Passion

We’re always being told to follow our dreams, but what if your dream doesn’t translate into a traditional career? Megan Hellerer has the answers

By Clare Considine

6 March 2021
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hen Megan Hellerer picked up the phone to call the HR department at Google, her then employer, following a brief sabbatical, she found herself handing in her notice. “If you’d have told me the day prior that I was going to do that, I’d have laughed in your face,” she says, on the phone from New York. “But it was the most honest thing that I had said or done in years.”

Ever the high-achiever, Hellerer had been scooped up straight out of Stanford University as part of a grand experiment by Sheryl Sandberg, Google’s vice-president of sales and operations: “the idea was: hire as many smart people as they could and then figure out what to do with them”. She became a strategic partnership executive. So far, so successful. “But, if I’m honest, I knew on day one that this didn’t feel like home,” Hellerer says. “I got further and further away from myself and it became harder to remember who I was outside of work. I’d arrived there two weeks out of finishing college, I barely took a vacation in the eight years I was there. I was getting more and more depressed and anxious.” She describes regular panic attacks, nausea and difficulty getting out of bed.

“I was so ashamed that I could be so outwardly confident, climbing the ranks, in the best job in the entire world on many lists, and yet so dissatisfied,” she says. “I thought the problem must be with me. How could I be so ungrateful?”

Of course, we know how Hellerer’s story ends. She is now a world-renowned career coach who guided Alexandria Ocasio-Cortez on her journey from full-time bartender at a Manhattan taqueria to the youngest woman ever elected to Congress. But there is no such thing as the end of a story, in the Hellerer school of thought – only an ever-evolving journey on which you can learn to enjoy the ride. “We should be living directionally, not destinationally,” she says.

If the past year has taught us anything, it is that we have no idea what the future is going to look like. With that in mind, Hellerer says, it seems bizarre to try to operate within a societal framework that praises choosing a path and never straying from it: “It’s a very 20th-century, ‘OK boomer’ way of doing things.” She points to the way developments like 24/7 technology have rendered the working world completely unrecognisable from what it was like a century ago. “Institutions want people to fit into an old way of being. But it’s hard to be living destinationally in a directional world.” It’s impossible, she argues, to think about where we want to be five years from now, when tomorrow may be completely different from yesterday.

As women we’re conditioned not to listen to ourselves, in favour of what is harmonising and good for everyone else.

Hellerer suggests that, instead of asking kids what they want to be when they grow up, we should be asking them what they are curious about. And we should carry on asking this question throughout our entire lives. “We’ve been taught to ignore the signs,” she explains. “Especially women – we’re conditioned not to listen to ourselves, in favour of what is harmonising and good for everyone else”.

So it makes sense to release ourselves from the pressure of searching for some kind of definitive calling in life. “The reason it’s hard to define a ‘passion’ is because it isn’t a fixed thing,” she explains. “There’s something called the arrival fallacy – the idea that our brain will figure out our passion, and then we will get to some place and feel satisfied and fulfilled. It doesn’t work like that.”

When Hellerer quit Google, she searched frantically for clues to her next move. "I was going to meditation, art classes, seeing every kind of healer you can imagine,” she laughs. “There was a thread in each one of those things that was helpful, but none of them offered me a holistic, comprehensive package of what I needed.”

The step that turned out to be most beneficial was the least proactive one: “I decided that I was not going to interview for another job, or even update my resumé, for at least six months.”

Hellerer acknowledges the privilege inherent in the financially secure position that she was in to make such a decision. “I sold some Google stock, I figured out the bare minimum I could live on.”

Image by Shannon Roddy

But, she says, she would’ve done whatever it took: “I felt that if it meant I moved to a place where the rent and living expenses were much cheaper, I would happily do that if I could feel free, clear, happy, fulfilled." She remembered being at Google and daydreaming about her carefree days as a waitress. She would do that job again, she says, rather than take a job that sacrificed her happiness.

“I’d made a commitment that I no longer cared about the optics of the situation,” she explains. After leaving Google she’d been looking for her own coach and was dissatisfied with the binary options available (“there were either the woo-woo, crystals-and-tarot coaches, or the executive ones”). So she decided to take a course and coach herself. And she loved it. “But I thought ‘who goes to Stanford and then becomes a coach?!’ It’s not a real thing!”

After six months of suppressing her instincts, she went back and finished the coaching course, taking on friends as clients as part of her training. Six years on, she has her own private practice, an online programme and a book deal.

“There’s a glossary that comes with me,” laughs Hellerer. “I ended up unintentionally inventing a whole vocabulary.” Her turns of phrase can take a moment to get used to, but they have a purpose: “We actually don’t have the words, in the English language – we need a new terminology to name, identify and talk about these new concepts”.

So, with that in mind, let’s step into Hellerer’s universe. What she is suggesting is something quite radical – almost anti-coaching. She wants you to scrap your plan, and to deliberately not make a new one.

So, let her guide you through the five core phases of the Hellerer methodology:

Image by Shannon Roddy

Unlearn

“That is about really figuring out: how did you get here? How did you get to this point that you feel stuck? Do a basic inventory of what is working in your life and what isn’t working. Ask yourself: what have been the things defining my decisions to this point? We’ve all been sold these myths about our careers. There is the structure in place that’s keeping us stuck. Consider your beliefs about work. Which parts are genuine values and which are things that you picked up along the way that need to be updated?”

Align

“We have a true self, and a fear self. I call it the true self because there’s a term in carpentry – ‘to true’ – which means to restore to accuracy. And that’s what we’re doing in this process. Our fear self is running the show most of the time, trying to keep us safe.

“You need to figure out your inner compass: your intuition. It tells you what your personal direction is. The difficulty is that society is a big magnet which has distorted our compasses. We’re told: ‘just follow your passion, follow your bliss’. For many of us it’s not that we know and are too scared to go after it; it’s that we have no sense of what it is. We need to learn how to trust our own inner compass.”

Navigate

“This is where we learn what directional living is. Destinational living – pick a plan, climb the ladder – is what’s been killing us. All we need to do is play a game of warmer/colder with ourselves.

“Take the example of my life. I was thinking: what direction do I want to go in? Towards psychology? Stay in tech? Pursue writing? My only job at that point was to check in with my inner compass. Which one of those directions felt warm and light, not hard and heavy?

Release

“Next, we map out our personal world and make a hypothesis of where we’re going. It’s a scientific method, applied to your life: you come up with a hypothesis, but the goal isn’t to hold stringently to it. It’s just a starting point and the goal is to find the truth.

“To do that we need to identify all of the HAYWALTs: ‘How Are You Walking Around Like That?’ These are the things that cause us pain that we just adjust and get used to. Go through all the parts of your life – every meeting, every coffee, every Zoom happy hour – and find each one that feels hard and heavy. It doesn’t mean you have to get rid of it, but make a pile of these things and start to evaluate and have a conversation around them. Once you start to identify HAYWALTs, it’s so hard not to see them everywhere.”

Image by Tracy Dungo

Activate

“This is what I call ‘make it real’. It’s five really simple steps. Firstly, get into the practice of paying attention to your thoughts. It could be as simple as: ‘I want Thai for dinner.’ Maybe you’re a 60-year-old and the idea is you want to be a doctor. Just because you have the thought, doesn’t mean you’ve committed your life to medical training, it just means there’s something in there that needs exploring.

“Next up, capture those thoughts. People often have ideas in the shower. When you come out of the shower, say the idea to your partner or roommate or dog. The first time you have the idea, it might feel too scary to pay attention to it, but get it out in the world with your voice, or on paper.

“Then, do some research on it. It can literally be Googling it. With the doctor analogy, it might be that you Google other 60-year-olds who want to become doctors. All you’re looking to do is move the platform forward.

“After that, have a proper conversation about it. In the case of the doctor, it might be that a relative works in medicine – have a chat with them. Again, no commitment here: these are all very low-stakes actions.

“Lastly, take an action, any action. The next idea in wanting to be a doctor is not to go to medical school. Read something, listen to something, go to an info session at a school… Obviously the pandemic changes a lot of things, but if you’re talking about quarantine, it doesn’t matter – you can apply this framework to any idea. There are so many things you could do to start moving things forward that do not even require leaving your house. Just go get some information.”

And now, look to the future…

Hellerer’s long-term hope is “that I work myself out of a job,” she says, without hesitation. She sees a future where we “de-HAYWALT on a daily basis”, where “you’re staying so aligned that your inner compass doesn’t lead you very far astray”. In simple terms, Hellerer doesn’t want anybody to go through what she went through: “no ‘game over, start from scratch’”.

“We transform our career on the way to transforming our life,” she says. “Imagine a world where everyone’s doing the work we’re suited to do. All of us benefit from that”.

Main image by: Shannon Roddy

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