How Underfulfilled Overachievers Can Find Career Satisfaction
August 26, 2021
Megan Hellerer is the founder of Coaching for Underfulfilled Overachievers and the author of the forthcoming book, Directional Living: The Underfulfilled Overachiever’s Path to Fulfillment in Work and Life (2022).

Through her proprietary Directional Living Method, Megan leads people through transforming their careers by shifting from a blind ambition to an aligned ambition. She has been featured in publications such as New York Magazine and The Times of London and has contributed to CNBC, The Wall Street Journal, Refinery29, Well & Good and Business Insider. Here, she shares how following your curiosity and pursuing joy will put you on the path of directional living.

What are the essential questions to ask yourself when it comes to career fulfillment?

The first question is: If you came across a career fulfillment genie who could grant you one wish, what would that wish be? My second question is: if this was the most productive, inspiring, inspirational, life-changing, transformative article you’d ever read, and you walked away feeling like everything was exactly as it should be, how would you know? How would you know if everything was perfect in your life in your career? What would that look like on the outside? What would feel different? What would look different? My final question is: how would it feel if you were perfectly fulfilled, whatever that means to you? How do you imagine that would feel? How would you know that you are fulfilled emotionally, physically, mentally and spiritually?

What does it mean to be an underfulfilled overachiever?

If you resonate with the term underfulfilled overachiever, at least to some extent, you’re either feeling completely stuck and lost and miserable, as was the case for me. Or you feel like there might be something more, and you want to step even more fully into what would be the most impactful, aligned, fulfilled career that you could have.

A lot of us are in transition right now. So if you’re here and asking these questions at this time, I often say the breakdown is also the breakthrough. If you’re here asking these questions, you’re seeing something compelling and transformative at this moment. If that’s you, I want to acknowledge you and give you props for being here and asking the questions that not everyone asks.

What is directional living, and how does it differ from being goal-oriented?

We need a paradigm shift in how we think about doing and finding our work in the world. I offer that we need to shift from the 20th-century career paradigm, which I call destination living or goal-oriented to what I propose as the 21st-century paradigm or directional living.

To understand what the shift is, I want to first look at what it is not. It is not thinking of careers as linear 10-year ladder-climbing plans. In those types of plans, you make your goalposts of success, and then you reverse engineer it. The problem with that is, it supposes the world and us as individuals and the future are fixed and knowable. And it’s neither of those things.

A new way of being in the world is the directional approach. This is where you build your individual life, one that is particular to you and no one else. One that is uniquely well suited to you in the world. And actually, one of my favorite ways to describe this method is via an E.L. Doctorow quote, he was actually talking about writing, and I’m paraphrasing a little bit, but he says, “Living is like driving in the fog at night, you can only see as far as the headlights in front of you. But you can make the whole trip that way.” That’s what we’re doing here. We only need to make decisions based on what we can see, which is the headlights in front of us. We cannot see further than that. The only question we need to ask ourselves is, what is directionally right? What is warmer, colder? What feels like the single next step? We are reliant on our inner GPS.

What are some ways of thinking that people can keep in mind when utilizing directional living?

I have two mantras or slogans that I teach people. The first is to forget your purpose. Forget imagining what it is that I am meant to do here. You will short circuit, you’ll blow a fuse and you will stay stuck. Not important to us. Forget your purpose and follow your curiosity. We tend to think curiosity is irrelevant. Or a distraction. It is a distraction. It’s a distraction from blind ambition. It is the best proxy we have for our purpose. If you can, stay grounded in that. Look at what you’re curious about and follow that. That is the number one thing I would love to leave you with regarding shifting to this directional approach or simply trying it on and seeing if it works for you.

The second is to take the path of the most joy. We also tend to think that is irrelevant in terms of career. Another way of saying this is to take the path of most ease. What brings you joy and what feels the most useful for you is also what is directionally right for you. Curiosity and joy are the building blocks of aligned ambition and aligned achievement. Aligned ambition and aligned achievement are what lead to directional living. It is what leads us to fulfillment and purpose.

The last thing I want to leave with you is a quote by Annie Dillard, “How we spend our days is, of course, how we spend our lives.” It’s a simple reminder of why following my curiosity is important and why the path of joy matters.

How do you actually get in touch with your inner GPS, to use your road trip analogy?

Think of someone who you trust and what that feels like in your body. You feel more relaxed. You feel more grounded. Your breathing slows down. You can think more clearly. There’s less fog and fewer racing thoughts. That’s the first place to start. Then you can do this sort of warmer or colder exercise by feeling out what feels right to you. For example, imagine a puppy, it goes to the people it likes, and it’s not going to go to the people it doesn’t like. It’s that simple.

How do you go about making these directional choices if you can’t quit your current job for example?

It doesn’t have to be a huge dramatic thing. It could be one small step that feels directionally right. The next action of following your directionally right steps can be taking a training course, reading a book, or listening to a super affirming podcast in terms of figuring out what fills you up and gives you energy. Take the smallest step, anything that is following your curiosity, no matter how small it is. Even if you don’t know how it connects to your purpose or career, just start taking those steps.

If you are following your curiosity but have now ended up with varied work history, how would you translate that experience into financial opportunities?

I think there is a thread if you were truly following your curiosity. If all of those things felt resonant and aligned for you, then there’s a thread through them that will lead you to the next thing. Most of us tend to think, especially if we’re unhappy in our career, that we will have to quit, stop everything, and start all over from scratch. I don’t think that I’ve ever seen that to be the case. So I would start by thinking about what is the common thread in all of this. Keep following your curiosity even if it doesn’t make sense. It’s like following the breadcrumbs. At some point, it is going to make sense why all of those things came together.

As individuals, we are allowed to grow and evolve and change and learn and become, rather than have to be in a fixed state and know who we’re going to be in 10, 20, 50 years. 2020 was a perfect example of the fact that the future is not fixed and knowable.



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