How to Swap Big, Confusing Career Goals For Small, Fun Experiments

An interview with "Directional Living" author Megan Hellerer

Photo c/o Megan Hellerer

For the past year, I’ve been struggling a lot with decision making. Even though I’ve taken on several new interests with enthusiasm, choosing my next big creative project has been difficult. I keep starting books and then stopping them. I keep choosing ambitious goals and then abandoning them. What’s going on with me?

Then one day I got a press release about a book with a very intriguing title: “Directional Living: A Transformational Guide to Fulfillment in Work and Life” by Megan Hellerer.

Normally I ignore these kinds of emails. Personally, I don’t love most self-help books. The ideas feel too simple, all sugary slogans with no nutrition. Or there are endless stats and real-life anecdotes but it all adds up to thoughts that could be summarized in one short essay. Or there’s a lot of empty positivity and not enough concrete guidance. I spend the whole book thinking, “GET TO THE POINT ALREADY!”

But not this time. Not only is Megan Hellerer’s writing sharp and succinct, but she dives straight into a problem that so many Ask Polly readers struggle with: How does an anxious former overachiever build a life that feels rich and relaxing instead of just crossing arbitrary items off an alienating to-do list? How do you make career decisions when every big goal starts to feel oppressive within a few days? What do you do when, after making all the “right” choices for years, you still feel unhappy with your life?

Hellerer’s approach seemed so practical, but I wanted to know more, so I talked to her on the phone and then emailed her some follow-up questions. Her insights have already helped me so much — more on that later! — so I’m very excited to share them with you!

Megan, in your book you describe how you always made the seemingly “correct” choices when you were younger: good grades, good scores, Stanford, then a job at Google. I think what people sometimes miss when they talk about the culture of overachievers is that there’s a kind of deeply internalized moralism to these selections, like only someone intent on betraying themselves and ignoring their gifts would choose a less ambitious path. How hard was it for you, when you were younger, to make choices that fell outside of what was seen as impressive?

I’ve been really puzzling over this question because I don’t think it even occurred to me that there was a choice in the matter. It’s not like I was deliberating between a more impressive and less impressive choice and couldn’t let myself choose the less impressive one. I truly didn’t conceive of anything else or any other way of being. And not all of my choices and actions were misaligned either.

Stanford is an interesting case because it was actually a “rebellious” choice for me, instead of an East coast Ivy League that was more expected, which is just ridiculous.

So, how hard was it? Close to impossible. I tried for at least six of my eight years to get myself to leave Google, coming very close a few times and then being unable to actually do it. I had to be so profoundly unwell that I essentially had no choice in the matter.

How long did it take for you to overcome that external ruler of achievement in order to follow your own map? Do you still hear echoes of that overachiever’s moral code inside your head today?

Dropping that underfulfilled overachiever mindset took a very long time. When I finally quit with no plan, I had what some people call, “the gift of desperation.” I was in so much pain that I truly did not care at all if my life was impressive, if it meant that I would be happy. I remember being jealous of a happy-seeming waitress at the corner cafe and truly wondering if that was the right path for me. If I thought it would lead to peace and ease, I would have done it. Not that there’s anything wrong with working in food service or hospitality, but it’s a far cry from what would be acceptable in my previous framework for life. I remember researching the cities with the lowest cost of living and really thinking about re-working my entire life — and as a born-and-raised New Yorker, that was a BIG deal to ponder.

Another answer to the “how long?” question is that it took about a year from when I left Google until I started my coaching practice, committed only to give it a try for six months and see what happened. But, even then, there was a lot of ego and fear saying things like “Who goes to Stanford and becomes a coach?” So even as I was starting this new path that was totally lighting me up and absolutely terrifying, I was still battling the underfulfilled overachiever in me. I think it was probably another year before I was fully confident in my path and felt proud of it and felt like this was my version of success and was just as worthy of a path as any other I might have chosen.

Publishing a book put me back into that position where there was ostensibly a way to measure success — akin to As in school —and comparative success at that. I thought I was cured, but suddenly, here was my old friend achievement wound showing up again, wanting to determine my worth by book sales, which, candidly, I did not expect! I probably should have, but I didn’t see it coming.

So, yes, while I wish I could say the exorcism was complete, I’m still working on it. The underfulfilled overachiever mindset pops up when I am doing something vulnerable and that I care about deeply, like publishing a book. In these moments, my brain believes that being measurably “the best” — straight As, high sales numbers — will keep me safe. On the flip side, anything less than “perfect” sales numbers — which, of course, doesn’t exist — means failure. So you can see how this all falls apart quickly and failure, in the framework, is pretty much guaranteed. (I see this all the time with clients, too.)

The difference is that now I can spot it a mile away and I can even feel it in my body when I’m coming from this place. And, I don’t buy into it, which doesn’t mean it’s comfortable or pleasant, but I don’t make decisions from here anymore and I have a lot of other saner, more accurate internal voices to counteract it.

You describe this feeling of deep despair that would overcome you in the bathroom at the Google offices. What was it about the practices or the setting or the tone of interactions in that world that dragged you down? I ask this as someone who was absolutely floored by how depressed and confused I felt at my first office job. Even when I was being offered a fast track to a high-level job, I felt ill over it.

I’m not sure that it was anything universally wrong with the culture, but it was certainly wrong for me. I often talk about how I think we get imposter syndrome wrong. I felt like an impostor at Google but it wasn’t because I thought I was secretly bad at my job. It was because I was being an impostor — I was performing being a “Googler” tech exec person when that is deeply not who I actually am. If we’re doing work, or being in relationships, or behaving in ways that are misaligned, we are going to feel like an imposter because we are faking it in our own lives.

I can point to the specifics that didn’t work for me, but I think the bigger point is just that it was just not the right fit for me, and that fact, and the fact that I ignored that and tried to convince myself otherwise for so long, was what was so debilitating.

Specifically, I’ve since learned that I love working for myself and do not like working for other people. I also am much more introverted than I understood at the time and working in an open office environment was pure hell for me and drained me of all of my life force. I also, frankly, did not care about the work we were doing and the impact we were having (with a few exceptions) so it always felt pretty pointless. That doesn’t necessarily mean it was pointless, but it felt that way to me.

Did you do summer internships at corporate offices and if so, did it give you any glimmer of what came next? What do you think might help college students attune themselves to their truest desires rather than using an external compass that tells them what they “should” do with their lives according to other (sometimes deeply dissatisfied) overachievers?

I did summer internships in journalism in college — working for NBC Nightly News and The Village Voice — since that’s what I thought I wanted to do, but that wasn’t feeling exactly right and as I got into my senior year I had no idea what I wanted to do. I got scared and felt like I suddenly need to grow up and get a serious job and also I needed to make money. Google was still pretty small but was growing a ton and in their prime “hire smart kids right out of college to do basic customer service work” era and I applied on a whim and got offered a job through a series of synchronicities. Google actually felt like the counter-cultural thing to do at the time (versus finance or management consulting).

The trouble wasn’t necessarily that I took that job — I learned a lot and it was a good career experiment. It was that I couldn’t make a change even when I knew it was wrong for me.

For college kids looking for jobs, I actually love internships, as they’re great low-stakes ways to experiment and test and learn. They help to take the pressure off. You don’t need to get the perfect internship that’s going to determine the rest of your career. It just needs to be directionally right. So, make sure you’re making these decisions, as always, according to what excites you and compels you, not what you feel you “should” do or what it will get you or where you think it will lead.

When you got into coaching and started to witness people learning to live directionally instead of destinationally, what did that look like? What were the markers and side effects of directional living in contrast to what they’d always known?

I often joke that Directional Living is the absolute best anti-anxiety drug around! Because the first thing that people report, and I observe, is less anxiety about the future and more ease in decision making, big and small. There’s less overthinking and rumination and more excitement about the future and what’s possible. There’s more general contentment and enjoyment of life. They’re more present and more at home in themselves. They feel free. They’re empowered.

Stage 2 is more authenticity, more self-expression, more creativity, and more inspiration, which are all side effects of beginning to in-source life decisions instead of outsourcing them. This leads to greater impact and contribution to the world around them.

Then, I start to see that show up in better and deeper relationships of all kinds — with more authenticity and self-trust comes more intimacy and connection.

And finally, the most incredible thing to see is it ripple out to people around them. Others start to become more free and more joyful and more inspired and more connected themselves.

When a huge, impressive opportunity presents itself to you and you have a gut feeling that it isn’t what you love but it fits neatly into your former overachiever’s value system, are you ever tempted to do it anyway? What have you witnessed happening to people when they fall prey to lucrative or high-status paths that they don’t necessarily love or want?

When people follow paths that they don’t love or want for any reason, they end up with “The Fulfillment Ache,” an existential and psychic pain that shows up when there’s distance between who you actually are and how you’re showing in the world. It typically doesn’t go away on its own. It only gets worse. It’s not there to be an asshole and to make you suffer for no reason. It’s there for the specific purpose

It shows up for different people differently, but some common places it leads are mental health struggles — anxiety, depression — chronic illness, and addictions of all kinds.

I know what this feels like and how painful it can be. I’ve made a serious commitment to living in alignment for all the incredible benefits that it brings, of course, but also because I want to do anything and everything I can to never be in that kind of avoidable pain again.

So, for me, if I’m ever tempted to override a knowing that something isn’t right for me, I remind myself of the cost of that decision and I ask myself if it’s worth the risk of that kind of pain and consequences, and the decision becomes obvious.

I have, for example, said no to media opportunities that didn’t feel aligned.

The first time that I started exploring writing a book, working with an agent and writing a book proposal, I was so excited and eager to get started. I had my “Directional Living” framework and I felt really clear that I wanted to write a book. And yet, it felt all wrong. It felt so forced and I felt like I was banging my head against a wall. So, I trusted that, even though I didn’t totally understand why and I was disappointed that it wasn’t feeling more “light and right,” and I put it down. A few years later, with some more public traction on my work, an agent who is an incredible fit for me found me and the proposal process flowed much more easily.

I’ve also left opportunities that I thought were aligned and turned out to not be. I was one of the original coaches for a well-known elite women’s executive professional membership community. It looked great on paper and paid well, but after a few months I realized that it just wasn’t aligned for me for a variety of reasons — mostly that we had completely different philosophies when it came to coaching, So, at the earliest responsible moment, I left.

The other thing I would add is that it’s usually not so black-and-white where it’s a lucrative and impressive opportunity and everything in you is screaming “no.” If you’re not sure, it’s usually because you need more information. So, ask more questions. Try to determine what would make it a definitive “yes” or a definitive “no.”

Lastly, nothing is permanent. Another strategy if it’s something that has a lot of upside but something in you is saying no, is to try it out. While this isn’t always possible, if you can do a trial period of sorts, which is usually the best way to get clear if something is aligned for you or not.

There’s also a funny (and wonderful) thing that happens: The more aligned you become, the more aligned the opportunities that come to you become. So, if you’re early in this journey, I think it’s helpful to know that it gets easier and simpler!

In contrast, how can you tell when a person is aligned with their curiosity?

I always say that being an underfulfilled overachiever can only be self-diagnosed. You can’t reliably tell from the outside how aligned something is for someone. For example, working at Google was decidedly not aligned for me; however, I have clients for whom it was deeply aligned. For me, writing a book was very aligned and felt like writing this particular book was something I couldn’t not do, but I know people for whom it was a very big “should” and a miserable process every step of the way.

So, you really can’t tell if something is aligned, unless you have access to someone’s inner world, which I am privileged to with my private clients. So, in that context, the energy is what I describe as “light and right” instead of “hard and heavy.” When I get to know someone, I can tell from their voice, their mannerisms and expressions, and just their overall energy when something is “warmer” and moving in the direction of becoming more themselves instead of “colder” and moving away from who they really are.

There’s an aliveness that comes with curiosity and alignment that once you see it, you can’t unsee it!

Why do you think the instruction to “follow your passion” sometimes leads people astray?

It’s a lot of pressure to feel like you have to find your one deep passion that you can devote yourself to for the rest of your life. And pressure tends to keep us stuck, not inspired. If I ask someone who’s trying to figure out WTF they want to do with their lives, “Well, what’s your passion?” they’ll typically blow a fuse, short-circuit and go into freeze. This is obviously not helpful. Furthermore, we tend to think this is something that we can figure out if we just think harder and longer about it. But clarity comes in motion, not from sitting still and thinking more. So, we want to get into action and I’ve found that “follow your passion” tends to do the opposite.

Second, if you do find something you’re passionate about, we tend to think it’s a permanent destination where we arrive once and for all - somewhere you’ve landed for good and then you “set it and forget it” and forget to keep evolving. And we end up stuck, again.

Passion feels so grand and intense and it often isn’t like that in practice. Most people don’t have the skies part and their passion announced to them from on high. We often imagine that we’ll be struck by lightning with passion one day and we sit around waiting for that fateful day to happen, when instead it starts with a tickle of curiosity. Curiosity and joy are our best proxies for purpose, and we often miss that looking for capital-P Passion.

I love how you compare directional living to driving a car in the dark and only being able to see a few feet ahead of you. You explain that no one knows what a grand destination will feel like, they only know what lights them up and makes them more interested, more engaged, more curious. So the best bet is to keep creeping forward, following those headlights, noticing how you feel and what you want next. Why does this work so much better than big schemes and plans?

Big schemes and long-range plans assume a level of certainty about ourselves and the world around us that just isn’t real — see AI, COVID, the US government, the economy etc. They ask us to predict who we’ll be, what we’ll value, and what will fulfill us years down the line, before we’ve actually lived the experiences that shape those answers. Directional Living works better because it reflects how humans actually evolve. You don’t need to know where you’re going — which is impossible even in more predictable times — in order to begin. And you can make the whole trip that way.

When you pay attention to what gives you energy, curiosity, or a sense of aliveness now, you get real-time feedback. That feedback is far more accurate than any abstract five-year plan made from your head instead of your lived experience. It allows you to be responsive to the changing environment inside, and outside, ourselves. Creeping forward lets you course-correct as you go. It keeps you in motion without locking you into a version of success that might look good on paper but feel deadening in real life. Over time, those small, responsive steps don’t lead to randomness. They add up to a life that actually fits you, because it was built in conversation with who you were becoming, not who you thought you were supposed to be.

Counterintuitively, it’s actually so much more effective and efficient than the linear, long-term guaranteed plan approach we’ve been taught to follow.

I know you’ve probably worked with a lot of productivity-obsessed current or former overachievers like myself who start to feel anxious when they don’t have a big-picture plan. What do you do to keep your coaching clients calm and focused on the present? How do you explain to them that this practice isn’t just about finding the best path to success, it’s actually something that will teach them how to bring joy into their lives right now?

I actually don’t explain to them! I let them find that out through living it. Once they start living this way and experience how much more ease, peace, joy, lightness and presence they experience as a result, they won’t want to go back.

There’s an expression in recovery groups that says, “We can always refund your misery.” I often suggest to clients to try this approach as an experiment. Give me three to six months to start, and you can always go back to what you were doing before, if you want! (You won’t want to.)

But, this is also the magic of focusing on the single next directionally right step. It forces you into the present — no meditation required.

How can you tell when a client is suffering for “good” reasons, i.e. they’re grappling with the difficulties and even anxieties of a truly worthy, life-altering challenge?

I love this question and this distinction because so many of us were raised with the idea that the harder it is, the more worthy or impressive it is. I have so many people come to me and say things like, “I chose my major because it was the hardest thing I could think of.” And that’s not the vibe. We don’t want hard for the sake of hard. There are no bonus gold stars for “hard.”

So, how do you know? The magic questions are: Where is the freedom and where is the relief? If it’s an aligned, truly worthy life-altering challenge, you’ll feel freedom thinking about taking it on, no matter how difficult. You will *not* feel relief when you think about refusing the challenge. If it’s not aligned and hard for the sake of hard, you’ll feel freedom and relief from not taking it on.

There’s an expression: “Choose your hard.” There are two different kinds of hard. There’s the existential hard of turning away from your true self, and there’s the hard work of creation and of building something that matters to you. For me, Google was the existential “bad” hard and my work now is “good” hard —the challenge of writing a book, or building your own business from scratch.

I also have a test for that! There are four tells of “bad” suffering or unworthy, misaligned challenges. I call them the 4 Omens: Obligation (Shoulds), Objectivity, Optics, and Outcomes. If any of these 4 things are part of your decision to take on a challenge, then that’s very likely not the hard you want to choose.

· Obligation: Doing something because you “should.”

· Objectivity: Relying on “smart” or “logical” generic moves rather than personal resonance.

· Optics: Prioritizing how a decision will be perceived by others.

· Outcomes: Focusing exclusively on what a step will “get” you in the future.

Does your directional focus eradicate your envy of those who stayed on overachieving paths — if you have any, that is? How do you soothe those people who are addicted to overachieving, addicted to the “fix” of having a grand strategy for worldwide domination, into noticing how much they long for a deeper connection to their present lives? I’ve often noticed that I’m the most fixated on big, productive, overachieving plans when I am the most in need of soulful connections and grounding experiences.

I know it sounds so cliché, but I’ve found that when we’re truly aligned, we don’t compare because we know we’re on our right path and we feel content where we are. It feels easy to access that truth that everyone is on their own path and timeline.

So, similarly to you, if ever I’m noticing some of that “compare and despair” trap in myself or others, I see that as a signal that there’s something out of alignment or there’s something more that I’m longing for.

What I do when this comes up for people is an exercise I call “Jealousy Juicing.” It allows us to flip envy on its head, snap us back into our own lives and leverage it instead of demonizing it.

The idea is that whenever we feel jealousy, that’s a clue for us about something that we want in our own life and there’s an opportunity there for us to gather information. So, we want to get clear on what it is that we’re envious of, as precisely as possible, and then make it actionable by thinking of a step we could take to get more of that in our own lives. Exploring your particular brand of envy of world domination can tell us a lot about your right direction. Looking at envy like this makes it empowering instead of discouraging.

Candidly, I have pretty much zero envy of anyone on a traditional overachieving path. I’m clear that there’s nothing for me there. I used to have so much intense and immovable envy of people who were working for themselves, carving their own path, creating and sharing new ideas, and building something that was inspired and fulfilling and clearly their work in the world. It was the clues in that envy that led me to start down the path I’m on today. I haven’t experienced anything even close to that level of envy I used to feel for a very long time.

I still have envy because there are still things that I want to do and ways I want to evolve and now I see that as part of being alive and growing. It’s not consuming or painful in the way that it used to be and I try to always get curious about it.

Does anyone ever say to you, “Okay I’m happy now but I’ve lost all ambition. Is this really a good thing?” Can you relate to that at all? What do you think is the right middle ground for most people between meandering curiously and storming ahead while despairing?

I have heard this before and I think it comes down to a misunderstanding of ambition. We’ve been offered a very narrow vision of what is worthy of ambition, as well as a very limited perspective of what the pursuit of ambition looks like.

To me, ambition is simply a desire for more life, a desire to have an impact. Ambition just means that you care about something and you want to put time and attention and energy towards it. Usually you haven’t lost all ambition, you’ve lost the form of ambition you’ve always known. I rarely find that people describe themselves as “happy” while not giving a damn about anything.

I call this aligned ambition — sustainable ambition that’s authentic and meaningful to you — instead of the old blind ambition — self-sacrificial ambition that’s dictated by external expectations.

So, the first question I ask is, “How are you defining ambition?” Usually people mean that they’ve lost the desire to hustle and grind, or the motivation to sprint up the ladder to the corner office at all costs. They don’t mean that they’re happy because they don’t care about anything or anyone.

The second set of questions I would ask is, “What is it that’s making you so happy? What are you cultivating or practicing? What do you want more of? What do you care about?” THAT is what you’re actually ambitious for. Maybe it’s a feeling — joy, presence, creativity, spaciousness, playfulness, connection, self-expression. Maybe it’s having a family or enjoying quality time with family or friends. Maybe you care about having a thriving garden, or a killer tennis game, or a fiction reading habit, or hosting events, or gaining more physical strength. Maybe you’re ambitious to live in a country where school shootings aren’t the norm, or where there isn’t such a massive wealth gap.

The other thing that people often mean when they say they’ve “lost their ambition” is they’ve lost the motivation to will themselves to operate permanently at an as-fast-as-possible pace. And, yes, I do believe that this is a good thing. I think we’re all seeing the limitations of “move fast and break things.” I’ve found that there is such a thing as right pace and right timing. “Slow down to speed up” is often an even better strategy.

It’s important to remember that ambition is cyclical, not linear. Sometimes we’re in what I refer to as an incubation period — it looks like nothing is happening, but in reality, a lot is happening below the surface that we just can’t see yet.

What’s hard about this is that it takes trust and requires that we let go of the belief that we have the ultimate control over outcomes.

When I left Google, it looked like I was doing absolutely nothing and I felt like I’d lost all motivation and drive. In hindsight, I was deeply ambitious about my own rest and recovery and the absolute most effective and efficient way for me to get to the next stage of my work in the world was to take a year sabbatical where I didn’t try to “produce” anything. Unbeknownst to me at the time, the entire foundation for Directional Living and everything I’ve been doing for the 12 years since was being created.

I have had many people who come to me and say, “all I want to do is read fiction, and lie on the beach, and take naps and I don’t care about having impact on anything whatsoever.” They thought it might be permanent, but in all cases, that has felt good for 6 months or a year but at some point, they found a desire to learn or to be of service or contribute in some way.

So, if you’re in the “I just want to drink margaritas on the beach” phase, go for it to whatever extent your circumstances will allow. I can pretty much guarantee it will shift.

And, lastly, if the word ambition no longer resonates for you for whatever reason, then let it go! I don’t think we have a moral obligation to be ambitious. I’ve rarely, if ever, seen someone be truly happy without caring about or for something or someone, and in my view, that’s authentic ambition.

You met and coached Alexandria Ocasio-Cortez before she ran for Congress. How did you guide her in a way that clarified her path, and what’s the big lesson offered by her example?

What’s important to understand is that I didn’t guide her by mapping out some strategic political trajectory or encouraging her to run for office. We didn’t talk about linear career paths, logical next steps, or ten-year plans. Instead, we focused on living Directionally rather than Destinationally. The work was about clarifying her Big Direction — a high-level sense of where she wanted her life to move, not a specific role or outcome — and then identifying the single next step that felt most aligned with that direction.

Rather than trying to pin down her “purpose,” we paid close attention to her curiosity and energy: what lit her up, what she couldn’t stop thinking about, even when it didn’t make conventional career sense. One of those directionally right steps was a road trip to the protests in Flint, Michigan and Standing Rock. On paper, it wasn’t strategic at all. It didn’t advance a résumé or fit neatly into a plan. It just felt aligned and directionally right. And it was on her way home from that trip that she received the first call about potentially running as a candidate herself.

Her eventual decision to run for Congress wasn’t based on thinking she’d win — by any rational measure, it was a near impossibility. She did it because it felt directionally right. She didn’t need to know the destination in order to take the step. As she’s said herself, things began to unlock when she stopped trying to have a plan and started following her curiosity, prioritizing building an overall good life instead of hitting certain titles by certain ages.

Even now, she isn’t operating from some grand plan to “ascend.” She’s only asking: Is this directionally right? You don’t need to know where you’re going in order to begin. The direction is enough. Clarity doesn’t come from guarantees or perfect planning. It comes through action. Curiosity and joy are the building blocks of fulfillment.

Self-trust and uncertainty tolerance are the most important — and often most atrophied — skills we need in order to build a life we love living.

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Thanks for reading Ask Polly! You can buy Megan Hellerer’s book “Directional Living” here. She does one-on-one coaching through her website which is here. I’ve been breaking my own big goals down into smaller experiments and I feel much more relaxed and inspired. Among many other things, I’ve started to realize that I only want to accomplish a big creative goal if I can truly relish the process along the way. That’s what I want my life to be about: RELISHING the present as much as possible. Join me in the comments for more discussion of Hellerer’s excellent insights. I’m hoping to do more interviews like this one this year, so:

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