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

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 t…