#217: Following your (non-specific) dreams

Good morning!

It’s not time for my usual advice column, but today I’m going to use a question I received from a reader to write a lengthier piece addressing something I’ve been thinking about, a slightly different format I kicked off last summer. This question concerns finding the “right” job, a topic I’d tended to avoid over the past few years (a little sheepishly) out of fear that my career has been unusual enough that advising anyone on it—telling someone to follow their dreams, say, or even telling them not to—would be annoying and unhelpful. But this particular submission had me revisiting whether that was accurate and made me want to try again.

“Dear Baby,

I feel like I'm almost constantly having an existential crisis about work, specifically the fact that I have to keep doing it for 30+ more years. I probably have really unrealistic expectations about how I could feel if I had a non-corporate job, but also feel so dissociated from my corporate job and numb all day and think there must be something else I could spend my time doing to feel more engaged. Work is so much time! And I hate that I feel so apathetic for 40+ hours per week. Right now, I work in a corporate job that pays me well, is not exceedingly stressful, and has great benefits. I also generally like the people I work with AND it's in an industry that I like. Even with all of this going for me, every few weeks I spiral about work! I just want to find contentment and I'm mad at myself for not being able to.

I was previously working in a similar finance role in a different industry with people I didn't like for about seven years. During that time I did yoga teacher training, which I loved, then started teaching yoga at a gym a few times a week, which I hated, but stuck with for two years. I also started a YouTube channel, which was super fun, but I only made like 20 videos before the idea of making more felt too scary and embarrassing. Then, about two years ago, I quit both teaching yoga and my corporate job to get a Master’s and become a therapist. Then, I gave up halfway through school because I realized that I felt the same numb disconnect and it felt like too big of a financial commitment to continue. Then, after months of searching, I found my current job, which compared to school and my corporate role before this is much better, but I'm only seven months in and already like, ‘FUCK, THIS CAN'T BE IT.’

I daydream about different versions of myself that I'm too scared of being, like the version who quits to be a preschool teacher, or uses my savings to open a wedding venue, or becomes a furniture maker's apprentice, or moves to Scotland and herds sheep, or becomes a writer with absolutely no experience, or who had tried harder to be engaged in the Master’s program and is now a therapist. I don't have a specific vision of myself other than ‘not this.’ None of them feel possible. I feel like I'm not allowed to feel stuck anymore or blow up my career again, and I'm worried that if I do, I'll still feel discontent.

Is the grass greener somewhere else? Do I need to suck it up and appreciate what I have? Am I doomed to feel this way forever? Do I just need to commit harder? Is my perfectionism the problem? I'd love to hear your thoughts.”

I’ve read this question probably 20 times and only just noticed that one of the final phrases is “Am I doomed?” which must be the most common sentiment in the questions I receive. It speaks to the state of mind that inspires us to write into an advice column—and I say this as someone who once had my own am-I-doomed question answered when I was 25 (the columnist told me to break up with my boyfriend) (classic). This fear of doom isn’t rational, it’s anxious. We catastrophize because, for some reason, it’s more comforting to assume there exists a right or wrong answer, no matter how high the stakes, than to sit in our own uncertainty and accept infinite shades of gray. Which is to say, you’re both doomed (to live with uncertainty) and not doomed (to suffer ceaselessly for it). The way out of this feeling isn’t finding the right job, but a different mindset.

The allure of the job hunt is strong, I know. At any given time it feels like you’re one “correct” decision away from solving everything. But as the job market reincarnates every few years and our crumbling institutions stop affording us a baseline sense of predictability, it’s seeming less and less likely that a specific set of steps will guarantee anything. When young writers ask how I got my start, for instance, sometimes I feel silly relaying the story—blogging for years then writing a long-shot email that secured me a 30-day editing contract when a website was desperate—because I know it was in large part random and lucky and “of its time.” It’s obviously incomplete to just call it luck; a lot of moving parts came together to create the opportunity (including several false starts), but regardless it’s not precisely repeatable, and had I gunned for my specific career outcome, it probably wouldn’t have happened.

Recently Avi told me that when people ask him for advice on landing a tattoo apprenticeship (a sought-after job in his industry), he doesn’t know what to say either. Be in a band with a drummer who happens to be a tattooer and offers it to you? He feels like it was luck for him too. But Avi is one of the most curious and engaged people I know, and if his new career seemed to appear out of nowhere, it was only because he’d spent his entire adult life conjuring it. There were fifteen years of studying music, illustration, history, film, and politics out of genuine enthusiasm while he worked a spreadsheet job that made him feel dull and depressed. Then, “suddenly,” he was showing his drawings to a tattoo artist in his band, who shared a bunch of his interests and, looking back, all of it made narrative sense.

Avi excitedly opening a book about tattoos in 2021, two years before he started his apprenticeship

One of the reasons I’ve become disenchanted with career advice is that the hyper-specific tips (send your resume here or there) can be just as patronizing as the general platitudes (never give up on your dreams! Judi Dench became a star at 60!). When I reflect on my and Avi’s career arcs, the practical choices we made and the career advice we got feel far less relevant than the fact that both of us spent many years curiously searching for who we were. As teenagers, both of us felt ushered toward economically stable jobs (business admin for me, engineering for him) and experienced intense ennui throughout our corporate careers, having no idea what we wanted to do. At various points, we both pined for specificity in our ambitions. If only we could be those people who always knew what they wanted to do! Looking back though, what brought us to career-defining circumstances wasn’t finally figuring out our purpose, it was an amorphous drive toward something, and an openness to whatever that may be. Had either of us nurtured a more specific dream, who knows how it all would have panned out? Instead, it was all the interests we’d cultivated all along that became the set dressing for the “luck” that eventually found us.

I think this is the aspect of luck that’s sometimes missed in career mythology. Not that if it doesn’t strike, you’re doomed, but that luck—which we all need a little of, and usually encounter at some point, although some more than others—can’t lead you somewhere specific, but if you meet it with the right attitude, can lead you somewhere unexpected. I like this perspective because it actually favors the people who don’t necessarily know what they want to do (most of us), but are willing to throw themselves in a few different directions. It would have never occurred to me, in my twenties, that being half-interested in many different things (coding, graphic design, illustration, fashion, writing, philosophy) could actually be a leg-up, but it was. It meant luck and opportunity had several entry points to find me, so long as I put myself in front of it. Having an extremely specific goal, meanwhile, is a higher stakes situation. It’s like trying to grab luck by the shoulders and push it in one particular direction.

I only say this to disillusion you from the idea that being clearer about what you want would necessarily solve your problem. Last weekend I was talking with a friend who’s wanted to be a teacher since she was 16. When I first met her seven years ago, she was 21 and I was impressed by (and a little nervous about) the precision of her ambition. Now she’s 28, five years into teaching and feeling less sure, and while she used to be the envy of her more aimless friends, today she finds herself envious in reverse. “They’ve been sitting with their indecision for years,” she told me, “and I’m only just starting now.” I was charmed by this phrasing, the way she framed sitting with indecision as an achievement, something her friends were more experienced at. This strikes me as the right way to think of uncertainty—the gray comes for all of us, not just once but many times, so better to become fluent in it.

The circuitous path you’ve taken over the last 10 years challenges some of the ideas I’ve presented so far, like that not knowing and trying lots of things is necessarily generative. Which feels like an invitation for me to clarify what I mean. What stands out to me about your few career pivots is that they feel primarily driven by fear, anxiety, and now shame. You keep starting over, hoping the next thing will be the answer, and when it’s not, your optimism crumbles. I just want to find contentment and I'm mad at myself for not being able to. First I want to give you a hug—this feeling is deeply relatable, and the seeking you’ve done has taken a lot of bravery—and second I want to suggest that your search may be too oriented toward a solution. What would it feel like to explore more curiously, with less pressure?

Anne Lamott has a bit of writing advice that might apply here (she borrowed it from novelist E.L. Doctorow): “Writing a novel is like driving a car at night. You can see only as far as your headlights, but you can make the whole trip that way.” A lot of people are paralyzed by an inability to see their destination—they wait around not realizing their tank is full and they’re free to get moving whenever—but that’s not you. You’re willing to drive, which is great, but only if you’re under the temporary illusion that you know exactly where you’re going. What if you accept that you can’t?

Although they both concern the unknown, anxiety and curiosity operate very differently as motives. When I think about the more anxious searching I did in my early career, it feels tonally different from the exploration I did once I released myself from the fear of wasting my own time or looking like an idiot. It might serve you to reframe this job search as a search for yourself—a grand experiment that may never end. I don’t mean to get too far afield of real material needs, but given yours are currently being met, I think it’s a good time to consider your spiritual needs. You’ve been endlessly testing things out, what about just trying them? You might find that by lowering the stakes, your relationship to some of these things will change. Finance, yoga, YouTube, therapy—what have these things shown you about yourself and your desires? What feelings did they give you that you’d like to feel more often?

I suspect the answer as to what you should do next is less tangibly about your career and more about (sorry) your soul. What if contentment has to come first? And I don’t mean contentment in the sense of loving every aspect of your life, but in the sense of liking and trusting yourself enough to face the unknown with curiosity instead of terror. This is a lifelong challenge for all of us, and it won’t necessarily lead you to your dream job. The right kind of work—the kind that helps you click into yourself and feel the force of your own agency—may very well have nothing to do with what your younger or more ideal self venerates. It may not even have anything to do with work itself, but who you are when you do it. Sitting with your questions isn’t a punishment, it’s a practice. Learning to move in concert with the unknown is a skill worth cultivating, and in my experience, it’s one of the best ways to stumble into the right kind of luck.

My favorite article I read last week was “The Life and Death of Hollywood,” by Daniel Bessner for Harper’s. Stunning write-up tracking the plight of Hollywood (especially its writers). Last Friday’s 15 things also included the coolest sunglasses I’ve ever seen, my favorite brownie recipe, my latest trick for navigating toddler night wakes, and more. The rec of the week was a discussion on the infamous blond trio of White Lotus season 3. So many great takes!

Last week’s podcast was a conversation with my best friend Michelle about how our friendship has weathered my having a baby (while she remains child-free). This is a followup to our conversation from September 2023, two months before I gave birth, when we laid out all our fears. We also discuss what happened in the comments under my Chappell Roan essay.

I know it’s not technically a Dear Baby week, but if you have advice for the questioner today, please share! My own advice was painfully vague so I’m sure some more tactical perspectives would be welcome.

Have a nice Sunday,
Haley