#145: Not caring about your job: freedom or misery?

+ the spectre of the writer-influencer and "paired-off" friends

Good morning!

Dear Baby hath returned. Today I’ll be answering questions about 1) whether it’s better to have a stressful job you care about or a stress-free job you don’t 2) my thoughts on influencing and social media as it pertains to building a writing career (and how I think about those things in relation to my own) and 3) what to do about the problem of friends pairing off and their plus-ones becoming a permanent fixture at social gatherings. Regarding the second topic, about writing and influencing, I get questions like that a lot—this one was inspired by this recent NYTimes piece about post-influencing—and I’ve tended to avoid them, but today I finally went in. I don’t really believe in the writer-influencer, and it was nice to get some of those thoughts off my chest!

On this week’s podcast, Danny and I will be answering questions about parsing the difference between actually liking someone and enjoying the attention they give you, the competitive weirdness of pursuing the same niche career as someone close to you, the potential danger of having a threesome with your husband and the one that got away (!), how to deal with resentment of the newly sober, and what to do if suddenly your eight-year partner’s personality is…annoying you. That last one had us reeling. Episode out Tuesday at 9am. To those who have told me my voicemail is down: I know and I’m sorry! The engineers are on it. For now, direct your written questions here.

On the appeal of braindead jobs

“I am in my early 30s, married, and planning a move across the country later this year. I currently work in a field that requires an advanced degree and credentials to practice. When I move, I want to let it all go. But, more than that, I want to let ANY ‘traditional’ job go...I think. I'm so unhappy in my current field, but find myself only taking baby steps to pivot away from it—like moving to another corporate-type job or into a different sector of the nonprofit world. It's so hard for me to think outside the box and step away from what feels familiar. The other thing is that I don't really know at all what I want to do. So it's not like I'd be giving up my field to pursue my true passion as an artist or whatever. Am I allowed to do this? Is this idiotic? Am I idealizing having a job with minimal mental/emotional strain because I'm burned out, but will find myself braindead after a month? I think this is generally related to capitalism and how we value ourselves based on our jobs—I know I should let that concept go. But I worry that existing outside the scheme of ‘ambition’ and ‘career’ will actually leave me unfulfilled. And then am I sabotaging my ability to have a career by taking this detour? Oy vey. Help!”

These are all totally valid questions. Although I’m curious what you mean by letting go of “traditional” jobs. Do you mean giving up the abstract notion of careerism? Or perhaps more simply, giving up salaried work? You mention wanting a job with minimal mental strain—does that mean pursuing an easy/boring desk job outside your studied field, or does it mean becoming a barista? I would have different advice depending on how you answer those questions, but regardless, you got my wheels turning for a few different reasons, particularly your line about idealizing potentially “braindead” jobs.

I think we’re in a transitional place, as a culture, regarding our preoccupations with work. Anti-careerism has been a focus for a while now among the young left, and while that’s been a healthy and necessary shift away from the hustle culture/girlboss era, I do think we’ve overcorrected a bit. That’s not a bad thing; it’s just the reality of the cultural dialectic. But I suspect we’re nearing the end of the romanticization of the clock-in-clock-out lifestyle, whereby it’s considered an act of self-care to not care about your job and to never do more than you’re asked. To be clear, these new norms are potent under the purview of the labor movement—to refuse to give more to your employer than it gives to you is a valid way to highlight exploitative policies. An employer and its employees are not actually “a big family.” This should continue to be highlighted. From a mental health perspective though, not caring about your work, which you most likely spend the majority of your waking hours doing, is actually pretty depressing, and I suspect a lot of people are learning this in real-time.

I was thinking about this last week while watching a basketball game with some friends. For the first 30 minutes, I technically watched but wasn’t actually paying attention or investing in the drama. After realizing how boring and unpleasant this was, I decided to try caring instead. I learned about the players and the stakes, asked questions about the parts I didn’t understand. Unsurprisingly, this changed everything, and quickly. By the second half of the game, I was hooting and hollering, making alliances with and enemies out of my friends, and generally feeling more present and awake. The time flew by. That night reminded me of how much more enjoyable it is to genuinely invest in whatever you’re doing, even if it’s not immediately appealing to you. This is especially true when it comes to work. It may sound easier to give nothing—to promise to keep your face pointed at the screen, and nothing more, to do “braindead” work—but I actually think it’s a lot harder. This isn’t a bid against work that others might deem unglamorous or boring (most jobs can be interesting to the right people), it’s a bid against apathy generally. I don’t think checking out for long stretches of time is good for the human spirit.

Keeping this in mind as you make your next move might be helpful. If your current field is making you unhappy, I don’t think there’s anything wrong with taking a break from it to experiment with lower-stakes, lower-paid, or less conventional jobs, especially if you can afford it. You can always change your mind and go back. I think we too often imagine that our thirties are a time to lock everything into place. But most older people warn us against that kind of thinking. Try to keep perspective: If you change things up now, you could have several years of a new path under your belt by your early forties, which is still young. And even if it weren’t—even if you were 65 contemplating a big change—I’d still urge you to stop asking if you’re “allowed” to reimagine yourself.

Regardless of what you choose, I’d warn you against glamorizing work that asks nothing of you. As hard as it is to care about something and find it disappointing, I think it’s much more spiritually draining to not care about anything at all.

On being a writer without a social following

“Dear Haley, I’m so curious about your thoughts on influencing and social media, particularly the ways it has paradoxically enabled you to opt out, since you have an established IG following that followed you to Substack. I’m curious what you’d suggest for writers aspiring to a set-up like yours whereby you don’t have to wait for sanctioned publications to validate you and have built a creative ecosystem for yourself that’s steady and structured. I read this article too and would be curious to hear your thoughts.”

This is a valid question I get fairly often. I understand why people might connect my current setup to my once-active social media presence. Especially given things I’ve written about myself, like how influencing helped me quit my job and start working on my own. But I think I’ve historically overstated (even to myself) what Instagram did for my career, while downplaying what actually established me as a writer, which was perhaps a bit more conventional: Writing and editing for a publication for four years. Social posting was a tiny portion of my creative output during that time, which included over 500 published articles. So while I’ve always been grateful for the additional eyes Instagram may have gotten to my writing, I think I really owe my setup to my years writing for a publication people genuinely enjoyed reading. In that way, I suppose I was “sanctioned.”

I know those jobs aren’t exactly a dime a dozen, which is where I got lucky. There’s no question digital journalism has been in a tailspin for years now, one that seems to be gaining speed (back when I started the crisis was that everyone was “pivoting to video”). The industry has never been particularly attractive in terms of hours and pay, which is why there’s currently a big struggle between unions and media conglomerates. I hope that gets us somewhere. But in the meantime, I still think working with or for someone else who has more skill or experience than you, even for a short period, is one of the better ways to cut your teeth and find your voice, even if you eventually dream of working for yourself. Those were tough, exhausting years, and they taught me so much. I was writing and editing at nearly all waking hours of the day, and the stakes were getting higher every year, as I became responsible for other people’s writing and careers. Learning to write for a specific audience also helped me figure out my beat. There’s nothing quite like that environment for growing as a writer, and while I don’t think it’s the only way, I can’t personally imagine being where I am today without it. (And by the way, I still work with a trusted editor—shout out Mallory Rice!)

There’s this idea today that you can skip all that now because of social media, but I’m not sure how well that translates to writing specifically. Of course there will always be exceptions, but it’s pretty difficult to develop your writing past a certain point if you’re only messing around in your free time with stuff you actually want to write. You can improve that way, absolutely—I did that for years in my early twenties—but I grew exponentially faster when I was forced to write when I didn’t want to, sometimes about things I didn’t want or know how to write about, according to someone else’s standards, at a pace that, when it wasn’t crushing me, inspired a lot of creativity. Through that I learned the intricacies of the editorial process, and gained mentors, industry knowledge, and media connections. Before I quit, I had coffee with several editors who said they were interested in working with me based on my work at Man Repeller. So while a bit of extra influencing money helped pad out my editor’s salary, all that other stuff is what actually gave me the confidence to bet on myself.

I don’t mean to minimize how useful it was to share my newsletter on Instagram and have thousands of people sign up right away. I don’t take that for granted! It’s difficult to get self-published work read without people already knowing about you, that classic catch-22. (This is where I think putting yourself out there, in the flesh, and meeting people who write and edit is invaluable.) But the skills that helped me keep the readership I’d built, deliver a polished newsletter on a consistent basis, and edit my ideas throughout that process—that all came from professional experience. The subsequent growth of my newsletter depended on all of that, too. 

I don’t think it’s impossible to accumulate those skills outside the media industry. I think my five years of corporate work experience prior to working in media were hugely beneficial when it came to the more tactical sides of working on a stressed-out team and eventually working for myself. If you have experience outside of writing, plenty of that will translate. It might even give you a leg up over people who’ve only ever worked in creative fields (plenty of writing geniuses struggle to work for themselves because they aren’t particularly gifted at the non-creative drudgery required of self-employment). Don’t assume you’re starting from zero. But if you’re looking to build a substantial creative ecosystem for yourself, as you described, I do think you’ll need a bit more than that.

If a full-time media gig is out of your grasp, which I understand may increasingly be the case in this dire landscape, my most tactical advice is to get practice doing the kind of writing you dread. That means writing when you’re not in the mood, writing about things you’re not yet confident about, showing your writing to someone who will tell you the brutal truth about the quality of what you’ve just written, maybe even practicing editing someone else. If you’re never pushed beyond what’s comfortable—to hit deadlines, to be humbled by exhaustive research, to change your mind and start over, to break your brain over an intense revision—I think you’ll struggle to hold yourself to a high enough standard as an independent writer. At least that was true for me; I never sweat over my old personal blog like I have my paid writing gigs. I think this is just human nature. It’s against our instincts to tarnish something we enjoy with so much unpleasantness, but creativity needs friction and constraint. We need to be made uncomfortable, over and over, in order to deliver more than we thought we were capable of. Maybe that’s less true for hobbyist writers, but for professional ones, I don’t know another way.

I hope this isn’t discouraging! Personally I think it can be more depressing to assume you have to somehow game the algorithm and commodify yourself to have a writing career. I don’t think that’s true. Building a big social media following for having a beautiful face or life doesn’t guarantee people will care about your long-form thoughts (in fact, the opposite can be true, and I think the unhappiness of figures like Lee Tilghman, per the article you linked, comes from the lack of genuine respect begotten by selling your image). Maybe this is optimistic, but I think a spirit of meritocracy still runs through the writing world. It’s hard to fake writing skills the way you might fake beauty, taste, or personality on social media. None of this is to say that being a good writer guarantees you a career (and plenty of bad writers have lucrative ones, even if they lack critical acclaim). It’s a tough and stingy industry, and you’ll still need to find ways to get your writing out there. But there are tons of working writers who have careers without clout, and their talent speaks for itself. Writing may be a famously romanticized career, but it’s also famously loathed. If you have the discipline to do it consistently, you’re already miles ahead!

On plus-ones becoming an unwelcome fixture

“Dear Baby, I'm a single girl in my thirties and as one of the only single people left among my friends, I'm having a hard time accepting that everyone's +1 is sort of always…around. I feel like I've had to mourn the dynamic we had as a friend group when we were all single. I guess this is all part of growing up, but how should I deal with it and how do I move on from the nostalgia of what-used-to-be?”

Friendships will inevitably change, that’s always true. You’ll probably never quite recapture the specific spirit of everyone being single at the same time in your twenties. But I don’t think that means you have to accept a fully couple-oriented social calendar in your thirties. Personally I think that sounds very boring! Studies repeatedly find higher rates of happiness among unmarried/childless women (at least in the West), and part of that concerns their superior social networks. In America we unfortunately romanticize the idea of self-isolation and codependency in coupledom. It’s why we have so many trends of sex dying in long-term relationships and parents having no support; married couples are way too closed off from their communities. I think we could all benefit, coupled or not, from creating and protecting social time away from partners.

I have one group of friends that’s historically always been a mix of couples and single people, and recently the women in the group made an effort to hang out alone, and it was so refreshing and fun. We couldn’t stop talking about doing it again. That’s not to say hanging out in a bigger group isn’t special in its own way—in fact I’ve found people coupling up as we get older to be socially expansive, too. It’s nice to be exposed to new faces and new social circles over time, and I think it’s also important to share friends with my partner. It sounds equally weird and isolating to keep my relationship and friendships completely separate. But I don’t think you’re wrong to drag your feet in accepting permanent plus-ones. It’s just as healthy for your friends to spend time away from their partners as it is for you to spend time with them alone.

When I recently went on a trip to London without Avi and got to run around a new city with a good friend instead of a boyfriend, I couldn’t believe how fun it was, and how little I’d prioritized traveling with friends in the past. It’s a completely different, life-affirming experience, one I think many coupled people simply forget is an option. This is sad, since studies show that friends are literally more important to our health and happiness than romantic partners. As time passes, or maybe with the help of your urging, I wouldn’t be surprised if your friends start recognizing this. Maybe their relationships or marriages are newer, maybe they need some time to be attached at the hip before they realize that’s a little suffocating, or maybe they’re just out of practice with planning stuff only for themselves. Either way, I can’t imagine your suggestion to hang out on your own sometimes wouldn’t be welcome. Everyone needs that, even if they forget.

Lastly, I want to thank everyone for trusting me with the intimate details of your lives, maybe even especially those whose questions I don’t get a chance to answer. Some of you send in genuinely moving stories and although I may not always feel equipped to advise you, I always wish I could reach out to offer you some solidarity and compassion at the very least. But since it’s all anonymous, I can’t do that! So I just want to acknowledge and thank you here.

Hope you have a nice Sunday,
Haley 

Cover image care of xPACIFICA / Getty Images