Good morning! I hope this email lands in your inbox with the forlorn, rotund grace of a cat’s paw on a windowsill. After some clinical trials I’ve decided Sunday is the best day to send out Maybe Baby. I hope you agree. This week I’ll be answering five reader questions for a new column I’m calling Dear Baby, because Dear Abby was taken and also felt pretty irrelevant. I’ll be running it once a month!
Dear Baby will be part-Q&A, part-advice, although I encourage your involvement via comment on the latter front as I always want to know what you think (and feel/hate/dread/love/eat). If you sent me a question but don’t see it below, I’ve either chosen another one that got at something similar, deferred it to a future week, or deemed my answer too boring to be worthy of your time. If you have a new question, feel free to send it via email reply, comment, or DM. I’m collecting them like specialty coins in a plastic sleeve.
Today I cover, among other things, whether I regret my last breakup, what it feels like to “have a following” on Instagram, and how I learned to write. As always thank you for reading/subscribing/giving my quarantine purpose. All of your thoughtful comments and replies make me feel safer than a baby chicken under a warm lamp.
I just re-read your essay, "Why I Ended a Happy Relationship," because it feels like you’re the only person I have ever heard articulate what I am going through right now. I love my boyfriend so much it almost hurts. But I have to break up with him. I just want to be done with this constant battle inside myself. It's been almost four years of going back and forth day by day. I feel scared, I feel guilty, I feel terrible. But I will read your essay again and take some peace knowing that someone has been down this road ahead of me. Is it better now on the other side? Are you happier than you were?
Damn, I get this question all the time! Nothing I’ve written has seemed to resonate so broadly as that essay, and I think that says a lot about the lack of dialogue around relationship doubt. I looked everywhere for answers and felt deeply alone in the height of my own experience with uncertainty, so I’m really sorry you’re going through it right now. I feel your pain viscerally because I remember it!
To answer your question: Yes, it’s better on the other side and I’m happier than I was. I still remember that relationship so fondly, but aside from moving to New York to change careers at 26, I’d be hard pressed to think of a decision I’m more proud of than letting it go. Learning what it feels like to do something extremely hard because it felt right changed me. It’s not the kind of lesson you forget easily, and my life will forever bend around it.
After the breakup, I grieved for a while, certain that we’d find our way back to each other. But then some more time passed and, from an emotional and temporal distance, I could see our relationship more clearly. Suddenly I understood what hadn’t been working and where my doubts had been coming from, which wasn’t something I could access from inside the relationship—at least not consciously, because I was so afraid of heartbreak (for both of us). I think this happens a lot with hunches: they make a lot more sense in hindsight, when they’re less muddled by fear and resistance. It’s why following them requires a lot of courage and self-trust.
For what it’s worth, the extent to which that decision was painstaking led me to a kind of brute confidence in what I wanted later. And it’s made me a much better partner in my current relationship. I also now understand what it feels like to not be plagued by doubt, which I didn’t know was possible. I still have such warm feelings for my ex, but I have no regrets, and I don’t think he does either.
I’m so sorry, again, that you’re going through this, but I think you should also be really proud of yourself for doing something hard that feels right. If you’re anything like me, you’ll never be the same.
How does it feel to have every thought that tumbles through your head be validated by an audience of 91,000 people? Is that what confidence feels like?
This question feels aggressive but I like it. Having “a following” is such a weird and disorienting experience!!! (I’m mainly referring to my Instagram.) Sometimes I find myself wanting to capture it in writing, but I usually shy away because it’s not universal, and who wants to hear about the emotional nuance of what amounts to a privilege? Compared to more pressing issues it feels laughably inconsequential, but social media has become a begrudged tenet of modern life, so maybe it’s worth writing way too many words about how it relates to our self-esteem? A question of our times.
I remember in the early days of Instagram, all I wanted was 11 likes on each of my photos, because that meant my stats underneath would turn into a number rather than a list of usernames. Later I remember feeling envious of someone I followed who always got over 100 likes on her photos because I thought it sounded freeing to know you could post whatever you wanted without fear of your shit tanking (which...of course you can do anyway). My presumption that enough validation could cure insecurity was very high school, and it carried through until I got more followers myself. Now my thoughts on it are a mess. So much so that I had to answer this question in a shameful, numerical list.
1. Re: validation: It can definitely feel validating to get high engagement on a post. But I don’t think that scales up with the number of followers you have (see: hedonic treadmill). There was a time when 100 likes felt just as rare/cool as 10,000 does now. Everything is abstract on Instagram, so any (horrifyingly fleeting) validation tends to come more from what percentage of my followers engaged with something versus the actual numbers. There are moments when I think about the actual numbers and think, whoa, but mostly it feels different/less invigorating than you expect it would. (If you have millions of followers please tell me if this still applies.)
2. Re: confidence: I do think I’ve gained some confidence through having a following, but mostly where it concerns my writing or ideas making a positive impact on people, not really through likes or followers (what if people are hate-following?!). And even then I have to convince myself constantly that anyone gives a shit. More than anything having a following has proved to me that no amount of external reinforcement can trick you into confidence if you ultimately don’t like yourself without it. The culture of celebrity probably could have told us that years ago.
3. Re: scale: When the numbers are higher, it’s hard to ignore the significance of the fluctuations. If I do something a little off-kilter, I might lose 500 followers in a day. Or I might lose them anyway and I have no idea why. Knowing that many people were like, Okay I’m over her, is wild. I laugh about it, too, but sometimes it doesn’t feel…great. And stupidly, I don’t get an equally opposite rush from gaining 500 followers, because I reason that they don’t know me yet, whereas the ones who left do. You love to see it.
4. Re: high stakes: Having my career be in some ways tied to my Instagram presence can be paralyzing. It makes me hesitate to post shit I know won’t “perform,” even if I think it’s funny or thought-provoking or I just want to. But this (probably unnecessary) editing makes me feel like a flat and superficial version of myself, which is unfortunate in another way, because my internet presence is (kind of) meant to represent me. This calculation is exhausting and makes me feel insufferable. It’s also in conflict with my Instagram rule, which is that I’m not allowed to overthink anything! (K, now we’re laughing…)
5. Re: community/access: The hands-down best part of having a following is the sense of community and access it gives me. Having an audience with which to share my work is such a privilege as a writer. Being able to ask a question and get a lot of answers is so fun, and can be genuinely useful. Receiving a ton of encouragement when I share things (like when I announced that I was leaving Man Repeller) can be overwhelming and touching, even if it also makes me feel a little embarrassed/unworthy. I also can’t deny that having a following also lends me an air of legitimacy when I want to get in touch with certain people for my career. These are the parts I feel the most grateful for and wish more people could experience.
The rest, less so.
“How and when did you learn to write?”
I’m not formally trained, nor did I grow up thinking I wanted to be a writer. But I’ve always read a lot, journaled furiously through hard times, and been introspective by nature. Even if it weren’t my job, the written form suits the way my brain works and my innate desire to methodically externalize my thoughts. It’s like a puzzle I’m desperate to solve.
After studying “business” and working in HR for five years, I came into writing professionally in a roundabout way, which I’ve recounted so many times (in interviews like this one and this one, or essays like this one, this one, or this one, blehhhh) it’s a crime. But the gist is that I learned to write by doing it informally for years out of an intrinsic, ambient desire (in Word docs, on Tumblr, on Wordpress), and then more technically when I landed a job at Man Repeller based on those writing samples. My first couple years as a professional writer were really tough—I was constantly pushed up against my stress limit and often staying up until 2 a.m. writing through my fear. It felt like an immersion program in that I had no choice but to catch up. The years after that were less existentially stressful, but formative for other reasons, as I learned how to write by editing other people and helping shape stories from top to bottom. I’m still learning all the time from the editors I work with and the intimidatingly good writers I read. I feel imposter’s syndrome all the time!
There are a lot of books that have inspired me and helped shape my idea of what’s good, too. In the last few years: On Writing Well by William Zinsser, Priestdaddy by Patricia Lockwood, How to Write an Autobiographical Novel by Alexander Chee, Never Let Me Go by Kazuo Ishiguro, No Time to Spare by Ursula Le Guin, and Sharp by Michelle Dean—all for different reasons I might expand on one day. But I have no idea where I’d be if I didn’t get the amount of practice I did at an intense, New-York-media pace. Even when I was writing something dumb, I took it very seriously, and I think that’s ultimately paid off.
I also think I have a natural instinct and passion for writing that I can’t explain or pinpoint, which I admit is a less satisfying answer. Although I can’t imagine trying to be a writer without that, as it’s a very frustrating craft even when you love it.
“I’m remembering Andi in How to Lose a Guy in 10 Days wanting to write about global conflict at the fashion magazine or late-season Carrie Bradshaw when she was hired at Vogue and struggled to adapt to the publication’s ‘fashion’-centric focus. Did you feel limited at Man Repeller in the topics you could write? But on the flip side, how do you now avoid your portfolio sounding like just a running diary when you write untethered to any particular guideposts of an established outlet?”
I’m haunted by the idea of things going just a tiny bit differently and not getting the job at Man Repeller or finding my way into this career. So my overwhelming feeling is luck/awe/gratitude that it worked out the way it did. But yes, by the end of my tenure there I felt my ambitions were departing from the company’s, and I spent a good year going back and forth between thinking that was very obviously true and convincing myself it didn’t have to be. By the time the fog cleared I had no doubts it was the right time for me to move on and then it was just a matter of summoning the courage and self-belief to strike out on my own. But I don’t have any disdain for MR the way Andi/Kate Hudson did for her magazine! (Lol @ this comparison.) We just grew in different directions. As for your latter question, I’ll be better equipped to answer that in a year! But my hunch is I’ll find the lack of guideposts freeing.
“I left New York over a month ago to shelter at my parents’ house in my Pennsylvania hometown and am grappling with this sense that life is on pause. Maybe I’d feel this way quarantining in my Brooklyn apartment too, since we’re all living just a portion of our past lives right now. But at the same time, this existence could be what we come to know as life for the next several months and I don’t want to reflect on it and think, ‘Oh, I was just existing, just waiting…’ Some of this feeling is probably attributed to some urgency of youth I’m feeling, BUT if this is what life looks like for the next however many months, what do we do/think about/focus on to feel like we’re not living half-lives? Is it possible? Has any of this made sense?”
There are so many elements of this question that I relate to—the anxiety that you’re misusing your time, the attempt to understand how you’ll see your present in the future, the fear of not liking what you eventually see and the desire to actively avoid that. It’s a very pragmatic way to deal with emotions, which is to say it’s the opposite of just feeling them.
Avi and I keep talking about how the days, weeks, and even months are blurring, and it reminds me of a stretch of time I spent in San Francisco, a couple years before I moved to New York. I remember I was having trouble marking time back then, that sometimes a year would go by and I’d think, How? I don’t remember anything that happened! This was my mid-twenties, and I’d gotten so good at thinking and distracting myself out of my wildest emotions that my life had become optimized for stasis. Everything was so rote and comfortable that I almost couldn’t feel anything anymore, like when a blanket is so soft it’s hard to register when you start and stop touching it.
Things started to change—and get more volatile—when I got more serious about figuring out what I wanted. That’s when I started trying new things, failing, dreaming, doubting myself anew, and finding out who I was from different angles. (This was a privilege and so was the comfort.) That era of my life was technically harder in that it was less predictable and more tiring, but I remember that time much better, because I felt like I was finally inhabiting my life and giving my memory something to hold onto. I felt alive.
When I compare that trajectory to now, since I’m experiencing a similar blurring of time, I see two ways of looking at it. One is that the initial inactive period I went through in San Francisco was a necessary precursor to the animated one that followed. I’m not sure anything else but profound complacency could have propelled me so effectively into action, which is why it’s not worth regretting how long I floundered. I wonder if the same can be true of the pandemic and life after it. Maybe this time will be rote and defined by waiting and existing because it has to be, and maybe that’s what will make the part that comes after all the more urgent, colorful, and memorable. The profundity of each will require the other.
The second is that sometimes what makes life interesting is less tied to what, specifically, we’re doing—traveling, going out, meeting people—than the mental state we’re inhabiting when we do it. I think you can just as easily feel dead while living a “dynamic” life as you can feel alive while living a quiet one. It’s all in the approach. Assuming you’re not feeling depressed (in which case I’d recommend focusing on the most basic components of taking care of yourself), maybe what will make this time memorable is learning how to push yourself out of your comfort zone in new ways. Trying something new, challenging old stories, finally learning that thing you’ve always wondered about. Sometimes constraints can offer boundaries that force us to get creative. Maybe this can be that, and maybe that can be enough, just a different kind of enough.
Obviously both of these might imply different courses of action, and I think both are valid, depending on what feels right. For someone like you, which is to say, someone like me, maybe attempting to tap into that—how you feel, rather than how you should feel, or want to feel in the future—would be the most provocative possible response to all this.
Ökay, that’s all I’ve got for now. If you’re a mom, thank you for reading this on your special day. If you’re my mom, I love you more than the moon/sun/stars! I’ll leave you all with this 2020 oil on canvas of me briefly removing my mask to smell cookies at Levain last week.
As they say,,,you miss 100% of the sniffs you don’t take.