#16: Dear Baby: On Man Repeller, queerbaiting, and "the one"

5 reader questions, 5 honest answers

Good morning babies, Baby here.

Welcome to the very first paid edition of my newsletter. Thanks so much for becoming a paying subscriber! Your support for this project means a lot. I hope to [sunglasses on] make it worth your while. This week is my monthly advice column, Dear Baby. Today I’ll be answering questions from readers about making a career change, my feelings on the Man Repeller reckoning, how to know if you’ve found “the one,” how to know if your work matters, and how I reconcile my style with my gender. Praying for your stamina since I’ve written a literal essay for each of these questions. And keep in mind that my podcast reading of the below text will be coming out on Tuesday!

Love and massage chairs,
Haley

On Changing Careers

How did you come to accept that you were ready for a major career change? I’m in a job now where I know I want to move on and change things in my career path but get overwhelmed with the idea of “starting all over again” with a job search, interviews, new workplace, etc.

I know this inner debate so well! After working in HR for five years, the sense that I’d already given that career so much time was a huge barrier to imagining a different life for myself. This was influenced by a few things—my sense that “success” was most reliably achieved by following a linear path, the idea that my income was the best measure of my worth, the belief that starting over was for “young people.” Of course, I was young at 26, but we always seem younger to ourselves in hindsight. If you’d have asked me about my prospects then, I’d have acted as if I were a 70-year-old woman contemplating going back to school. (Which, by the way, is a super celebrated decision! So I’m not sure why we often look down upon these pursuits for ourselves.) But more than all of that was the simple fact that I didn’t know what I wanted enough to understand what I was willing to risk for it. That amorphousness, beyond any sense of pride about starting over, was paralyzing.

For years I hoped time and careful thought would unlock me. And then all my hand-wringing and journal entries only made me more confused, and then resentful of my own confusion. But of course I was confused! I was young, had basically only tried one career, and didn’t have nearly enough information about myself to draw any satisfying conclusions. At a certain point it became clear that if I hoped to make any headway, I needed to get more comfortable with actually trying things (and failing at them), rather than just considering them. Some part of me probably knew that all along; I just had to get desperate enough for answers to be willing to look really dumb in the process of seeking them. That was a big turning point.

Over the next few years, I would try my hand at a lot of things and apply for a lot of jobs. I failed a fair amount and got rejected exclusively, but after a while my mind had new information to hold onto. What I liked, didn’t like, loved, sucked at. When I noticed how much energy and enthusiasm I had for different kinds of work, I stopped thinking the lack of it I had for HR was a sign of my character, and started seeing it as a datapoint. That was especially helpful. Recognizing the extent of my ambivalence for my job helped me better understand the stakes of staying versus leaving. The debate went from, “What do I want to do?” to something closer to, “What role do I want work to play in my life?” And the better I got to know myself, the better I got at answering that question.

If I’d stayed in HR, I would have had to recalibrate my expectations for what it could do for me, and that would have been a totally respectable choice. But I was privileged to feel secure enough to give it all up for something else. This is something that’s often left out of the follow-your-dreams narrative—the depressing fact that the potential spoils of a good gamble are most accessible to those who feel secure enough to gamble in the first place. I don’t have a trust fund or anything, but I knew I would have a soft place to land if I crashed. That can’t be discounted. Still, the risk terrified me, and I was only able to take it because by then I understood my priorities enough to know that not taking it would feel worse. So in 2015 I sat my boyfriend down and told him I was going to stop at nothing to get a creative job in New York, even if it meant breaking our lease, or leaving him behind. It was the first time in years I felt specific about my direction (even though it was still vague!), and I’d have never gotten there had I spent all those years journaling about it.

March 2016, my last week in HR, already doing mirror selfies.

You asked me how I accepted that I was ready for a career change, and I think the simplest answer is I finally knew myself well enough to conclude that no other pursuit felt authentic. I know that’s a little wishy-washy, but I think we sometimes underestimate the value of self-knowledge when it comes to big decisions. We get caught up in the logistics, or sunk costs, or the choices other people are making, instead of asking ourselves what the choice is really about for us deep down. So I’d urge you to consider what specifically is driving you toward change, and how that measures up—in a broader, existential sense—against the risk inherent in “starting over” (although you’re never really starting over). You might have to get to know yourself better to answer that, but I think it’s a solid place to start.

On the Man Repeller Reckoning

I want to ask your thoughts about everything that went down at Man Repeller in June. I understand if that is a hot-button issue you might not be able to talk about because of what I assume to be your ongoing friendship with Leandra. Maybe I am overstepping, but I am curious to hear your thoughts.

Not an overstep! A fair question. Although it would take a long time to explain my experience there, I’m going to try to shed as much light as I can in a few paragraphs. For anyone not familiar, Man Repeller is a women’s media site I worked at for four years and left in March. After the murder of George Floyd, Leandra Medine, the founder and face of the brand, published a piece in support of the Black Lives Matter movement. In response the brand faced a pretty severe backlash for not internally upholding the values she expressed. Among the comments were accusations of having a homogenous staff, cultivating a toxic culture unwelcome to Black employees, not being class-conscious, and generally sticking to a mission that felt out of step with progress. Leandra apologized a couple times, which didn’t go well, and eventually announced she’d be stepping back to let the rest of the team rejigger the editorial strategy and imagine a different future for the site. Man Repeller was one of many women’s media brands that went through this in June. 

Watching this unfold was in some ways reaffirming and in others ways difficult. Reaffirming because a lot of the criticism Leandra and MR received echoed criticisms I and others had made inside the company, and also because some former Black employees were getting much-deserved support. It was difficult because some of the people I love who still worked there were facing brutal feedback, some of it missing context I believed might change minds. But it wasn’t the right time to defend anyone, and to that end it was also a little frustrating, because the rumors that started to swirl were a mix of true and false, and although I got to the point of recognizing that the exact truth wasn’t as important as the fact that an urgent reckoning was occurring, it was still disheartening at times. I also wasn’t sure of my role—after trying to address things within the company and coming to the conclusion that I needed to leave, I felt like I’d already made my statement and moved on to new challenges. I did spend a lot of time reflecting though—on things I could have done differently, times I could have spoken up more, ways I benefited from the system. I wasn’t perfect; my time there was one massive learning curve.

Before I go on, I do want to acknowledge that I think MR has done a lot over the years to become more progressive, and the fact that its cultivated such a politically engaged audience speaks to the way it didn’t get everything wrong. I’d have never stayed as long as I did if I believed that. Even though I struggled ideologically with its mission and tone, the team when I was there became increasingly thoughtful about who we cast and profiled and celebrated; we absorbed hard lessons and responded to them by doing better within the guardrails we were given (even if we lamented those guardrails). Through working there I became exposed to and friends with a far more diverse range of people than I knew before, and myself learned to connect with a broader audience. But none of it went far enough, and there were certain fundamental problems that needed to be addressed.

Some of these issues were typical of the media industry—the long hours, the low pay, the pressure to drive traffic so that brands would pay us enough money to stay in business, which has ripple effects beyond the obvious (hence my fervent support of subscription models). To its credit, MR didn’t sell out nearly as hard on this front as its contemporaries, which kept me there for a long time, but it was still there. Other issues were more specific to Man Repeller—a tension our audience would never be privy to: a continued cultural struggle between those of us who wanted MR to evolve and those who wanted to hold onto what it was when it first became a cult favorite. I believe it was that nostalgia—and its associated fear of change—that was the knot at the center of most of the problems that came out in June. Nostalgia and ignorance may be softer motives than outright malice, but the impacts can be just as cruel, and that’s what matters in the end.

About a month ago Leandra asked if I’d be willing to talk, and I said I would. First she told me she was sorry for resisting change, and then she asked if I’d be willing to offer some feedback about my experience at Man Repeller. Even though our ideological differences had become a dealbreaker for me by the end, Leandra and I always had a solid working relationship—I tended to be more outspoken with her than other team members (most saw her as an intimidating boss), and now that I wasn’t working for her, another wall had dropped. What followed was an hour-long, brutally honest unloading, and I believe she absorbed it in good faith. I hung up feeling like she wasn’t doing PR, and I hope that’s true.

It’s always jarring when private struggles go public, but there was another layer when it came to MR, which had cultivated an intense parasocial relationship with its readers—and a real-life one too, through DMs and emails and community events. And while that sense of connection was authentic (at a least to me!), it wasn’t the whole story. As writers and sharers we were deeply vulnerable and open about certain aspects of our lives, and that lent the impression that MR was more like camp than work. Or that you could glean everything you needed to know just by reading, which was far from true. To that end, some people (fans and critics alike) expressed anger at Leandra’s decision to step back, but from my perspective it was the right one. I don’t want to speak too much for her, but I do think more people should understand how integral she was to the company—its wins and its failures—and how necessary it was for her to give the team a chance to right some wrongs on their own. Many current employees took issue with things long before they came out in June, but weren’t able to reconcile them the ways they wanted to. If they’d expressed that publicly a couple months ago, it would have seemed defensive or performative, so I understand why they didn’t. But now they’re getting a chance to show growth instead of just talk about it, and I’m rooting for them.

There is so much more I could say, but I’m going to leave it at that, as it doesn’t feel like my place to speak on specifics for MR or former employees. In the end, I don’t regret leaving. My frustrations with the company weren’t the only reasons I left. I’m still grateful for everything I learned there, and for the opportunity Leandra gave me (I’ll never forget it), but by the end I felt called to a different kind of work. Four months later, I feel confident I made the right decision.

On Trusting Your Work Matters

Writing used to be "what I do"—not for work, just for fun. It was who I was, really. But now every word and every sentence feel stuck in my throat, and if they ever make it to the page, I cringe and feel embarrassed that I somehow didn't produce a Booker Prize-winning piece of writing in five seconds. I've been toying with the idea of forcing myself to put out something like a newsletter, even if I'm the only one who reads it. So my seriously long-winded question is: How can I trust my own voice? How do I know I'm doing something right/writing something of value? Does it ever stop feeling self-indulgent?

I get a lot of questions like this, and it makes me happy to think many of my readers are writers themselves. (I wonder why that is?) Yours stuck out to me this week because just this morning I required a pep talk from both my boyfriend and my mom about whether anything I make is worth anyone’s time. I’d just finished editing my podcast and was having trouble imagining anyone would give a shit. It felt so self-indulgent, so boring, so small when everything urgent right now feels big. To be honest I cycle through these thoughts pretty often—my decision to keep going is never finished; I’m revisiting and recommiting all the time. And this is coming from someone who gets a lot of public encouragement! It’s depressing how short the statute of limitations is on compliments, and how long it is for criticism. Our insecure parts are much more absorbent, I guess by definition.

When I remember them, the kind comments I’ve gotten over the years do keep me going (I’m lucky to have them), but probably more potent than any external push is my internal one. Writing is how I best process the world, and sharing myself that way makes me feel more known by, curious about, and connected to the people around me. It sounds like you have a similar drive, which means your biggest challenge is believing that the fruits of writing are worth the trouble they require to grow. Sometimes you’ll have an easier time accessing that belief than others, and I think that ebb and flow is natural. When I wasn’t writing professionally I went through phases of blogging a lot and phases of not laying down a single word. It’s easy to reason that my more active periods were me at my best, but it’s probably more fair to say both periods were important to finding my voice. Action is best followed by rest, and vice versa, and artistic activity follows a similar cycle. Maximizing output doesn’t necessarily mean you’ll grow faster. (This essay I once wrote about embracing life’s ebbs and flows touches on this!)

That said, you do need to write in order to get better. Sometimes that might mean giving yourself prompts, other times pushing through a profound desire to never externalize a thought again. This is something that professional writing helped me with a lot—I didn’t have a choice but to hit my deadline, whether I was in the mood to write or not. My first year as a junior editor I was sometimes churning out two or three articles in a day. I had my first panic attack that year; the pressure was overwhelming. Relying on your brain to just think right is a maddening pursuit! But it did help me understand the value of pressure. Finishing by way of pure will is difficult. Occasionally someone on our editorial team would commit to writing something on the side—off deadline—and those pieces almost never got filed. So I’d be gentle with yourself on that! And find a way to introduce accountability, even if it’s a low-stakes form, like an agreement with a friend, or the structure of a newsletter. Some guardrails can be disproportionately helpful to just finishing.

As for not producing prize-winning prose right away, try to consider this a sign of your taste. Per Ira Glass’s famous two-minute monologue on the creative process, which I think about all the time, most of us get into an artform because we appreciate the best it has to offer, and that means we will immediately clock when our own attempts don’t measure up. This misalignment is most present in the beginning, but it doesn’t necessarily go away—as my taste increases, my own work falls shorter! I will always want to be better than I am, which to me has become a driving force. I can sense from your question that you know all this and are trying to square it with the sense of failure you feel anyway. And to that I can only say: You have to decide if you think you deserve to pursue your most authentic self. If you feel like a writer deep down, you have to allow yourself to be one, no matter how shitty. Anything short of that will probably be unfulfilling. Art is self-indulgent, but it can also be a life force if you let it.

On Finding “the One”

When do you know someone is "the one" to commit to? Do you ever know?

This is such a common question I’m going to try to not answer it with platitudes. What could be more useless than “when you know, you know” to people who don’t know? It’s always struck me as more of a fist-bump between people who thought they’d figured it out than genuine advice. But I understand the appeal of such a flimsy axiom; the problem itself is flimsy. It depends on who you are, what you want, and who you’re with—of course! So answering with any clarity means answering those questions first, and anyone who can answer all of those with certainty is probably a tiny bit delusional. So now that we’ve established the inherent un-answerability of this question and our enduring, collective delusion, let’s get started.

The first thing I did in pondering this was go back and read my response to a similar question from a little over a year ago—“Ask MR: Can You Ever Be 100% Confident in Your Relationship?” I was curious to see if I still agreed with myself, and I do, mostly. But there are a few things I feel differently about now. My position in the letter was this:

1) It’s hard for us to answer this question because we’re biased, fickle, and blind to the fact that “rightness” is a construct.

2) There is an important difference between confidence and certainty, and we only need to cultivate confidence. (Per the Voltaire quote someone shared in the comments: "Doubt is not a pleasant condition, but certainty is absurd.")

3) If you consistently don’t feel confident, you should take that seriously instead of waving it off as naïveté or anxiety or a projection.

That third part was probably the most controversial—some commenters believed their doubt was naïveté or anxiety or a projection (or in some cases, relationship-OCD), and felt I’d been too dismissive of that. I think it’s a fair criticism—I took that position so strongly because I myself used those as excuses to stay in a relationship I didn’t want, but that doesn’t mean there isn’t a whole population of people who do the opposite.

I tend to believe most of us know the truth about ourselves somewhere deep inside of us, and then construct elaborate fantasies and ideologies to protect ourselves from it. This is why I’m suspicious of convenient explanations (distinct from simple explanations) in most personal matters, because facing the truth can be painful and ego-destroying. “The grass is always greener on the other side!” for instance, is an easy, faux-moralistic reason to avoid a breakup that’s sorely needed. “I’m just unhappy with my life and blaming it on my partner!” is another reliable, seemingly mature reason to stay (because most people are unhappy with their lives in some way, especially in their twenties when their interior lives are fucked, or especially living under late-stage capitalism). What I failed to capture in my response, though, is how this cuts the other way for people for whom leaving, versus staying, is convenient. Things like “I just need to figure things out on my own for a while,” or “I just don’t think we’re compatible” can just as easily be convenient ways to avoid the hard work of committing to someone. You can’t really answer this question, then, unless you understand your predispositions.

Another thing I failed to address in those three points is that, in a long-term relationship, who you are, want you want, and who you’re with will probably change without ever leaving it. Years ago, an ex and I broke up, and after a few conversations that felt genuinely transformative, got back together. In telling his dad, a little sheepishly, that we’d reconciled, his dad said something that I still think about all the time: “Sometimes you can realize a lot in a moment.” Although we ended up breaking up for good about four years later, I do think something changed fundamentally about our relationship after that. And I think that can happen on a much larger scale over the course of being with someone, or being alive. Sociologist Esther Perel talks all the time about how you can have multiple different relationships within one relationship, and I always found that encouraging. 

In sum, I agree with my original take (and if you have a bottomless interest in this topic, that one is a bit more granular), but want to emphasize that I think the answer to this question has more to do with understanding your own pathologies, and your own truth, than whether you’ve found “the one,” which is outrageously subjective, and means different things to different people. Some questions that might help you get there: Why did I choose this person? Why have I continued to be with this person? What about leaving them appeals to me? I think your most brutally honest answers to all three might get you closer to the truth than listing out your partner’s pros and cons. Because at the end of the day, no one else’s measure of fulfillment matters if it doesn’t genuinely resonate with you. If you try to force it, some part of you will know you’re lying. (See: Cheryl Strayed’s “The Truth That Lives There.”) This doesn’t just apply to love but life in general. Examining your reason for doing something is a much faster path to determining its “rightness” than examining the act in a vacuum, or feeding it through someone else’s moral filter.

On Gender and Style

As of late, I've been thinking so much about style and gender fluidity. I have friends and see folks where their style is so clear––I know what their "look" is and their look (at least in my brain) has stayed rather consistent over time. When I look at myself, some days I want to dress like a skater boy from the 90s. Other days, I want to embody all that is femme and sensual. So my questions for you are: What are your thoughts on the fluidity of style? How do you see your own sense of style and how that has changed over the years and how does it change day-to-day?

Although I think about this all the time, I haven’t written about it much, and I think that’s because I still have a lot of questions myself. I’m pretty confused about my relationship with gender and style—I’ve been accused in the past of queerbaiting and lesbian appropriation due to my “boyish” way of dressing, and I’m still not sure if I think those criticisms are fair, or if I fully understand them. The truth is, I don’t feel a deep connection with my gender. There are times I feel like a woman, like when I’m nesting or having sex or surrounded by other women. But oftentimes I just feel kind of genderless. I wouldn’t call myself non-binary, I just don’t feel a strong sense of ownership over my womanhood. This struck me most specifically when I was talking to my friend Crystal some time last year, and she said to me: “I just feel so deeply like a woman. It’s who I am to my core.” And I thought, Wow, I feel nothing like that.

This photo of me shot by Lulu Graham for a story about dressing like Daniel Day-Lewis was the most memorable time I was accused of queerbaiting.

I’m still not sure what that means, or if it will change as I get older. But I would say my style is about more than just liking “baggy” clothes, or growing up as an athlete; it traces back to being young and feeling that I wasn’t “good” at being a girl. Looking back there were moments where wires got crossed for me—where I couldn’t tell if I was imitating boys because I liked them or because it felt more natural to me. I spent a lot of time course-correcting; imitating the femininity my friends seemed to display so effortlessly, and it would be a long time before I realized I felt most like myself somewhere in the middle, and that most markers were constructed anyway. These are private things I haven’t written about much, maybe because I don’t want to overemphasize their importance in my life—I don’t suffer much for this ambiguity, and so many can’t say the same. But to your question, I do think style has been a key part of my navigating this. At its best, it offers me a chance to reconcile how I feel inside with how I see myself and want to be seen. In that way it’s a form of communication I cherish (if a limiting one).

As for your undulating style preferences, I think your contrasting desires can be an opportunity to embrace contrasting sides of yourself. Just because you admire someone else’s consistency doesn’t mean your lack of it isn’t just as interesting. Our modern obsession with personal branding and self-commodification wants us to flatten ourselves into something someone else can understand in five seconds, but that’s just not how people are, and it seems cruel to deem anyone so simple, least of all ourselves.

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