#197: What is "personal style"?

+ my thought on the Substack discourse & being "a failure"

Hey and welcome back to Dear Baby!

I’ll be answering three questions today: One about how to cultivate personal style from someone who regularly has mini-breakdowns while getting dressed, my thoughts on the “Substack discourse” (niche one for the newsletter heads), and lastly, how to manage feeling like a failure while hunting for a job that isn’t materializing. Warning, this round is long as hell. Thank you thank you for all your question submissions, I cherish reading them! 

On cultivating personal style

“Dear Baby,

Wondering your thoughts on style, taste, and confidence. I just turned 28 and one thing I’m focusing on in transitioning from my post-college years into an ‘adult’ is cultivating my personal style and investing in quality pieces that I enjoy and will wear for years to come. I feel like I’m struggling with this. My dream is to have a closet where I can easily find an outfit for work, errands, going out, etc, that expresses my style, is flattering, and that I feel confident in. I find that more often than not, when I get ready to do any of those things, I fall into the trap of trying on everything in my closet while having a mini-breakdown that nothing fits any of those criteria. I go back and forth between thinking this is just an issue of cultivating my taste (i.e. a solid understanding of the true silhouettes, cuts, styles, and colors that suit me) or thinking this is just an issue of self-confidence that no amount of Instagram Reels on dressing for my body type and hours scrolling online shopping will fix. Is there an ‘end’ to cultivating your style? Does ‘the perfect wardrobe’ exist? How do I enjoy the journey?”

I definitely could have written this question at various points in my adult life! Part of the reason fashion is so complicated to love is its inextricable link with vanity—to put time and energy into it is to walk a tight-rope with your self-respect. Do you get dressed to honor, express, or delight in yourself, or to fit into someone else’s idea of worthiness? Do your clothes enable you to be present and engaged or do they push you further inward? Is your style connected to your values or does it feel like a commercial product, disconnected from how you otherwise operate? Is it additive or parasitic? Fashion can be just as inhibiting as it is liberating, and most of us experience both sides on and off. It’s hard to pin down.

I sense this ambivalence in your question. You’re either on the cusp of this sustainable source of well-being by way of finally buying the right stuff, or you’re lost, looking for confidence in all the wrong places. My first suggestion is to disabuse yourself of the notion that you’re going to solve this riddle by studying harder. I think you know that deep down. The Instagram Reels about how to dress for your body type and the endless online shopping are junk food for your anxious mind to chew on—they work because they feel immediately satisfying but are unsustaining in the long-run. You can chase those little highs forever, build a closet packed with technically flattering and stylish clothes and still be scrolling, looking for your next hit. Consumerism is an addiction! That kind of void doesn’t close by being filled. It has to heal.

The idea that we’ll gain confidence by buying the right stuff is one we’ve lifted from marketers whole-cloth. In my experience, it tends to happen the other way around. When I’m feeling confident, my taste is more reliable, grounded, and steady, and I’m able to shop slowly and with more patience. In the end, what I buy may contribute to my confidence, but only because it was already there, developed over time and, importantly, through other means.

Time is probably the most important factor. Like I mentioned in my critique of Emma Chamberlain’s house tour, “personal style” feels soulless without a little patina to it. Years may pass before you feel like you’re onto something, and this process will likely involve plugging your ears to the siren song of trends until you realize you actually have the same sensibility you had as a kid, it’s just grown up now. I like the word sensibility, I’ve started using it instead of taste when I’m trying to tap into something deeper. My sensibility is more personal, time-tested, idiosyncratic: the colors, textures, and moods I’ve always gravitated towards. It applies across contexts and is easier to trust than my tastes, which are more likely to shift with trends and culture. My sensibility is basically consistent, and dovetails easily with the rest of my life and personality, because I came about it organically versus by algorithm.

When I’m feeling overly eager (almost panicked) about some kind of shopping endeavor, like wanting a whole new wardrobe when a season changes or hoping to make over my entire apartment, this is always a sign to back off, because I’m going to buy things I won’t like or cherish in the long run. I’ve brought this quote up before in this same context, but it bears repeating: “Desire that arises in agitation is an expression of the ego; desire that arises in stillness is an expression of the soul.” That agitated feeling of hating all your clothes, wanting everything to change suddenly—this isn’t a shopping problem, it’s a spiral of insecurity that needs a different kind of tending. How can you slow down, take stock of what you have, what you like, what makes you feel good, and accept where you are for a while? There’s no harm in feeling unfinished. The harm is in assuming that’s a problem.

Some classic shopping advice you probably already know but may need to heed better: When it comes time to acquire something new, try to do it from a place of relative stillness, or at the very least, out of a careful curiosity. When possible, buy higher quality clothes less often, in natural materials. Cheap or polyester stuff can look great or even look expensive, but it often doesn’t wear well over time (or even in the short term if you look closer, the way it clings or attracts dust or feels on your body). Return stuff you don’t love or that doesn’t fit exactly right. If you tend to buy a lot of one type of item, e.g. you always buy pants, rarely tops or shoes, try in earnest to refocus; another pair of pants is not going to fix your lack of tops. If it helps, figure out a few words that describe your sensibility and use those as a litmus test when you want to buy something. Imagine having the item for years. This is a slow process that can be kind of boring. It’s not a movie makeover montage, which is sad for all of us, but in the long-run, it’s a much more reliable (and sustainable) way to build a wardrobe.

I’ve written about this before, but I think buying too much can inhibit the process of finding your style, or make your style worse. Leaping from high to high, you mistake the rush of novelty for confidence, spend less time with the stuff you own, and begin seeing the inevitable shopping comedown as proof that your closet still isn’t right, when you’re probably just bored because it isn’t new. Spending more time with your closet, forcing yourself to get creative with it, trying out combinations you wouldn’t initially think to try—these are all ways you can explore without constantly feeling like you’re starting over. I’ve only become a slow shopper in the last few years, and I think this is the single biggest contributor to my lack of mini-breakdowns while getting dressed (although this may jinx me).

One of the pitfalls of fashion is how it can encourage you to see yourself in the third person—an object held up for judgment. Try to keep in mind that your goal isn’t to look like a walking advertisement for a certain sort of person (a contest with no prize). It’s just to feel good in your clothes, embodied and present. “Finding your personal style” suggests you’re pursuing something specific, but I think it’s more abstract than that—more like self-possession. If you can gather the requisite patience, this is as much of an inward search as a practical one. 

On the Substack discourse

“Hi Haley, I'd be curious to hear your POV on all this newsletter discourse. As someone new to publishing on Substack with no following, I constantly struggle with imposter syndrome. Obviously, anyone looking to write full-time on Substack is probably well-versed in the platform and reads widely but I worry that I've internalized so much of other people's style that I won't be original enough or my content won't be good enough or worth reading. If you were getting started now and hadn't had a following from MR, what advice would you give to someone who cannot get a media job but has some experience in adjacent fields and some academic training as a writer?
Emily Sundberg’s “The Machine in the Garden”
Alex Brown’s “Who’s Even a Writer Anyway?”
One Thing’s “What Makes a Good Newsletter?”

Thank you for linking these pieces so conveniently! I’d read parts of them but hadn’t read them fully until now. I’ll share a few thoughts but my main advice is going to be related to why I’ve never contributed to this Substack-on-Substack meta-discourse before: I find it distracting. It drains me and drudges up worries that I don’t have space for creatively nor a desire to indulge. I don’t find it helpful from a professional perspective either—trying to gain insight from it feels like trying to take a deep breath from inside of a paper bag. I’d much rather go outside. That said, I understand that new writers may find the discourse impossible to ignore (I’ve been asked about it a few times now), so I’ll weigh in briefly then answer your question specifically.

I know Emily Sundberg’s essay got people riled up and I think that’s because it was framed up as a systemic critique while her frustration felt oriented more towards users. I also think it was non-specific enough to make many people feel like it was about them, which was both a strength and weakness of the piece. It got a conversation started but didn’t really know what that conversation ought to be about—not a crime. I think she made some fair points, but I think it led to a pretty defensive discussion because it backed people into their respective corners. At least that appears to have been the initial effect…I guess we’ll see as time goes on. Regardless, Emily definitely tapped into something people were anxious about.

Like Emily, I think the ecosystem Substack has built out and encouraged people to use is a bit fatiguing. But I think that has less to do with the users and more to do with Substack’s growth strategy. In essence, they’ve become a brand-forward social media platform rather than a software service that disappears into the background. I get why—they’re trying to become another leader in the attention economy and turn big profits. But in the process they’ve handed their users a lot of the social-media trappings newsletters were initially trying to solve for: the swirl of people vying for their attention, the overload of information, the like counts, the ads, the algorithms.

At least, that’s what I thought newsletters were solving for. They were a slower, more siloed, more intimate form of communication. Now the Substack app feels like Twitter (but earnest), and “posting” once again feels like this dreaded imperative for participating. I think this is why Notes feels tiring after a while—most people use it to market their work, and marketing just isn’t very exciting to consume or create. Emily might argue that a lot of it feels dull and repetitive because the work itself is dull and repetitive, and that may be partially true, but I’d argue the medium is the message. We’ve known the negative externalities of the social media format for a long time; any disenchantment with this latest iteration isn’t surprising.

Notes has probably helped writers with smaller audiences clear some hurdles, which is great, but it’s also created a feeling of overwhelming abundance: so much writing published all the time, seemingly circling the same handful of topics. Users subscribing to 20, 30, 40 Substacks, and why not more? They just keep coming! This solves a problem (helping writers find an audience) while creating a new one (transmuting their work into “content,” and all the drudgery that implies). I acknowledge this is a tough nut to crack for Substack; I’m just not sold on how they’ve approached it so far.

This brings me to someone like you, a writer starting out who has a pathway to potentially find an audience on Substack, but in order to do that needs to learn to cannily navigate another social network that makes you feel like what you have to offer is disposable and unoriginal. The thing is, the world is so vast and populous that everyone is doing something that many other people are doing—it’s not useful to take in reminders of that all the time. This is a moment in your writing life to home in on what you would like to say and focus on learning how to say it as best as you can.

Learning how and when to put those blinders on is invaluable. This is why I don’t read very many Substacks. Sometimes I feel guilty about this, like maybe I’m not doing my homework, but I’d rather find inspiration elsewhere—different formats, tones, contexts. I don’t want to feel like I’m competing with other newsletter writers; I think that muddies my motivations. I’m not trying to “write a newsletter,” I’m just trying to write and connect with people who read my writing, however and whenever I can do that. I think as long as I can access that unadulterated motive, the result won’t feel like a farce and the platform itself won’t actually matter that much.

That’s why I say this discourse is a distraction. One of the wonderful things about Substack is, at the end of the day, the work published on here is reader-funded, which means cheap tricks (like a zingy headline that gets readers to click and see ads even if they don’t enjoy the article) won’t get creators very far. That means quality does matter—or at the very least, genuine entertainment value does. Otherwise people will just stop paying to support its existence. I think that helps the platform maintain a measure of authenticity, even as it (in my view) loses its way a little.

So my advice to you is the same advice I’ve given writers in the past about improving their quality (most of which you can find here): Try not to write exclusively in a vacuum—support your work with outside resources; share it with friends, with an editor, or with peers who offer to edit; edit some work yourself; hold yourself to a high standard. Don’t fixate on what you think people want to read (this reverse engineering produces hollow stuff), but also maintain a healthy fear of wasting your readers’ time. You want just enough of an inner critic to give you something to prove.

As for Substack specifically: Commit to a sustainable rhythm and stick with it as you establish your voice. If and when you’re ready to charge, know that people do not typically convert to paid until they’re enticed by something behind a paywall, even if they love your free writing and hypothetically want to support it! Know that it takes a while to build an audience. Remember that being creative always requires risk—if you weren’t ever nervous, you’d be a hack, repeating what you know works over and over again.

That’s all I can offer you for now. No tricks really. I’ve never done tons of marketing for my newsletter, which I know is lucky (timing, prior audience, etc), but I think it’s also helped by the fact that I put a lot of work into the product itself. Maybe I’m naive, but I really do think that’s the most reliable “marketing” strategy. Who knows though? Substack is rapidly changing and I sometimes have doubts that my low-key promotional approach will keep working—after slow but consistent paid subscriber growth for four years, it’s been falling for nearly six months now, and I’ve heard the same from some of my peers. The time may be ticking on our way of doing things, but maybe that will prove helpful for some of the new faces. Either way I still believe there’s a group of loyal readers out there for everyone who wants to write. I hope you find yours!

On feeling like a failure

“Hi Baby!

I recently finished grad school and I'm on month two of the job search. I went into grad school with such high hopes—that it would be a kind of reset, setting me on track for a new career path in a new city. But two years later, I feel more stalled and uncertain than before. Right now, I’m unemployed, and it’s not just a career gap; it feels like I’m carrying around a heavy weight. My friends and family have been nothing but supportive, but I increasingly find myself avoiding them out of embarrassment and shame. They don’t see me as a failure, but I can’t shake the feeling that I am. I’ve always believed that work shouldn’t define us. I know that our worth lies in how we show up for others, how we support our communities, the passions and purpose we bring to the world. But all I can focus on right now is how off track my life feels. I’m haunted by fears I didn’t used to have, like whether I’ll still be able to have the future I imagined if I don’t ‘fix’ my career soon. I hate how much these thoughts consume me, especially when I know I don’t want my job—or lack of one—to define me. I've never felt so devoid of confidence. How do I navigate this dissonance? Is there a way to genuinely reconnect with the values I believe in, even when I feel so lost?”

I’m so sorry you’re feeling this way. First of all, no person is “a failure.” Nobody fails and stays there forever. Failure is part of the cyclical nature of life. I am failing at some things right now, and one day I’ll be thriving at them, then back again. Some years I feel lots of growth, others like I’m generally blowing it. None of us get to stay up all the time, and we don’t stay down either, and thank god for this variability, because it gives all of us a chance to be celebrated then humbled, generous then needy, grateful then wanting, confident then searching. (If you’re lucky enough to not have external circumstances send you around this loop, don’t worry, you’ll find a way to do it to yourself.) All this to say: You’re not a failure—that implies a simplicity to your life that insults it. If you must, call it a flop era.

This is a destabilizing place to be—you are sane for feeling terrified! I think it’s important that you’ve allowed yourself to get swallowed in this feeling and just as important that you now navigate your way out of it. The pre-grad school high hopes need to be set aside. They helped you take the leap into higher ed and now they need to be forgotten so you can deal with the situation in front of you, which you are more than capable of doing. 

The situation, to be fair, is shit, and that’s not your fault. These academic programs promise the world (very lucrative for them) and the job market simply can’t support their claims. That’s not on you. Everyone who wants work should be able to find it. And you will find something, it just may not look or unfold as you imagined. That’s probably a hard pill to swallow when you assumed the hard part was the degree itself, but as long as you hold onto that narrative, you’re going to keep seeing this predicament as a referendum on your character.

It’s time to reframe this. Your predicament is not about living up to your former expectations, it’s about assessing a need (employment), and taking stock of the resources you’ll need to address it (friends, time, money, and, yes, your developed skills and degree). Assuming you have a little of all of those, this isn’t a bad situation, all and all. But being unemployed is hard for reasons that aren’t always comprehensible outside the experience—it’s a lot of pent up energy and pressure to use it wisely. Currently you’re using that energy to fuel anxiety and rumination. It needs a place to redirect.

How can you break this endeavor into smaller steps? “Find a career that justifies years of school, impresses my family, sets me up for the exact life I want to live until I die” is too big. What’s your goal at its simplest? Assuming you are applying for jobs already, what else can you do that will make use of some of your stagnant energy? Reach out to some people you admire to get coffee? Volunteer? Offer to help a friend with a project just because it sounds fun? What parts of yourself are being neglected right now, and how can you nurture them a little? I know these things may feel like distractions but I promise they aren’t. Sitting around worrying and waiting is disempowering. You need to make use of yourself. It’s shocking (actually a little scary) how often people’s lives turn on happenstance—getting out there won’t just make you feel better, it will broaden your horizons.

That feeling that this isn’t just a career gap but a heavy weight really is all about framing. It is ultimately just a career gap; things just feel a lot bigger and more complicated when we’re inside them. Every career has gaps and lulls. Just because they’re unavoidable doesn’t mean they aren’t terrifying when you’re in them. The challenge is to figure out how to breathe through it and trust that they’ll deliver you somewhere new. 

If you have advice for our questioners, please share!

Have a happy Thanksgiving everyone,
Haley