#137: When to give up on a dream

Also: quitting Instagram and making art

Good morning!

Welcome back to Dear Baby. Today I’ll be answering three questions: on knowing when to give up on a dream, the benefits and drawbacks of getting off social media, and how to share writing (or any creative work) when you suspect you’ll change and eventually hate whatever you’ve done. As someone who once wrote about the “powerful” color of Hillary Clinton’s red pantsuit during the 2016 primary, I have a lot to say here.

On Dear Danny this week, we’ll be answering questions about how soon is too soon post-breakup to get into a new entanglement, what to do about a friend’s bad marriage, dealing with a forgetful mom, navigating a family member who wants money, and what to do when you’re 37 and still haven’t found your “thing.” Ep drops Tuesday at 9am! As always you can write in your questions here or call 802-404-BABY to leave us a voicemail.

1. On knowing when to give up

“I'm writing because I might be having something of an existential crisis. I think, after chasing it for 15 years, I'm reaching the point where I'm willing to give up on my dream. The dream was to be able to tour with my music internationally and have an audience large enough to sustain the project. My image of success is one that I've created myself, so in that way I'm creating my own unhappiness, but chasing that dream has also been my fuel for so long.

I live in a tiny country, Belgium. Times are weird (in general), but I've really seen the music sector change drastically in the last ten years. In three weeks I'm releasing my third full album. But after releasing the first three 'singles' from that upcoming album, I'm actually feeling depleted and defeated already, while I'm trying to keep up with the non-stop demands for content on social media. (I only have 1080 followers, but it seems like all the players in the sector expect you to do some promo magic by yourself.) I do have a booking agent and a small record label, people I really like, but they also seem tired of fighting for attention and trying to compete with the bigger fish in the sea. And then I feel guilty that they have to bump into all those walls for my project. And all the rejections...they get under my skin. So many gatekeepers you must depend upon.

Even though I know there are thousands of artists like me who want the same thing, I feel like a total failure. Maybe I expected too much, pumped myself up with optimism, thinking my moment now would come, with this album, to really get a significant step further. But I feel like I'm failing myself, my dream, and those who believe(d) in me. I'm so frustrated and really don't like myself like this. It's been hard to find my center or flow or trust. So Haley, tell me, when do you know it's time to give up on your dream?” 

Love x

Echo Beatty

I’m sorry you’re feeling so defeated right now, it’s palpable. If I were to guess, you did some fantasizing about the impact these singles might have on your life, and so the fact that not much has changed since you released them has served to highlight, once again, the gap between your imagination and reality. This is a microcosm of the larger narrative playing out with your music career—a parade of unmet expectations—which is why drastic measures are carrying a certain appeal. If you can never achieve your version of success, why try for anything at all?

First of all, your frustrations sound totally reasonable. I believe without proof that the music industry is a PR game that rewards clout and cynicism before talent and spirit. I can see how it would be depressing to spend so much time on a piece of art only to turn around and have to sell it to a jaded population that’s only interested in being entertained in 15-second intervals. Perhaps a useful reframing of this moment is that you’re not failing to achieve your dreams, but rather reckoning with what exactly your dreams entail. Obviously the industry has changed a lot, but from what I hear, it’s always been a little gross. Maybe you were going to reach this point no matter what.

The second-most popular notion about dreams, after the one that says we should follow them, is that the day-to-day reality of achieving them feels different than we expect. For so long your idea of success as a musician was to tour internationally and not have to do any other work to support that. It sounds like a very nice dream. But you’re 15 years older now—you have new information about what that life will require of you. You’re not sure you’re willing to give what it will take, or have what it will take. That’s a sobering thought, but it’s not exactly a sign of failure. It’s a sign that your real self is rubbing up against your idea of yourself. This happens to all of us eventually.

What would it look like to be a musician who didn’t tour internationally, or who had to work a little on the side to support herself? What would it look like to invest time and energy in your art without the hope of achieving commercial (or at last niche/indie) success? I’m not suggesting there’s no hope for achieving your original goal, but as a sole motivator, it’s inadequate. I totally get why “making it” has served as fuel for you, but it’s running out, and there are other, more sustainable types of fuel. You might need to shape some ambitions for yourself that rely less on luck and industry power-brokers over which you have no control. You might need to return to what called you to make music in the first place, before you ever considered you could tour internationally. Callings are different from career dreams—they suggest sustained action, rather than black-and-white achievement. All a calling requires is that you listen to it.

Maybe this album will take you to a new level of monetary success, maybe it won’t. What if your future wellbeing didn’t hang in the balance of that binary, but instead turned on your ability to continually reassess what feels meaningful to you and steer your life towards new versions of that? There are so many possibilities between one end of the spectrum (“making it”) and the other (“giving up”). There are so many ways to be an artist. All of them will involve weathering dry spells and stretches of self-doubt, but they’re not all contingent on self-commodification and kowtowing to gatekeepers. You’re allowed to decide how much of that you can bear. You’re allowed to set your own rules around what success looks like. You’d sooner fail by letting someone else choose.

2. On quitting Instagram

“Might be a goofy question, but what do you do now that you are off of Instagram? I find myself in a constant delete-and-redownload loop with the app. I want to stay up to date but I also don’t love being on there for so long. As soon as I delete it, I do feel good, but can’t help but feel a little bored on occasion. It’s not like Instagram is that stimulating but it does sometimes help to defeat the boredom feeling. Any recommendations? And also what made you decide to get off of the app? Do you still use it?” 

I still go on Instagram sometimes, but I don’t find it nearly as entertaining as Twitter or TikTok and I suspect that’s because IG is a poster’s paradise, and I don’t post there anymore. I don’t have a rule against it, but once I stopped sustaining the myth that my account was a reliable reflection of me or my life, I was sapped of motivation to participate. This was a long process, and I’m still working out all the implications. When I first started getting “real” followers on Instagram (as in not friends but parasocial connections, the real movers and shakers of the app), my ex at the time would sometimes get annoyed at the time and energy I started dedicating to posting—my goal was once a day. I remember leveling with him at one point, saying something like: “Once you get people interested in your life, it’s very exciting! I want to sustain that interest!” Lol. This was 2015. I wasn’t remotely interested in unpacking that sentiment.

Today I’m more aware of the fine print on the social contract we enter when we post on Instagram—at least when we’re posting lifestyle-esque content on personal accounts. I think the repercussions are more psychological than social. It’s an agreement to understand our lives at least partially through the content our lives produce, that we then edit, caption, and post for likes, views, and comments. Even the noblest disregard for metrics and engagement still necessarily involves a commitment to this algorithmic form of storytelling, which I no longer trust is additive. I can honestly say that the highest highs I ever experienced on the app merely mimicked the feeling of connection and belonging I experience when I’m with good friends. The other upsides were more compromising: the relief I felt when I managed to accurately update my public image; the zaps of thrill when someone with a lot of followers followed me; the satisfaction of privately scrolling my own account and getting a rosy “outsider’s” perspective on who I was. All useless in the long run.

I always feel a little dramatic when I talk about Instagram like this. It’s not like it ever felt that serious when I was doing it. My account is (was?) mostly outfits with silly little captions. It was never an accurate or abundant portrayal of my life. Often it was fun! Yet I can’t deny that not posting feels somehow correct. And while I sometimes miss having a little record of my aesthetic choices, somewhere along the way I got more interested in my offline life, and my offline aesthetic choices, and then it was hard to go back. It felt corny, or too high-stakes, or like a regression, after so much time away. Once I realized my life was the same, if not fuller, without the specter of content creation, the lack of content mining felt like a win. 

I get what you mean about boredom, though. For me it presents more like FOMO—I sometimes miss the times Instagram felt really entertaining and connective, or, less wholesomely, the times it gave me jolts of validation. But I think there’s something useful to courting the void Instagram leaves in its wake. In the book Four Thousand Weeks, Oliver Burkeman talks about the intent behind the Jewish Sabbath—a tradition of “rest” that requires a lot of preparation and isn’t necessarily easy. He quotes the writer Juidth Shulevitz: “The [Sabbath] rules did not exist to torture the faithful. They were meant to communicate the insight that interrupting the ceaseless round of striving requires a surprisingly strenuous act of will.” Rest, in this case, is about more than taking a pleasurable break. It’s about recognizing how difficult true rest actually is, and recontextualizing our relationship with striving by separating ourselves from it. Similarly, the boredom or loneliness we may feel off IG can be instructive.

When it comes to creating and consuming lifestyle content, the best Instagram has to offer is a simulacrum of true connection, and it comes at a cost. Stepping away means sacrificing both sides of that equation, and confronting that loss can be motivating. There are other, less compromising ways to pursue belonging, love, connection, and self-knowledge. I feel a deeper sense of all of those things since I stopped crafting my image for internet strangers, and I feel a little less seen, too. I’m not sure what I plan to do about that long-term, but for now I’m sitting with the feelings, considering what they mean, even when they’re boring and uncomfortable.

3. On publicly changing your mind

“How do you maintain the resolve to publish your writing knowing that a few days, weeks, or minutes from the moment you put it out into the world, you will likely have a new perspective or different opinion on the subject matter or the presentation? I haven’t put any of my writing out publicly because I find myself tripped up by this often. Does it get easier once you start just putting it out there anyway? How much do you think this fear matters?”

I won’t say this thought never occurs to me, because it does, but I’ve learned to power through it. It helps to think of writing (or whatever creative medium you choose) as a form of processing or expression, versus a product. Products are put out by brands, and brands thrive on consistency. But humans aren’t consistent, and shouldn’t be. In fact I think a lot of us are drawn to creating art because we’re looking to make sense of the disorienting experience of growth and change, so naturally our work will reflect that mutability. Art that feels too final can feel a little dead.

I wonder how old you are—I do think that can make a difference. I distinctly remember a moment in my mid-twenties when I finally felt ready to start a long-form blog, and that readiness almost exclusively concerned the fact that I was feeling myself cohere a little. (Maybe this is literally when my prefrontal cortex finished developing?) Obviously I was still changing a lot, but my worldview and self-view seemed to click into a more consistent place. Some of that was probably just time and practice, but I’ve felt subsequent clicks over the years as I’ve become more acquainted with writers and thinkers that influence my own writing and thinking, thereby fortifying it a bit. Consuming work that plays around with your same subjects (especially from the past/outside our current zeitgeist) may help you feel less like you’re making things up on the spot, or falling for the latest in the discourse. A lot of the naivety I clock retrospectively in my writing has been the result of me thinking that I—or my generation—was the first to have a fairly prosaic thought. Developing my awareness outside myself and my time has since helped protect me against that sort of thing. Although I’m positive I will make this mistake again. I think it’s part of the deal. Sometimes we may even need it a little.

Still, the old writing I’ve done that makes me cringe the most actually isn’t the stuff I disagree with now, but the stuff I’ve written inauthentically. Whether I was trying to inhabit a tone that didn’t suit me or being a little too impressed with myself, my old writing that reads false haunts me more than the stuff that reads naive. Even master-level fakery tends to reveal itself in time—if not to others, then at the very least to you. So in my view, the best approach to combating future-cringe is to try to be true to yourself in your writing. Your present self, even if it’s bound to change. And if naivety is your fear, there are ways to write with the possibility of your own evolution in mind. Although I’d guess that’s coming through in whatever you’re communicating already. (I wrote about this a little in my first newsletter, when explaining its namesake.) 

Obviously those with institutional power need to tread carefully with their lesser-formed ideas. But when it comes to lower-stakes writing, remember that nobody is thinking about your canon as much as you are. My politics have changed a lot since I started writing professionally, and while I genuinely shudder remembering some of the over-ripe-but-under-baked takes I shared early on, I’m just happy I have the opportunity to evolve those ideas now, and to keep doing that as long as possible. This is one of the rare times when the media adage that “you’re only as good as the last thing you wrote'' can actually be a relief. You’ll change, of course, but your work can change with you.

Have some advice for the questioners? Please share!

See you on Tuesday for Dear Danny!
Haley

P.s. Hello again and thank you to everyone who came out to Daughter last week in New York! I had so much fun meeting you all.