#47: Writer’s block, HR secrets, and feeling like it's “too late”
I made you a flowchart
You’re receiving this email because you’re a paying subscriber of Maybe Baby. Thank you! This is my monthly Q&A column, Dear Baby, in which I answer multiple reader questions. To view this in a web browser, click on the title above.
Hi!
Welcome to Dear Baby, my monthly advice/Q&A column. This week I’ll be answering these five questions:
I’m 22 and feel eager to be older than I am. How do I stop cringing at my own mistakes?
After 5 years in HR, do you have any behind-the-scenes secrets to share?
How do you deal with bad or difficult writing days?
I recently received some disappointing career news. Should I tell myself everything happens for a reason? Is there another way?
Can you talk about the feeling of it being “too late"? I know logistically it isn't true but the feeling is overwhelming.
As usual, my wordcount is completely out of control, although Google told me it will take under 20 minutes to read, which is less offensive than I thought. Thank you for being here!
1. On Shame
“I am almost 22. I have always felt eager to be older than I am (I maybe took 13 Going on 30 too seriously? like why the hell would she want to go back?!) to the point of almost being embarrassed to be young. I wonder if some of this has to do with shame of growth, or shame of not popping out of the womb fully grown and perfect. Do you have any advice on how to allow yourself to grow, free of ego, and also forgive yourself? How to stop cringing at a big mistake you made 12 years ago? How to stop cringing at a big mistake you made 12 days ago?”
One of the most confusing things about being in your twenties is everyone telling you about their twenties, and giving you advice they wish they’d gotten. The irony of this tradition (and I’ve participated often) is that it means those people probably did receive that advice when they were 22, and they either didn’t listen to it or weren’t ready to hear it...because they were 22. Many lessons we simply have to learn for ourselves, and receiving it too early can invite a lot of pressure or self-flagellation. And I say that as a person who is literally, at this moment, writing an advice column. So rather than try to convince you out of your ennui (“Enjoy being 22, it won’t last!”), or render it unimportant (“One day you will kill for this problem!”), maybe I can try to help you reframe it. Because how you’re feeling now is a completely normal and formative way to be 22, but you might be able to experience it less anxiously.
We definitely overemphasize age in our culture, but I understand why the twenties have such a stronghold on our collective conscience. They combine something wildly scary (being on your own for the first time) with something wildly fun (being on your own for the first time). It’s also a period of transition, meaning it will be unavoidably confusing and uncomfortable. And just like heartbreak, the experience will feel completely novel to each person going through it, making preparation virtually impossible. It’s very strange to be told something will be hard and have no reasonable way of avoiding it; I remember hating that a lot. You asked how you can forgive yourself through this process, and I think that’s a very wise question to ask. Because shame, as you mentioned, can make forgiveness and acceptance (and thus growth) really difficult. It might help you to start thinking of this tension—between shame and growth—as the central challenge of this era of your life, rather than the more concrete pursuits you probably think are the challenge, like asking for a raise or whatever.
Heather Havrilesky once wrote an essay for Man Repeller about shame that I never forgot. “Shame is an onboard navigational system,” she wrote, “one that’s intent on keeping you small and apologetic indefinitely.” She writes that shame is the natural extension of a belief that others know better than you. That their mistakes or fraudulence aren’t as fucked up as yours. It makes sense that we feel this way—not only because we know ourselves completely and others barely, but because most of us behave as if we’re better than we are, which feeds the same beast. On top of everything, shame is socially enforced; others become envious when someone doesn’t experience shame, and often try to right the balance. “Coolness is shame incarnate,” Havrilesky wrote. “The blasé are full of shame. Shame is believing that if you’re not winning, you’re a loser, and if you’re not in love, you’ll never be loved, and if you’re not perfect, then you’re disappointing and flawed in permanent ways that anyone can see just by glancing at you.”
When we cringe at our former selves, that’s shame. The things I cringe at the most from my past are my varying shades of self-delusion or misguided confidence—times I was so sure of something only to realize later I was wrong. That process is very embarrassing, but recognizing that everyone goes through it, and literally must, does help. I think we often assume that self-compassion or self-acceptance always start “within,” but I think learning to extend it to others is really good practice for internalizing it ourselves. I have a clear memory, from my early twenties, when my friends and I stopped making fun of other people’s failed efforts and started admiring their bravery for trying. This transition helped me learn to be brave too. Try extending empathy to other people for their fuckups and fakery; see if it makes you feel any differently about your own. I know you said you make yourself cringe, but I’m sure there are things about your former self you still like and want to hold on to (if you don’t, you should try to find them). In the meantime, assume others empathize with your mistakes, and if they don’t, take comfort in the fact that they cringe at themselves too.
Cringe can also be really funny when embraced. The more I talk and write about my stupid former self, the freer I feel. (I really regret tearing up some of my old embarrassing journal entries when I was 17 and mortified, because I know I’d love them now, which is to say cringe has a lifecycle that can end with affection.) As much as I hate the use of “adulting” as a verb, I can appreciate what it’s offered people: a sense of humor and camaraderie about something that actually feels heavy and overwhelming when endured privately. There’s a lot to be gained by giving things air and recognizing you’re not alone in how you feel. I remember having so many long talks with friends when I was 22 about how lost we felt. We would scream and laugh and cry we were so confused, and while talking about it didn’t necessarily solve it, it connected us in really bolstering ways. I wouldn’t have predicted it then, but I would later look back on those conversations as unlocking something in me. It’s almost as if that era wasn’t really about solving our problems or figuring out what we wanted, but about enduring a disorienting time and learning who we were in the process of that. The answers almost came incidentally. Hopefully this feels something like a relief to you.
You mentioned you’ve always been “eager” to be older than you are. In most cases, the word eager has a positive connotation, and I wonder if you can strive to see it that way. You can look forward to something without being impatient for it, or too attached to it. I happen to think anticipation can offer a pretty good high. But there is a particular emptiness to living as if your best life is always around the corner, never happening now. I’d challenge you to let your eagerness coexist with an appreciation for what is specific to your life now—what features of your current situation and sensibility you once longed for. This is ultimately a challenge for all of us and it never goes away. Once we get the things we want, they cease to entice us. So keep in mind as you navigate this mental balancing act that this is what living is, what life is. There is no version of you that will become static and satisfied. The sooner you realize that, the sooner you’ll realize you’re already doing exactly what you need to do.
P.s. I felt the same way when I was your age—ashamed to be young. If it’s any consolation it very aggressively dissipated when I turned 30 and now I would like time to please slow the fuck down.
2. On My HR Secrets
“After 5 years in HR, do you have any behind-the-scenes secrets to share? Never know what the people in HR are thinking and it would be cool to have some insight...maybe some big sister advice for dos and don'ts from someone in HR?”
The first and most important thing I can say about HR is it exists to serve the interests of the company. I don’t mean that everyone who works in it views the job so cynically (I didn’t!), or is hiding an ulterior motive from you, but ultimately that is the purpose of HR. Even if reps fight for you behind closed doors, unless they can convince the higher-ups that what they’re asking for will ultimately serve the company—financially or reputationally—it’s not likely they will win. Of course there are always exceptions to these rules, but generally the framework is not a moral one. HR will not protect you like a union will.
I worked in office management/overhead-type roles for my first five years out of college, but the latter three were explicitly in HR, when I learned the ropes of hiring, firing, promoting, and everything that falls under “people management.” I enjoyed my years in HR because they spoke to my interest in the softer side of business. People told me their problems; I often dealt in feelings; in meetings my colleagues and I would discuss abstract ideas like motivation and fulfillment. But at the time I don’t think I fully grasped the limits of my role as an agent of the C-suite. I got caught up in the politics of who “deserved” a raise, who wasn’t pulling their weight, or how to fairly split a meager bonus pool. While I might have bristled at the difference in compensation between levels, I rarely thought to challenge the salary bands or the budgets. My role was to work creatively within the rules, which were set by two 60-something white men with previous experience at a company that made a few people billionaires. The company I worked at was dealing in much smaller numbers (and they were nice enough), but my point is that business norms are set by the people at the top, and the people at the top center financial growth because that is the primary goal of for-profit business.
This isn’t to say HR reps don’t have the choice to behave ethically within those bounds, or that they can’t offer genuine empathy, support, and championship. But I think it’s safest to operate under the assumption that what HR can do for you is help you play the game better. When I was in HR, I was best able to serve people who genuinely used me for that purpose: by telling me what they wanted, what wasn’t working, what didn’t sit right with them. Part of my job was to figure out how to help people by placing their needs in the context of the needs of the company, so if people did that for me, even better. It tended to be more difficult to fight for requests that answered to only one individual’s needs, unless that individual was a star employee who brought a lot of business to the company. So if that’s not you, I would suggest trying to frame your requests under the guise of helping you/your team perform better going forward, versus something more backward-looking. For example: Asking for a day off for the whole team after a hard week so that you can come back fresh on Monday will be more effective than lodging a complaint about overwork. To that end, asking for things in specific and tactical terms worked well, i.e. timelines (“when will this request be best received?”), trade-offs (“I can do this, but I’ll need this in return”), and specifics (“what exactly do I need to do for a raise?”). Of course every company and HR department is different.
I am not condoning this modus operandi at all, just expressing it as I experienced it and have grown to see it in hindsight. I do think good HR people can convince their higher-ups to think in terms of people over money, but bad ones can do the opposite, as we’ve seen with so many harassment-suits-gone-wrong. Ultimately I think unions are a much better resource for fighting to protect employee needs and rights. So if your workplace isn’t unionized, perhaps look into it starting the conversation with your coworkers. (I haven’t done it myself, but there are lots of great resources out there on how to organize your workplace.)
3. On Writer’s Block
“How do you deal with difficult writing days? How do you know when to give up on an idea? I'm trying really hard to be consistent with my own writing project but some days I find it impossible to come up with something good or valuable. I adore your writing and this newsletter and I just want to know how you face those challenging days when ideas feel stupid and words don't flow right.”
I’m sorry you’re struggling with your project! The first thing I will say is everyone’s relationship with writing (or any kind of creative work) is specific to them. While I do think some writing aphorisms are universal, like the idea that you can’t get better without lots of practice, I find that many of them—like “write every day” or “start early” or “shitty first drafts”—don’t account for the infinite differences across personalities, strengths, resources, general life situations, etc. In my view, the idea that what works for one famous writer will work for others is born of the same myopic delusion that inspires celebrities to tell us to follow our dreams. So before I tell you what I do, I’d encourage you to treat your own experiences as the most relevant data for building a framework for how and when you work best. Think about times you’ve been more motivated, energized, and able to follow through and times you weren’t. What differentiates them? Or how about times you dragged your feet but ended up pulling through—what helped you? What definitely didn’t?
For me, dealing with a bad writing day is all about diagnosis. There was a time in my writing life when I conflated writer’s block with just not trying hard enough, and another era when I conflated it with being burned out, and another when I was sure that every snag could be fixed with an outline or a phone call with a writer friend, but none of these were always true. Writing can be hard for different reasons—being tired, aimless, afraid, confused, intimidated—but often the feelings present similarly: we feel frozen, want to procrastinate, do anything but write. One of the biggest challenges for me has been learning how to suss out the differences between different blocks, and thus understand how best to respond to them. I still make mistakes sometimes, but I’m getting better at it as time goes on, and you will too.
Here is a loose visual representation I made for you re: how I deal with bad writing days:
As you can see I place a lot of emphasis on the quality and clarity of the idea. This is something I learned a lot through working as a professional writer and editor, where there is no way out of writer’s block but through. I found that oftentimes when I was struggling with a piece, as a writer or as an editor, the problem was foundational: the initial idea was not perfectly coherent. It might have sounded good in pitch form, or compelling as a headline, but drawn out it didn’t track. This is why writing is sometimes harder than we expect it to be; we think we have tons of good ideas but fail to account for the fact that it’s much easier to toss off a thought in conversation or on Twitter than it is to actually communicate it thoroughly or artfully. This happens to me all the time, and sometimes it takes trying to write it out to realize. If you find yourself there, try explaining your idea to a friend, or make an outline, or sum up your idea with a title and thesis statement. Crystalizing your idea can free up some of your headspace.
But sometimes the ideas are good and the words still don’t come, or the very process of clarifying the idea feels too mentally taxing. Having to work through burnout because you’re on a deadline or have no time is a very painful experience. To be honest, I’ve been going through that with this very newsletter. After writing so many intense essays over the past months, writing this much this week has been really hard. I know it hasn’t led to better work and I can only imagine the ripple effects it will have next week.
You can swap in a variety of external or personal problems for burnout on the chart—mental health, the conditions of your life, a pandemic. Sometimes your inability to express yourself creatively isn’t something you can fix through individual action. Writing may seem like a widely accessible hobby, but it takes a surprising amount of time and energy that not everyone has. I can write as much as I do because I have three full days every week just to write, not including the weekend. Which means that if I wake up on the first day and feel totally incapable of writing, I can choose to do something else that day and revisit it the next. I’ve never had that kind of flexibility before, and now that I do, I understand it’s the ultimate privilege—one our work culture often doesn’t account for, let alone encourage. I protect that time even when it means sacrificing more money, which sometimes feels counter to my instincts. I also can comfortably pay my bills and generally feel supported in my work, which isn’t something many writers have, and I still get blocked and burned out. We live in a mentally taxing time and writing itself is mentally taxing, but it can also be deeply satisfying, so you just need to check in on where you are.
All this is to say: It’s highly personal and also societally informed. Learning about yourself (when you work best, how to diagnose your block, when you’re lying to yourself, etc) will help a lot, but understanding what external pressures exist for you will paint a fuller picture. Modern life in the West has done so much harm to creative pursuits—by working everyone to the bone, by making commodification the only goal, by glorifying the hustle—that blaming only yourself for struggling to keep up is not only unhelpfully harsh, but inaccurate.
4. On “Everything Happens for a Reason”
“I recently received some very disappointing career news. I matched for residency at a site very low on my rank list. I was so certain that I would match at one of my preferred sites and I am feeling the sting of rejection. With the way the match works, I am locked into this position for the next year and there is realistically nothing that can be done to change the situation. I have to accept these results and make the best of it, but I am struggling. The spiritual tradition of my upbringing would say that it’s part of a masterplan that I can’t see, and nothing that is for me will pass me. Basically: everything happens for a reason. I’m not sure that I believe this to be true or even find comfort in these thoughts the way I once did. It’s possible that this position will be better than I expect. It’s also possible that it will suck. My question for you is: How do you work through disappointment and rejection? Do you tell yourself it happens for a reason, or is there another way?”
Receiving news that the next year of your life will look very different than you imagined—especially after you worked so hard for this moment, probably through a pandemic—must be really unmooring. I have a lot of compassion for how you must be feeling right now, and I think it totally makes sense that you’re struggling. If I were you, my instinct would be to immediately rebrand this disappointment in terms of its silver lining. Like you, I grew up putting a lot of emphasis on that kind of reframing, mine usually centering gratitude. But over time, I fashioned it into a kind of bludgeon against negative emotions, explaining them away as quickly as I could. By doing this I reinforced a very sanitized worldview; one where my sadness or disappointment was always a failure of optimism, gratitude, or perspective. It’s not a very humane approach, in my experience. And it can breed resentment. So my first suggestion would be to allow yourself to feel sad about this. I think it’s an important part of getting to know yourself.
But that doesn’t mean I don’t see any merit in believing “everything happens for a reason.” Assuming you’ve given yourself enough time to process your disappointment—how it’s made you feel, and why—I think there’s a lot to be gained by thinking about how you might benefit from this unexpected turn. I may not believe things happen for a reason according to some divine order, but I do think people have an incredible capacity to find reasons to accept what happens to them, and that can be just as powerful. Acceptance allows us to get out of the past and into the present, where we’re much more needed. I’m sure you already know this, but in case it’s helpful to hear: You’ll no doubt get something out of this experience that you will eventually cherish, even if it’s just more information about what you want, which is not a small thing.
I think it’s also worth considering whether your idea about what it might have been like to match with your top choices was skewed, or flawed. Humans are famously bad at predicting how we’ll feel if and when we get what we want. Or rather, we assume it will make us much happier for much longer than it does. This is called the impact bias. We’re also not very good at knowing what is most critical to our wellbeing—the salience bias “describes people’s tendency to focus on things that seem like a big deal while ignoring other things that may be more worthy of their mental energy.” Or how about optimism bias! Our tendency to assume bad things won’t happen to us; it contributes to the failure we feel when we’re proven wrong. Oftentimes the thing we want—the crush, the dream job, the big move—turns out to make us unhappy. While things we didn’t want do the opposite. Which isn’t to say this next year will be the best of your life (although it might!), but that it may be just as much of a crapshoot as one of your top choices. This is what makes life so amazing and awful.
Being rejected can be a huge blow, especially because it’s often mysterious, and we’re left to imagine what’s wrong with us. Often it has less to do with us than we think. This is not remotely comparable to your situation, but every once in a while I remember how many times I applied to work at Everlane when I was 25. I made them the most over-the-top applications (one was basically a custom zine), got coffees with multiple enthusiastic employees who then referred me, then never heard a peep. At the time I wondered if that indicated something about me, but I’m sure it was just a dumb twist of fate. I’m of course so glad I didn’t get that job, as it would have set me on a different path than I’m on now, which I love, and didn’t I say people are very good at doing this? My point is, while some rejections merit analysis, I’m not sure this one does. There’s likely nothing you could have done differently. Like you said: Your fate’s been handed to you. I think your most compelling challenges are ahead rather than behind you.
5. On “It’s Too Late”
“Can you talk about the feeling of ‘it's too late?’ I turned 30 this year and feel like because I haven't achieved ‘success’ yet, it's too late. I know logistically this isn't true but the feeling is overwhelming.”
I’ve been thinking about this question for a long time, and I’m finding it trickier to answer than I anticipated. As much as I’d like to give you a pep talk about how it’s never too late (and I will give you that in a second, kind of), I want to first acknowledge that you feel this way for a reason. It’s not some sign of mental weakness or a lapse in good nature. We have all been fed a narrative since we were kids about the general trajectory of a life, yes, but on top of that, most of our systems and traditions are set up to support that trajectory. From job descriptions, to the price of education, to the price of buying a house, to the price of living remotely comfortably, there are practical consequences to these “ideas.” To break away from them isn’t just a matter of practicing radical self-love or learning to not compare yourself to your peers; oftentimes it requires financial, ideological, and social sacrifices. Your anxiety is systemically reinforced.
I think our critique of that system has to start with the nature of work itself. We are told repeatedly that we must do what we love and glean purpose and happiness through work, and yet the system is only set up to do that for an almost microscopic margin of people. Obviously this is unfair, and yet we rarely collectively call this out, because those in power have so thoroughly convinced us that our failures are individual, and that our fulfillment therefore must be individually sought, and so we see our unhappiness as our fault. Those who manage to escape that trap and find fulfilling work are then given the microphone and proliferate it further. I’ve done it myself! After I moved to New York and “followed my dreams,” I told other people to do it too. And it’s not that I think it’s malevolent to try to motivate people to play the game differently or recognize their agency, but I think we’ve created a massive problem by prioritizing that conversation over one that might call for a new game entirely. One where your general wellbeing—your home, health, safety, happiness, and freedom—did not rely on your employability or your prowess at navigating the job market. Our country is so fucking rich. Insanely, mind-bogglingly rich. This money is created by the hundreds of millions of people working every single day. It is not created by a few men who are really good at spotting gaps in the market and exploiting them. It is created by working people, and it is stolen from them every single day.
When you say you feel overwhelmed at trying to succeed within that system? Of course you do. It’s flawed, immoral, and exploitative by design. There are so many concurrent forces making this true: not just a culture that venerates workaholics and defines people by their productivity, but unlivable minimum wages, unaffordable education funded through predatory loans, and a competitive market created through false scarcity (if there is actually not enough work to go around, why are most people overworked?). Essentially, the system is set up so that everyone’s waking lives are completely subsumed by work, most of it rigorous and/or unfulfilling, and then tells them to do just what they love. It makes me so angry I could scream for a year.
But okay, I know you’re asking about yourself. And as much as I believe in my entire soul that we need to address the system, I also understand there is a lot to be gained individually in reframing your role in it. I did it myself when I moved from the corporate world to the arts, and it’s the best thing that ever happened to me (the extent to which only proves the system is unfair). So if it is within your power to change your life, which isn’t true for everyone, I do think there’s a lot to be said for trying to deprogram some of your thinking about what it means to succeed, and what it means to follow a different trajectory than the one you previously ascribed to it. By “success” I’ve so far assumed you were using the most common cultural shorthand for money, recognition, and fulfilling work, but even if you meant something more intangible, like a particular lifestyle, I think many of the same ideas apply. Deprogramming yourself could mean trying to figure out how to get what you want within reason and without crushing your soul, or it could mean redefining your needs entirely. If you weren’t told over and over by other people, what do you think your personal definition of success would be if it were up to you? Luckily, it is up to you.
When you say “it feels too late to be successful,” the rest of that sentence might seem implied to you, but I’d encourage you to finish it. Whatever’s hiding at the end of that statement might be a good starting point for working through your anxiety. For instance, if it’s: “It’s too late to change careers because it will cost a lot of time and money and I might fail,” you now have three things you need to sort out your relationship with: time, money, and failure. Dealing with each of those might require further deprogramming. Turning 30 is a great example—it’s a cultural milestone with tons of baggage that doesn’t stand up to much scrutiny. Plenty of people radically change their lives after the age of 30; almost everyone acknowledges their twenties are a disaster; and it has now become more of a trope to feel anxious about not having your shit together by 30 than to actually have your shit together by 30. Also, what does it actually mean to “have your shit together”? Do you agree with that definition? Are your failures in that respect actually your fault? There are so many ways to unpack and disarm these ideas if you give their counterpoints the time of day. Therapy is great for this.
I won’t lie to you. There are some practical barriers to bucking the typical trajectory (some perhaps biological), but it’s also true that feeling like it’s too late is endemic to modern life. I felt it when I was 23 and had no business feeling it, and I feel it now, much to the chagrin of my future self. You will think, one day in the future, that you were much younger at 30 than you thought you were. And you know it would still be worth fighting for a life you liked even if that weren't true. So maybe your biggest challenge right now is to ask yourself what’s actually stopping you from doing that. Really spell it out, give it air, share it with others, demystify it. If your concerns are material, give yourself grace in accommodating those (it can be freeing to admit you simply don’t want to blow up your life, and rejigger your goals accordingly). If your blocks are mental, consider what might help break you out of them. For me, this had a lot to do with learning to govern myself with curiosity instead of fear, and finally recognizing that trying things was more useful for making decisions than ruminating on them. Essentially, I had to unfreeze myself before I could move. I think you need to do that, too.
This is all so vague I want to slap myself, but without more information about you I’m nervous to be prescriptive. Assuming that “success” is achievable to anyone with the right combination of ideas and actions is exactly what got us here in the first place. We live in a strange, alienating time. It’s not your fault you feel this way—so many things need to change so that this burden is no longer considered inevitable. But until that happens, try to forgive yourself, and see what you can do to reframe the problem, if only for your own sanity. Just because society has deemed youth the ultimate cultural currency doesn’t mean it’s necessarily more enjoyable to do things young (there are clear downsides to “early success”), nor are certain works better just because they come from someone young. It’s simply a cultural fascination; it doesn’t have to have so much bearing on your life. These anxieties may be a product of our fucked up era, but that also means many of them are full of shit, making it easier to see them for what they are.
Alright that’s it for this week! Thanks so much for writing in and reading. On the podcast this week I invited one of my friends and mentors, Verena von Pfetten, co-founder of Gossamer magazine, to explore these topics from new angles. Since many of this week’s questions struck me as existential-crisis fodder, I couldn’t think of a better person to bring on. I loved our conversation so much and I think you will too.
See you then!
Haley
This month a portion of subscriber proceeds will be redistributed to GlobalGiving Coronavirus Relief Fund, a non-profit focused on equitable vaccine distribution and getting resources to those made especially vulnerable by the pandemic.
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