During my final year working at McKinsey & Company, the elite global consulting firm, I did a year-long project at the World Economic Forum in New York City. It sounds highly glamorous, as did so many things in my life then. McKinsey, which we consultants called The Firm, flew me back and forth between New York and my home in San Francisco every two weeks and paid for my half-time housing in Manhattan. It was 2013, and The Firm’s frothy pot of cash seemed downright bottomless, so I spent my early twenties jetting around the country business class and staying in giant hotel suites. During my year at the World Economic Forum, I went to London, Cape Town, Jakarta, Geneva, and Bali, for work, and then, to top it off, I attended The World Economic Forum in Davos, the ultimate meeting place of the rich and powerful. This life seems unimaginable, even to me. I was twenty-four.

Blinded by the glare of all that, it’s easy to forget what I was actually doing for work, what took up the majority of my time and life force (and that, I think, is the point of all the glitter, to be blinding). At the World Economic Forum, my job was to write a report about the changing digital media landscape. This involved convening stakeholders from across the media landscape and then synthesizing the takeaways into a white paper, (dropping some consulting-speak on ya, wah-bam! I’ve still got it!)

Compared with my regular work at McKinsey, which was more spreadsheet- and powerpoint-heavy, the white paper catered to my strengths—collecting and organizing ideas, writing. But I did not, um, care about the project. I did not believe it was good or helpful. Mostly I believed it was part of the elaborate charade at the World Economic Forum to appear as a legitimate think tank, when really it is a corporate-funded event planning organization. So did I feel good about the work? Not really. But I was used to that.

During my final week on the project, the junior McKinsey partner who had overseen the work took me out to a sushi dinner. I was leaving The Firm and had given my notice, and I had nothing to lose. So when the partner asked me, “Rachel, what did you think of the project?” I was honest. I thought it was neutral at best. Kind of pointless. Kind of a waste of time and money, unless you count the insane amount of world travel that I personally got to do.

“Wow,” he said, “you are really good at working really hard at something you don’t care about.” He looked me straight in the eye across the bluefin tuna sashimi,

“You should be careful of that.”

*

If there is one theme that has been consistent in my life since I was prepubescent, it’s my propensity to push and win, and specifically to push up whatever mountain is the most impressive without much thought to whether this is the mountain I want to be climbing or the toll it might take.

This approach made sense in my life for a long time. In fifth grade, I switched to a fancy private all-girls school, entirely thanks to my own ten-year-old determination to go to the best school around. My mom preferred a school called The Learning Project, but I wanted to go to Winsor, and both schools are exactly like the names suggest. My first year at Winsor I won the academic achievement award, given to the best student in a class of hand-picked, academically-minded ten-year-olds. In retrospect the existence of this award seems kind of silly and a little concerning? Nonetheless, my identity became indistinguishable from my academic, and later professional, achievements, which piled up. Brown University, Fulbright, McKinsey & Company, The World Economic Forum—it’s like I was collecting coins and beating levels, plowing forward along the 2D course in an unnaturally straight line.

My success at each level entailed a massive exertion of effort, an all-out marathon-sprint, long and fast and completely depleting. I remember one weekend during my senior year in college when I was preparing for job interviews and also applying to the Fulbright. I had stacks of grant application papers and notebooks full of practice case interviews spread out on the floor of my bedroom in neat piles, and I was overtaken by a wave of overwhelm. I collapsed onto the floor in uncontrollable sobs, shaking and crying. My parents were visiting that weekend, and they were concerned. No matter, though. I picked myself up and finished those applications and nailed those interviews. This was my main skill. This was my unique strength. I had all the privileges in the world, and I was going to take that launchpad and propel myself with the utmost force to the highest possible landing place.

*

But of course, there was a cost. I’ve written about the breakdown of my mental and physical health at McKinsey and afterwards, when I propelled myself into the world of Silicon Valley and continued my coin-collecting with a stint at Y Combinator, the most prestigious startup incubator around. I had panic attacks and chronic diarrhea and mysterious skin rashes every night for months. I had heart palpitations and extreme fatigue and chronic sinus inflammation. I continued climbing higher, but my body was barely able to support the ascent, my engines failing mid-flight, pieces of my wings cracking and chipping, but still I pushed higher.

You can see the pattern. I can see the pattern. I’m thirty-six now, an age where we can still access youth but no longer feel immortal, and I’ve been at this game for twenty-five years. I can absolutely see the pattern. I’m really good at working on things I don’t care about, if they seem like things other people think are impressive. The young McKinsey partner’s words ring in my ears: “You should be careful of that.”

Now, let me talk about Substack

I’m having a moment of angst and confusion about this Substack, and I’m curious what you all think about it. The context above is important; I must consider my decisions here against the backdrop of this habit to drive forward and win the game. Here’s my conundrum.

I love certain aspects of this platform, most notably the interactions I have in the comments, with you. I adore the opportunity to compose my ideas, flex my writing muscle, create something brief but thoughtful, and then hear what other insightful people here on Substack think about it. This is the most surprising and wonderful part of writing online (which I was very hesitant to start doing). I really love it. I think it’s unequivocally good, which is not common for me (hah!). I feel lucky each week to have this opportunity.

But at the same time, this is not the type of writing that I love most, deep in my core. It is not the type of writing that made me start writing; the writing whose lines are burned into my mind, the writing that pushes me, the writing that makes me cry and sometimes makes you cry (as they say: no tears for the writer, no tears for the reader). That writing takes weeks, months, or in some cases years. That type of work is where I have been able to access deeper truths within some of my life’s most complex and interesting topics: success and privilege, infertility, introversion and sensitivity, friendship and mental health. That is where I have felt like an artist, creating moments of beauty, capturing feelings like hopelessness, the fleeting moments with young children, or tragedy.

These literary essays tend not to perform as well on Substack (with a couple cool exceptions, like this one), and in all cases the ratio of effort to Substack payoff is wildly out of whack. And this is where the danger lies for me. Substack, after all, is a winnable game just like all the rest, and I am a serial game winner.

Now let me be clear: I don’t come to the writing desk to write Substack bangers, at least not consciously. I don’t want to cheapen the work I publish here, I’m proud of it. I know that I tend to be overly cynical about the internet, and maybe I’m whipping up a whole lot of concern over nothing (please do tell me if so, in the comments!).

But the reality is that after almost two years of writing here I can predict with scary accuracy how popular an essay will be before I publish it. And that makes me sad. It pains me that my formulaic “what I learned from one year of writing on Substack” post is my most popular ever, and furthermore that I knew this would be the case before even writing it. Soon I will write the “two year” version, and it will be uber-popular as well, if I pick the right title, which I absolutely know how to do. “How I grew from zero to five thousand subscribers in two years,” or something like that. How tempting it is to just do that, just do it, just eat the apple, it would be so sweet and delicious.

And then there are the punishments. Recently, I published something that caused a lot of people to unsubscribe, and for a couple weeks after that, my newsletter stopped growing at all, a marked change from usual. I had clearly been demoted. I had done a bad and was automatically put in front of fewer eyes. Then, following a popular post, my growth resumed. This kind of event strikes fear in the heart of a compulsive game winner. You know the rules, Rachel, follow them.

Both types of writing—my Substack and my literary essays—do not earn a living for me. Both are mostly labors of love. But Substack has the promise of growing an audience and building a platform. Maybe fame! Maybe money! It also provides a dopamine hit when subscribers jump up and a big emotional slap on the wrist when they don’t. This is something I am familiar with. There are rules. I can learn them. I can win.

But, ugh, this is what I’ve been doing for two and a half decades. I’d like to find a different metric to follow than “what’s most impressive on LinkedIn.”

So what’s a compulsive game winner to do in this world of games?

This is hot on my mind right now because with the arrival of my second child, I simply haven’t had enough life force to do both types of writing well: the long, slow writing, and the faster, interactive Substack growth writing. Since my daughter was born, I have barely been able to produce my weekly Substack post and haven’t done any of the deep writing. My life feels a little impoverished, having no new art in the works. I have one unpublished literary essay about the experience of doing IVF for my second child, which I finished many months ago and am very fond of, but I cannot bare to put it on Substack because I feel its value will be reduced to a number of views and likes and comments, which will inevitably be low since it is long and winding, like my best essays are.

Let’s imagine I turn back to deep writing only. I will publish only occasionally, maybe once a month. I will not have enough writing to support a paid offering, and I will lose the little orange check mark by my name. *A shiver of fear runs down her spine.* I can only guess that my limited Substack activity and lack of paid offering will cause my newsletter to be far less widely circulated, which is the primary way I find new readers. *She shudders.* Perhaps my newsletter will…*gasp*…no longer grow at all. I would be breaking all the known rules of the game.

There are of course Substacks that are both big and arty in the way I’m defining it—the long, slow, hard-won work that really gets to the core of something. But my sense is that getting there on Substack requires either bringing your own audience or having a lucky break. And even Roxane Gay, a consummate artist, publishes resource roundups, which are one of the most tried and true types of posts for driving newsletter growth and require minimal effort to produce.

Let’s say I ditch all the strategy. Fewer people would see my work, that’s certain. I would also be returning to the core of my artistic self, feeding and nurturing her. I would also be giving up something that I love—the more frequent interaction with you all, readers.

I don’t know what the right decision is here, but I do know I am most inclined to make the same choice that I have made for the past twenty-five years. I have no practice making the other decision. I still can’t quite get myself there. I still want to find a way to do it all.

I’d like to hear from you….it’s my favorite part of all this 😊. Do you think it’s possible to publish work on a platform like Substack without conforming to its rules? Do you struggle with these tradeoffs? Or are you someone who just does your own thing, rules be damned?

Also, what are your favorite counterexamples on Substack? I could use some inspo right now!

Recently I took myself on an artist’s date, an idea from The Artist’s Way, where you make a date with yourself to go look at art, or listen to music, or make something with your hands, or do some other activity related to beauty and making that is outside of your normal routine. The idea sounds extravagant within a regular modern life, packed to the brim with a job and perhaps a family and a home and maybe a dog, all of which need attention. For Julia Cameron, the author of The Artist’s Way, though, it’s an indispensable practice for nurturing creativity.

My artist’s dates are rare, but recently I have felt a sudden urgency for this kind of solo, slow, aimless outing centered around seeking beauty. Perhaps this is a reaction to my spending more time online and feeling a little creatively choked. So, full of guilt for all the other responsibilities I was neglecting, a few days ago I took the bus to the San Francisco MoMA. I didn’t look at which exhibitions were open, and I didn’t plan. I just walked in, bought my ticket, and immediately stumbled on The Visitors, a multimedia installation showing a group of people in different rooms of a house signing a song for an hour. In various soulful harmonies, they repeated the phrase:

“Once again I fall into my feminine ways….”

Like art is supposed to, it cracked me open. I sat on the floor of the museum in the dark with twenty strangers for forty minutes, reveling in the sound.

*

It is in moments like these that I often get a spark of an idea that becomes my favorite work. My recent essay about my son started in a moment like this, as did my recent essay in AGNI magazine about pessimism, sensitivity and depressive realism. While I firmly don’t believe in writing only when I feel inspired, I do believe that the best ideas often start in moments of inspiration.

Furthermore, I’ve found that I prefer to place the resulting work—the stuff closest to my heart—in literary magazines, rather than in my newsletter.

Literary Magazines vs. Self-Publishing on Substack

The literary magazine world is just about as opposite from the internet as you can get. Magazines often have limited reading periods during certain times of year, the rest of the time you can’t submit. They usually take months to respond to submissions, and if a piece is accepted, the publishing timeline is typically many more months, so the whole thing from submission to publication can easily be the better part of a year. Once the work is published, no one can comment, and it almost certainly will not go viral. Many literary magazines are print-only (can you imagine!?), and the ones that publish online do so at a slow and steady pace with no “like” buttons or other forms of interaction. The work is just the work, take or leave it, I will never know.

So as someone reading this on an internet platform, and maybe a writer on said platform, you might be thinking, are you crazy? Put your best work there? Where few will read it or share it? Where it can’t go viral?

My answer is yes, and let me make the pitch for why. I think the literary magazine process—the slowness and the preciousness with which each piece is treated—feels right for a work that emerged in a dark room full of music and tears, and which I often draft and edit over the course of many months. The whole format honors the work in a way that throwing it up online does not. At some magazines, there is also the opportunity to work with an editor, a totally wonderful experience which further hones the piece and recognizes it as something to be cared for and crafted. As a bonus, in certain communities, these publications are highly respected, even if the majority of people have never heard of them. There are downsides of course—low readership, and the impossibility of ever making a reasonable income from literary magazine publications—which is why I write on Substack too. But I will not give up the literary magazines; I deeply appreciate the role they play in the writing world.

So I thought I’d share some lessons learned from publishing in literary magazines. You can see my work online and in print in AGNI, Green Hills Literary Lantern, Literary Mama, Under the Sun, Stonecoast Review, Ghost City Press, Talking River Review, and others. If you are interested, here are the nuts and bolts of getting started and some lessons learned.

There are lists

Whether you are a writer or an avid reader, you can discover excellent literary magazines by perusing lists of top magazines. When I started out, I wasn’t familiar with any of the nonfiction literary magazines outside of the The New Yorker and The Paris Review. David Mcdannald’s nonfiction rankings list is widely used among nonfiction writers.

At first, it can be wise to submit to smaller magazines, which are often more open to writers without an established publishing track record. The best targets are the ones where you love the work they publish and where you can envision your writing fitting in. As I have written about before, I don’t actually love reading, so sometimes this part of the process felt like a chore. However, as I continued doing submissions over multiple years, I started to get a feel for different magazines and could determine more quickly where any given work might fit.

Most submissions happen on Submittable

Doing submissions felt really intimidating to me at first, but luckily most magazines accept submissions through Submittable, which is an easy-to-use platform for submitting work. Magazines typically post their guidelines on Submittable (or on another page), including genres, word counts, and sometimes themes that interest them. I’ve found that the more I submit, the easier the process feels—once you have an essay and a bio ready, it is mostly a matter of copying and pasting with some customization for each publication.

There’s help if you want to pay

I was really overwhelmed when I was trying to get my first literary publications, and so I enlisted help. Writer’s Relief is a company that will create lists of good target magazines for each piece of work based on the length, themes, magazine submission windows, author publishing history and more. For an extra fee, they will also do the submissions for you. This was a really helpful service for me at the beginning, and it resulted in my first handful of publications. It also educated me in formatting the submissions and writing a cover letter, and helped me understand the full landscape of magazines out there (there are a lot). I’m sure some writers find this a little icky—too much of a shortcut, too little author engagement, we should be carefully reading all the magazines we submit to. I have felt some of that too, but at the same time it helped me get started and gain some confidence, which has been really valuable.

Once I felt I had gotten in the door, this service was no longer an appealing option. I wanted full control over my target list, and I was familiar enough with the landscape to do the targeting more easily myself. I also wanted to do fewer submission with more care as my acceptance rate increased due to my track record of publishing. So that’s the path I took: Writer’s Relief to break in, then moving to a self-directed process, which I now use.

My current submission process

I typically aim to submit an essay every couple of months, though this year it was more like every three to four months as I worked to get my Substack off the ground. I choose 5-7 publications for each round of submission, and if an essay is rejected from all of them, then I do a second round of the same size. This allows me to wait to hear back from my top choices before submitting to more. Needless to say, each essay is usually rejected many times before it is accepted.

Bonus tip: Consider taking a writing class

One of the best things I have done for my writing in general, but also for learning about the literary world, is take adult ed writing classes. I take classes through Grub Street, which I have found to be consistently high quality, covering all kinds of topics, and which I can do via Zoom even from across the country (Grub Street is in Boston and I am in San Francisco).

The people who take the classes range from professionals to serious hobbyists to beginners, and through these classes I have not only upped my writing game significantly, I’ve also met other writers and been exposed to different approaches to “being a writer.” Seeing this range of styles has been very important in informing my own approach to writing. It is at Grub Street that I was first inspired to start submitting to magazines, and where I met writers who had established their literary credibility through this type of publication. I find that participating in classes, meeting writers, and submitting work outside of the internet world helps me balance and feel good about the other, more fast-paced work I do online.

***

I thought this fast-slow balance might resonate with some of my fellow writers here, and I hope this sparked an exciting idea or two for a few of you, or at least offered permission to still engage in very slow writing. This other way brings different value into the world, keeps me sane, and is an important counterbalance to writing on the internet.

I’m curious…

1. What was the last “artist’s date” you’ve taken yourself on? If this is a new concept to you, do you have an idea of the type of artist’s date you’d like?

2. What’s your experience publishing in literary magazines, if any? Is this an interest of yours? Do you have any tips for the submission process?

3. Do you have a favorite way of reigniting your creative spark?

   Leave a comment

It seems to me that there are a lot of people here on Substack who identify as highly sensitive. My writing on being highly sensitive—or having sensory processing sensitivity, or being a highly sensitive person (or HSP—a term that I have used but which is controversial)—continuously finds a receptive audience here, and I have noticed that new Substack features, like Notes and the new app homepage, are regularly bemoaned for introducing too much stimulation. There are also a number of other writers here who are doing great writing on their experiences with and perspectives on high sensitivity. Perhaps my exposure to the topic is just a function of my particular Substack circles, but even so, it has gotten me thinking: what is it about this place that is working for sensitive people, and what’s not working? What can that tell us about how to cultivate wellbeing in the world outside of Substack?

The power of matched/mismatched culture

The pocket of Substack culture I’m mostly exposed to (and part of) is what I would call slowly self-seeking. Many of us have gotten off some former path—whether through a career change, or a transition to parenthood, or illness, or retirement, or divorce, or menopause (the types of things everyone faces at some point)—and found ourselves a little lost, or very lost, not sure what comes next. We are generally aware that we would love to get to the answer immediately, but we also know that this is not how life works. The way we handle this, on Substack specifically, is by investigating ourselves on the page, reading other writers who are doing the same, identifying our foibles, interviewing people who have walked an interesting path that relates to ours, researching topics of interest from the solitude of our desks, and in these many ways, fertilizing and growing new ideas with an emphasis on nuance and shades of gray. We plod slowly down this path. We interact with each other (particularly pre-Notes) through asynchronous comments which are 99.9% supportive and filled with phrases like “I feel so seen,” and “this one hit hard,” and “I will be thinking about this today.” We read things when we want, at the pace we want, and (I would guess) mostly don’t mess with Substack push notifications. We cheer each other on for identifying our imperfections. We try not to brag. We observe the world. We don’t do a ton of Zoom meetings.

Now, I’ll only speak for myself when I say that this is just a bit different from the other world that I previously inhabited. In business almost none of this behavior is acceptable, let alone revered. Plodding slowly? Not bragging? No Zoom meetings? These are the antithetical to entrepreneurship in the classic Silicon Valley format, where the winning behaviors are speediness, fake-it-till-you-make-it, projecting a big vision, networking, and generally appearing to have all the answers already.

This culture difference snapped into focus for me recently as I read the introduction to a study on sensory processing sensitivity (SPS) and wellbeing. “Research indicates,” the authors wrote, “that when people are matched with their cultural environment, they experience higher rates of psychological wellbeing (Fulmer et al., 2010) and less negative emotion (Stephens et al., 2012) than those who feel a mismatch with the surrounding culture.” I had felt this mismatch so acutely working in tech, but seeing it stated in matter-of-fact science journal syntax, with citations, made it feel so much more real. 

The findings from this small study, which looked at how individual sensitive people pursue wellbeing within a mismatched culture, “suggest that highly sensitive individuals perceive that wellbeing arises from…low-intensity positive emotion, self-awareness, self-acceptance, positive social relationships balanced by times of solitude, connecting with nature, contemplative practices, emotional self-regulation, practicing self-compassion, having a sense of meaning, and hope/optimism.”

So many of these are experiences I can find on Substack and aren’t generally part of the broader culture of San Francisco where I live. What I’m suggesting is that perhaps I, and other sensitive people, have found a better culture match on Substack than in our previous environments, and that’s why we seem to be gravitating here. Though recent changes to Notes have got me a bit worried, this certainly seems true for me to date.

The wider world

But we can’t live on Substack, or at least most of us probably don’t want to exist only online (even if it can offer a nice stimulation buffer). So what can we take from these insights about Substack culture to apply more generally?

Picking your people

One strategy is to surround yourself with people who operate in a subculture that more closely matches your character. For sensitives, this might mean spending time with people who either 1) have similar sensitivities and prefer similar types of stimulation, or 2) really get how important these things are for you. Last week I sent this text to a friend, and in doing so I realized how special it was that I was unafraid to tell him exactly what was going on with me with no apology, rather than make up a story:

Now, obviously it may not be easy to suddenly find a bunch of people who create your ideal culture—it’s harder to do in the real world than on Substack due to the realities of geography, work, and existing relationships. But a first step could be just to notice: who around me generates the types of experiences that help me thrive, things like, as the researchers in that study put it, low-intensity positive emotion, self-awareness, or positive social relationships balanced by times of solitude? 

Maybe there’s someone around who is super fun and the life of the party, and you feel like you should be really joyful around them, but actually they bring a whole lot of high intensity positive emotion, and it turns out that’s not really your vibe. Sometimes this mismatch is hard to recognize, given how our culture tends to consider “being the life of the party” to be an objectively positive trait that everyone should find appealing. Maybe one new way to think about it is, “how would this person fit into that comments section I love on Substack?”

Honesty about work culture fit

I spent many years telling myself that if I try hard enough and am a talented person, than I should be able to thrive in the work culture that surrounded me—that fast-paced, extroverted, competitive, hard core, pedal to the metal, go-big-or-go-home culture. A failure to thrive there was clearly my own failure to hack it in the world, a failure of effort or talent. For a long time it was too painful to acknowledge the other option: that I couldn’t thrive in that context because of a fundamental mismatch between that culture and my personality. Given how idealized that culture is, given how “success” is so often equated with “success in that specific culture,” I refused to see the mismatch for a very long time. What would that say about me? My talents? My prospects?

It took me a decade to identify that mismatch and extricate myself, and I am an extremely lucky person who started out with a lot of options and had the ability to leave if I wanted to. Many people don’t have that option. The fact that I could leave but didn’t is a testament to how difficult it can be to say, “hey, I just don’t fit here.”

That said, even while I was still in that crazy game, my growing recognition of the mismatch situation was helpful for me. I was able to slightly reframe my intense day-to-day struggles as perhaps, maybe, just a little bit, not my fault, but rather the product of a clash between my traits and the culture. I was able to begin to see, just a little, that this was not necessarily a problem with my traits, and maybe even actually was more of a problem with the culture. In the case of being sensitive, even if you can’t leave a culture, just naming the mismatch can be beneficial, giving yourself permission to not vibe with the current culture.

My whole decade-long realization that I had lived in a culture that was a total mismatch for me has only really crystalized since I started writing seriously on Substack around the beginning of this year. I started feeling actually good about what I was doing, and things seemed to be so much less of a struggle, and in having this experience that I never had before—a culture that better matched my traits—I began to see that that was even possible.

Tuning into emotions & body signals

So how do you tell which people and which work tasks and which environments are matched or mismatched to your personality? In her book, Making Work Work for the Highly Sensitive Person, Barrie Jaeger discusses the importance of becoming an expert in our own inner body signals. This can include paying attention to signals like pulse, breathing rate, and body temperature, and starting to notice when these shift into a higher gear. Looking back, I see that stomach aches and breath holding have long been two body signals that tell me I am in an unhealthy environment for me. 

It is not always the case that we can just notice these warning signs and immediately leave a situation. But in the long arc of life, I hope for me, and for you, that we can move towards days where these alert signals happen less, whether because of the people around us or the work we are doing or where we live. I have started treating these signs with the utmost seriousness, a huge change from the constant ignoring and dismissing that I did for so many years. 

I have rarely found myself holding my breath while reading Substack newsletters. This is starting to change on Notes, where I am noticing little spikes in heart rate and lingering feelings of internal discomfort. It seems like I’m not alone. In order to decide whether to stay, you better bet I will be paying close attention to my pulse.

Tell me…

1. In what ways do you find yourself matched or mismatched with the culture at work, within your friend group, on Substack, etc.?

2. What are the unique ways the people in your life show up for you that make you feel deeply seen and cared for?

3. How does it feel to treat the signals from your body with the utmost seriousness? Do you feel more attuned, more overwhelmed, more honored, more anxious?

   Leave a comment

One year ago I decided that I was going to pull out all the stops to do what I have always wanted to do, which was to BE A WRITER. I decided I was even willing to—gasp—write online in service of that goal.

I came here naive about the internet. I came with a feeling of resignation, a belief that in starting an internet newsletter, I was giving in to the pace demanded by modern capitalism—faster, faster, faster and more, more, more—but that this is what was required if I wanted to BE A WRITER, which I really did. At best, I hoped the ends would justify the means. Maybe, I thought, I could make a compromise: bring some of myself to the work and also change some of the work to fit the demands of the platform, and in that way work within the system and outside the system at the same time. Maybe I could come here and not completely lose myself. (Losing myself in my career has been a problem for me in the past.)

In other words, I was cynical. I did not do the internet, I was not an internet type of person. I prided myself on this—the purity! The art!—and I also saw the downsides. For one, when my work came out three times a year in print-only magazines with a circulation of a few hundred, it was hard to imagine how I would find my readership, the people who really loved and wanted what I was offering. It was nearly impossible to imagine a path to making any meaningful income. So, at the end of August 2022, I prepared to launch my Substack newsletter. I decided that I would publish at the breakneck speed of twice a month. Imagine publishing twice a month! A breathtaking pace.

Ah, how innocent those times were, one year ago.

As I’ve written about before, Substack did not go as I expected. It was not actually just a big cesspool of market demands that I just needed to keep fighting against (of course there is some of that, which I will get to). Instead, what I have gained from writing on the internet for one year was an avenue to stretch my skills as a writer, genuinely connect with other people who share my interests, and experience an unprecedented feeling of providing real value and having purpose. Color me shocked.

I’d like to tell you a little bit about what I’ve learned here and the growth (both personal and newsletter) that I’ve seen as a result. Then we’ll talk about what’s to come in Inner Workings’ second year!

Exploring fulfilling ways to write

Working on an essay for a year is a fabulously fulfilling process. Drafting it, moving away from it, coming back, workshopping it with other writers, leaving it on the shelf again, circling back again, applying the different perspectives that accompany each of these different periods of work. It is deeply fulfilling to bring something to fruition over many months, even years, and everything I’ve done that I’m most proud of has been made this way.

But—and this shocked me—this is not the only fulfilling way to write! It is also a totally different and awesome experience to try and articulate what’s on my mind this week in the most original and relatable way possible. It is also very cool and different to try and capture new research in an understandable way. It is the utmost fulfilling experience to interview a kindred spirit about a topic of mutual interest and help craft that story in writing. All of these types of writing use different brain parts and different skills, like trusting your instincts (when writing fast or interviewing), doing efficient editing (on everything), and not letting perfect be the enemy of the good (and what perfectionist among us wouldn’t benefit from a little practice on this front).

Here is a reality about Substack writing: there is absolutely no correlation between how long I work on an essay and how much people love it and are touched by it, measured by comments and likes (which of course is just a proxy, but the best I have). I’ve worked on an essay for two years and published it to, more or less, crickets. I’ve worked on an essay for two hours, published it, had it featured by Substack, and got a thousand new subscribers.

The cynic in me would say: “Exactly! This place doesn’t reward the real work!” But the newly enlightened internet writer in me would say: “There’s a certain type of thing that tends to fit here, and that thing is also meaningful and important in a different way.”

Welp. Given that, here are some of my learnings about what works here!

Things I’ve found that fit really well here

• Brief personal essays exploring a single topic in an original way, and ideally bringing in one or two perspectives from other thinkers. These offer a digestible dose of wisdom, but not a simplistic one—people here like nuance, yay!

• Interviews

• Short lyric pieces. This was a surprise to me, and very cool, because there aren’t a lot of obvious places to publish this form.

• Synthesis of books, research, and articles

Things I’ve found fit less well here

• Complex, 4,500-word personal essays that braid together multiple themes. (Lit mags are still the place for these, IMO! I’ve got one coming out in AGNI this fall that I’m excited to share.)

• Longer reported pieces with lots of sources. While some people like these, it seems like they are too long and heavy for the brain space and time allotted to Substack—which seems totally reasonable.

Things I’m not sure about yet

• Serialized, memoir-style writing. I’ve done this once, and it seems like there was a core group of people who absolutely loved it, but for most perhaps it was, again, too long.

• Podcasts and audio. I’m podcast-curious, for sure, but I’m also careful about how much I’m signing up for so that I don’t dilute the quality. I still care about the quality!

Things I haven’t tried because I hate them

• Really short bits of content fired at you every day or multiple times a day. Who cares how good it is, as long as it’s frequent. I hear this is the number one way to build your audience here. I am unwilling to do it, even if it is effective. Especially when wading into territory that can feel compromising, one must have a line.

Real collaboration and connection

As my first year progressed and I began to realize that my goal here was not to publish extensively re-worked literary essays but rather to try new stuff, I also realized there’s no way I could do that alone. Imagine me, sitting alone at my desk trying to come up with new stuff I’ve never done, then trying to do it, and then publishing it to the internet without anyone else ever weighing in. Some people can do this and hats off to you, but I can’t, and this is where my collaboration with a couple key people enabled my first year on Substack to become such a positive experience.

First, I began to exchange writing with my friend and emerging Substack Notes God

. Even though we had known each other for over a decade, and even though we had long just gotten each other (despite being very different people), we had never meaningfully worked together. We set up weekly calls to exchange work, which did not end up happening weekly (are you crazy we both have toddlers), but which did and still do happen with a shocking regularity, even now, one year in. Alex never fails to amaze me with his feedback on my work, which quickly gets to the heart of what I’m trying to say and improves it. Perhaps even more importantly, he is someone I can go to with an unworked idea and talk it through. Having that person is absolutely essential for me in this work, especially if there is experimentation involved. He also just always makes me laugh because he’s goddamn hilarious, so yeah…BONUS.

Then Alex introduced me to , whose continuous collaboration helped me spread my wings even further. With Erin, I can bounce ideas and discuss possibilities–what would it look like to do a serialized memoir-style piece? What about publishing this weird lyric essay? What about grouping the work together in themes? Collaborators like Erin can further bring fresh ideas and perspective to the little isolated world of my mind. Again, this is essential to my highest creativity: we can add our brains and together figure out how some little idea might actually turn into reality, like the Lady’s Illness Library. She also helps make my work more polished, both in content and in form, and I like presenting something polished to the world, even if it is produced quickly. 

THEN. Then the real thing happened. I started meeting people online that I actually really like and want to be around. WHAT?! I had heard this kind of thing could happen on the internet, but I one hundred percent did not believe it. I know, I know. I was wrong..

This kind of connection mainly happened through interviews, both ones I’ve given and ones I’ve conducted for Inner Workings. During these conversations the internet people turned into real people on my screen, and we had awesome, wide-ranging, and in some cases even life-influencing conversations. One of them is looking for a place in my neighborhood (IRL! Not even in VR!). One of them sent me a book after I mentioned that when I’m knitting I get stressed that I’m going too slowly (long story).

There is also a group of people I haven’t interviewed, but who regularly write beautiful comments on my work, like , , , , and many more. And there are the Substacks I regularly read and comment on, whose authors I feel a kinship with even if I’ve never spoken to them, like , , and .

And all of this together has led me to feel a sense of fulfillment and purpose that I have never felt in my career, not even close. That’s profound. That’s hardcore. Phew. Yeah. I’m definitely thinking a lot about what I was doing for those fifteen years before Substack.

Resisting the pressures to do even more

Even if writing on the internet is way better than I expected a year ago, it still does have traps. I check my subscriber number way too often, most days, sometimes multiple times after I put out a new post (right now the number is 2,357). No matter how high this number, I always want it to be higher, and I expect this will always be the case, and I think that this is the most perfect example of the element of human nature that powers our current late stage capitalist society.

For me, it is a conscious, ongoing effort to not try harder and do even more on Substack, to just not add that new thing, and just not take that advice from some Substack guru swearing that the only way is to publish more, more, more. The fact is, I have already published more, more, more—approximately 400-600% more per month than I originally planned—HELLO, the forces have already acted on me! But in this process I have also been experimenting and finding what feels good in terms of balancing the frequency, thoughtfulness, and polish of my writing. Even with my (drastically) increased pace of publishing, I have at many points declined to do even more. This is all a complex set of compromises and learnings, and I wouldn’t say I’ve nailed it perfectly, but I do feel more confident now that a balance is possible. In other words, I don’t feel that I’ve fallen to my greatest fear at the outset—I don’t feel I’ve lost myself here.

What’s ahead

Whew. Inner Workings Year 2! Time to take all that I’ve learned here about myself and about internet writing and use that to make the coming year an absolute banger for Inner Workings. Here’s what’s coming up! (With the caveat that everything is an experiment and will doubtlessly evolve!)

More thoughtful, succinct essays on relatable topics

The absolute highest compliment I can receive as a writer is when someone says, “oh my god I’ve felt that way for so long and never put it into words, and you articulated it perfectly.” That’s the gold standard for me when I take on a topic in these mini-essays, bringing my own experience, my analysis, and often the words of others. My goal is to present topics in an original way that cuts to some core truth that is hard to reach but feels exactly right once found.

More Lady’s Illness Library

The energy and inspiration I personally get from interviewing these (mostly) women would be enough for me—no one benefits more from this project than I do. But even better, the responses from the community here have been full, multidimensional outpourings of feeling with a heavy dose of gratitude, and I am totally energized to keep this going and build on it. Let’s elevate women (and men!) with chronic illness!

We have four more wonderful, unique interviews in the editing process right now which will come out over the next two months, and over thirty (!) amazing people who have filled out the interest form to participate in interviews. (I apologize to those who haven’t heard from me yet! Your inquiry was not lost!)

Research synthesis & reporting

This is an area where I am still experimenting, but I aim to continue having research and reporting in the mix, covering our favorite top topics here: chronic illness, the microbiome, the nervous system, wealth & power, work culture, caretaking, and the like. I have tried longer deep dives and quick, digestible summaries, and these formats may continue to evolve, with a focus on making the information easily accessible.

Best of Inner Workings

I wrote some pretty rad stuff on here when I had about forty-two subscribers, thirty-nine of whom were my friends (or my mom’s friends). As I take my maternity leave this winter, I will be digging up the gold from the bottom of the pile and republishing it to, hopefully, delight you with some of the past writing I’m most proud of. For the twenty-five of you who have already read these ones…thanks for your patience 😊

Community-building

I have long shied away from using the term “community” to refer to groups on the internet—call it a high-horse thing, given my big life focus on in-person community-building. However, I now cannot think of a better word to describe the emerging connections happening here between like-minded people. I am committed to nurturing that. To date, I do that in the comments section, where I make every effort to read and respond to all the thoughtful stories and ideas that people are generous enough to share. I’m not sure what other avenues will work for us, but I am open to trying them—Substack chat, Discord, Substack threads—expect some experimentation in this area this year!

And lastly…

I just want to express a huge amount of gratitude to everyone who has joined me on this journey over the past year. I feel full and connected in a way that I never have in my life. I feel optimistic and full of potential, things that seemed impossible in the depths of my burnout. I know everyone gets a shitload of emails, and I know it’s no small thing to sign up for yet another goddamn email. So thank you.

Well, here’s to year 2 and all the wild, awesome, and unexpected things that will doubtlessly unfold!

—Rae

I’d love to know…

What are you most looking forward to from Inner Workings - essays on my life in Silicon Valley? Stories about infertility? More about chronic disease and Lady’s Illness Library interviews? Analysis of the newest health-related research?

Leave a comment

I have written before about Highly Sensitive People, people who have a set of genetic traits that cause us to be more sensitive to external stimuli than the general population. When I learned about HSPs in my thirties, it explained a phenomenon that had dominated my adulthood (and still does): many experiences, like watching a scary movie or going to a big conference, have always seemed way more intense to me than they do to other people.

In my previous post, I detailed some of the information about HSPs that gave me an enormous sense of relief—learning, for example, that around 20 percent of people and the same percentage of many other mammals are born with this genetic predisposition. I’m not a wild aberration, but a part of a strong minority. At the time, I wrote about my first encounter with a website for HSPs:

The website described HSPs as people whose nervous systems are more sensitive to all stimuli. We take in more information and process it more deeply. The result is that we both notice more about the world around us, and also become overwhelmed more quickly from stimuli that others would find completely tolerable. With even just this small window into the workings of myself, I felt transformed from something broken into something interesting.

Recently, I’ve been noticing the HSP topic pop up here and there, including on . I’ve been noticing how many of us on here identify with this descriptor, and how high sensitivity is also a hallmark of living on the spectrum—and how writers on the spectrum also very often have something special to say. And I’ve started wondering if perhaps I didn’t take my line of thinking far enough last time, because it felt too braggadocios. But I’m convinced it’s true: high sensitivity is nothing less than a primary ingredient of a great writer.

Advisors and Kings

“For better and worse,” writes Elaine Aron, the first researcher to identify the HSP trait, “The world is increasingly under control of aggressive cultures—those that look outward, to expand, to compete and win. This is because, when cultures come in contact, the more aggressive ones naturally take over.” This phenomenon, she claims, has led to a long history of dominant cultures led by the Warrior King type: outward looking, aggressive, and action-oriented. If you’re like me, you might let out a big sigh of recognition here. Recognition of someone else, though: the winners, not you.

However. These warrior king societies, observes Aron, always include a strong so-called “priest-judge-advisor” class. The advisors balance the action-orientation by insisting on stopping and giving the whole deal some serious consideration. “HSPs tend to fill that advisor role,” writes Aron. “We are the writers, historians, philosophers, judges, artists, researchers, theologians, therapists, teachers, parents, and plain conscious citizens. What we bring to any of these roles is a tendency to think about all possible effects of an idea.”

I would never have said this so bluntly two years ago, but our own warrior king-dominated society needs these highly sensitive advisors; we need the thinking and sensing people to balance the equation.

Because what would the world be like without these sensitive thinkers? Well, I believe it would tend towards a more fast-paced, less considered approach to everything. As a default, that does seem easier. “Adrift in the noise and bustle,” writes Meghan O’Rourke, “we duck confrontation with the metaphysical and existential. We avoid the enduring regret at how we treated an old, estranged friend, the fear that our life has been a project of self-delusion—that its gilded hand-stitched brocade may in fact be moth-eaten. Who wants to think about all that, really?”

Well, actually, we do. The sensitives do. It kind of sucks sometimes. But thank goodness we go there, because this kind of thinking is the foundation of a deep soul, IMHO.

Sensitivity and the writing practice

It is almost too obvious a connection between sensitivity and writing, but worth stating: if you observe the world more closely, you probably have more interesting and original things to say about it. One of my favorite generative writing exercises for nonfiction and memoir comes from Lisa Dale Norton’s book, Shimmering Images. When approaching stories about our lives, Norton encourages us not to go back and tell the story from the beginning, but to let the most fiery details float back up to the surface from our well of subconscious memory. She calls these hot, remembered moments “shimmering images.”

Here’s my version combining some of her exercises:

1. Set a timer for ten minutes and list out any images/moments/scenes that come up related to the time period or theme of interest.

2. Pick the hottest, most shimmering image from the list. Set another timer, and on a piece of blank paper, draw the scene. It doesn’t matter how shitty your drawing skills are. The act of hand moving on paper tends to bring up more remembered details.

3. Set another timer and write the scene, now pulling from a rich pool of memory.

Now consider someone who generally notices more, and spends more time processing, or making connections between events and ideas. In just this exercise, this person’s initial list of scenes will be more varied, making more connections between experiences, likely more capable of identifying the points of interest in a long history filled with many unremarkable stretches of time. Her list will probably also be longer, since she tends to remember more. Her drawing will be more detailed and probably include more surprising elements, noticed by that sensitive brain. This will all yield prose that is more original, more incisive, and generally more interesting.

This does not mean that HSPs are born writers. It does not mean that less sensitive types can’t write. It does not diminish the importance of craft and practice and more practice. But it does point out the power of being sensitive, particularly for a writer.

HSPs Love Inner Workings

Sensitivity on Substack

I have seen many grateful comments from writers about the slower pace of Substack, the calmer vibes, and my guess is these are emanating from the sensitives (and my other guess is that there are more of us on here than in the general population). I have also seen grieving comments about the introduction of Notes and the ticking up of pace demanded by newsletter writing (I have written about this myself). At the end of the day I don’t think this is really about Substack, but rather about the innate tension between being an HSP and the experience of the internet. Oh, you’re someone who reacts to every bit of external stimuli with a bigger-than-average nervous system response, and you commit more attention and mental energy to every piece of information you see? Cool! Here’s literally infinity pieces of information, many of them stated very forcefully, in an arena where loudest and most frequent voice wins. Have fun!

Yeah, so obviously this won’t go very well for us. Acknowledging this reality has been very helpful for me. It is not that I don’t have enough grit and sticktuitiveness to just buckle down and bellow out my opinions more often, thus growing a big-ass following and becoming Successful. It’s that the experience of shouting my inner thoughts into an abyss of other voices on the internet is, for me, nervous system torture.

And when I start feeling bad about this (often), I return to my journals, which I have been keeping on and off for the last nineteen years, building my observational skills. I look back at my sixteen-year-old self with admiration. Look at this little sensitive observer advisor being formed:

“The chart would have to be like a mile long.”

And with that timeless wisdom, I leave you.

—Rae

I have to ask…

• Do you consider yourself a Highly Sensitive Person? Raise your hand ✋

• What measures do you take to safeguard or soothe your nervous system in the face of the internet’s infinite information? ♾ ℹ️

Join me in the comments!

Leave a comment

I wrote in my latest roundup about our modern relationship with time, and in doing so I started thinking about writing and time, and then, inevitably, the writing on internet. I have always viewed writing as a fundamentally slow act, one where any given day’s work is not likely to be material, but in fifty days I might see some progress. In particular, I hold a very long view when it comes to the project of improving at writing.

My mental model is this: if I write and write and write, then every year I might get just a bit more skilled, almost imperceptibly, like stacking one additional sheet of paper on a small stack. And then years later, I will look at the stack and it will be tall, and that is, I believe, the only possible way to become the writer I want to be.

There are certainly times when this idea feels impossible, or at least tiresome and annoying, times when I wish the process could just happen faster. But also, when I am able to escape for a moment from the Tim Ferris-esq cultural preference for doing everything faster and more efficiently, the notion that I might give whole decades over to slowly improving at something I find worthwhile can feel hugely liberating, like taking a big breath of forest air after a day in an air conditioned office. It releases me from a day-to-day feeling of having to jam everything in; as long as I do this one worthwhile thing diligently, then I can feel confident that I am putting one foot in front of another on this long and winding hike that I have deemed worthwhile. Ah, doesn’t that sound nice.

Enter Substack.

My first nine months of writing on the internet have been undeniably rewarding and positive. For the first time in my fifteen years of serious writing, I have people reading and even responding to the ideas that fuel my inner life. This is perhaps the most rewarding possible outcome for a writer. I am regularly encountering other writers with similar interests and whose style I admire. I am building a genuine foundation for a career as a writer, a much more solid one than all my previous attempts, including spending five years writing an unpublished book, and publishing essays in print-only literary magazines.

And also. I have slid smoothly, seamlessly, almost without thinking, into the speed of this platform. I started out with the idea of publishing monthly essays, with a pause in August and December. Ten essays a year, a cadence which at the time sounded difficult to achieve but possible. These essays would be in the vein of this one on infertility and this one on being a woman in Silicon Valley: meaty, long, crafted, workshopped, written and re-written, hammered into shape over many months. For my paid offering, I would send around favorite quotes each week. Simple. Elegant. Plenty of time for slow writing.

Then, a few months in, that offering started to seem a little thin. Regular posting is important on Substack in order to be discovered and featured. So I started writing short essays every week, and one long essay monthly. Then I added a monthly roundup for paid subscribers, because that format seemed valuable and valued on Substack. So suddenly I was doing six posts a month, following all the Substack best practices. Then Notes arrived, and my new weekly cadence quickly took on more of a daily urgency, one that I haven’t been very good at, to be honest. But even if I’m not posting daily, then I’m definitely feeling bad daily about not posting daily.

The games we choose to play

I can’t help but think at this juncture about all the sacrifices I made when I was starting my company, all the little concessions to fit into the system and succeed within it. It turns out that I’m good at adopting the rules of the game set out for me by society, even when they make me miserable. So the cynic in me is saying, “here we go again, Rae.” I am a little disturbed by how naturally and easily I slid into my conformity with this platform’s demands. But then again, I want to be a writer. This is how you do that on Substack.

This is not a new story, the tension between creative work and commercialization, between the demands of your job and the demands of your soul. But it has been instructive to watch it happen once again to me and so quickly. I have been able, this time, to observe it with eyes wide open. As this all was unfolding, I came across this essay by about being a writer today, which basically makes the case that the most highly rewarded skill now is being able to write anything coherent quickly.

“The cornerstone of internet success is not intelligence or novelty or outrageousness or even speed, but regularity. There are all kinds of things you can do to develop and retain an audience -- break news, loudly talk about your own independence, make your Twitter avatar a photo of a cute girl -- but the single most important thing you can do is post regularly and never stop."

I hated this conclusion, and it also struck me as deeply true.

So, what’s a writer to do?

I could easily and cynically conclude here that we are all doomed to be trapped in whatever platforms capitalism has delivered to us in our particular time and place. But that’s actually not how I feel, and particularly not about Substack. Actually, Substack has opened up a couple really interesting new modes for me as a writer: it has strengthened my ability to compose ideas quickly, and helped me build a habit of listening to reader feedback and responding to it.

The other major option for me, the one I’ve tried in the past when I failed to publish a full-on book, is to spend months or years putting my best work on paper, then to lay it at the feet of forty or sixty people in New York City and cross my fingers that one of them likes it. This path has certain advantages, particularly related to pace of work, and a lot of obvious disadvantages.

So to use the favorite phrase of , both are true. All platforms demand certain types of conformity to succeed, including this one. And also, for me, right now, Substack is an awesome place to write. My goal now is to approach the platforms I use with eyes wide open, aware of what types of changes they demand from me, constantly evaluating if these are changes I want to make, and particularly when it comes to my art. I don’t want to be a purist, devoted to my own way or no way at all, but I also don’t want to bend too far, suddenly finding myself to be not an essayist but a rapid snippet creator.

I have heard many times the adage, “the medium is the message,” and this theoretical idea becomes very concrete when I think about the changes I have made to my own writing in order to work well on this particular medium.

We need to be vigilant about how our message is being shaped by our medium, and watch for signs that that shaping is changing our voice beyond our recognition.

For me, right now, Substack’s demands are more helpful than hurtful. They give me a template and push me to try new formats, lengths and styles for my writing. They still allow for some, (though less than I would like), time for the long and tedious process of crafting what I would call Essays with a capital “E,” the work that cannot be done quickly, and which usually strikes much deeper in the hearts of my readers, obviously because it comes from a much deeper place in my own heart.

But, back to the game

Ok, but, let’s be clear, I am still playing the game. It is my nature. This newsletter is devoted to unflinching honesty, so I feel I must tell you. I am now seven paid subscribers away from getting a little “bestseller” checkmark next to my name, a completely arbitrary threshold that has been made extraordinarily significant in my mind because some team of people at this company called Substack decided to attach social proof to this particular number. God, this tactic worked so well on me—good job team. I want that checkmark. I want that checkmark so bad. I want that checkmark like drugs. Grrr I’m hungry for it. Even though I know that after a week the thrill will fade and I will be onto the next incentive provided for me.

But that awareness is my point. Making changes to our work and our rhythms based on the medium we choose doesn’t mean we have no agency with our voices. I think it means that we need to choose our platforms wisely, and use them with full awareness of their demands.

✍️ I’d love to know…

• What Substack “demands” are you most consistently aware of?

• In your own Venn diagram of “what Substack demands” and “who you want to be as a writer,” what is the amount of overlap?

• What threshold are you hungry to reach right now?

Let’s talk about it in the comments!

Leave a comment