Should I orient my Substack towards art or growth?

Or maybe you can tell me the magical way to do it all

Art by Stephanie Davidson

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!