How the end of Trump's blog made me rethink my approach to writing full-time
A month ago, Donald Trump started a blog. Then, a week ago, he shut it down. What happened?
The answer is, well, not a whole lot. From the Washington Post:
“On its last day, [Trump’s blog] received just 1,500 shares or comments on Facebook and Twitter — a staggering drop for someone whose every tweet once garnered hundreds of thousands of reactions.”
When Twitter decided to ban Trump, critics of the decision argued that it violated his freedom of speech. And yet, that Trump was able to start a blog illustrates that it wasn’t really his freedom of speech that Twitter was restricting, but his freedom of reach. If freedom of speech were the problem, where Trump was publishing would be irrelevant. It shouldn’t matter if his rants are on Twitter, or Facebook, or a blog. Clearly, though, it does.
In a recent issue of Platformer, Casey Newton cites the technologist Aza Raskin, who was the first to distinguish between freedom of speech and freedom of reach. Freedom of speech is the right to say what you want, but, as Renee Diresta put it in a 2018 essay for Wired:
“There is no right to algorithmic amplification.”
She’s right, of course. In theory, Twitter is well within their rights to take algorithmic amplification away from Trump.
Most of us, though, aren’t Trump. If we use social media, it’s to send memes to friends and doomscroll Twitter on public transit. At best, some of us have a few hundred sort of engaged followers who retweet us occasionally; we haven’t done anything that would make platforms want to take that right away from us.
In fact, most of these platforms wouldn’t want to take these rights away from anyone if they could at all avoid it. Algorithmic amplification is what fattens their bottom lines, after all—it is only amidst massive social backlash that they’d even consider taking it away. With this in mind, I’ve decided to change my strategy as it pertains to writing full-time.
The TL;DR is that I am going to start publishing not only on Substack, but on Medium and other platforms, too. This is a function of (a) wanting to take advantage of the freedom of reach that I very much still have, because I am not Donald Trump, and (b) wanting/needing to make money. If you’d like more detail, feel free to read on.
I’ll start by noting why, exactly, I started Anything Different. This requires some background—first about my writing, second about what I was doing immediately before the launch.
Let’s take each in turn.
I started writing a few years ago. I found that it helped me deal with post-college anxiety.
I also came to enjoy finding new and interesting ways to articulate things. I liked editing, specifically, because I could revise thoughts in a way I couldn’t revise speech.
I found a home on Medium. Founded by Ev Williams, who also co-founded Twitter, Medium offered writers a seamless publishing experience and the opportunity to reach a built-in audience.
Over three years on the platform, I published several dozen long-form essays. A few went viral. I went from zero followers to over 10,000.1 My work was featured alongside publications like the New York Times and the Atlantic. I even collaborated with Medium on a collection of essays called Buy Yourself. That collection was featured next to No Mercy / No Malice by Scott Galloway. I was experiencing my “15 seconds of fame,” as they put it. And it felt good!
Success amidst a platform with a built-in audience, though, made it easy to think—incorrectly—that my writing would’ve succeeded anywhere. It further led me to believe—also, incorrectly—that regardless of how often I published, people that had once messaged me or shared my work would still want to read me, perhaps even to the point of wanting to pay me directly.
So it didn’t give me any real anxiety when my actual job got insanely busy in late 2019 and early 2020, and I lost the time and motivation to continue publishing for my audience.
Here, it’s worth understanding why, exactly, that happened.
Life Before Anything Different
As of late 2019, I had been working full-time at a corporate culture hub called Platterz for 18 months.
Platterz’ primary business was acting as a broker between restaurants and companies that brought catering into the office. This was a very good business until suddenly, it wasn’t. The pandemic took our company’s revenues from a lot to a little, basically overnight.
Now, we didn’t just lie down and die. We responded by building an entirely new business vertical. As we had once been brokers of food, now we were brokers of virtual experiences. Virtual escape rooms, virtual trivia nights, virtual mixology classes. If you did a virtual experience in 2020, you might’ve worked with one of our partners. We also rebranded to Thriver from Platterz, as a reflection of “supporting Thriving workplaces” no longer being synonymous with just brokering food.
As you might expect, the demand for virtual experiences was insane. We turned off inbounds multiple times because we couldn’t keep up. Still, just because demand exists doesn’t mean selling something is easy. There are other aspects of sales—dealing with logistics, or unreliable partners, not to mention expectation setting amidst uncertainty about what, exactly, the client’s expectations should be. We quickly realized that our expertise in managing food programs, which happened in-person, and dealt in physical goods, did not necessarily translate into expertise managing virtual experiences. It is astonishing how many things can go wrong with a Zoom call, or how difficult it can be to manage shipments of packages to people’s individual addresses. Hiccups—or, as we lovingly referred to them, fuck-ups—were varied and constant. It felt like we ran into a new crisis every day. And thus, the second half of 2020 was one of the craziest times of my working life.
Partially as a result of how much time I was spending on work, I stopped writing. Whereas I had been publishing on Medium about once a month, I couldn’t get myself to write even a word for the second half of 2020. I was making good money selling virtual experiences for Thriver, which made giving up on what I actually liked doing tolerable. Still, selling virtual experiences felt sort of opportunistic, and thus, I don’t know, hollow. I was making money doing something that I didn’t really feel like I should’ve been making money for doing. But it was a pandemic, so like everyone else who had a job, I found myself “sheltering-in-position,” as Linkedin dubbed it. The basic idea being, if you have a job, no matter how meaningless it is, or how much you hate it, just shut up and do it, because a lot of people are out of work right now and are way more worse off than you.
Granted, I should clarify that I really didn’t hate what I was doing. It’s admittedly fun to sell something people want, assuming it isn’t something that could destroy people’s lives. (Drugs come to mind.) I wasn’t initially convinced that what we were selling was worth wanting, but as demand exploded, it became easy to think that it was. This may just be human nature—that it becomes easy to convince yourself something is worth wanting when you see other people wanting it, too. I know this is true as a consumer—mimetic impulses undeniably drive consumptive behavior—but now I know it to be true as a salesperson, too. When people want something you’re selling, it becomes very easy to ignore that it might not be worth wanting in the first place, and it’s fun.
The other part of this that’s worth acknowledging is just how little else there was to do during the second half of 2020. My sources of excitement were cooking dinner with my girlfriend and spontaneous games of Sporcle Trivia or Quiplash with college buddies via FaceTime. There was literally nothing else to look forward to. No trips to plan, no dinners to go out to, no bars to stumble out of. My girlfriend and I spent Thanksgiving and Christmas at my apartment because we didn’t want to risk flying home. I couldn’t even muster up the motivation to get a tree, or hang lights. I’ll thus cut myself at least a bit of slack for trying to find some sort of direction amidst a pandemic, even if that meant trying to make as much money as humanly possible selling escape rooms and trivia nights to companies that didn’t yet realize paying $50/head for either one was absurd.
This last sentence basically describes my second half of 2020. From March of 2020 onward, I sheltered-in-position, survived two rounds of layoffs, and just kept my head down and ground it out, counting myself lucky to still have to wake up for a 9am Zoom call. As the virtual experiences vertical caught fire, I even found myself optimistic, thinking that we’d emerge from the pandemic in early 2020 with a new vertical added to our bottom line, and that once catering came back, too, maybe we could even hire back some of the people we’d had to let go.
Then, the Tuesday after Martin Luther King Jr. Day, I woke up to a calendar invite I didn’t recognize, and immediately knew what was happening.
I—along with Thriver’s entire sales and customer success teams, among many others—was being let go.
In retrospect, I probably should’ve seen it coming. Truthfully, though, I didn’t.
Virtual experiences had become a behemoth of sorts; a fraction of what our monthly catering revenue had been, mind you, but a lot of money for a vertical that had only existed for a few months.
Still, it wasn’t enough to justify a spend on a sales and customer success team, so our executive team made the decision to let go of everyone but product, engineering, and customer support. The idea was to keep supporting existing customers, but otherwise hunker down, wait things out, improve the product, and emerge from the pandemic stronger and leaner. This was the right move for the company, but it left a lot of people out of work.
I counted myself lucky not to need a new job immediately. Like many others, COVID eliminated a lot of my normal expenses, so I had some runway. Amidst a world where it seemed everyone was looking at life and wondering if what they were doing meant anything at all, I kept coming back to writing.
In a graduation speech at Maharishi University of Management, Jim Carrey tells the story of his father, who gave up on his dreams to take a stable job before being fired from it years later.
The lesson is simple:
“You can fail at what you don’t want, so you might as well take a chance on doing what you love.”
There are a few things I love. I love my parents; I love my girlfriend. Those aren’t occupations, though.
I love golf, too, which could be an occupation, but part of what I love about golf is that it isn’t what I do for a living, and I have never made money from it. Asking myself what I loved that I had also made money from previously led me back to writing.
I hadn’t written anything in a year, but I had some ideas. Still, I wasn’t married to going back to Medium, where I’d started writing. There were a few reasons for that. The first was that Medium doesn’t allow you to own your audience. Put another way, I had 10,000+ followers on Medium, but if the platform shut down tomorrow, they’d all be gone. This wasn’t as much of a risk when writing was a side gig, but it would be exceedingly stupid to build a business around an audience that could disappear in an instant. This led me to Substack.
The appeal of Substack is simple. You can import an email list, or start one from scratch, and reach your audience directly. You can also build an email list up with Substack. Critically, if Substack were to shut down tomorrow, I would still have that email list, and could use a different service to email them my work, as well as find another service that would allow them to pay me. From a business perspective, Substack made more sense than Medium.
I also had an email list of 400+ subscribers from a Wordpress blog I’d set up at the end of 2017. These were people who had emailed me at one point telling me they’d enjoyed my work, or had simply signed up to receive updates. Substack might’ve been less appealing if I were starting an email list from zero, but I wasn’t. I convinced myself that 400 people that hadn’t heard from me in over a year would gleefully accept my emails, and that a significant portion of them might even sign up to pay me monthly. This was, to put it gently, optimistic.
I should make a caveat here that my launch of Anything Different didn’t go terribly; it just didn’t go as well as I’d hoped. Many of you embraced my call to action and signed up for paid subscriptions. At this point, I have a few dozen paid subscribers. A few are friends and family; the rest are people I don’t know personally, but clearly found enough value in my work to want to pay me directly. I am grateful to everyone who reads my work; I am especially grateful to those willing to pay me for it.
Still, going paid as early as I did was a mistake. My eyes were bigger than my stomach. Not to mention that I had been let go from my job two months before starting Anything Different, and was anxious to start earning money again. So I turned on paid subscriptions, hoping for a deluge. I got a trickle.
In retrospect, this shouldn’t have been surprising. Substack works best for writers who have highly engaged audiences already. This usually means two types of people.
The first is someone like Matthew Iglesias, who started Vox. He already has hundreds of thousands of people who want to read him, specifically, and are willing to pay him directly. Substack enables him to charge those readers directly without having to go through a publication.
The other type of writer Substack rewards is someone who writes about something very specific, such that there is already an audience for them. I, for instance, would love it if someone wrote a Substack with hole-by-hole descriptions of every top-100 private golf club in America. For obvious reasons, there are only a few people who might have the access or social connections to enable them to do this, but there are a lot of golfers who would love to read it. This is a particularly niche example, but the niche is the point; there are people who would want that to exist prior to it existing; creating a Substack about it is just a way to connect with an audience that already exists.
For me, the calculus was different. I had people who wanted to read my work, but I didn’t have enough people such that the typical portion who would pay—10%, according to data from Substack—would offer me enough income to live on. I anticipated this, and worked out—basically via cocktail napkin math—that it would take me a little over a year to get to my target number of free subscribers—20,000. (10% of 20,000 is 2,000, and 2,000 * $5/month = $120,000/year, before taxes/fees, etc.)
Still, I was basing my estimates on the three years it took me to get to 10,000 followers on Medium—a platform with a built-in audience—while writing part-time. I also made the mistake of thinking that my productivity would scale linearly. If writing for ten hours a week for three years got me to 10,000 followers on Medium, I thought, then if I wrote 40 hours a week for Substack, I could reach 10,000 followers 4x faster. Aside from simply being incorrect—the nonlinearity effect, whereby there is not a linear relationship between an independent variable (time spent writing) and a dependent variable (follower count), is likely at play here—this also assumed that I could, actually, write for 40 hours a week. As any writer knows, the hardest part about writing is sitting down and doing it. Even if I sit at my computer for 40 hours a week, the chance that I’m actually writing for all of those hours is… low.
Having been unemployed for several months, though, and wanting to believe I was making the right decision, I ignored this reality, and—like a good economics major—simply assumed that writing for 40 hours a week would be a piece of cake. With this assumption intact, my cocktail napkin math said I could get to 10,000 followers in nine months—4x faster than I got to 10,000 followers on Medium. Once I was at 10,000, too, it would be much easier to get to 20,000. As anyone who writes online will tell you, it’s much easier to go from 10,000 to 20,000 followers than it is to go from zero to 10,000. (This is the same mechanism at play with the exponential growth of COVID-19 cases.)
Now, I’ll clarify again that things aren’t going all that terribly. My email list started at ~400 in March; it’s now up to 639. Things are moving, but they’re moving slowly. And it’s not hard to see this slowness as a function of my utilizing only Substack, and thus no longer having access to the freedom of reach that Medium provided me. Substack’s audience may grow in the months and years to come, and their discovery tools may improve, but for right now, their platform is best suited for those with dedicated audiences. If I am to make a living from writing, I need to focus first on building an engaged audience—not one that was engaged once, but was left to languish for a year while I tried to make as much money as humanly possible selling virtual experiences (because how the hell else was I supposed to find direction amidst a pandemic). This requires using not only Substack, but other platforms, too.
So starting today, I am going to begin publishing everything I write not only on Substack, but on my blog and on Medium. I am also going to pitch publications on new work so as to get my name out there. The goal, for now, is to use Medium and my blog to add to my audience and reengage my existing one, then direct people to Substack. As I continue publishing and earn new email signups, I will communicate with people directly, and gauge people’s willingness to pay for a subscription. Assuming the numbers appear to make sense, my plan is to begin monetizing once I hit 20,000 free subscribers on Substack.
Further, there is the more practical reason for publishing elsewhere—that is, I need to make money. I feel it worth noting that there is actually good money to be made from Medium, especially if you have a following, or decent relationships with the curators. My basic understanding of Medium’s algorithm for payments is that readers pay $5/month to Medium for access to paywalled content, Medium takes a small cut of that, then the rest is distributed to writers according to the percentage of time a reader dedicates to each writer’s work. So if someone paying $5/month reads only me for a month on Medium, I will get their entire $5, or whatever fraction of that $5 Medium doesn’t take.
Part of the reason I’m publishing this is so paid subscribers, specifically, are aware of my strategy. I’ve wanted to be extremely transparent since the beginning that if you are opting to pay me, you are doing so to support ME—NOT because you can’t read my work unless you pay. (To those who are paying, I really can’t thank you enough.) My work continues to be free for anyone to read. As I return to Medium and my blog, though, I feel it is worth acknowledging so anyone who is paying me who, in light of this new information, would like to stop, can do so.
The fun thing about doing all of this and defaulting to action is that you learn really quickly what works, and what doesn’t. For better or worse, in my effort to migrate to Substack, I found out very quickly that freedom of speech is not the same as freedom of reach. Given that, for now, I have the ability to take advantage of freedom of reach—unlike Trump, who is confined to launching his own social media platform—I think I’d be foolish not to take advantage of it.
Diversifying where I post is the best way to take advantage of freedom of reach, and move towards my goal of having a self-sustaining business built around writing.
Thanks for reading! If, after reading this, you feel compelled to subscribe, you can do so below.
Update: I am now back down below 10,000 because Medium purged a bunch of spam accounts. So that meme I posted would actually make more sense in its original form!