8 Lessons from 8 Years of Writing at Medium

On May 27, 2013, I wrote and published my first blog post at Medium. Designed in Toronto by Teehan+Lax, Medium made writing look and feel like it was worth your attention. Especially if a person didn’t blog regularly, Medium gave them a place to tell their stories. A lot of things have changed over the years, but one thing hasn’t: over eight years and 168 posts later, and I’m still writing at Medium.

There are many reasons for me to keep publishing at Medium: over 10,000 people have chosen to follow my work there. Also, thanks in no small part to its editorial team, I’ve written some of my favorite work at Medium’s publications, like this piece covering how to make money at YouTube for Marker, or this piece on reclaiming time for creativity for Forge. Like I told Jeff Sarris, I made a few thousand dollars directly from writing at Medium in 2020—the equivalent to a small book advance. Outside of Medium, I also started and led an editorial studio, I independently published a book that I’m now revising and publishing with Holloway, and I even worked as a staff writer for Lifehacker, writing 176 posts for it in a few months.

During these years, Medium grew up too. According to SimilarWeb, Medium received a whopping 204.5 million pageviews to its platform in April 2021. (For comparison, Lifehacker got 12.4 million.) If you want a detailed history, Laura Hazard Owen did a great job documenting it here. In particular, I loved the way she phrased her conclusion:

“Maybe because we wanted to know whether [Medium] was a friend or an enemy. The answer is that it’s neither. It’s a reflection of what the media industry has worried about, and hoped for, and not received. But Medium was never something that we would get to define. Instead, it’s turned out to be an endless thought experiment into what publishing on the internet could look like. That’s not much fun for people who got burned along the way, but Medium was never exactly ours to begin with.”

Hazard Owen’s point is something to keep in mind as there’s a lot of controversy around Medium these days. Just in 2021, there’s the union-busting, the culture memo, and of course, the change in strategy. I’ve been following along from afar. I wanted to provide a perspective of a writer who has written at Medium and away from it—at other publications like Lifehacker, Fast Company, and The Globe and Mail, and working with corporations to build publications—as well:

1. Medium Gets Emerging Writers Paid

I’d been reading about passive income since 2005, but I really earned my first passive dollar in 2019 from Medium. I’d pitched and written a piece for Forge, which earned me hundreds of dollars through the Medium Partner Program in the months after I published it, in addition to the bonus fee Forge paid its writers. This residual, passive, income would never happen if I was writing for a publication not at Medium.

For me, it wasn’t that I didn’t know how to earn passive income, but I just never felt ready to actually pull it off. My mailing lists never seemed to have enough people. My ideas for a book or a course were half-baked. I wanted to make something I was genuinely proud of. Plus, I had an editorial studio to run! So, Medium made it really easy for my writing to earn a bit of passive income.

There are many other stories of much greater successes that started at Medium. I’ll name a few: Sarah Cooper got her first book deal from constantly publishing hits at Medium, including this first one that she published at Medium in 2014. Same goes for elle luna, Sara Benincasa (for this book), and Refe Tuma. More recently, Sahil Lavingia and Julie Zhuo. Benjamin Hardy is authoring his third book (and is much more active at YouTube now). It’s definitely worth mentioning that, aside from Benincasa, none of these authors are active at Medium any more. In 2021, Cooper, Lavingia, and Zhuo are more active at Twitter. 

Still, there are plenty of great writers at Medium. (CEO Ev Williams puts the total number at 50,000.) With the launch of its Partner Program, it finally did something that publications with a much stronger brand and audience failed to do for decades. Instead of subsidizing content with ad revenue, Medium got people to actually pay for the content. 

However, there is a tradeoff: for me, my articles get a fraction of the traffic now compared to Medium before its Partner Program and paywall, but it actually directly pays now. I believe this is why a lot of that first generation of writers left: they prefer impact and reach.

It’s also worth noting, Medium pays its writers on time. Medium doesn’t need to apologize for its legal team being backlogged or for a convoluted process, and there’s never a need to follow up. Medium will pay you at the end of the month, through Stripe, and sometimes in 2021, with a little extra. You can check your earnings any day.

Medium also doesn’t own your work. I’ve seen some wild contracts for freelance writers at publications, where you’re effectively signing over your article as intellectual property to a publication for the comparatively small fee they’re paying you. (At best, it should be a non-exclusive license!) Medium doesn’t own any of the work, and it enables writers to republish their work there too. As with all things, there’s room for improvement—for example, Medium could almost certainly do a better job keeping an eye on plagiarism—but I think for the most part Medium has done its best to make the world better for writers

2. Medium Short-Circuited Snobbery

If you work with art, words, music, or video, you’re working on a world of snobs. You’ll know a snob when you see one: they’ll want to see what you do, listen to the words you use, and judge you as a person—and treat you well or poorly—based on their perceptions of your work and success. You need to develop a thick skin to keep creating. 

This is just the world we live in, and it’s certainly not restricted to publishing or media. We all have an endless amount of work and opportunities, but only so much time, and we need to figure out how to prioritize. 

However, in a time when most of us use popularity to determine quality, it’s a difficult one to operate in when you’re not popular yet. 

Enter Medium.

I think it’s absolutely underrated what Medium has done to level the playing field for writers and get emerging writers discovered. People with literary backgrounds—the aforementioned handlers—actually read and hold Medium’s owned publications like Forge, Marker, OneZero, etc. in high esteem. There’s something powerful about writing at the same platform where Joe Biden, Elizabeth Warren, and Barack Obama write. I realize that’s like saying, “Elizabeth Warren has Twitter, and I do too!” but the subtle brand association hits different for me.

Medium also has started deals with prominent people to build publications as well. There was Matter. The Ringer was started at Medium, before moving to Vox. The Awl moved to Medium, then left, and shut down. Unfortunately for Medium, these are very high-profile, notable, fumbles.

Writing on the web isn’t easy. And, it’s also not like Medium fought or created really unfair terms to keep the publication’s owners there. It was a mutually beneficial relationship, and when publications wanted to walk, they walked. Medium took all the blame and heat from it, and didn’t punch back. Sure, when push comes to shove, the communication probably could have been better, but business is business. A lot of publications ended—I miss Cuepoint, dammit!—but I wonder how many of these publications would’ve even been started in the first place without Medium.

As time goes on, we’ll see Substack face similar challenges. It’s just how things go

3. Medium Needs to Experiment to Survive

In Orbiting the Giant Hairball, Gordon Mackenzie writes, “It is not the business of authority figures to validate genius, because genius threatens authority.” The media industry is clearly an authority here. I wouldn’t necessarily say that Medium is a genius, but it has done a lot of things right. 

Still, media has not been kind to Medium, to say the least. There’s a narrative that Medium doesn’t know its head from its tail, and that it’s a complete mess. Tony Stubblebine, who sits on the board of Medium, disputes this.

Stubblebine says Medium has only actually pivoted once, which is to the paywall and Medium Partner Program. But the media will point out all of the shuttered publications, programs, algorithm changes, strategic and tactical shifts, as pivots. So, to me, it seems like a disagreement in definition. 

If the narrative that Medium is confused is valid, then this narrative applies equally to Google’s search algorithm changes, Twitter’s acquisition of Revue and shutdown of Vine, Square launching Cash App, Facebook’s feed and advertising changes, Amazon launching AWS, and all of the other little changes that platforms constantly make. By that definition, every software platform is confused because it is constantly pivoting. Confusion has nothing to do with it, of course. Medium, like all platforms, will always experiment.

Image: Cytonn Photography/Unsplash 

At my first job at Xtreme Labs, we had a small team in the sales division known as strategic alliances. The team had a strange name, but it basically started and maintained working partnerships between businesses. From what I saw, this included sales referrals, previews of and working relationships with new technology, and connecting people inside and outside of the company.

This is how I saw Medium from a business perspective: I was developing a writing business under my own name, my writing and craft was product development, and working with Medium was a strategic alliance. Medium certainly wasn’t my only alliance, nor my main way of generating sales or distributing my products. But, it was where I started writing and provided an opportunity that could benefit us both. As a platform business, Medium needs to constantly experiment and ship new features, and that’s exactly what it does. 

4. Medium Tries to Make the Best Bundle for Readers

If you want to make money writing at Medium, you need to understand its business model. Its founder and CEO Ev Williams writes about it here. Here’s the way I understand it: 

Medium makes money by charging USD $5 per month or $50 per year from its subscribers. Axios reports it has 725,000 paid subscribers as of March 2021. If that’s accurate, let’s assume each subscriber pays the lower cost of $50/year and divide by 12 months, which is just north of $3 million per month. After taking a slice of that $3 million (I haven’t seen that % or $ figure), Medium will then split the rest out to people writing in its Partner Program, based on its own algorithm which constantly changes. (If I had to guess, it’s some combination of time spent on the post, % of people who finish reading the full post, and pageviews.)

Image: Aggregation Theory/Stratechery

Medium is an aggregator platform. If you’re familiar with ecommerce, Medium is like Amazon, and Substack is like Shopify. Medium will show some new readers your work, but it also doesn’t want the readers to go somewhere else. Medium’s goal is to keep people constantly reading at Medium. The value proposition: Pay $5 for access to a lot of good writing, personalized for you. Given the many bundles and paywalls popping up, I actually think this could work out for Medium if they can keep writers writing there, and onboard enough publications like The New York Times and The Atlantic and make them money. 

By contrast, Substack’s goal is to keep writers publishing at Substack. It’s not a bad deal, but it takes 10% of subscription fees. Writers will leave when they know they can draw in more readers because while 10% of $1,000 isn’t much, 10% of $100,000 starts adding up. (See The Browser moving to Ghost.) Like Medium, it also cuts deals to people with large audiences, mitigating the risk for writers. Substack allows writers to export their subscribers’ email addresses, which means writers effectively own the data—they can import it into Mailchimp, Memberful, or Ghost, and continue publishing there. 

Either way, as a writer, Medium getting in between me and my followers doesn’t help me out. There’s also constantly new writers joining the Partner Program, so in order to show their work, Medium shows less work from authors with longer tenure and larger followings. I don’t love it, but I can understand it. This decreased reach has been my experience, although I’m sure this might be changing. And also, like many of the first generation of successful authors, it’s no coincidence that after Medium implemented its paywall, Gary Vaynerchuk stopped writing at Medium

All of these changes are tied in with the most important lesson I learned working with Ryan Leslie while he was starting Superphone:

If you’re an artist, you should be trying to connect directly with your fans and customers. You want to give them good reasons to provide their contact information, whether it’s emails or phone numbers, no matter what. That way you can directly keep in touch with them, build a relationship, and let them know what you’re up to. 

Medium is helpful for showing people your work, but it’s not great for maintaining your audience connections. There are a lot of factors here. For example, I mentioned having 10,000 followers at Medium—but I wouldn’t be surprised if at least 50–75% of my readers weren’t using Medium as much anymore, especially after the paywall and Partner Program. That’s the bargain that I, in full awareness, struck with Medium. I knew Medium would change, I knew it could even disappear like Vine or Myspace did, and I knew it was an alliance. It’s why I write the Best of Books newsletter. It’s why I write at my blog, too! I want to own my marketing. (See The Billionaire’s Typewriter.)

Currently, I write and publish two articles per week. I’ll publish at my blog first, so Google has a chance to index it, then I’ll republish it at Medium with a canonical link. I’ll also probably share just an excerpt of the longer pieces, like this one. For example, I wrote a piece on 8 lessons I learned from the Zettelkasten, and I’ll share 3 of them at Medium and link back to the original. 

5. Medium Is Not Meant to Generate Stable Income

If the Medium algorithm was a client at my editorial studio, I would have fired it in a heartbeat. Day-to-day, the algorithm feels completely all over the place—sometimes it seems to incentivize certain metrics, and it’ll flip the next day. It’s incredibly frustrating to work with as a writer, because—in a sense—the algorithm also determines how well writing at Medium pays. Medium income has tanked by up to 75% some months, so every writer needs to know that going in.

But, Medium’s algorithm is not a person. Medium is a strategic alliance (see lesson #2). 

While you can treat and work at Medium like you would at a conventional job, you’d be disappointed if you expected to get paid like it. I actually expected to earn $0/month from Medium, because when I joined the platform, it didn’t pay at all. That also influences my own personal lack of reliance and infrequent writing at it (for 168 posts divided by 416 weeks (8 years), I’m at around 0.4 posts per week). I earned most of my income from my editorial studio. Also, I wrote a book that I promoted at Medium, but is an entirely separate income stream.

Image: Glenn Carstens-Peters/Unsplash 

Making money at Medium is similar to how vloggers get paid at YouTube. When I wrote a piece examining YouTube and Patreon payment structures, reader Cynthia Wylie, asked rightly, “What about Medium?” Selling your work at platforms absolutely does not mean you’re hired by them. The working relationship is completely different. Some say better, some say worse, but it’s not the same and can’t be considered the same way.

If you want a stable income, don’t try to make money writing at Medium. I would actually probably shorten the sentence to, don’t try to make money writing. Medium is not going to fix the unstable nature of writing for the average person, which happens because of all sorts of other factors. If you still want to write, get a content marketing job (very stable), a journalist or editorial job (less stable), freelance write or edit (even less stable), or sell courses (the least stable on average of the four options, in my mind). Augment your income with consulting, like Susan Cain and Soman Chainani. If you experience discouragement reading this, nothing would make me happier than you responding by saying, “I’ll prove that Herbert Lui wrong!” That’s the spirit you’ll need in the business of writing.

6. Medium Is Not a Panacea for the Writing Business

Every time I said I wanted to start my own business, my dad would always tell me it wouldn’t be easy. That insight came from his own observations with his father’s generation and their failed businesses. It was discouraging for me to hear this, which is probably why I didn’t try anything more risky than I did—an editorial studio is a services company! After all, if I was more bullish on Medium in its early days, I might’ve written more posts and seen even more positive outcomes from it.

But, my dad wasn’t wrong. He set the expectation that it was supposed to be difficult. A friend and mentor recently told me this too. In his early career, when he felt he wasn’t compensated fairly by the company, he just woke up and told himself it was supposed to be difficult.

A critic might say that Medium is a sad reflection of society that doesn’t value writing, but writing has never been an easy business to be in. If you choose to go into this business, it’s not worth complaining about. This is a deliberate decision and a choice I’ve made to decide to write. There is money, there are opportunities, but it is not an easy industry to work in. Do not expect a 4 hour workweek. 

The reality that it is difficult absolutely does not mean that it is impossible, to be very clear. But you need to brace yourself, and not expect Medium to have fixed everything.

7. Medium Works Best as a Long Game

Image: Miguel A. Amutio/Unsplash

Medium and creative work in general pays better the longer you play. It pays poorly if you quit too early. You need to practice and make a lot of acceptable work. When I tried betting bigger at Medium, I was constantly frustrated by the algorithm. I was allowing it train my brain to write a certain way—to look for topics, to change my voice and tone, in ways that I thought would encourage it to distribute my work to more people. I could really relate to this piece

The solution, to me, was clear too: I wanted to have fun writing again. I realized that when I was having fun writing, there’s a good chance the person who was reading it would have fun too. “In writing for yourself, you write for others,” I wrote at my Paradoxes page. So I just gave up on writing for the algorithm.

For me, I naturally became my own audience and paid attention to other people like me. I am a self-taught author, making more stuff I’m proud of. I do my best to write daily and take notes. I’ve spent years writing to refine my voice, tell story, and to have fun and make some money. There are a ton of people who are just like me—at least 50 million according to Signalfire. I’m betting there’ll be more! 

With this approach, I believe I developed an intuitive sense of what the audience wants. But I also do deliberate research (I didn’t find that stat by accident!). If you’re going to write, maybe you could do something similar. Find the person or people whose work resonates with you, and see who they’re writing/drawing/filming/recording for. 

So generally now, I start with the topics that interest me. I ask myself some questions as I fill out an outline, to see if there’s a strong idea there. I spend a few minutes doing some basic SEO keyword research too, with Keywords Everywhere and Ahrefs Keyword Difficulty tool. Then, that’s it! I start writing. I pitch less, I write what I think is interesting, and let the people decide what gets chosen. This sounds silly, but I used to pitch 12 ideas only to get 3 accepted. So freedom makes a big difference.

8. Medium Is a Place that Brings Authors Together

I see most platforms as digital equivalents to physical places. They’re set up to make money, but they bring people together. It’s not about followers, algorithms, and optimizing—it’s about people, community, and relationships. 

Writing is seen as a task of solitude, but like Annie Duke told me, it can be a team sport. Medium is a great place to meet and have conversations with other people can read your drafts, refine ideas, and support you in other ways.

It’s not dissimilar from being at a conference. You can choose to schmooze, or to hang out by yourself and wait for people to approach you! But if you want to meet new people, there are tons of Slack channels, Discords, email newsletters, and all sorts of other things happening between authors, and information spreading at these hubs. If you don’t know where to start, start at Medium. Take your time with the free information before choosing to pay for a course or membership. If none of it looks like a good fit for you, start your own community.

I don’t do this nearly as much as I probably should, but Medium is a great place to meet people and make new friends. They might work as part of Medium’s editorial team, own a publication you like, or be an author whose piece you just read. (You can use a tool like Norbert to find people’s email addresses!)

Just make sure you still make enough time to write.

A World With Medium Is Better than a World Without

I’m sure I have my own biases—writing eight years somewhere, even occasionally, will do that to a person—but at the end of the day, I really appreciate Medium. Even if it wasn’t as successful and powerful as it was now, it did writers a service by offering an alternative. If you don’t want to write at Medium, you can still start a WordPress or Ghost blog, or continue freelance writing at traditional publications. Those options still exist.

For me, I’m a selfish writer. I’ve always wanted to write things that, first and foremost, I want to write. But I’ve found this difficult writing at publications, because it often required pitches, avoiding past coverage, and timing and relevant topics. It was soul-sucking pitching and arguing about whether a topic was worth covering or not, and that it was different enough to warrant a piece. These types of non-writing tasks actually add up and eat into precious writing time. It just wasn’t part of the game I was good at, and I didn’t want to play.

So, the fact that Medium has created a space where I can publish almost anything—and get paid a little bit for it—is something I appreciate. If you’re an author who wants to write what’s on your mind, it’s important for you to remember what a world without Medium looked like. You can choose that world too—just don’t write at Medium—but if you ever change your mind, Medium will be there.

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