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I’ve Written 100 Posts on Medium, Here’s What I’ve Learned

I have officially crossed the century mark on Medium, racking up over 100 entries. Technically, this is #101. I have a few thoughts.

I learned about Medium when it launched in 2012. Back then, I’d check it out every few days and find at least one or two things to read. The topics were insidery — start-ups, technology, media commentary and design. The pieces were written by the internet, for the internet, which was kinda cool.

At the time, Medium was organized by Collections. Collections were like mini magazines. If you wanted to house your writing in one place — like say, here are all my thoughts on trying to lose weight — you could just create a new collection and put your pieces inside.

Medium also had its own Collections, edited by other people, and if you were able to get something you wrote in there, depending on the size of the audience that followed that collection, it could be widely-read.

I’ve written professionally since 2004 but there’s no doubt about it — I missed the personal blogger era of the internet. I was too busy, too lazy and didn’t think making posts every single day about every little thing was that exciting.

A few years ago, when I finally started warming up to the idea, Tumblr was ascendant. But Tumblr, to me, was far more in line with small ideas— images, .gifs, a snappy little comment about something— than anything thoughtful or, dare I say it, #longform. I wrote a lot on my Tumblr, always painstakingly, because their CMS is wonky, and I never got the sense that anyone following me there actually wanted to read anything.

Not to get too web-nerdy and abstract, but when Medium launched, I saw it first and foremost as a community. That’s what all these things are. Twitter. Tumblr. Facebook. Vine. Instagram. Reddit. They’re all communities and if you’re on them, you basically decide who and what you want to be within that community. If you’re a passive member of the community, you get little out of it. You consume and move on. If you’re active, you get rewarded. It’s strangely like real life.

That knowledge aside, I didn’t intend to write a lot. I just had some thoughts in my head, stories I wanted to tell, things I wanted to say, and I wanted to share them without the added burden of having to maintain a separate website, which I already had. Medium was an easy place to do that, so I did it.

On October 1, 2013, I wrote my first entry: “Why I Started Paying for Newspapers, Music, Movies and Magazines Again.” It took me thirty minutes to write and publish. I shared the link on social media and many people retweeted it. I believe Medium may have tweeted the link as well, and eventually it hit the front page, which at the time was filled with stories that were trending.

In the days that followed, I made posts about binge-watching television, the return of the monoculture, a book review, movie review and a high school friend who got his face slashed with a razor. I even wrote about how, during his month-long New York residency, I made Banksy’s piece in East New York happen.

I’m sure if I worked at a large media company, or if I even had the patience to deal with pitching this stuff to other folks, maybe I could have published this stuff elsewhere. I write for a lot of other places; so, I don’t know. But what I do know is that this stuff was being read and that was pretty important to me. I was at a low point in my career, thanks to a layoff and subsequent job search that proved fruitless, and to know my pieces were being well-received, in light of getting the cold shoulder on the job search, gave me a real jolt of energy.

About a week after my first post, I was driving home late at night, poring over my dwindling checking account balance, the months I’d spent unsuccessfully interviewing and all the exciting news my ‘successful’ friends were sharing on social media. Mentally, I felt burnt out. But I wasn’t even doing much. How could that be?

I had this idea in my head— hey, guess what, starting over can be healthy!— and when I came home I spent twenty minutes writing down everything I was thinking. I titled it “The New Retirement Age is Thirty.”

Then, I went to sleep.

While I rested the piece struck a chord, because back then, on Fridays, Medium sent out a weekly newsletter with its best stories and they included “The New Retirement Age is Thirty” in it. It subsequently exploded, which led to it being translated into many different languages, audio versions and more.

Looking back, it’s certainly not the most widely-read thing I’ve ever written, but I presume it’s the one people felt the most. And I, too, benefited. In a moment when I was feeling down about things, it let me know that I wasn’t the only one.

Energized, I spent the next year or so filling up Medium with many stories. I didn’t have a beat per se, so I just wrote about whatever I wanted.

Some of these stories were extremely well-received, like the one about the struggles rap producers go through nowadays (“Why Being a Hip-Hop Producer Sucks”), how Beyonce’s new LP had permanently altered the record business (“Beyonce Broke the Music Business”), and why the cinema industry is fucked (“Hollywood Has a Major Problem”).

Some flew under the radar, like the one about scalping tickets (“How to Buy Cheap Tickets to Sporting Events”), or how seeing Kenny G changed my negative opinion of him (“I Saw Kenny G Last Night”), or why a city that everyone can’t stop crowing about is still pretty cool (“New York is Still Awesome”).

Others, which I felt were particularly eyebrow-raising, weren’t read much at all, and that was very disappointing. Take “Real Scenes from a Chinese Restaurant,” for example. It’s a true-to-life Staten Island story, dealing with race relations, which takes place five minutes away from where Eric Garner got killed. It was written about a week before the verdict came in that absolved the police from any wrongdoing. Less than 1,000 people looked at it.

Another story, which I wrote in late November, in the midst of the uber spying controversy, was called “I Don’t Give a Shit About Uber.” The title may have been misleading, but it dealt with another true-to-life story, that of a supermarket cashier who, while we were busy worrying about our fancy livery cab service on our smartphones, didn’t even make enough money to pay for bus fare. He walked 3 hours a day to and back from work.

It got no attention on Medium, so I sent it to Business Insider. There, it exploded, leading to roughly 100,000 views and discussions about potentially turning it into a book.

In the early months of summer ‘14, Jonathan Shecter sent me a message.

Shecter co-founded The Source in the late 80s, and after bowing out of that business ran an independent record label, working with the likes of Eminem and Royce the 5'9. He spent the next decade becoming that dude in Las Vegas, where he worked as director of programming at the Wynn, before being hired as the Editor-in-Chief of Cuepoint, Medium’s then-forthcoming music vertical.

Shecter asked if I was interested in writing for Cuepoint and I, flattered, told him I was. We bounced around a few ideas. We had to get the right one, as there was a lot riding on this; the piece was going to launch the vertical, effectively announcing that this is what Cuepoint is and this is what it will be about. We eventually settled on:

“Kanye West, Chris Brown, deadmau5: When Great Music is Made by Despicable People.”

Typically, I’d spend between thirty minutes and a few hours writing a Medium post, but this piece, including research and writing, took about a month. I probably could have written it faster, but because it attempted to advance an idea that wasn’t a retread of something that already existed— which is, let’s face it, about 90% of what writing online is these days— I wanted to make sure what I was saying really made sense.

The essay was extremely well-received and I think it’s one of the best things I ever wrote. It’s a real personal favorite, too. But most of all, what I enjoyed about writing it, and all of the pieces I’ve written thus far for Cuepoint, is that I was free to do my own thing. Whether it’s concerns over structure or language, editors typically won’t resist the urge to meddle, and the words you hand in are rarely the words you’ll see on the page. With Cuepoint, unless I’ve specifically requested the help, that has not been the case.

That means I’ve done far less pulling my hair out than actual writing, and writing, after all, is what I got into this racket for in the first place.

A few months ago, Medium made some changes.

They moved away from the open submission format of the original Collection model, then ditched it altogether for Publications, which has made it more difficult for less-celebrated writers and their work to be discovered. It’s a growing issue and I think they’re aware of it.

At the same time, they’ve combated that, arguably unsuccessfully, by changing the homepage around and adding other features, like the one which allows people to follow each other, with emails and notifications going out whenever someone you follow publishes a story.

The platform has obviously grown, and that’s great. But, I’m not really sure what the net effects of that growth have led to. Closing in on my 100th post, I asked myself what all of these pieces have amounted to. Frankly, it’s tough for me to say.

As Medium has gotten more popular, discoverability has become a fairly complex issue— a lot of it has to do with the inability of vast social networks to drive eyeballs to small, individual publishers — and I think, going back to my original point about community-building, the opposite has been proven true.

I have been very active and I’m not that sure if that activity— at least on my own, not as a contributor to Cuepoint— has really led to anything substantive. Initially, it did. But now, much much much less so.

Or, has it? Am I just ungrateful? Am I splitting hairs? Why should anyone care about me?

Here’s the bottom line.

Writing this much, on topics this varied and dear to me, has made me a much better writer. It’s pleasing that many conversations I have now involve my interest in pursuing books, screenwriting, longform journalism and more dynamic, comprehensive, creative types of storytelling. Exciting stuff.

I guess, in a sense, that’s a much better position than the one I started in.

Ask me again when I get to post #200.

if you’d like to get in touch, email:

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Wrote for the New York Times, New York Magazine, Esquire, Rolling Stone, Vice, Fader, Vibe, XXL, MTV News, many other places.

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