I Joined Medium Out of Desperation. A Year Later I Was Making $10,000 Per Month.

From the rags of freelance to the riches of self-publishing

I love happy accidents.

It feels like the universe is finally tossing you a sweet, tasty treat after years of struggle and confusion. Modern life is no easy task. Making a career as a writer is tough. It requires hard work, focus, discipline, and a willingness to put yourself out there with complete abandon. A great writer is a fearless one.

It’s not only our task to say the hard thing, to discuss the difficult topics that need to be discussed, to peer boldly into the various realms of the world that ordinary people don’t dare to go (entertainment by definition isn’t ordinary, after all), but we must give a tiny slice of our soul with each and every piece that we write.

Every article is a confession of perspective.

We can try to water down our tone as much as we want, but, in the end, the fingerprints of our minds will always find their way into our words artifacts that impregnate our pieces with the shading that is our signature.

We must give all of ourselves — nothing less. There is no room for half-measures.

Plenty of writers just try to go with the flow, especially after a few months or years when they start to feel the slow burn of burnout clutching them in its nefarious barbs, only to later find that they’ve lost their audience — nobody’s listening; they scream endlessly into the void.

And just like that, they’re right back to where they began.

The Twist of Fate

It was late 2018, heading into 2019, and I’d been writing freelance for a website for about 2 years. The pay was good, albeit intermittent. Towards the end of 2018, things went awry. Payments would come through 6 months late, sometimes. On average, a payment that was supposed to show up in two weeks would show up in three months. When you’ve got bills to pay, this is catastrophic.

After a few vehement email exchanges (demands for my money were included), I’d finally had enough. I needed to adopt a new strategy that would be more consistent. I remembered my friend had tried Medium and failed some years prior and, in an act of complete desperation, signed up to start writing here.

And it was just in time, too.

My company held all payments for another few months. I’m assuming they were having financial troubles. I didn’t get my last few paychecks for work completed. It was a mess.

Medium provided a new opportunity that I was thankful for. I understood that if I couldn’t make Medium work — and by work, I mean, make me enough money to live on — I’d starve.

My bills would go unpaid. My life would fall apart.

Lesson #1: it’s absolutely vital to be thankful for the opportunities you have to make money. I know, I know, this sounds like more toxic positivity bullcrap, but it’s true.

It’s easy to get jaded. It’s a cinch to fall into the trap of believing our bullshit. It’s effortless to get swept up in the world of toxic platform politics and start feeling entitled.

Entitlement has its place — we can’t let people walk all over us. But sometimes entitlement can convince us that we’re worth more than we really are. It’s easy to lose sight of the opportunities we have in abundance that others don’t.

Write like you realize what a wonderful opportunity you’ve been given to make money with words, sitting at home in your underwear, with your cat trying to climb on your laptop.

From Madness to Marvelous

My first month was really uninspiring. I raged and churned out as much content as quickly as I could. Thankfully, I’d been writing my own thoughts down all along, creating notes in several note-taking apps, on social media, and elsewhere. I had tons of opinions and a new place to put them.

Freed from the constraints of having to write content for the specific niche of my former site, I went to town. I pounded out stories like you wouldn’t believe. Over 100 in my first thirty days.

At the end of the month, I crossed the finish line and I’d made a whopping $57.

Not exactly inspiring. It certainly wasn’t going to pay my bills, either.

But…you know what? I chose not to focus on that. Why?

Because I would’ve starved if Medium failed.

Lesson #2: if Lesson #1 fails, remind yourself that you need to do this otherwise you won’t be able to pay your bills and survive. Even if you have a job, one you want to escape, pretend for a second that you don’t. For some people, this is too much pressure to put on themselves. If it is, see Lesson #1.

I eventually got frustrated with curtailing my work to what I thought the Medium audience wanted.

I realized that the whole time I’d been writing in a way that tried to emulate what I thought would be successful. I wasn’t very authentic.

At a certain point, you just say screw it, I’m going to be me and if nothing works, I’ll shift gears and do something else entirely.

Turns out, that was the secret sauce.

From Vague to Viral

My first viral article was about anal sex. I remember watching as tens of thousands of people were viewing my article per day. Just a month prior, I was lucky if I’d garner 200 views per day.

It was only my second month and I was already hitting viral articles. And therein lies Lesson #3: stop writing what everyone else is writing.

I’ll keep it 100% honest, here, and give it to you blood raw — I can hardly read 99% of most writing anymore. Frankly, it’s redundant. A lot of people are telling me the same things I’ve read a million times. Everyone’s chasing the hottest news story.

We end up with a tens of thousands takes on the same subject and it’s the few people who can think outside the box who become interesting.

At the time, February of 2019, anal sex articles weren’t everywhere. And nobody was doing a deep dive (huh huh) on the subject of anal sex and why people love it so much.

Lesson #4: try to be original. Success at writing means letting wonder guide you to uncommon realms, places of study where you can find the substrate that will eventually become your articles. Don’t use Medium alone for your research. Branch out.

Truth be told, I just found the subject matter fascinating. I wasn’t having that kind of sex but it always made me super curious to think about — humans are fascinating once we get past the their awkwardness.

There’s another lesson…

Lesson #5: Let your curiosity guide you. Ignore the pressure of what you *think* people want to read. Ask yourself, what have you always been curious about, fascinated by; what repulses you in a way that you can’t comprehend it? Write that.

Research it. Write it. See what happens.

From there I took on cannibalism, men’s issues, infinity, dating, and more.

I continued writing about a variety of subjects that interested me and, a year later, I was making nearly $10,000 a month on Medium alone. No need for diversifying; no chasing down magazines and pitching them stories, dealing with the constant stream of rejection.

(If you need receipts, I bring receipts).

It wasn’t a fluke, either. I had some great months and some bad months, but as long as I clear at least $5,000 per month from Medium alone, I feel unfathomably fortunate.

Everyone tells you to “find your niche” but that’s not what well-rounded people do. Niches are inauthentic. Imagine being so one-dimensional that you can only talk about one thing.

Simone de Beauvoir didn’t have a “niche” and neither did Sartre. Voltaire did philosophy and novels. And don’t even get me started on Leonardo da Vinci.

History is riddled with people who learned to express themselves, and they expressed themselves very well, in many different ways. Strive to be that kind of person.

Niches get tiring.

When we put ourselves in a box we can no longer think outside of it.

Writing is Bigger Than Writing

Sometimes, it may not feel like it, but writing is always bigger than writing. It’s easy to forget how incredible writing truly is. I don’t just mean as a career, I mean the fact that humans write things down with this weird thing called language — shapes etched into stone or scribbled onto paper, information that can be decoded by other humans. But it’s so much more than that.

It’s personal expression. It’s therapy. It’s taking a tiny slice of our internal, mental world and putting it out into the physical world in a code that can be understood by others.

When we write, we turn ourselves inside out. We place our hearts on a platter and say, “Gaze upon this if you wish. Carve into this if you dare. Here is all of me.”

We expose ourselves for who we are and what our interests are. We stamp the fingerprint of our inner experience like a time stamp records a document. These articles and stories, they are the stories of our lives.

Thank you for reading. Sign up to my Medium email list, so you don’t miss a beat, and check out my new Substack publication, The Science of Sex.