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What I Learned About Writing on Medium After One Year and 100 Articles
Experience is always the best teacher
At the end of October, 2019, I committed myself to posting at least two articles per week — roughly 100 articles — on Medium for an entire year. As I write this, I’ve reached my goal: 52 weeks of publishing, 106 total stories (I published three stories in a week a couple of times). What better way to celebrate than with an article describing some fo the most important lessons learned?
In other words, get ready for yet-another person to write yet-another mostly worthless article about “How to be a successful writer on Medium” article. You’re welcome!
But first, a quick bit of context…
I study and teach about social media at Duke University. Through my studies, I’ve learned a ton, but I’ve always had one huge gap in my knowledge: I personally never created large amounts of social media content. To correct this shortcoming, and to more fully understand and appreciate what social media influencers do every day, I decided I needed to become a social media content creator.
Unfortunately, since I’m a researcher, that dramatically limits my choice of platforms. After all, aside from my mom, who wants to see TikToks of me giving lectures or Instagram posts of me sitting at my computer? That pushed me toward creating longform content like blogs, essays, and articles. The best place to post those is on Medium, so here I am.
In order to successfully build an audience on Medium, I knew I would need to focus my content on a single subject. Since I spent 15 years running venture-backed tech companies, and I also teach entrepreneurship courses at Duke, I decided I’d write articles about startups. Makes sense, right?
So far, I’ve been pleased with the results. I’ve grown my following to 5,000+ people and generated nearly half-a-million views. I’m not exactly a super-influencer, but I’ve got my niche, and, most importantly, I feel like I’ve helped lots of people. I get messages nearly every day thanking me for my articles, and, if I’m being honest, that’s a great feeling. I love teaching entrepreneurs, and I love how Medium has expanded my ability to help more of them, so I plan to keep writing.
I suppose that plan starts here with the very article you’re reading right now. Are you trying to grow an audience on Medium? Then what follows are 10 of the most important lessons I’ve learned after one year and 100+ Medium articles. The vast majority of my articles are about startups and entrepreneurship, but the lessons I’ve learned from writing them go well beyond that.
Enjoy!
Lesson #1: You’re first article won’t make you famous
After 52 weeks, my very first article is still my least-read article with a whopping 20 views. I just reread it, and, honestly, it’s not my worst. So why has nobody read it? I don’t know. But if you’re just getting started, don’t give up if the first article doesn’t go viral. In fact, it’s the opposite. If your first article goes viral, you probably should quit because it’s all downhill after that.
Lesson #2: Your title is 90% of the battle
If my first article was a complete whiff, my second article was a homerun. It remained my most popular article for the next nine months and still gets ~100 readers per day. Why? Just look at this juicy title:
The Three Words no Early-Stage VC Wants to Hear
How could you not want to click on an article with that title? Even now — even if you’re not an entrepreneur — you’re probably dying to know what the three words are. In fact, go ahead and click on the link to find out. I’ll wait…
…
…
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Welcome back!
If I’m being honest, choosing a great title for my second article was complete luck, and it took me a while to fully appreciate the value of a good title and replicate my success.
Also, please don’t mistake this advice as me encouraging “clickbait” headlines. Clickbait is a misleading headline that misrepresents the content. A compelling title is one that hints at the actual content without explaining the entire article. Which leads me to lesson #3…
Lesson #3: Don’t reveal too much in your title
If a great title encourages people to click through to your article so they can learn more, then a bad title does the opposite. After reading the title, they think, “I can’t learn anything interesting from reading that article,” and they don’t click.
People will feel like they can’t learn something for two reasons: 1) they’re not interested in the topic; or 2) the title reveals too much about the content.
The first issue is something you should embrace. Be clear about your topic up front so your content appeals to people who want to learn about that particular subject. This will help you build an engaged audience.
The second issue is something to avoid. For example, I once wrote an article called How Milkshakes Helped Get Me 30% More Investor and Customer Meetings. A few days after publishing it, a friend mentioned successfully using the advice in the article. But, to my surprise, when I thanked him for reading what I’d written, he said: “I didn’t bother to read it. I could tell from the title it was just going to tell me to invite people for milkshakes instead of coffee.”
That moment is seared in my mind. While I was glad to know my advice was useful, I was annoyed he didn’t actually read the article. Since then, I’ve tried to be better about not over-explaining in titles.
Lesson #4: Don’t bother publishing on holidays
Within a month of starting my one year commitment to post twice per week on Medium, I ran into Thanksgiving. A month later was Christmas/New Years. Determined not to interrupt the publishing schedule I’d only recently committed myself to, I decided I’d publish on the holidays. I reasoned that nobody else would be publishing, so even though there wouldn’t be as many people reading, I’d have the attention of the ones who were.That led to this article on Thanksgiving and this one on Christmas. Neither did well
So don’t bother killing yourself for holiday content. Do what everyone else does and give yourself a break. You’ve surely earned it.
Lesson #5: Keep it casual
If I had to guess, I’d say 20% of you are reading this article as a temporary distraction while you’re supposed to be working. Another 10% of you are on some form of public transit (would be higher if not for COVID-19). And at least 30% of you are sitting on a toilet.
None of those are good environments for reading complex thought pieces or sophisticated prose. As a result, Medium isn’t a good place to publish overly intellectual polemics or witty satires. What you write has to be easily browseable and something readers won’t feel bad about putting down halfway through when they reach their bus stop or need to wipe.
While I’d hardly describe anything I’ve published on Medium as scholarly, I’ve noticed the things I’ve written that I’d describe as “thought pieces” never do particularly well. It’s a bit frustrating, because I enjoy writing them and think they’re some of my best articles, but Medium audiences don’t seem to agree. Which leads me to Lesson #6…
Lesson #6: Write for your audience, not yourself
In my case, I don’t personally care for articles about startup fundraising; however, I’ve found that my articles about fundraising are my most popular. In contrast, I enjoy thinking about sales and marketing. But my articles about sales and marketing have almost no readers.
I fought this for longer than I should have. I was sure I knew what readers needed to learn. But I was wrong and stupid. Eventually I realized it wasn’t my place to tell my readers what they should want to read. I don’t know them. I shouldn’t be making decisions for them. The only person I know is me, but I’m not writing articles on Medium for myself. I’m writing articles to provide value to other people.
That’s true for you, too. If you want engaged readers, listen carefully to their feedback and write for them. Selfish content will get you nowhere.
It’s also worth noting that, while Medium’s stats aren’t the best, they do reveal lots of useful data for understanding reader interests thanks to stats like read ratios, claps, fans, and, my personal favorite, highlights. All that data is telling you what readers enjoy and want more of. Listen carefully, and give them what they’re asking for.
Lesson #7: Stay in your lane
As I’ve mentioned, I write about things related to startups and entrepreneurship. One day, seven months into my experiment, I decided to write about something completely different (healthcare!). In my mind, it’s my absolute best article. However, with a miniscule 48 views, It’s also my least popular article behind only my first article.
This was a stark reminder to choose a topic and stick to it. Yes, I have opinions about things unrelated to startups. But my audience wants to read about entrepreneurship. They don’t want (or need) my advice about how to live longer, healthier lives.
Lesson #8: Write about your children
In two articles, I include brief stories related to my young daughter. One article is my most popular in terms of overall reads and money generated. The other article is my most popular in terms of claps. They’re both good articles, but I didn’t expect either of them to blow up the way they did.
I think the lesson here is that if you want a viral article, tell adorable stories about your children. If you don’t have children, I guess you just have to make something up? ¯\_(ツ)_/¯
Lesson #9: The world is beyond your control
In a lot of respects, 2020 has been a difficult year for online audience building because there’s been a lot of competition for eyeballs. For example, my March and April readership stats plummeted as a result of all the attention COVID-19 was getting (as did lots of other people’s I’m sure).
At first, I tried tying into what was going on in the world by writing articles connecting entrepreneurship with COVID. In other words, I created articles about pitching VCs remotely and making remote teams more efficient. At first they got some readers, but, eventually, those kinds of articles got ignored. That’s when I realized my entrepreneurship articles weren’t supposed to be related to COVID or elections or anything else the rest of the world was talking about. People were reading my articles about entrepreneurship because they wanted to learn about… well… entrepreneurship.
That’s going to be true for you, too. Whatever subject you decide to write about, there’s an audience out there that wants to read it. So don’t worry about connecting your work with whatever else is dominating headlines. Keep your content focused on what you know. Not only will you be happier, your readers will appreciate the opportunity to escape from the things they’re reading about everywhere else.
Lesson #10: Keep experimenting
The things that work well for me might be terrible for you. For example, I initially tried posting content around mid-afternoon because I read somewhere it worked well for someone else. After a few months of that, I tried posting early in the mornings and saw a big increase in readers. I’ve been posting in the early mornings ever since.
The only way I figured that out was by experimenting. Be sure you’re constantly experimenting, too. The worst thing you can do is read a few articles — like this one — and assume someone else’s successful strategies will work for you.
Instead, treat your content like you’d treat any new product: prototype, test, learn, iterate, repeat. Keep doing that over and over and over again in order to figure out what works.
Heck, this is the first time I’ve ever written a “How to be a successful writer on Medium” article, and I have no idea how well it’ll perform. It’s an experiment, and I hope you’ve enjoyed it.
