9 lessons from one year of writing online
Looking back on a productive 2024
For years I’ve told people I want to write online. Partly because I feel like I have interesting things to say. The other part is I strongly believe the best opportunities in life stem from increasing serendipity and writing online is one of the best ways to achieve that.
But it wasn’t until 2024 that I started writing more consistently (this is post #18!). What really kickstarted me was taking David Perell’s Write of Passage (RIP) last March. It taught me a lot about writing but, like anything, the only way to really learn something is by doing it.
My surprising and not-so-surprising reflections on one year of writing:
1) There are many intangible benefits to writing online (even without building a huge following)
There are a lot of obvious benefits to writing online if you build a huge following: money, fame, opportunities.
But even with my small number of followers so far, I’ve received a ton of value from writing online. I’ve gotten job opportunities, met many interesting people, and have seen it give me instant credibility when talking to people for the first time. I’ve honestly been shocked by the amount of conversations where people mention it.
Everyone worries about the potential blowback from writing online, but I’ve yet to see any. Some of the articles I was most worried about publishing have had the most positive reaction (like my recent one about crime in NYC). This probably changes as you get bigger, but the broader point is that the costs are usually more imagined than real.
2) To write well, you need to read well
When you start out writing, it’s easier to come up with ideas. Everyone has something they’ve been talking about for years that they need to just put pen to paper on.1
But eventually, the low-hanging fruit runs out and you need a new source to tap into. I’ve relied too much on trying to just sit down and write from what’s in my head because that worked fine in the beginning. As the year went on, the need for more deliberate reading time (and not just writing time) has become more obvious.
3) Having a clear theme makes it easier to build a following
I wrote about a lot of topics in 2024. VC fund returns, New Urbanism, index investing, crime in NYC, and why advice can be dangerous. While I’ve enjoyed doing this and have been exploring what to write about, I think it’s made it harder to build a following, at least initially. I’ve found that the most successful writers may have lots of interests but there is almost always some unifying theme that drives 90% of their output, especially in the beginning.
4) If it doesn’t hurt to cut more from your piece, you haven’t cut enough
“I would have written a shorter letter, but I did not have the time." -Blaise Pascal2
The biggest mistake all new writers make is that their pieces are too long. I don’t necessarily mean this in an absolute sense, but more that however many pages you think you need, you can probably cut it in half and be just as effective. You need to earn your reader’s time and if you are putting out a longer piece, it better be worth that extra length. One lesson I keep in mind from Write of Passage: if it doesn’t hurt to cut more from your piece, you haven’t cut enough.
5) Good writing is simple
I used to look at the long and verbose writing in academic papers and say “That’s just the way academic writing needs to be.” If I didn’t understand it, that’s because I wasn’t smart enough.
But now I realize it’s actually just bad writing. Not everything has to be understandable to a fifth grader, but if most people can’t understand your writing clearly (and quickly!) then that is usually on you.
6) Like VC, writing is a hits business
Similar to venture capital, writing online is a hits business. That is, people remember your bangers and don’t really remember your bad pieces. Consider the writers you follow. They might put out >50 articles in a year and can you really remember more than a handful? Probably not, but you still talk about how much you love their work.
It’s also hard to always predict the hits. My most “viral” post all year was a Twitter/X essay I spent 30 minutes drafting.
The lesson that’s been hard to fully internalize is it’s usually better to just get something out there instead of making each piece as strong as possible. I always want to put out things which are great, not good, but that philosophy ends up holding you back. As Nate Silver says: Always Be Blogging (ABB).
7) People always underinvest in distribution (including me) because it’s not as fun
Something Write of Passage drills into your head is that every writer thinks way too much about content and not nearly enough about building a following because that’s not as fun to most writers. Figuring out who to email to plug your piece, who to interact with on social media, and which new social media channels to leverage is not why people get into writing but it’s even more important to gaining a following than what you write about.
Being good at distribution today means being a bit unsavory and shameless. As much as people look down on the Linkedin-fluencers who often eschew nuance to be provocative, it works.
8) Catchy names/titles can be more important than content
I started hosting events called “Chart and Tarts” where people bring a chart to discuss and we eat some tarts (examples 1 and 2).
Besides them being super fun, my posts about them have been a big hit and I genuinely think 75% of the reason is the title (something I spent 20 seconds thinking of). Rhymes are fun, memorable, and great for branding. This was for an event but I think the same advice applies to article titles and ideas you coin in them.
9) Writing never really gets any easier
Tim Urban has been writing for 15 years now. He wrote 300 blog posts before Wait but Why, then wrote 50 long posts for Wait but Why, and then recently wrote a long book. He’s considered one of the most respected writers of the internet era. And yet even for him, writing never really gets much easier.3
I’ve experienced this too in my much smaller sample. While I have a better nose for what good writing looks like, there are no shortcuts to getting there. It’s still often input → output. Just lots and lots of writing and rewriting until you eventually hit diminishing returns.
Below are my favorite resources for getting started at writing online. Happy New Year!
The Ultimate Guide to Writing Online, by David Perell
A lot of the wisdom of Write of Passage is distilled here
“How I Write” podcast, by David Perell
Always be Blogging, by Nate Silver
A good prompt if you want to start writing online is “What’s something you could give a presentation on for 10 minutes with no prep?” Whatever that is, you should be able to write a post on it.
Apparently not a Mark Twain quote as I previously thought.