The wonderful, asymmetric opportunity of writing online

I feel old right now.

I realised yesterday that it’s been nearly 15 years since I started writing stuff on the internet.

I first started down this path in late 2008,¹ back when we just called it “blogging.” I began on Wordpress, then quickly graduated to my own domain name. I’ve had that domain name ever since. At various times I’ve published on a blog, an email newsletter, a podcast, Twitter, LinkedIn, and even Quora, where for a brief period in 2015-16 I was one of the most popular writers on the platform.

But why?

Someone asked me that question the other day over a Zoom call. We were talking about career paths, and they looked at me, somewhat skeptically, and said, 

“You talk a lot online about what you’re up to, and ask questions about what you’re working on -- in fact, you’re quite open. Why? What’s your end goal with all that?”

The answer is that writing about what I’m doing, reading, learning, or thinking, and sharing it online, has been the most valuable thing I’ve ever done in my life.

Here’s why.

Why publish online?

The number one reason to publish online is so that you can be found. Austin Kleon describes this process in his book Show Your Work.

In order to be found, you have to be findable.

Almost all of the people I look up to and try to steal from today, regardless of their profession, have built sharing into their routine. These people aren’t schmoozing at cocktail parties; they’re too busy for that. They’re cranking away in their studios, their laboratories, or their cubicles, but instead of maintaining absolute secrecy and hoarding their work, they’re open about what they’re working on, and they’re consistently posting bits and pieces of their work, their ideas, and what they’re learning online. Instead of wasting their time ‘networking,’ they’re taking advantage of the network. By generously sharing their ideas and their knowledge, they often gain an audience that they can then leverage when they need it.

The best way to be findable is to publish your work online. As Austin says, “It sounds a little extreme but in this day and age, if your work isn’t online, it doesn’t exist.”

Why do you want to be found? So you can avoid being a martyr. This piece by Joey Roth illustrates this principle wonderfully:

Charlatan, Martyr, Hustler by Joey Roth.

A charlatan is all talk, no end substance. What ranchers used to call “all hat, no cattle.” Think Twitter threadbois, ChatGPT book summaries, and wantrepreneurs posting motivational shit on Instagram and TikTok. I hope it’s obvious you don’t want to be there.

A martyr is a more insidious place to be. You’re putting in the work, honing your craft, building your career or your company — but you’re doing it in the dark. You may be great at what you do, but no one knows about you. You’re toiling in obscurity.

You want to be a hustler. Someone who talks the talk, and walks the walk. Someone that builds a reputation, and has the substance to back it up.

The way you do that is by building expertise, doing great work, and then putting it out there for others to find.

Patrick O’Shaugnessy, an entrepreneur, investor and podcaster, describes this process as learn, build, share, repeat.

Patrick OShaughnessy @patrick_oshag

Learn, Build, Share, Repeat

It’s a principle that works well for Patrick. A few years ago he was just a public markets investor. Now he’s published nearly 400 episodes of his podcast, Invest Like The Best, and along the way has created a media company, a VC fund, an asset management company, and a regular conference called Capital Camp, all as a direct result of creating his podcast.

Along the way, he’s had a blast, interviewing some of the most interesting and accomplished people in the world. It’s been incredible to watch and listen along.

Why writing specifically?

Assuming I’ve convinced you that sharing your work online is a good thing, you might now be asking why I choose specifically to write. Why not make Youtube videos, or a podcast, or get on TikTok?

I could pick any medium — and I’m palying around with podcasting right now — but writing is what I’ve been doing consistently for 15 years, and I’ll keep doing it long after Chat GPT achieves God-level intelligence.

First and foremost, I like doing it, and it comes somewhat naturally to me. I don’t know why. I remember when I was 12, I had to write a pretend newspaper article in an English class. The teacher asked me if I’d copied it from an actual newspaper (I had not).

The thing that’s worth doing is the thing that you’ll stick with. For me, that’s writing.

Writing also has a few other side benefits:

Firstly, writing helps you come up with new ideas. My friend

Jakob Greenfeld

has this wonderful line:

Lots of ideas are hiding in the shadows and only come to light once your fingers hit the keyboard.

Julian Shapiro calls this the creativity faucet, and it’s a wonderful thing to experience. For example, this article was originally going to be a breakdown of why being on Twitter is such a career enhancer. Once I started writing it, I got a ton of other ideas, thought about that Patrick O’Shaugnessy quote, how it related to Austin Kleon’s book that I just read, and it sparked a whole new piece, which is the one you’re reading right now.

It’s an idea echoed by Paul Graham, entrepreneur and founder of Y Combinator. Graham says:

Writing doesn't just communicate ideas; it generates them. If you're bad at writing and don't like to do it, you'll miss out on most of the ideas writing would have generated.

Secondly, writing helps you become a better thinker. According to Shane Parrish of Farnam Street:

Writing is the process by which you realize that you do not understand what you are talking about. Importantly, writing is also the process by which you figure it out.

Importantly, good writing is clear writing, and clear writing is the result of clear thinking. Here’s Paul Graham again:

Paul Graham @paulg

A company asked why it was so hard to hire a good writer. I told them it was because good writing is an illusion: what people call good writing is actually good thinking, and of course good thinkers are rare.

So writing is:

1. something I enjoy

2. that helps me generate ideas

3. and makes me a better, clearer thinker.

I’d do this even if people didn’t read it (but thankfully, they do 👋)

What are the upsides?

Sharing my work has led me to any number of wonderful conversations, opportunities, learning experiences, and in some cases, direct paid work.

I’ve gotten full-time jobs and consulting gigs from people that found me online. I’ve found amazing people from whom I’ve learned a ton. I’ve built a small but growing audience, some of whom have told me that if I ever want to do something, they’re happy to invest to get me going. Even writing on Quora, which I mostly did for fun, led to places like Inc and Huffington Post picking up my writing and publishing it.

None of these things were the specific goals I was aiming for when I started writing. But they’ve happened anyway.

In fact the conversation that prompted this post — me discussing an opportunity with a friend, and them asking why I bothered to write online so much — was a direct result of someone finding me on Twitter and DM’ing me because of something I wrote.

The truth is: there is no end goal. This process — learning, write, share, repeat — is the reward. I have no way of predicting exactly what opportunities will come up, but I know for damn sure that something will. I’ve seen it again and again over the last 15 years. Now I just trust the process.

This costs nothing except time, and the tiny amount of money it costs to renew my domain name and hosting each year. It’s a classic asymmetric bet. No downside, all upside. That’s a bet I’ll make every day of the week.

1. I can pinpoint the exact date because it was immediately after reading this post by my buddy Charlie Hoehn, as evidenced by the fact he gave me a shout out in the post.