The secret to blogging is secretly blogging

I started my first blog in 2007*. Ever since, blogging has gone in waves for me. Sometimes, a wave would start with a new platform I wanted to try: I was big into Tumblr for a good long while, and then embraced Medium for a stretch. Sometimes, it would start with a shift in career focus: I wrote more online when Lisa and I were focused on growing our podcast, Should We. And I certainly wrote a lot when I was interviewing for product roles back in the U.S. after two and a half years of living in Germany. Other times, it would begin with a simple intention to write more, paired with a plan for how to get there by blogging daily for a month. (These quests typically succeeded, but in name only; by the end, I’d be posting random photos from my camera roll and about two sentences. They were still fun, though.)

My last wave of blogging came in 2018, when I blogged daily for nearly a two-month stretch. (I’d filed it in my memory as a 30-day challenge, but looking back at my archives here, I see a lot more.) I stumbled on a secret: blogging secretly made me like it more. I had a ritual around texting my daily post to a few of my closest friends, but they were my only intended audience. Otherwise, I told no one. Didn’t tweet about the posts, didn’t send newsletters about them, didn’t expect anyone to read them. And mostly, no one did read them. But I liked writing them then, and I like looking back on them now.

Blogging without the expectation of an audience—without any effort toward building an audience at all—made it an easy, joyful practice for me. Day by day, the garden of ideas grew. I liked tending to it, I liked looking at it, and I liked plucking individual posts out and sharing those with people one by one.

Here at the start of a new year and a big shift in my career, I’m thinking about blogging again. But I want to do more than think about it: I want to do it. Writing regularly is so good for me, and I think it could be helpful to my work as an investor—to articulate ideas and observations while they feel new, to connect them to a constellation of other ideas, and to be able to share them with founders and friends in a way that shows the breadcrumbs a train of thought leaves over time.

So I’m going to try to do what I know works for me: blog secretly. Secret doesn’t mean private; these posts are public, and anyone could find them. I’m sure I’ll post one to Twitter every now and then, when it feels right, and others occasionally will, too—and that’s fine. And those posts will inevitably include breadcrumbs to all the rest. But the key is to keep my expectations low, and let it be easy. I love the modest test proposed by my friend Chris Xu at the end of her own experiment with writing regularly back in 2015: “what pieces do I want to be able to link to?” To be able to link to it, I need to write it in the first place. If each post gets read by three people—me, one person I send it to personally, and one unknown future person at the end of a tumble of serendipity—it will all have been worth it to me, and then some.

*My first blog was on Blogspot at the time, but the content seems to have been moved to Wordpress; maybe the two sites struck a deal for archival, old content?