How To Blog

Sometimes I wonder if I’ve simply forgotten how to blog. Little (shit)posts about whatever interested me used to come so easily — I’m sitting on over 1,000 entries from 2002-2008, from my original Movable Type blog, along with a few hundred from my old Tumblr. Most of those were gushing about some tech company or product I liked, or complaining about something petty, or some personal in-joke where I even don’t remember what it was about.

These posts weren’t great, but they were an accurate picture of what I was into at the time, and collectively they’re a chronicle of what and how I thought for almost 15 years. Why did I stop?

I mean, one reason is this:

I was just writing part of a blog post about why blogging has gotten so hard in the last 5-6 years

then I heard shouting from the kitchen and my child ran in like a banshee and would have crushed my laptop by body-slamming into me if I hadn’t tucked it away

Anyway, that’s why
— David Demaree (@ddemaree) April 11, 2021

But also, the last few years were very much the social media era. “Social media” is an interesting bit of double-speak, because it turns out what distinguishes social media from older forms of media is not the social-sharing aspect — actually we had social sharing in the early blogging days, it was just smaller and less organized — so much as the metrics.

The audience for Content is bigger than the old web ever was, and we have data telling us what it responds to. I think it’s hard for most people to go through life knowing that someone is posting think pieces about how to break into product management to a quantified audience of thousands or millions, but it’s OK to share thoughts on mechanical keyboards in public to a dozen friends. It’s like every casual blogger is seen (or is encouraged to see themselves) not as a normal person with a hobby, but as a failed influencer.

That said, there are some encouraging signs that blogging is on the way back! Ben and Sebastiaan at Lux, who make the excellent iPhone RAW camera app Halide, recently relaunched their team blog with the intention of sharing deep dives on photography and tech alongside product news. And YES PLZ founder Tonx, who’s been maintaining a product-update-oriented company blog for a while, recently posted about wanting to get back into sharing ideas more on his blog:

Blogging offers a way for me to work out some ideas in a lower stakes environment. I already do a lot of idea journaling, but putting things out in public adds some accountability for follow through. It also helps me come to grips with the fact that some of the inspiration rattling about in my head is still less than half-baked.

There’s a case to be made that blogging will make a comeback as there’s a growing glut of email newsletters and our inboxes are surely not the best place to curl up with a couple thousand words. The era of thriving blogs ended with the murder of Google Reader and the period where Facebook (briefly) favored content from major media companies tricked into played along with its world domination schemes.

Both of these are technically still in the world of content marketing, but I like to see small, indie companies come back to sharing the ideas behind their work, trusting that audiences will be into it. This is how we did it back in the day at Typekit, and what drove all-time-great team blogs like Editorially’s STET (?) and Basecamp’s Signal v. Noise. And, FWIW, it’s also the best reason for individuals like me (and you?) to blog.

A house for ideas

Blogging requires three things: ideas, words, and somewhere to put them all.

I have some thoughts on the first two, but regarding the last one, I’ve noticed that a lot of blogs that until recently lived on Medium — like Lux Camera and Signal v. Noise — have all ended up on WordPress.

I’ve spent the last 3+ years obsessed with creating the perfect blog setup (a pursuit I was already having doubts about when I wrote in 2018 that blogging is a pain in the ass), trying dozens of combos of traditional and headless CMSes, Markdown-based static-site generators, build tools, hosting platforms… it’s been a journey. ? Having been through all that, I’ve concluded that unless you have very special needs or a lot of free time, it’s hard to beat WordPress for personal or small-business blogs, because it just has everything you need:

The best block editor in any self-hosted blogging tool. Some people don’t love Gutenberg, and many people are more into Markdown than I am. I find that I am a very visual blogger, and WP’s editor strikes a good balance between power and simplicity. (And if you don’t need a visual editor, you can turn it off!)

A staggeringly huge developer ecosystem making plugins, themes, and add-ons, many of which can be 1-click installed from WordPress’s plugin directory, covering virtually any need that isn’t handled by the (still quite capable) core app.

It’s all just PHP (which in turn just generates HTML), so in theory, you can make it do anything you need it to do, and is relatively cheap and easy to host

Speaking of hosting, in addition to a huge developer ecosystem, there are companies that specialize in WordPress hosting that will take care of scaling and security so you don’t have to.

A good, native, well maintained mobile app, which is important for those of us who have trouble stringing together a few minutes to use a laptop (see tweet above)

Once upon a time, there were a bunch of other, competing blogging platforms — my first blog was on Movable Type for almost a decade, and a lot of my web designer-y friends were really into Expression Engine for a while. Many of those tools are still around in some form, but usually mere shells of their former selves. The big money — and in turn, the most of the interest from developers — has shifted either to enterprise-grade CMS tools that one might use to power a major media site or a big company’s helpdesk content, or to super developer-focused, open-source tools built by programmers to meet their own nerdy needs.

WordPress is the last blogging tool standing, and that’s only because its creators have done a great job of building a sustainable business around it without twisting it (much) to meet the demands of the market. They can do this because WordPress’s massive scale (it’s said that WP powers a majority of all websites) creates its own gravity. And, to Matt Mullenweg’s credit, despite having built a big business selling value-added services and establishing WP as an enterprise-friendly platform, the core app still works first and foremost as a super hackable blogging tool for individuals.

All that to say: I’m writing and posting this using WordPress because I haven’t any strong or compelling reasons not to use WordPress. WordPress is good. WordPress is easy. WordPress can scale, if I need it to, and look however I want.

Overcoming blogger’s block

Photo by Aaron Burden on Unsplash

Sara Soueidan wrote ages ago that the way to get out of blogger’s block is to “just write”:

I got used to writing lengthy technical articles over the last few years that I’d been finding it increasingly harder to publish articles that are not lengthy and overly technical over the last few months. This had led me to abandon a lot of rough ideas and article drafts, eventually leading to my blog feeling abandoned for months in a row.

This isn’t just bad because, well, it is bad. What made it worse is the fact that one of my most recurring pieces of advice is telling people to just write — write down what you learned, no matter how big or small. Start a blog and publish your writings there. Don’t think about whether or not people will like or read your articles — just give them a home and put them out there.

I’d yes-and that by saying don’t just write—publish. (Or maybe just edit a teeny bit, then publish.)

Julian Shapiro posted a few weeks ago about a mental model for generating ideas and breaking out of creative ruts:

Visualize your creativity as a backed-up pipe of water. The first mile of piping is packed with wastewater. This wastewater must be emptied before the clear water arrives.

Because your pipe only has one faucet, there’s no shortcut to achieving clarity other than first emptying the wastewater.

What these two posts have in common is acknowledging that not every idea will be gold, but that the way to find the gold is to first dig through the rock that stands between you and it.

Sara’s advice is to write more and post it; Julian’s seems to be to write more and discard it until you find something great. Both are valid, so it depends on why you’re writing and what you hope to get out of it.

During my longest-running stretches of blogging, I wrote to share things that excite me, but also to figure out (semi-publicly) what I think about the things I’m sharing. And, though I didn’t realize this at the time, I was leaving myself a present — a record of what I thought at the time of writing, which I could return to later to see how my thinking has evolved and remember some of the little things I found delightful in earlier years.

I don’t know if I’d have retained all of that if it had just been in a private journal, and if I had, I don’t know if Past Me would have written it in a way that Present or Future Me would understand. By writing for an audience other than yourself, you are also writing for your future self.

The trick to doing that, however, is to do it. I get stuck on whether anyone will want to hear about the mechanical keyboard I built a few weeks back, or how I’ve set up my WFH desk, or how much I’m enjoying a new book, and what any of that says about me.

At the moment, it seems what matters more is to capture those thoughts before they pass, because whether or not they’re super interesting now, they will be interesting later, and may lead to ideas that will pay off sooner, once I’ve dug through the rock to find some gold.

Pointing at things

Photo by John Schnobrich on Unsplash

In his newsletter Robin Rendle described blogging as “pointing at things and falling in love,” a sentiment Austin Kleon recently seconded and annotated.

This is the part that’s seemed, weirdly, hardest for me — I have a strong, almost obsessive-compulsive drive to write something that will tell you all What I Think, as a Thought Leader (especially in The Product Management Space), but when I think about writing something short about enjoying Super Mario 35 I clam up. (This despite a silly newsletter about the Koroks from Breath of the Wild and their poops being my favorite thing I wrote in 2020. ??‍ )

I think my weirdness here is driven by how the practice of blogging (and now also newsletter writing) has become synonymous with content marketing. When blogs are businesses, and there’s a rich, vigorous (and, it should be said, entirely valid) discourse around best practices for how to craft and package content in the marketplace, silly personal blogs seem, well, silly and personal.

Lisa Schmeiser, a journalist who writes the So What, Who Cares newsletter, wrote about this feeling the other week:

During the “whither So What, Who Cares?” phase, an editorial professional whose judgment I trust commented, “The thing about your newsletter is, it’s not about anything beyond what interests you. You don’t have a hook or an area of expertise or a market niche.”

This is an entirely fair assessment, and it reminded me of a passage in one of my favorite reads from last year, Jennifer Homans’ history of ballet, Apollo’s Angels. She wrote of New York City Ballet co-founder Lincoln Kerstein, “A driving but unfocused ambition made it difficult for Kirstein to settle … He wanted to be an artist—he had studied painting and even briefly considered a career as a dancer—but he had the hard, analytic mind of a critic instead and found himself depressingly ill-suited for the occupations he most admired.”

I don’t really think I have any sort of driving ambition, but boy howdy did the “difficult to settle,” “unfocused” and “the hard, analytic mind of a critic” parts require me to look up from my Kindle and stare at the wall for a few minutes until the stings of recognition subsided.

I think this feeling is probably more acute in people who can write content professionally (a category I’d include myself in) but want an outlet for stuff that doesn’t fit anywhere else. I don’t want to start one publication for coffee stuff, another for hobby-scale web development, a newsletter for home office desk optimization, and a photo blog — I want one website that can encompass all of those, plus articles about my work as a big-tech product person. I want to bring my whole self to the internet, point at things, and fall in love.

In the absence of a through-line, that’s to say I want my blog to be a reflection of me rather than in service to an idea or an audience, which (again) feels silly and petty, but that’s where I’m at. I may, in feeling cute might delete later fashion, bail on this later. But for now, I think I’m OK with that.