People and Blogs: Matt Stein

Let's start from the basics: can you introduce yourself?

I’m Matt Stein. I live with my wife and cat-sized dog in Bend, Oregon. Grew up in Ohio, studied graphic design in upstate New York, and I’ve been bouncing around the U.S. ever since.

My design degree led me to a small interactive agency in Seattle where I worked with HTML, CSS, Flash, and a CMS called ExpressionEngine. I taught intro-level HTML and Flash workshops in the design school we shared a building with—a former hat factory downtown built in 1920 that was later swallowed by Amazon expansion. I learned an amazing amount in those few years, and in that environment.

I left with my youthful enthusiasm and surprise knack for coordinating agency work to run a solo gig for twelve years, and learned a lot more about people, technology, business, and unfortunately the minutia of taxes and accounting. Having complete responsibility for my workload and decisions—from triumphant to cringey—was extremely satisfying.

I left that to work as a technical writer with the team behind Craft CMS, a successor to ExpressionEngine I was proficient with and fond of. I moved to Bend, Oregon with that job, lived my first spectacular burnout adventure, and left that in 2022.

I just turned forty and I’m working on whatever act two looks like. I want it to involve using my generalist bag of skills to make the world better in some way that’s focused more on human beings than investors or shareholders.

I tinker with things for work and for fun. Lately it’s been a parade of Astro, Eleventy, Kirby, creative writing, reacquainting myself with the piano, and playing high-adrenaline video games as a thought break. I spend a lot of time reading despite being a fairly slow reader, and that’s ramped up as I’ve started following newsletters and RSS feeds in an attempt to distance myself from algorithms and hype.

What's the story behind your blog?

I got to tech-nerding as soon as my uncle booted up our family’s first MS-DOS computer, so having my own site was more nature running its course than a careful decision. I lucked out and beat a surprising number of Matt Steins to mattstein.com, and the first site I remember having on it was college portfolio. It was an oppressively blue Flash site that heavily relied on a barcode as a design element as if that wasn’t a cliché. I don’t remember if it had a blog, but let’s hope not.

I’ve changed platforms a few times over the years, mostly writing brief notes about books or minor technical breakthroughs and migrating everything from Statamic to Craft CMS to Gatsby and now to Astro. I’ve used it as a place to experiment, always with a custom front end I intend to someday finish. I used Procreate to hand draw favicons for my current site until I finally got to one I liked, and I regularly build little features and ideas I don’t launch. Send help!

My old company’s blog got more attention for a long time, but it’s a retired Gatsby site and I’m back to mattstein.com again with stronger feelings that I need a personal site and I need to be writing more.

I’ve always felt like an internet outsider, I think because I was always an okay visual designer in the midst of either “real” developers and software engineers, or designers that could make you a really kickass band poster. I was quiet in forums, didn’t go to conferences, and offered all the fun and personality of a cardboard cutout. This started to change with the Peers conference and meeting people in the Craft CMS community, which is a wonderful place full of professionals and design agencies that do really cool work.

Writing’s always been a tool for me to sharpen my thinking, and I spent years shortchanging myself being sort of aloof—so I’m working on writing and publishing more and participating in the kind of internet I badly want to thrive. I’m inspired by what so many people choose to write and share, and I want to be part of that. I want to write something that matters to someone, and I need to be publishing for that to have a chance.

So that’s what my blog is to me right now. And I love that if I wake up tomorrow with some other idea, it can support that.

What does your creative process look like when it comes to blogging?

It’s generous to call it a “process,” because for me it’s the spontaneous choice to corral half-thoughts, impulses, and rambling into a Markdown file with a title and a publish date.

I rewrite and edit heavily to try and find what I want to say. I wrote obscenely long answers to these questions and had to start over, and I’m one of those serial Discord+Slack edit-after-sending people. I would go broke as a stone engraver.

If we visualized my thought process, it might be a tornado moving through a junkyard while I cling to a lamppost and catalog the various tires and scraps of siding. I use notes, journaling, and outlining to sort things out and pat my hair back down and build something with whatever I’ve collected.

I squirrel bookmarks and notes in Raindrop and Obsidian, and keep a long list of writing ideas in an Obsidian (Markdown) file. Some ideas are just bullets, some link to impossibly cryptic notes, and some link to long drafts too weird or uninteresting to publish. The ones that seem faintly coherent graduate to a Markdown file in my Astro repository where they’ll probably turn into posts. Rare ones hop into Scrivener books because it seems like they want more structure and may go on for a while.

If I get stuck or bored with something, I’ll rewrite it from scratch to approach it from a different angle. If I can’t manage to get words out, I’ll use a mind map to free-associate ideas as fast as I can and then look for opportunities to explore.

Trying to summarize my years as a technical writer was really important to me, for example, and I wrote about it a lot without ever feeling like I said what I wanted. I laughed out loud when I stumbled on Ian Henry’s writing, and I tried channeling that style in another rewrite that I finally liked. (I told Ian I ripped him off and he was fine with it.) I want you to like it too, but the little miracle for me is that I don’t need you to. I rarely get something to that point.

I’m trying to also be better at not reply-guying Mastodon posts, but turning strong feelings or tangents into blog posts. Better thinking for me, one less notification for somebody else rationing finite attention.

I’ll ask specific people to read drafts if I know they’ll be inclined to spot any sketchy or inaccurate details, but usually it’s me going it alone and re-reading with specific people in mind as a way to pretend at a fresh perspective.

If this answer isn’t long enough, I wrote a post about how I write.

Do you have an ideal creative environment? Also do you believe the physical space influences your creativity?

I’m a sensitive creature and absolutely believe spaces influence my creativity, both physical and psychological.

I process and reflect best in stillness. That means visual and auditory quiet as much as putting away any extraneous thoughts. God forbid I need to write a coherent sentence but I forgot to flip the “clean” magnet on the dishwasher. I write best at my desk in my little cave of a bedroom office, or on the couch piled with blankets and a cup of coffee.

I find new ideas outside the cave, whether that’s reading or talking with people or physically exploring new places.

Taking an idea on a walk or into the shower is usually a good way to clarify it. I keep wondering what a walking shower desk would look like but it all falls apart with conference calls.

A question for the techie readers: can you run us through your tech stack?

mattstein.com is an Astro site hosted on Cloudflare Pages. My domain registrations are split between Porkbun and Cloudflare Registrar, and this one’s with Cloudflare.

I use Cloudflare R2 (which is like Amazon S3) to store a handful of images, and a self-hosted imgproxy instance that resizes them on the fly. This probably sounds fancier than it is—mostly an experiment related to work projects.

I don’t use a CMS because in this case it might overcomplicate things, but as a chronic replatformer I’ve been looking at Payload CMS and Kirby because what if I overcomplicated it?

Given your experience, if you were to start a blog today, would you do anything differently?

What I admire most about bloggers and newsletter writers I follow is that they manage to write.

Anything from interesting blurbs to deep, moving essays. I’ll be impressed or entertained by the format sometimes, but ultimately the magic is the writing. The number of people with crusty, dated-looking blogs still publishing incredible posts is a testament to that.

So I’d liberate myself from my greatest constraints: the fear of putting dumb words next to my name, and excessive platform puttering. I’d pick a low-key domain name that’s not literally the one I was born with, and I’d pick a platform like Blot that lets me tailor the look without rebuilding the whole machine every two years and finding new ways to break my RSS feed. That way I could focus on the writing, or at least have fewer distractions to blame when I’m not writing.

Financial question since the Web is obsessed with money: how much does it cost to run your blog? Is it just a cost, or does it generate some revenue? And what's your position on people monetising personal blogs?

As hobbies go, I’d probably lose less money maintaining an old boat.

The operating costs are $9.15/year for the domain name, and $22/year for a cheap VPS to run that imgproxy thing I mentioned. Astro is free, as is Cloudflare Pages with my meager traffic. I spend heaps of time on the site that I can’t justify financially.

I have no problem with people monetizing their personal blogs and admire anyone taking it seriously enough to try and make it a sustainable endeavor.

But that’s not what it’s about for me.

I’m anxious about the effect big companies and commerce have had on the internet, and my blog is my little personal space—a tiny world as I’d like it to exist. No ads, no tracking, no referral links, no pressure to subscribe. I want to tell you about some things I’ve bought that I really like, but I don’t want it to even seem like that kind of blog.

I don’t even have a rough idea how many people subscribe to my RSS feed, and I like that. The feed isn’t for me.

The winds of income shifted for me recently, and as I re-evaluated expenses I suddenly noticed how many independent writers and developers and artists seem to put their work before their income. I think that’s a courageous thing to do, and my usually-free-tier patronage didn’t square with that. So now I keep a list of projects and resources and try to do a better job of supporting them when they offer a way to do it. (It’s never enough and I have a lot more to go!)

I know our priorities and circumstances are all different, but I wonder what the internet would look like if we collectively did more of that.

Career-wise I need to figure out what I’m selling and do that, but I’ll keep the selling to some other place because mattstein.com is my place to be a person more than a product.

Time for some recommendations: any blog you think is worth checking out? And also, who do you think I should be interviewing next?

I’d like to answer this three times.

Answer 1: Dave Rupert.

I’m still working up the confidence to not have a side blog for weirder posts I’m self-conscious about, and Dave’s been over there this whole time, regularly publishing interesting, entertaining, and useful things, but now he’s added self-described shitty science fiction complete with covers! From my point of view this is some wizardly next-level blog stuff.

Answer 2: Sara Joy, who’s playful and inventive and always mentioning parts of the internet where fun is still served. As far as I know, she also invented the term “short thorts” which is endlessly amusing to me. (Sara was the 29th P&B guest)

Answer 3: the folks at Good Enough. I’m only a new fan, but they make and share fun internet projects together that to me epitomize playful, stylish, inventiveness that’s cheerful and not overly commercial.

I’d like to find my inner versions of all these people. And there are many more, because I’m instantly enamored with anyone that chooses to write their own blog and build things for fun.

Final question: is there anything you want to share with us?

I’d say “watch this space” while I figure out what I’m doing, but there’s a nonzero chance I’ll end up pivoting away from tech to work maintenance at a horse therapy ranch or something. But surely I’d write about that.

Thanks for publishing this series and having me as a guest here! And thanks to anyone reading!