Reflections on the First "Season" of Stray Thought
11 Jun 2025Back in January when I launched this blog, I wrote that I planned to post content actively in “seasons,” recognizing that neither my inclinations nor my track record made it wise to expect consistent, uninterrupted posting over the long haul. The first season, I thought, would run through May, at which point I would figure out what to do over the summer.
Now that we’re well into June, it’s time to take stock of how this first season has gone and where things will go from here.
Learning to Write Again
First and foremost, I learned that I was terribly out of practice at this kind of writing. Nearly all of the writing I’ve done since retiring my old blog 20-some years ago has been in either a business or an academic context. I think I got pretty good at both, but there is a bigger difference between that kind of writing and what I’m doing here than I anticipated.
The change has been a positive one. It’s good to practice a kind of writing that requires me to devote some effort to welcoming the audience and convincing them to keep reading. It’s also been worthwhile to put effort into cultivating a more aesthetically appealing writing style, a major departure from typical business writing, which usually aims to be generic and unadorned. I don’t know how successful I’ve been, but the mindset shift alone feels worthwhile.
Another thing I’ve learned is that my instincts are driving me toward longer posts. Most of my posts so far have exceeded 1,000 words (including this one), and a few drafts passed the 2,000 word mark before I edited them down. Although I did end up breaking one post into multiple parts, I decided to let my interests guide the writing, so I haven’t prioritized brevity. Instead, I’m writing as much as I feel I need to get my message across.
On my old blog, I experimented with microblogging avant la lettre, posting occasional tiny updates ranging from a phrase or two to a couple of sentences. This feels especially out of place today given the immense malign influence of Twitter on contemporary online culture. These days, the topics that draw my attention seem to demand substantially more space to articulate my ideas. In fact, I’ve determined that some of the topics I’m most eager to write about won’t fit into even a couple thousand-word posts. As I started to gather my thoughts on them, they felt like longer series that might stretch on for a half dozen or more entries. But given how much effort it took to complete more modest posts, I put those series ideas aside for the time being.
The Practical Challenges
Beyond the craft of writing itself, I’ve also encountered some practical challenges. Each post has taken me longer than I expected to complete. Much as I enjoy the process of outlining, drafting, reworking, and editing, each of these things has taken me more time than I had hoped. My rustiness and preference for longer posts certainly contributed to the slow pace, and I’m considering tracking my time more systematically to identify ways to speed things along.
Speaking of time, my other work has also reduced my writing productivity. Surprisingly, my consulting practice proved less disruptive than a side project I started. It has been quite fulfilling, drawing on my coding experience while giving me a chance to explore creative work that’s well outside my comfort zone. But a combination of factors caused that project to take up more of my time in March and April than I expected, which led to an unplanned two-month hiatus. The obvious remedy to that situation is just to post about my side projects, which I will probably start doing, perhaps once the current one is a little farther along.
Plans for the Summer
I’m thinking about the next phase of this project with these lessons in mind. Summer is coming, and between work, family stuff, a bit of travel, and projects on the side, I’ve got a lot going on. I’m going to use the next couple of months to regroup a bit. Taking an intentional break should feel a lot better than living with the angst of an unplanned posting drought hovering over my shoulder.
That said, I don’t mean to disappear entirely. My plan, after probably one more regular post this month, is to post one update a month for July and August, then pick up again with a second season in September. I might experiment with micro-posts as well, but I won’t be putting pressure on myself to post a ton of new content while I take some time to recharge and reorient myself.
A Preview of Next Season
Part of what I hope to accomplish over the next couple of months is to form a clearer picture of what the next season of this blog project will look like. But I do have a few ideas in mind that I can share now.
First, as I mentioned above, I am itching to write about a couple of topics that I think will each require a series of posts to cover in the depth I feel they deserve. Assuming I am able to complete my research and get myself organized, I would like to launch at least one of those series this autumn.
Second, I’d like to figure out what it would take for me to post weekly. That will require me to address at least one of the issues I described earlier around my preparation, pace, and post length. I’m working to resolve the tension between my inclination to write longer posts and my desire to post more often. It’s possible that I’ll come up with a plan for that over the summer, but since I intend to use the time primarily as a break, I will most likely aim for a more manageable posting schedule—something like a major post every other week—when things pick up again in September and try to make incremental improvements from there.
I remain energized by this project, and I encourage anyone who’s thinking about getting (back?) into blogging in 2025 to do it. Despite big platforms’ outsized influence over public attention, the Web as it was originally conceived—distributed, democratic, and a little bit weird—isn’t dead yet. It’s up to those of us who hope to revive it to create and maintain online spaces we control, and I couldn’t be happier to be playing my small part in that movement.