I think I started blogging, if that's the word that applies to what I was doing, in 1996 or so, when I first got an io.com shell account. I know I started blogging around 1999 or so, when I bought my own domain name and began filling it with content generated by ... ColdFusion? And then Microsoft FrontPage, and then Movable Type, and now a CMS of my own devising. I was a DIY guy all the way, even if that wasn't what I would recommend to others. And I've learned a few things along the way.
Now, there were alternatives to the DIY route even in those early days. Blogger (which is still a thing), LiveJournal, and later Facebook and Twitter, gave something like blogging to the masses. No software to install or upload, nothing to configure, just log in and start posting. I liked how democratization of the tech had become the norm, as an elitist attitude towards such things doesn't always spur people to rise to the occasion; sometimes it just pisses them off unnecessarily. But I knew I wanted to have complete control where I could, and to use what I was doing as a way to get as much understanding as possible. Blogging wasn't just a route to self-expression, but also technical mastery of a slew of related subjects.
I'm still doing the DIY thing all these years later. And it's still not what I would recommend, because after having hung around enough people who blog, or who want to blog, I've learned that the ones who really, really wanna Do It Themselves won't ask whether or not that's a smart thing. The doing of the thing will be its own reward, and somewhere in their marrow they know it. The rest of them will just set up WordPress (at best), or settle for some managed blogging system (which is typically, again, WordPress), or just fall back to Twitter. But there is no moral differentiator here. The ones who DIY are doing what's best for them, and the example they set will be followed by those who are inclined to follow it. What matters is that everyone have the choice if they choose to make it, and that the choices of the few aren't negated by the choices of the many.
I still prefer blogging to the alternatives, if only because of the form factor. Tweets are fine for when you just want to shout "Hey!" to the world about something. But they limit themselves, and ultimately they aren't owned by anyone except the service you post them on. A blog post is more overhead to get started and to finish, but that forces you to think about what you're saying and to what end. I know it's possible to go overboard with that (see: Slate Star Codex, whom I dislike for more than just his logorrhea), but it's easier to manage time in one block of 20-30 minutes for a blog post than to have one's time nibbled to death over the course of the day by the tweet-and-response cycle.
The best thing about blogging for me, though, has not been the way it let me master the technical side of the subject. It's been discovering how individual bloggers make distinctive voices with their work, exploring highly specific subjects and drawing an audience. Maybe not a huge one, but a devoted one; and the devotion matters more than the breadth of the reach. Jeremiah's Vanishing New York (now more or less on hiatus) documented the incremental decay of that city to high-rent blight and faceless consumerism. Stephen Downes covers a panoply of subjects around pedagogy and technology, with the kind of highly selective intelligence I find best cultivated in bloggers with a strong "vertical" beat. For a while, My Ghetto had some of the best writing on popular music I'd ever seen, and while it isn't being updated anymore, the archive is there for all. Something Old, Nothing New did the same for "vintage" media, until he found he was twisting his own arm into producing material that wasn't in line with his true passions:
A personal blog is not work, and once you can't generate ideas for it, you have to ask yourself if you should keep trying, or find something else to do in your spare time. I think I should try to do the latter, partly because I think I might be able to write better that way.
When I first started blogging, I had roughly three areas of focus: my own writing and my notes on the techniques of same; the media in my life that either excited me or disappointed me; and the occasional foray into other subjects that I felt I had some ability to comment on sensibly and constructively. The first one is a well I don't think I'll ever be able to exhaust. The second I put on hold because of poor time management, but anyone who's been hanging around here the last couple of months will notice I'm slowly bringing it back.
The third one, though, was something I wasn't always very scrupulous about. Most of the time I don't post here about the specters of current events all haunting us — not because I don't care about them, but because I care about them enough not to treat them cavalierly. I doubt most of anything I could say about Trump (or Biden, for that matter) would surprise or enlighten anyone of conscience and intelligence, so I leave that to the people who are genuinely excited about such things and don't have to twist their own arms into talking about them. I never wanted to put myself in the position of talking about something because I felt I was in danger of losing my blogging cred if I didn't. And I wasn't just happier when I followed that rule, I was more productive, more satisfied with the results of what I put out.
From all this, I can derive a few cardinal rules of blogging:
It's nice to have an audience of more than one, if only in the sense you get constructive feedback. But don't start blogging to get an audience; blog because you have some specific thing you want to address in your own way. Maybe you'll only find out what that thing is after some false starts. Fine. Keep slugging.
Whatever subject lights you up, that should be where you make your point of entry. And how you go through that subject should also be informed by your own curiosity. If you learn that someone else is blogging about the same subject in a vaguely analogous way, don't feel like all you have to say has been pre-empted. They are not you. Find what is only yours to give, and give it.
Some of the most entertaining bloggers out there, chiefly in the political blogosphere, employ razzle-dazzle, two-fisted writing styles as part of their selling point. That's fun, but not essential. Perspective and personalization are what matter, and those things don't have to be delivered by a particular style. It helps to polish one's writing whenever possible (I recommend Macrorie, Telling Writing, 4th Edition, for pointers on this), but style is not a matter of word choices. Your style, whatever it is, will suggest itself.
The toolset is also not that important, except inasmuch as it makes your job easier. WordPress is not my favorite software in the world, but for many people a managed WordPress installation, or just Blogger, will be fine. Just be as conscious as you can of the consequences of your choices with any particular product. E.g., if you use a service like Blogger, take regular backups of your work.
For some people, blogging is a job, in the sense that they monetize it aggressively and make their livelihoods possible with it. I am not against this in principle, but again I just want people to be conscious of the costs involved. Few things kill one's delights faster than making them into responsibilities. What's one of the things most rock bands say when they break up? "It just wasn't fun anymore."
If you have a comments section on your blog, set a policy for it and stick to it. The best blogs have comments sections that are as lively and informed as the blog itself, and the vast majority of how they get and stay there is by not tolerating bad actors or bad faith. Don't make excuses for the way people once were, or use justifications like "that's just them being them". It's never nice to ban people for being jerks, but better you do that than send a message that it doesn't pay to not be a jerk.
Trite and clichéd as those words sound, they are more important than ever. If you cannot be honest with yourself about your motives or your curiosities, you will not be able to do that with anyone else. If anything, you'll treat others with even greater contempt.
I am not just talking here about avoiding the propagation of lies or antisocial nonsense, although those matter. I also mean the simple act of trying to be something you know you're not. My other blog about Japanese popular and high culture, Ganriki, is still going after multiple change-ups of mission. I realized early on that I didn't want to investigate those things because someone would give me free stuff if I did (never a good motive). I wanted to talk about them because, well, I wanted to talk about them. Instead of contorting myself into rubbishy positions to try and secure review copies of things, I was freed up to pursue discussions of the things I really did care about. Nothing I ever wrote because a review copy was involved got me anything I hoped to get out of it. All the stuff I did because I truly wanted to has paid off dividends beyond measure.
Again, the largest question is one's own motives. What do you want and why? If you aren't possessed with some kind of urge towards the personal truth, and you can't document that in your blogging, it'll show. It is not always easy to recognize, or abandon, one's complicity in such things.
I followed more than a few bloggers who went from being enjoyably curmudgeonly into straight-up bigotry and reactionary fight-or-flight, not only because there was no one to Dutch Uncle them out of it (at least one of them had a cheering section goading them on at every turn) but because they clearly enjoyed talking about the lies more than anything else, and telling themselves that such things constituted "hard truth". Hard truth is always hardest to one's self, not others; the truth hurts because you have to confront it inwardly, not rub it in the face of another.
The truth is in short supply these days because there are so many glamorous alternatives to it. Insincerity and duplicity are cheap and easy highs. Blogging is one of the few places we can cultivate truth on our own terms, and turn it into beauty on everyone else's terms too.