My Boston Globe op-ed yesterday argued that blogging still matters. But it’s also got me wondering: Is the time ripe for newsletters again?

I wrote a personal newsletter for about ten years. It started out as an in-house mailer at Open Text where I was VP of Strategic Marketing in the mid-1990s. It came out every week or two and was titled DWOTIO: David Weinberger’s Open Text Inside Out (I think). News, views, humor, witty repartee with people who sent me email about it.

I’d coined the phrase “hyperlinked organization” there, and when I left I started a new newsletter called “Journal of the Hyperlinked Organization,” or JOHO. Hence the name of this blog. The phrase “hyperlinked organization” didn’t quite catch on (Deniro decided to make “Analyze This” instead), but I stuck with it and started sending out a free newsletter about every three weeks.

Each issue had one substantial essay, a couple more that were lighter and quicker, and witty repartee with people who sent me email about it. It also had a a humorous contest that no one ever entered, a “cool tool,” and a very brief write-up of an article about a company doing something interesting with the Web.

It took a lot of time, and not just to write it. It took me way longer to create HTML and text versions than you’d think; back then not all email readers supported HTML. Even just had formatting the HTML was a pain in the tuchus. (It’s way easier now, kids.)

But it was totally worth it. I had a direct connection to 7,000 people. They wrote in and I responded in the newsletter itself. It got me writing. When I wrote “In the future, everyone will be famous to 15 people,” that’s what I meant.

Then blogging happened.

For about ten years, I posted every day, often more than once. It took more and more of my energy. RSS let you subscribe to my blog. So what did my newsletter add? It faded away.

But now I’m thinking it might be time to start it up again.

Blogs are a pull medium, but not a lot of people pull on this blog. Newsletters are an opt-in push medium. I don’t know (and I don’t want to know — really, don’t tell me) how many people check my blog with any frequency, but I suspect it’s in the dozens. I love those people deeply, but that means that if I want to each a wider audience, I have to publish in the equivalent of online magazines. I do that and I’m truly glad for the opportunity. It’s a privilege. But that doesn’t establish the sort of intimacy that ritualized reading can.

It also means that my voice as an author works only for that one article, and the reader only hears me in that one voice. Turn the web page and the next author has to her establish her own presence. But a newsletter is a space that more fully expresses the author. JOHO was famously garish, ugly and amateurish. Welcome to me, people!

So, it’s tempting. I would still blog, of course. But: Can I come up with enough mid-range articles? Can I come up with a set of repeating pieces — like the old “Cool tools” — that will be interesting enough but won’t paint me into a corner? Would anyone read it? Would it be worth the commitment?

I don’t know.

But I’m not the only blogger in this situation. With mainstream web magazines providing a way to reach a lot of people with longer-form articles, blogs working for shorter and more informal pieces (or for anything you want), Facebook for quick personal posts, and everything else for everything else, the ecosystem might be ready for the next round of personal newsletters. Maybe.

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I’ve spent most of today working on something I haven’t done since August 18, 2009: Publish an issue of my old newsletter, Joho.

I started it in around 1995 as an internal up-to-dater for Open Text where I was marketing vp. The idea was to share links, explain some stuff when I could, and crack wise. In other words, it was a lot like a blog that I folded up and sent through email once every few weeks. (In case you were wondering, Joho gets its name from this period: Journal of the Hyperlinked Organization.)

When I left Open Text, I opened up Joho as a free online newsletter. I’d post the hmtl and send out the text. Because we still didn’t have blogs, much of the content consisted of amusing emails from readers, with my occasional semi-amusing riposte.

As the new millennium dawned, I was blogging up a storm and thus felt less of a need — and had less time — to write up articles for a newsletter. And formatting it was a pain in the tuchus. Yes, I know it’s got all the usual hideous elements of my “design aesthetic” (as Jeff Goldenson, who works with me at the Library Innovation Lab, once called it with a straight face). But putting it into that format, and then taking it out so that I could do an ASCII-based version of it for pre-html email took more of a part of a day than I’d like to admit, even after automating as much of it as I could.

But now I’m getting ready to send out another issue. What prompted me was an article I’ve been working on about echo chambers, culture, and Reddit. It’s long for a blog post, but a good length for Joho. And, I have to admit that the publication of a new book undoubtedly is also at least a bit behind my decision to reach out to Joho’s subscribers. Shameful, I know.

I’ll post the linked table of contents here in a few days when I actually send out the newsletter. Until then, I’ll be revising drafts of the three articles in it, and feeling like a young man of 50 again.

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