Forgive me if I see Andrew Sullivan’s departure from blogging as more than just a routine retirement by a pioneer in a new media field. Rather, I see it as an extremely negative omen for that very field.

Andrew Sullivan was not just one of the pioneers in creating the blogging form, and in demonstrating how you create a personal brand on the web. Beyond that, he was one of the first to understand that what he was doing, most fundamentally, was not writing, or even editing, but curating – organizing the vast trackless swamp of the internet into material that his audience would be interested in.

And beyond that, he was pioneering a business model that I believed held the best hope for anybody getting paid for producing “content” in the age of on-line distribution. He asked his audience to pay, to subscribe to what amounts to “the web as I see it.”

I say that that is the best hope for anybody getting paid for producing content based on the following syllogism.

First, there are only three ways to monetize traffic. Either you give everything away for free and sell advertising. Or you get people to pay for specific content. Or you get people to pay for a subscription to a whole suite of content.

The problem with the first is that on-line advertising is massively deleterious to the on-line reading (and watching and listening) experience. And it doesn’t work very well in terms of motivating purchases. And most efforts to mitigate the one or the other are massively corrupting of the creative or journalistic enterprise (as Sullivan was well-aware).

The problem with paying for specific content is that you don’t know whether the content is worth purchasing until after you’ve purchased it, which creates a substantial barrier to purchase. If you’re talking about a feature film for which you can consult Metacritic or Rotten Tomatoes or whatever to learn whether it’s likely to suit, that’s one thing. But if you’re talking about a news article, or a web short, or a poem, that’s not an option.

The problem with subscriptions is that, generally, the way they are enforced is by creating a paywall around the content. Nothing gets inside the wall unless it was worth paying for up-front. And once it’s inside the wall, the only way to access it is to be a subscriber. This creates a two-tier world where most people are producing and distributing stuff without compensation, hoping to get them “hosted” by sites that don’t pay them, and eventually to “graduate” to paid work. But the prevalence of so much free work means that there is constant, brutal pressure on compensation for content-creators.

The solution to this dilemma is one that I’ve described – with apologies to “Big Bill” Haywood – as One Big Paywall. In very broad strokes, this would be a scheme whereby content-creators band together to require micro-payments from content aggregators for traffic driven their way, in exchange for not cluttering up access to that content with extraneous advertising and the like. Such a scheme would make it possible for content-creators to put their material out there for general consumption without worrying about either hiding it behind a paywall or getting paid nothing.

Without going into a great deal of detail of my thoughts about how to bootstrap into such a scheme, I’ve long felt that it depended, ultimately, on the success of curators in turning themselves into subscription services. A free curator is always going to pursue a mass audience, and this will skew the kind of content (and advertising) that it features toward the lowest-common denominator. A subscription service has the possibility of pursuing a niche audience – and niches can be quite lucrative. And much of the most interesting content is going to be aimed at some kind of niche.

Andrew Sullivan was my test case, in a way. If he was able to “make it” on a standalone basis, with a subscription model, then it was possible. If it’s possible, other people will do it – not exactly the same way, but with variations. And once it’s clear that it’s a “thing,” one could pursue my idea of One Big Paywall – because there would be moneymaking curators to negotiate with, and with whom the content-creators signing up for such a scheme would have a natural symbiosis.

But we don’t know whether he made it. It’s too soon to know. All we know is that it didn’t go bust immediately, and that there was no way to keep the venture going without Andrew Sullivan consistently and obsessively at the helm.

That’s a very negative fact for the future of that model. There just aren’t very many people like Sullivan in the world, who combine his speed as a writer, his breadth of taste, his skills as an editor, his manic energy, his head for the business side – it’s just a huge conglomeration of valuable traits. And he didn’t institutionalize them the way Steve Jobs or Walt Disney or Harold Ross did in their own various ways. Even though Andrew Sullivan did only a small fraction of the writing or the curating of the Daily Dish, without him blogging full time, apparently, there is no Dish.

I’ve been told that, in order to build a real, monetizable audience on the web, I need to post at least three times a day. Obviously, some of my colleagues here do exactly that. But it’s a completely insane demand. Virtually none of the critics or opinion-writers of yore could have met it – and those that could have would probably have destroyed themselves doing so, to say nothing of destroying their lives. The only reason anyone adheres to such a standard is precisely that there is no reliable way to monetize good work as such.

I probably sound like Leon Wieseltier here, but I could not disagree with him more. I have no interest – none – in preening lamentations for the great age of culture now past and gone. I loathe nostalgia – but I also recognize that culture is shaped by market structure, and that the market structure we have – and which is a consequence of decisions made a long time ago, some consciously but many unconsciously – is exceptionally brutal to anyone trying to make a living writing, making music, shooting movies, while also providing more ready opportunities to “break in” than ever before. I want to retain the latter while mitigating the former. That means changing the market structure, not posing as a solon while manifesting mostly ignorance.

Andrew Sullivan’s retirement is a blow personally, because, while I never met him, he has always been generous in linking to me, both here and at my prior perches. That he has been so generous in spite of the fact that my first on-line interaction with him was acrimonious in the extreme (and unnecessarily personal – on my part) is a testament to his admirable ability to look past the sort of thing that would lead many successful people (particularly in media) to hold a lifelong grudge, simply because what Sullivan cared about most was whether the work was interesting – to him and to the readership he cultivated. But that’s not the main reason his departure is a blow. The main reason is that the torch has not been passed. There is nobody else out there doing what Andrew Sullivan did, nor is there any prospect for someone to do it. There’s nobody else I can think of who I would say: if he or she links to me regularly, then people will read what I write.

Which make me very sad, for any younger versions of myself out there looking to give what they have to give, creatively, and to get something for it, without being fatally consumed by the endeavor.