[UPDATE, 3:35 p.m.: As this post went up, tr.im announced that it’s back in business. But the thoughts below still apply.]

I had the very-2009 experience on Sunday night of losing my URL shortener to a lack of business model. Tr.im, the Nambu Network‘s intuitively named and competitively concise truncator of web addresses, announced that it was folding after a year in its curious but increasingly vital field. As a friend put it, tr.im “is the Sarah Palin of URL shorteners,” although I have more reason to fret about this abrupt departure: Barring some 11th-hour resolution, the hundreds of links I’ve shortened for the @NiemanLab account on Twitter will break at the end of the year. (URL shorteners have boomed precisely because their shrink-ray powers allow more text to squeeze into Twitter’s 140-character limit.)

Tr.im’s demise prompted me to call up Garrick Van Buren, who designed the in-house URL shortener used by MinnPost, the non-profit in Minneapolis. They’re among a small set of news sites with their own short URLs, including TechCrunch’s tcrn.ch, ContentNext’s cnt.to, and Daring Fireball’s ✪df.ws. The New York Times has an unofficial shortener — that phrase makes me think of Crisco — created by one of its developers, Michael Donohoe, at nyturl.com.

In all of those cases, the short URLs can only point to pages on the publisher’s own site, but Van Buren told me that’s a feature not a bug: “The benefit — and this is something that the guys at MinnPost told me — is that we want readers to know that the link is going to take them to us.” It’s a marketing opportunity as well as a mark of assurance for readers who are clicking blind and don’t want to end up somewhere NSFW. For more on the subject, check out Van Buren’s posts about URL design.

Baking a URL shortener into your own servers is just short of trivially easy, and Amy Gahran has a great post with various tools and thoughts to consider. In our conversation, Van Buren noted that many content management systems already assign a numerical shortkey to each post that could be used for a short URL. “The really, really big benefit in that case is that it’s no longer a redirect,” he said. “It’s just one more URL that points to same place.”

There are also solutions like awe.sm for shortening any URL on your own server, and we’re thinking about something along those lines. (One of the most frustrating side effects of tr.im’s demise is the end — at least for now — of the aggregation tool that ranked our 40 most-recent links on Twitter by the number of clicks they received. Built for us by Dave Winer, it was teaching me a ton about mixing recency, popularity, and importance on the Internet.)

Finally, when I spoke to Van Buren yesterday, he raised an idea that’s been bouncing around in my head since I hung up the phone: What if a short URL were static, but the page it pointed to wasn’t? You could change the redirect to whatever is catching your interest at the moment or, say, randomly selected links from Andy Baio. There’d be elements of mystery and serendipity, like flipping the pages of a great magazine, and devotion might center around the URL itself. (Unless you put some kind of annoying frame on it, there’d be no way to monetize this brand, but that’s not what’s great about the idea.) Van Buren has tested the concept with re07.us, which anyone can point to any page for five minutes. Earlier, it was redirecting right here.

Where will you point it?