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At sea about monetizing content? Become a sailor: Learn navigation, use your compass, and know the waters your sailing in.

ABOARD THE SLOOP APOCRYPHA — We’re sailing somewhere between Rhode Island’s Block Island and New York’s Montauk Point. We can’t see land under these tepid, hazy skies.

My friend Richard is at the helm. He loves this 29-foot sloop, which he bought in 1998 and sails every summer weekend. Richard is a corporate lawyer with a master’s degree in business administration. He can expertly navigate a courtroom and chart a spreadsheet.

Richard’s thrilled to be out of sight of land, if only briefly. Excursions like these let him stylize himself as a sailor, an explorer, a pioneer in the medium of the sea. Yet he dares not go out of sight of land or other boats, because he has no clue about marine navigation.

He knows little about the compass, except it rotates whenever he turns his boat. He can’t read a nautical chart and probably hasn’t one aboard. Richard’s oblivious to what the clouds and sky portend about the weather. Or how winds and tides affect a ship’s course. Even simple dead reckoning navigation techniques are unknown to him. He sails his boat the way he drives his car, because land is his familiar medium and a car is what he has always been driving.

Richard turns the boat now; heading back to land by following his own wake. How will he find his way back to Connecticut’s Groton Long Point harbor? He’ll follow other boats he sees; he presumes they’ll know the way to go.

Richard is my friend, but I’m glad this self-styled pioneer isn’t sailing further out to sea. He’d get lost. Although we’re cruising back toward land, should the weather turn foggy or stormy he could lose his way along the reef-studded Connecticut coast. He’s a fine lawyer and businessman and can afford to fund a superb sloop, but Richard’s lack of knowledge about this new medium actually endangers all aboard.

Richard reminds me of new-media types I meet every day. Well-meaning and well-funded, they’re white-collar executives, most with experience in traditional print or broadcast publishing or marketing. They’ve embarked on this fluid new medium without much of a clue about it. Since 1993, I’ve seen hundreds of lawyers, MBAs, and other executives embark into new media without learning navigation or the nature of these turbid and perplexing media. Most went to woe in the decade since.

The dynamics of new media are very different from those of print or broadcast. Hidden reefs abound. Latent tides can pull the best-aimed venture off course. Economic storms and fog hit much more quickly than in traditional media. The U.S. Coast Guard can rescue Richard and the rest of us aboard this boat, but there’s no new media Coast Guard to rescue a floundering online venture.

I’d frankly rather ship with Richard than those executives, because the odds of everyone safely surviving his sailing adventures are better than those of surviving new media ventures unscathed.

You’re now ready to toss me overboard because I’ve gone two-thirds through my column without telling you more about the nature or navigation of new media. Cut me some slack, mates! It’s mid-August and this is as close as I can get to an annual vacation amid 26 biweekly columns here.

My June 18 column outlined three criteria I use to decide whether a consultant should offer free or paid access to content. My July 2 column outlined the economics of content online provision. On July 30, I alluded to why the AOL Time Warner merger and other synergies won’t really work

In my next column, we’ll look at the incidental importance of visitation frequency regarding decisions about whether you can charge for access to your content. How can you expect people to pay for something they don’t frequently use now when it’s free?

Next, I’ll explain why only three media exist. You read that correctly: only three. Newspapers aren’t a medium. Magazines aren’t a medium. Nor is the Internet. They’re vehicles in one or more of the three real media. Read here in September what those three are. They’re the keys to understanding new media.

The three criteria on which to base a decision to charge; the incidental importance of frequency; and existence of only three media and the definition of new media. The topics aren’t rocket science. Instead, they are akin to basic techniques of seamanship, piloting, and dead reckoning navigation any sailor should know. They’re what Richard would learn if he kept a copy of “Chapman Piloting: Seamanship and Boat Handling” or “Dutton’s Navigation and Piloting” (instead of Forbes or the New York Law Journal) on his boat. If you want to charge for content, know where you’re going.

Later next month, I’ll also write about the practical paid content successes (or failures) of ireland.com, the Financial Times, Frankfurter Allgemeine Zeitung (Germany’s most prestigious newspaper), the uboot.com youth portal in Austria, and Hong Kong’s South China Morning Post. So many cutting-edge ideas about how to charge for online content are coming from all points of the compass.

There are lots of interesting places for us to go. Don’t give up the ship. The voyage is only beginning.

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