Eric Schmidt ✈ North Korea

A private trip to Pyongyang.

PICEDITOR-SMHWhat happens when an outspoken executive from the world’s largest Internet search company visits the world’s most restrictive Internet economy? We’ll soon find out! The Associated Press reports that Google executive chairman Eric Schmidt is scheduled to travel to North Korea as early as this month on a “private trip” led by former New Mexico governor Bill Richardson.

The gloriously candid Mr. Schmidt has taken on more of a policy role since stepping down as CEO in 2011, focusing on the company’s external relationships with business partners and governments. He’s working on a book called The New Digital Age with Jared Cohen, the fratty-looking former State Department policy and planning adviser, who now heads Google Ideas, a New York-based think tank that “convenes unorthodox stakeholders.”

It’s unclear how the message of Mr. Schmidt’s book–that the Internet and mobile tech can free people from poverty and political oppression–will go over in Pyongyang, or even who they’ll visit, considering that North Korea has no diplomatic relations with the U.S. and hosts “almost no business with companies in the U.S.”

But if the GOOG is searching for unorthodox stakeholders, they may want to look at the newest iteration of its supreme leader:

North Korea is in the midst of what leader Kim Jong Un called a modern-day “industrial revolution” in a New Year’s Day speech to the nation Monday. He is pushing science and technology as a path to economic development for the impoverished country, aiming for computers in every school and digitized machinery in every factory.

Milder rhetoric aside, the visit to North Korea follows the recent jailing of an American citizen of Korean descent on suspicion of committing “hostile” acts against the state. And Mr. Richardson has previously been on trips to North Korea to negotiate the release of American detainees. But it’s worth noting that Google has also been willing to play ball with restrictive governments before, to a point:

After being accused of complying with China’s strict Internet regulations, known as “the Great Firewall of China,” Google pulled its search business from the world’s largest Internet market in 2010 by redirecting traffic from mainland China to Hong Kong. The company maintains other businesses in China, but a recent transparency report shows Google’s services there sporadically are blocked.

Mr. Schmidt was talking about implanting chips in your brain when he said, “Google policy is to get right up to the creepy line and not cross it,” but it seems to work for policy as well.

Eric Schmidt ✈ North Korea