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Take it from experience, it’s not easy being a native advertising sympathizer.

Sitting through a half hour panel on ‘modern monetization’ at the Native Advertising Summit in San Francisco on Tuesday — or as the moderator put it, “the sobering reality of paying the bills” — I couldn’t deny that there is a lot that’s awkward in this new ad movement.

You had the Washington Post’s Kelly Andresen, its Director of Ad Innovations and Product Strategy, discussing the inherent difficulties in having advertisers request specific writers from the newsroom to write branded content. Of course, she clarified, the division between news and advertising is kept strict. But it still brought into focus that as good as branded content can be — buy space in the Washington Post to tell your story, almost as if it was a real article! — the true advertising dream goes well passed that.

There was Gawker’s James Del, the Executive Director of Studio@Gawker, piously rambling about working only with companies whose corporate message he respects. Be warned, McDonald’s and Walmart, you are not welcome on the furtively sacred moral high grounds of Gawker.  “I can’t work with your brand because you’re message is a lie compared with the actual experience,” he said, as if growing confused about what Gawker actually is, and whether advertising was really just a very emotive form of journalism after all.

Chris Pirrone, the GM of USA Today’s Sports Media Group, rounded out the panel. His early contribution to this somewhat stuttering discussion was to concede that sometimes his team had to be creative in what metrics from the site it presented to advertisers and which it held back. “It’s not all that great,” he said.

If you were concerned about subterfuge and the insidious and incorrect equivocation that if a brand is just honest, native advertising can be as good as any independent editorial, there was enough here to stoke your paranoia.

For a start, Andresen and Del, with the Washington Post’s WP Brand Studio and Gawker’s Studio@Gawker, both front operations that are designed to help advertisers exploit the same cultural cache that brings in readers to their publications.

“It’s really about us advising them and understanding what story they want to tell, then having an opportunity to create that story with them,” Andresen said. Her job in essence then, is trying to help brands make ads so good they could almost pass for Washington Post articles.

Advertising dressed up as content. It’s not not awkward.

But underneath the acknowledgment of the early glitches in the system, was a strong justification of why this all has to happen. Namely, that we live in an economic reality where more people view information as being free than don’t. Advertising revenue has plummeted dramatically and remains in free fall. Readers are quick to express moral outrage about native advertising, but they’re never going to stand up and offer to pay good money to underwrite that content themselves. Frankly, we’ve kind of become dicks about the whole thing.

“You’re always going to offend someone,” Gawker’s Del said. Readers don’t pay, he added, “but there is still a sense of ownership they have over everything we do.”

Native advertising feels weird because we’re trying to absorb and legitimize something that used to held at arms length and tainted with the advertorial label. But it won’t always feel so strange and counter-instinctual.

Listening to these three speak, hearteningly, the thought hit me that maybe, despite all projections to the contrary, native advertising could be freeing for media publications rather than damning.

As advertising has gone digital at alarmingly fast rates, major media publications have been left way behind, forced to switch up from commanding top dollar rates for full page ads for advertisers hungry for a chance to reach their audience, into selling cramped banner ads and charging by the click or page view.

“My editorial team would love to kill the banner ad,” the USA Today’s Pirrone said. “Click through rates are the bane of my existence.”

Digital advertising and its reduction of everything to a metric — how many saw, how many clicked,how many bought — has so far neutered mainstream media online and set new media on a never ending quest for link bait. In this, The New York Times doesn’t get plus points for being The New York Times, it’s left competing for ad dollars with one hand tied behind its back, against companies like Google and Facebook who have warehouses of data to use as a competitive advantage.

Native advertising — if all the caveats about transparency of labeling and separation between ad men and journalists are held true — frees someone like the Washington Post to return to charging a premium to brands for being associated with the Washington Post, and all the benefits that come with that.

In an era of advertising defined by a raw adherence to numbers, it puts cultural currency back on the table. There’s some hope in that.