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5 Things I Learned as an Anonymous TSA Blogger

From 2007 to 2013, I patted down people's crotches to put food on the table. Yeah, I know.

I worked for everyone's favorite post-9/11 security agency, the Transportation Security Administration. I was also a humor writer that entire time, contributing to publications such as the one you're reading right now. It didn't take long for me to put the two together and begin secretly humor-blogging about my federal experiences with private parts; it was actually a pretty smooth transition from Cracked. By day, I was a TSA employee, viewing nude images of airline passengers and confiscating people's bottled water. By night, I was an anonymous controversial blogger. I went viral for the first time about three months after starting my site. A lot of eyes, including the government's, were suddenly on me.

Two months ago, I revealed my identity to the world, and a goddamned 80-megaton media bomb went off. It's been a crazy ride, but I've learned a lot of surprising things about this whole anonymous blogging game along the way.

#5. Staying Completely Anonymous Was Such a Pain in the Ass That I Gave Up Trying

cookelma/iStock/Getty Images

Quick: How do you completely cloak your online activities from the world? There's got to be some relatively easy, surefire means by which to do it, right? Some advanced IP-masking software out there that hackers use, or some such?

It's not that easy. Not that easy at all.

WikiLeaks recommends that its informants use Tor for anonymity. That's what I used to run my site for the first couple months, operating online with a masked IP address, thinking it was a watertight guarantee of anonymity, until I learned that it doesn't really guarantee shit.

selimaksan/iStock/Getty Images
"The mask is just to keep my face warm."

Then there's the fact that the Internet doesn't take kindly to people with masked IP addresses. Try logging into Gmail while signed into Tor and you'll discover that Gmail instantly locks you out. Trying to build and operate a WordPress blog with a masked IP address is like trying to play piano wearing boxing gloves. Features are stripped to the bare minimum, and loading times are in 1990s territory.

What about public computers, you say? That's mostly how I ran the blog for the first few weeks, going from public computer to public computer, using libraries and FedEx stores, until I realized there were cameras in all those places watching me peck away at my controversial little project. Anyone truly determined to find out who was behind the site would be able to do it.

And so I just gave up.

Daniel Schweinert/iStock/Getty Images
Come and get me, coppers.

Internet personalities who try to remain anonymous after gaining public attention almost always end up being de-anonymized. A popular piece of wisdom when it comes to anonymous blogging is to always assume that you will one day be unmasked. It's a piece of advice that I took to heart: Day 1 of my blog marked the beginning of my mental countdown to the hour when I would come out from anonymity, preferably in a halfway respectable publication.

But little did I realize just how hard it is to get respectable publications to cooperate.

#4. Actually Getting Out from Anonymity Was Extremely Difficult, Too

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After I resigned from the TSA and was no longer doing the whole TSA employee by day, "former" TSA employee/blogger/lame version of Batman thing by night, I decided it was relatively safe to make the reveal: I began submitting coming-out-from-anonymity pieces to publications. I was sure that by that point -- eight months after I started blogging, having gained a decent following, as well as a few mentions in major news publications -- it would finally be a little less of a battle to get the attention of editors.

It's been said a million times before, but it bears repeating as fair warning to those thinking about getting into writing: The odds of getting accepted by a publication, no matter what you have to say and how well you say it, are always ridiculously long. Even after my blog had been covered in print by the Los Angeles Times and appeared on the websites of Fox News and ABC News, I was still getting my ass handed to me by editors from publications via form rejection letters. You'd probably be shocked to learn just what it takes in the writing world to impress an editor at a large publication.

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OK, maybe it's not that shocking.

Faced with slush piles like black holes, it's easy for anyone to lose faith in their ability as a writer or in the value of what they have to say, since one could conceivably submit evidence of first contact with extraterrestrial life to a major publication and have the body, UFO debris, and accompanying report returned with a form rejection letter.

I submitted nine op-ed pieces to major U.S. newspapers in which I attempted to come out from anonymity (all of them rejected or ignored), as well as a 5,000-word essay (the same essay that would pull down over 8 million views four weeks later) to 11 small literary publications. Every publication that got back to me did so in order to reject me.

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Some more memorably than others.

Then one day an editor at POLITICO contacted my anonymous alter ego after coming across my blog, asking if by chance I would be willing to contribute to the magazine. Finally, the stars aligned. It's a damn good thing I checked my anonymous email account that week, or else I'd probably still be getting my attempts to come out from anonymity alternately ignored and shat upon by editors across the nation. Which brings us to another of the biggest things I learned ...

#3. Timing Is Everything

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My first thought on how to successfully go about blogging with guaranteed anonymity was to write a year's worth of blog posts, set the entire blog up from a public computer with no video surveillance around, schedule the posts for intermittent time release over a year, and occasionally monitor the site's impact on the Web via Google search to see just how viral that bad boy had become. Then, after I'd resigned from the TSA, I could swoop in and claim credit for the site if I chose to.

Although this would have been a near-guarantee of anonymity, it would have also been a recipe for ensuring that almost no one would ever see my site.

In order to steer a site out of the obscurity zone, you have to be able to react quickly to unfolding events in real time. If a major news story breaks that readers would expect your blog to address, you had better be fairly quick to offer your take on it. It can mean the difference between everyone reading you and no one reading you.

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Or starting to read you, then switching over to that website with the cats that all look like Hitler halfway through.

For example: The night POLITICO published my piece, I knew that a good number of people would be visiting my Twitter account, since I'd plugged it at the bottom of the article. Generally, when you know you're going to have visitors from a website plug, you want to have something awesome waiting for them when they show up to your site. Having a humdrum post about what you just ate for breakfast on your blog when thousands of visitors come banging down on your site is like greeting a dozen party-loving chicks at your front door unshowered and without an ounce of alcohol in the house.

A few hours before the POLITICO piece ran, I decided to strategically post a tweet that I was sure readers would like. One of the best strategies for this is the "deleted scenes" approach. You see a lot of Cracked writers going this route on their personal blogs when you click the plug at the bottom of articles, offering readers a few things that didn't make the cut for the article -- bonus material, essentially. In my case, I decided to have a tweet waiting for POLITICO readers that would impart a piece of amusing information that I couldn't quite fit into the article. The tweet read: "One thing I left out of that Politico piece: HELL YES airport employees often drink those bottles of alcohol you surrender at the checkpoint" (it's true, they do).

David McNew/Getty Images News/Getty Images
"I'll need to confiscate any lime wedges or club soda you may be carrying, too."

When I signed in to Twitter a few minutes after the piece went live, it was up to 21 retweets -- already approaching the most popular thing I'd ever tweeted. An hour later, it was up to 54 retweets. I felt like a goddamned superstar already -- I had visions of becoming another Twitter success story like the many former Cracked writers I've watched ascend to fame. It could have stopped right there and I would have died happy.

The next morning, I signed in to Twitter and discovered I'd dropped my own personal MOAFT -- the mother of all fucking tweets. It was up to over 300 retweets. The day after that, it was up to 550 retweets and 220 favorites. Sure, we're not dealing with Ellen Oscar numbers here, but for a lowly, relatively unknown writer, it was big news.

Via Twitter

The strategic decision to have that tweet awaiting readers ended up making all the difference in the world (as you'll soon see), and it's an example of the kind of ad hoc strategizing you have to do in order to pilot a site to popularity. Already I sound like a grandpa reminiscing about a game-winning home run back in his old-timey ball-playing days, so I should really stop (more on this in a minute). The point is, it was necessary for me to think fast if I ever hoped to emerge from the chrysalis stage of semi-obscurity and morph into a beautiful goddamned viral butterfly that ladies found irresistible. Which reminds me ...

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Jason Edward Harrington

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