When asked, I will always tell people the best job I've ever had as a writer was working for Playboy magazine in 2008. At the time, I was just starting out as a online media reporter, penning eight posts a day for $12.50 per post, a position I felt lucky to have landed. Like nearly every other person working in media that year, I was caught up in the all-encompassing excitement of the 2008 election and the simultaneous rise of online journalism. I was familiar with Playboy's illustrious journalism history -- its "read it for the articles" bylines are a veritable who's who of New Journalism heavyweights.
One day, I cold-pitched the then-Editor-in-Chief Chris Napolitano the idea of doing a political blog. Playboy had next to no Internet presence at the time, and I thought it would be smart to have a woman covering an election in which a woman was running for president. After months of back and forth-ing -- Playboy had sold their web domain years before (a decision that would soon contribute to their near ruination) and was only then in the process of getting it back -- my proposal was green-lighted.