Sometimes when this feels too good to be true, I think that if this were all a dream, that would be what should have tipped me off. I'd wake up saying, "I was in this incredible TV show and it was a big hit and the star was John [Krasinski] from high school. Isn't that weird?"
He attended Newton South High School with Future Office costar John Krasinski, and they graduated in 1997. Novak graduated from Harvard University in 2001, where he was a member of the Harvard Lampoon and the Hasty Pudding Club. He majored in English and Spanish literature, and wrote his honors thesis on the films of Shakespeare's Hamlet.
Novak's television acting career began on MTV's Punk'd. He was the lead accomplice to Ashton Kutcher on the show's second season in 2003, playing pranks on Hilary Duff, Rachael Leigh Cook, Usher, and Mýa.
Novak is primarily known as one of the Writers and executive producers of The Office (2005–2013), in which he also played Ryan Howard.
On July 21, 2010, news reports indicated Novak had signed a contract to remain with the show for its seventh and eighth seasons; under the new terms, he would be made an executive Producer midway through Season 7 and direct two episodes of the show. In a June 2009 interview with The Philadelphia Inquirer, Novak spoke about sharing the success of The Office with his Newton South High School classmate John Krasinski:
On April 11, 2013, publishing house Alfred A. Knopf announced it had signed a seven-figure, two-book deal with Novak, with the first book slated to be a fictional collection of Woody Allen-like stories.
On February 4, 2014 a book of 22 stories, One More Thing: Stories and Other Stories, was published and spent 6 weeks on the NYT Hardcover Fiction Bestsellers List. Novak also signed a deal with Penguin's children's books label and wrote the title The Book With No Pictures, which was released in September 2014 and has spent two full years and counting on the New York Times Picture Books list, with 34 of those weeks charting the book as the #1 seller in the country.
On October 14, 2015 Novak released an Apple iOS app app along with co-founder Dev Flaherty called The List App. The app has since been nominated for a Webby Award (losing in its category to Beme and Pocket) and in May 2016 rebranded as 'li.st' and became available on the Android platform.
In September 2017, the app was shut down, citing that the growth wasn't enough to sustain the current product.