Starting in 1996, Lopp wrote The BitSifter Digest, a website that published "the more interesting collections of bits which arrive at our desks" once a week, which increased in frequency and became daily by 2001. According to Steve Baldwin of disobey.com's Ghost Sites, it received recognition for its "pioneering use of borderless frames" and "topical, eclectic editorial content", and "was an important forerunner of the 'Blog.'" The BitSifter Digest stopped updating in 2001 and no longer exists at the domain name bitsifter.com.

Lopp created the Jerkcity web comic in 1998. In the strip, Rands is the "boring" one among a cast of absurd characters.

In April 2002, Lopp started a blog titled Rands in Repose. It explains aspects of technological or corporate culture, with particular focus on techniques for improving management skills. For example, one post explains the nuances of an interesting application, and another identifies and names workplace stereotypes. Posts contain a level of observational humor, such as direct explanations of management jargon.

In June 2005, an essay by Lopp was published in the book The Best Software Writing I, edited by Joel Spolsky. The essay was the July 2004 post on Rands in Repose titled "What To Do When You're Screwed."

In June 2007, Lopp published a book titled Managing Humans: Biting and Humorous Tales of a Software Engineering Manager. A supporting website, Managing Humans, gives a brief pitch for the book.

In August 2010, Lopp published his second book titled "Being Geek: A Software Developer's Career Handbook". A website, Being Geek, supports the publishing of the book and includes an original teaser video for the book.