How Not to Live Your Life

In 2006, Clark was commissioned to write two short comedies for Paramount Comedy 1 – Dan Clark's Guide to Dating and Dan Clark's Guide to Working, both of which he co-wrote with Gary Reich. Clark was the main character in both shows, and Isabel Fay appeared in Dan Clark's Guide to Dating, which was shown as ten one-minute clips on the channel, with lists of ten things people shouldn't do on a date, such as "Ten things you shouldn't wear on a date". The clips began to appear on the Internet and the BBC approached him about doing a 30 minute show in the same format. The result was the pilot for How Not to Live Your Life, using the same style of short clips within a traditional sitcom. The pilot was filmed in a real house in London and first aired on BBC Three on 27 September 2007.

The pilot featured a number of actors who did not appear as regular characters in the series – Sally Bretton, Rich Fulcher, Claire Keelan and Bruce Mackinnon. Although, Isabel Fay who also appeared in the pilot was in the final episode of the first series, "The Break Up", as Fiona. The BBC then commissioned a full series, which was filmed in a studio in Glasgow. Clark wrote each episode and directed four episodes.The first series started broadcasting on BBC Three on 12 August 2008 with the first episode, "Home Sweet Home", which introduces the four main characters of Don, Abby, Karl and Eddie. BBC Three showed the first series on Tuesday evenings at 10:30pm.

The series often features the character of Don giving a narrative and talking to the camera, as well as cut away dream sequences where he gives alternative scenarios such as put downs or physical moves he wished he had thought about at the time. For instance, in episode four of series one, "The Young Ones", these include, "Eight Ways Don Shouldn't Dance", "Alternative ways to deal with annoying teenagers" and "What Don wished he had said to his flatmate, Abby, while she was necking with her annoying and square boyfriend Cockface on the sofa".