This achievement depends on the decisions you take on how you portray Sophia Rymmington:
The first time Sophia makes an appearance, on day 8 (The Fallout), during the headlines portray her as a graduate.
The next time she appears will be on day 153 (The Tempest). During the headlines, portray her advertising the Flardmaster 5000.
During day 232 (the Silence), the A Flard Day's Night headline, you will be asked to portray how the public reacts to the Flardmaster. Have them portray negatively to it by selecting the red sad face.
During day 371 (the 20th Week War), you will have to play the Flard Festival tape during one of the breaks.
Doing all of this should make the achievement pop.