The film begins with Peter, Michael Bolton, and Samir attempting to fight their way through traffic in order to get to the office, find their cubicles, and begin another day of meaningless work. Peter is a man who is ready to run from his job but doesn't have the courage to do so. We see this when he is trying to sneak out of work and is caught by Lumbergh, who promptly asks him to stay until 9 pm and then come in on Sunday. Peter willingly complies, and this is the beginning of the end of Peter caring about the consequences of acting within the bounds of corporate compliance.
Peter decides to go to a hypnotherapist to get help, but the doctor performing the treatment dies while hypnotizing Peter. This leads Peter waking up the next day completely relaxed and capable of not caring about anything, including his girlfriend who breaks up with him. Peter, newly awakened, decides to act against the grain of what is normal behavior in the white-collar world of Initech where he works, and skip work to go to lunch. This plot point opens the door for him to meet Joanna who is a woman who seems to be right for him, unlike his ex. The film is revealing the necessity to let go of our fears and preconceived notions of what is expected of us, and instead allow the sense of freedom to lead us in new directions as they have the potential to open up new opportunities and relationships that can be healthy for us.
The film then turns the everyman's need to comply with giving the right answer to their boss on its head. Peter is interviewed by the higher ups, the 'Bobs' as they are determining who to fire and who to keep. Because Peter doesn't care about keeping his job he gives them answers that confound them, but lead them to believing Peter is just the kind of freshness that the company needs and they promote him. We see that the writer/director, Judge is making a commentary on the way employees of bigger companies lead their lives. That they base their entire existence on pleasing 'the man' and in the process lose themselves in a vortex of bitterness and anger and hopelessness. By Peter simply telling the truth, he creates a smooth pathway to growth in the company.
However, Peter's lack of caring is upended when he believes Joanna had previously slept with Lumbergh, his boss, and he is returned to being animated about the offense, and the couple eventually split. It is through this incident that we are allowed to see that even when we try our best not to care, or are hypnotized in to believing nothing matters there is still a deep desire to be loved that we want. And Peter wants to be loved by Joanna. It is her love that reawakens him from his sleep and returns him to the world a new man, full of feelings but finally on the right track.