1. Why do you think Bill Clegg turned to drugs? Do you believe that the source of addiction is more emotional or physical?

2. Have you ever had a coworker or loved one who was an addict? What would you do if you were in the same situation as Bill Clegg’s friends and family?

3. Do you think that the “Penneys” the author saw were real or hallucinations? At what point did you have a hard time deciding which they were, and why?

4. Bill Clegg was often able to find public spaces where he could take drugs --- bathrooms, dressing rooms, offices, etc. Were you surprised by how much of his drug use was hidden in plain sight?

5. The author seemed to have a sixth sense about which other people “liked to party.” What do you think the signs he picked up on are?

6. James Joyce wrote The Portrait of an Artist as a Young Man. Why do you think Bill Clegg chose to call his memoir Portrait of an Addict as a Young Man? Do you think the two books are similar?

7. What do you think is the significance of the author’s childhood affliction? Why do you think he wrote those passages in the third person?

8. Do you think Portrait of an Addict as a Young Man can serve as a cautionary tale for readers? Do you think it can help people who are dealing with addiction?