Recently, there has been research on what factors influence a user’s password setting practices, which include various types of emotions such as anger, risk-taking tendencies, etc. However, research has shown that factors such as memorability and perceived memorability have a greater influence on password choice. Some recent research has shown a negative correlation between the perceived memorability and the perceived security of passwords, particularly passphrases (that are technically more secure). However, it is unclear whether this effect can be extended to groups with good experiences with digital spaces (IT professionals, entrepreneurs, etc.). Furthermore, it has not been determined whether random, uncommonly-worded, or complex structure passphrases would also maintain the correlation, as opposed to relatively less secure, common/simple passphrases. This study examines this problem using a diverse demographic and different categories of passphrases.