A cross-sectional survey was distributed to 1322 members of a 1-on-1 personalized strength training studio. A total of 366 respondents (n = 134 male and n = 232 female), all aged over 20 years, reported considerable training experience, with 55% of the males and 42% of the females reporting 5+ years of experience. The data were analyzed and reported descriptively with differences >5% identified based on the use of a 5-point Likert scale, the sample size, and the nature of the observations. Disparities between the males and females were identified; the males reported higher perceptions of managing effort, technique, and programming without supervision compared to the females. Safety was noted as being more important to the females compared to the males. Qualitatively, additional themes were raised including an analogy of the personal relationship between the trainer and trainee being similar to that between medical professionals and patients. This was validated where the participants discussed their adaptations from supervised strength training for maintaining quality of life in aging and recovering from medical conditions and injury. The data are discussed in the context of a previous body of literature suggesting males falsely report higher levels of confidence in tasks compared to females, particularly in relation to effort, role models, and verbal encouragement. We posit that the greater confidence expressed by males at least partially explains the greater engagement in strength training practices by males compared to females, as well as explaining the higher level of participation in supervised strength training by females compared to males. This research proves beneficial for strength training practitioners in enhancing their understanding and expectations of clients, as well as hopefully proving insightful in engaging more people in strength training.