Parachutes, while lifesaving, are not without notable problems—problems that, interestingly, parallel those faced in implementing Lifestyle Medicine. Firstly, despite their effectiveness, parachutes are difficult to validate through the most robust research methodologies. Secondly, parachutes are ineffective if they are not large enough. Thirdly, parachutes require ongoing maintenance. And finally, parachutes must be deployed to be lifesaving. In this presentation, we will critically examine these “problems” with parachutes and explore how they provide valuable lessons for enhancing the implementation, effectiveness, and sustained impact of Lifestyle Medicine interventions.