The intersection of health and technology has received much attention due to the popularity of wearables like fitbit and dieting websites/apps such as myfitnesspal. But how do these high- tech tools work for the everyday person trying to lose weight and stay healthy? Based on my own personal journey, I describe how these technologies helped and sometimes hindered my 75 pound weight loss. Over the course of a year, I used fitbit, myfitnesspal, wifi scale, heart rate monitors, digital food scales, and various motivational apps to help me lose and maintain the weight loss. But it was not easy- I found that some tools created healthy sustainable habits, while some created almost unhealthy obsessions. Some products made the process easier, while others made dieting more complicated. In all the discussions about weight loss technology, it is important to have a real person's experience and perspective to help others best utilize these tools for their own health and fitness!