With more and more wearable devices and smartphone apps being released that are capable of unobtrusively recording various aspects of our life, we are currently witnessing the emergence of a new trend. Followers of this trend rely on these apps and devices to track their every day activities and to gain insights into their personal well-being. Although promoted by various players on the market, the use of such techniques does not come without risks or drawbacks. In this chapter, we use the SWOT matrix, which is commonly used by business strategists to evaluate the strengths, weaknesses, opportunities, and threats of self-tracking activities.