This chapter uncovers the opportunities that online media portals like content sharing and consumption sites or photography sites have for informal and formal learning. The authors explored online portals that can provide evidence of evaluating, inferring, measuring skills, and/or contributing to the development of competencies and capabilities of the 21st century with two case studies. The first one is focused on identifying data science topical experts across the Reddit community. The second one uses online Flickr data to apply a model on the photographs to rate them as aesthetically attractive and technically sound, which can serve as a base for measuring the photography capabilities of Flickr users. The presented results can serve as a base to replicate these methodologies to infer other competencies and capabilities across online portals. This novel approach can be an effective alternative evaluation of key 21st century skills for the modern workforce with multiple applications.