While developing of a new project, novices often neglect the creation of useful documentation, which is usually composed of comments whose helpfulness is minimal for future reference and understanding. Moreover, such documentation lacks relative and contextual information, including errors encountered and the corresponding solutions found, lessons learned, consulted documents, choices and missteps made. By giving a seamless way to create artifacts with rich data, novices can generate valuable documentation for themselves and other developers. Thereby, in this thesis, I designed and developed Dear Diary, a Visual Studio Code extension that allows non-expert programmers to generate pieces of documentation directly in the IDE.