There is a fantastic Article on Medium by designer Thiago Oliveira describing how his graduation project (informed by a preceding lecture about the work of Jan Tschichold) and a fuel for calligraphy turned into a self initiated font development project.
The article chronicles Oliveira's design discovery and learning process throughout the project. He talks of the importance of defining boundaries as not to get overwhelmed by the endless possibilities of an open brief (this designing inside the box approach is something we discussed in volume 02 of TypographJournal)... And also the need for disciplined, methodical and focused practice to build up some mileage and proficiency with his chosen tools (which in Thiagos case a broad nib pen). As is often the way with designers our taste outweighs our ability at first so Oliveira describes how much time went into sketch development, practice and refinement to get harmonious analogue letterforms, before he proceeded to digitization and the delicate balancing act of the black and white shapes/spaces within a type system.
Thiagos font is called Paciencia and a free weight is available for download here and you can view and buy the full family of fonts here. And you can see more of the visual research and outcomes of the design development process via Thiagos Dribbble account here.
This is an engaging, insightful and very honest read into the process involved in developing a functional font. And I highly recommend you check out the full article here.