A few years ago, my brother sent me a link to this site – myscriptfont.com – He was encouraging my creative tendencies and had come across this page where you can design your own font. It is amazingly simple. All you need to do is download this form and draw your own letters on it in black ink, scan and upload and you get your own .ttf or .otf file to download and use.
More on .ttf vs .otf files later. This web app takes the amazingly intricate world of font creation and makes it nice and simple enough for beginners. It is a free resource, and that and incorporates a super simple UI so it is easy to use for beginners. If you are a typography nerd like me and want to start creating your very own fonts I cannot more strongly recommend myscriptfont.com.