Yes, start out with a small project that you feel fairly confident you can finish. Think of each new project as a small building block you can use to build bigger things in the future. That's pretty much what I do every day.
All of the projects I create at home (or wherever I can drag my tablet or a laptop) have been designed as a 'learning' project for me. Scareplane, for example, was created because I wanted to learn Anime Studio and more about 2D animation. The Brudders music video project started out as a way to learn more about motion capture tech and to develop a system on a shoe-string budget, but along the way the project extended into many other areas of education for me, like cg hair and fiber, physical dynamics, instancing, and music production. (My wife and a friend did the 'heavy lifting' with the music and I learned to play harmonica while sitting in two hours of L.A. traffic every day.) The comics help me improve my drawing skills and writing the gags teaches me a lot about, well, almost any topic since they typically involve a lot of research. (The recent Brudders 'Carmen' episodes, for example, taught me a lot about opera, Georges Bizet, and bullfighting.)
It can be very hard work but it's fun too, and what I learn from the projects helps keep me employable. It's all connected and kind of organic in the way it grows.
I think the hardest part is managing my time. I dropped my cable TV subscription well over a decade ago and I hardly ever go to the movies--which is probably ironic, since I work in entertainment media. If I watch any TV, it's usually related to something I'm working on or it's a show I'm really interested in. I still try to have a social life with friends but not as much as I used to. I try to keep my wife and daughter involved with my projects when they want to be but sometimes that can be hard work too. I think these projects are worthwhile but I try not to lose perspective on the things that are really important to me.
(See, I can go on and on about my own projects. I guess better stop now.)
