In this article, the author shares the successful digitization effort of their library and demonstrates how they were able to expand their first digital collection. The author started working at James G. Gee Library when the director asked him to try digital collections and was asked to study an open source collection management program called Greenstone. After a couple of months of exploring issues and concepts related to basic digitization, it was time to think about what they hoped to gain from a digital collection and how they wanted to move forward. A pilot project would provide an opportunity to continue learning how to use their content management software, and it would allow them to experiment with workflows, digital content creation, and project organization on a scale that would not be overwhelming. Their ultimate goal was to be able to take a finished pilot collection and use it to solicit grant funds for expansion. He mentions that despite the growing pains they had in establishing their first collection, their efforts have paid considerable dividends for their library. They not only continue to develop their own collections, but their digital collections have also become an excellent platform for collaborations with other libraries and organizations.