At the college level, it can be difficult to engage students outside the classroom through the use of effective homework assignments. Although it is straightforward to create assignments that test the ability to carry out computations as discussed in class, it is more challenging to create assignments that encourage students to think more creatively and deeply about course ideas. I discuss my implementation of written homework assignments in two calculus courses at a small liberal arts college, describe four of the written assignments I gave my students to engage them at a deep level, and explain what challenges I faced and how I attempted to resolve these issues.