Proposal writing is a venture common to non-profit organizations, academic researchers across disciplines, scientists and engineers in academic and professional contexts, and educators. This paper addresses proposal-writing challenges of researchers in three very different academic fields: Technical Communication, Engineering, and Biology. An inherently interdisciplinary undertaking, proposal writing entails challenges of two kinds: general (common to most writers) and field-specific, or limited to people from one discipline or environment. Both types of challenges are addressed here.