In United States trademark law, the value of a brand turns less on who thought of a name than on who cleared it and filed first, which makes timing the quiet variable that decides whether a brand becomes an asset or a liability. This guide reframes "when should I trademark?" as a sequence of decision points along a priority timeline, from the naming stage through launch, expansion, financing, and rebranding. It explains why delay creates two distinct and compounding risks, adopting a name you cannot keep and losing priority to whoever files first, and how clearance searches and an intent-to-use filing under Section 1(b) neutralize both. Drawing on the Lanham Act, USPTO practice, and leading cases from Abercrombie to M.Z. Berger v. Swatch, it walks through distinctiveness, clearance, the registers, the registration calendar, and the first-to-file regimes abroad that make the China squatting problem so costly. It closes with a worked example, an FAQ, and a map of related UpLaw resources. Nothing here is legal advice; trademark strategy is fact-specific and warrants qualified counsel.