In any reasonably long personal or professional timeline, periodic spells of extreme self-doubt, boredom, and general dissatisfaction are a recurring theme. Philosophers and psychologists know these as existential or midlife crises, classic film buffs are familiar with the infamous "Seven Year Itch", and developers as the long-term project-from-hell. At one time or another, almost any developer has been stranded on a project that could (perhaps generously) be compared to a long, slow trudge through a desolate wasteland comprised solely of fodder for TheDailyWTF. The Ruby community's increasing maturity, combined with the recent explosion in the language's traction and popularity, has resulted in the frequency of such projects going from exceedingly rare to much more commonplace. But for every midlife crisis that ends in personal disaster, many more end with fresh energy and a renewed outlook on life. This talk will be about the latter, and using specific case studies from a recent large-scale, real-world example, offer some solid techniques and strategies (personal, technical, and methodological) for turning a deadly slog around into something interesting and exciting.