Conducting rigorous due diligence fuels informed decisions yet obsessive analysis risks paralysis. While investigating mitigates risk, over-scrutinizing minor variables obscures vision. As such, balancing pragmatism and precision allows progress despite uncertainty. This article examines due diligence optimization, contrasting exhaustive hypthesizing with efficient evidence gathering through lenses of viability assessment, skepticism, and strategic scoping. Insights help entrepreneurs hone diligence processes, signaling both ambition and discernment to evaluate opportunities on confirmed merits over speculative drawbacks.