The characters literally combine to mean “lifting a chess piece (举棋), but not (不) being able to decide/settle (定) on where to place it.” The imagery is the core of its meaning.
The idiom `举棋不定` is deeply rooted in the cultural importance of board games like Go (围棋, wéiqí) and Chinese Chess (象棋, xiàngqí). In Chinese culture, these are not just games; they are seen as disciplines that cultivate strategic thinking, foresight, and patience. A single move can determine victory or defeat. Therefore, being `举棋不定` is more than just being a little hesitant. It carries a negative connotation, suggesting a lack of confidence, poor judgment, or an inability to handle pressure. In a culture that often values decisiveness (果断, guǒduàn) in leaders and respected individuals, chronic indecisiveness is viewed as a significant weakness. Compared to the English phrase “on the fence,” `举棋不定` is more active and critical. “On the fence” implies a passive state of neutrality. `举棋不定`, however, depicts someone who has already engaged with the decision (by “lifting the piece”) but is now frozen, holding up the game for themselves and others.
`举棋不定` is a common idiom used in both formal and informal contexts to describe a state of indecision.
The connotation is almost always negative or at least critical. It implies that the indecision is a problem that needs to be resolved.