You often read that Obama was too cautious in the size of his stimulus, making it too small (for example here). But really in this context the word cautious should be in quotation marks.
Having a smaller stimulus may have been what seemed cautious to many, or what was considered cautious by Washington conventional wisdom, but it was actually much riskier politically for Obama and the Democrats – and for the country.
The truly cautious thing was actually doing the opposite -- erring on the side of making the stimulus too big (assuming you could pass a bigger one).
Making the stimulus substantially bigger than the estimated expected amount needed was the cautious thing. Making it much smaller was the "cautious" thing.