During the Revolutionary War, Washington’s army was positioned outside of Boston, which was occupied by the British. As explained in David McCullough’s book 1776, George Washington was facing troubles in terms of money, gun powder, guns, and troop readiness and numbers. Winter was coming, and some of the soldiers’ enlistments were ending, leaving the need to convince soldiers to reenlist or to be replaced by new recruits.
Washington, lamenting that he did not attack Boston earlier, at one point, recounted that if he had known what he was getting into he would not have accepted the command. He said:
“I have often thought how much happier I should have been if, instead of accepting of a command under such circumstances, I had taken my musket upon my shoulders and entered the ranks, or, if I could have justified the measure to posterity, and my own conscience, had retired to the back country, and lived in a wigwam.”
Ultimately, Washington secured Dorchester Heights which gave him a superior position over Boston and the British. This resulted in the British withdrawing from Boston.
Many undertakings do not rise to the level that war entails. However, doubts are common when facing issues not for seen at the beginning, no matter the endeavor.