Yes, and it’s a classic case of sunk cost fallacy.
Jon’s initial decision to send the Night’s Watch’s fleet to Hardhome does fit his overall military objectives – he wants to rescue the thousands of free folk at Hardhome, he doesn’t want them added to the army of the dead – but the risks are huge, in terms of ships, men, and officers.
Then when the expedition goes as bad as it could – half the ships lost in the storms, the wildlings unwilling to accept rescue after the slavers betrayed them, “dead things in the wood. dead things in the water” – Jon wants to commit hundreds if not a thousand men to an overland rescue mission, without any plan of how this expedition will accomplish what the second one failed to do.
And I think this is where GRRM’s thing about being a good leader vs. a good man comes into play. The heroic thing to do is ride in to save the day, but the right command decision is to cut your losses and preserve your resources when the army of the dead is bearing down on the Wall.