He wanted a vacation... and didn't get it. You and him went on this cruise with the sole goal to get to relax for once, and then literal pirates took over the ship and it's now your and his responsibility to stop them. Despite your internal insistence that Tim has got to have a plan, he doesn't. But he's charismatic and smart enough on the outside to convince you and everybody else that he does; internally he's bullshitting and making up everything as he goes.