Works best when your job throws uncontained work at you. Email, chat and meetings each spawn more of the same, and most of the day goes to managing the work instead of doing it. That describes most founders' weeks. Newport says this is the situation time blocking exists for. Without it, the overhead eats the day and the real work moves to the evening.
Fails when you try to run your whole life on it. Newport concedes the method is oppressive. The writer Oliver Burkeman said on a podcast that time blocking felt oppressive to him, and Newport answered on his own show by agreeing. A time-blocked day has no breathers, because you are always locked in to the current block. Run it on weekends and you burn out.
It also fails as a way to squeeze in more hours. If you keep working past the shutdown to finish the plan, Newport's read is that the plan was too ambitious or you lost focus during the day. The evening is not overflow.
His long-term answer is fewer things in flight. Newport would limit each person to two or three projects at once, keep a visible list of work nobody has started, and leave about 30 percent of the day as slack. With the load contained, a looser approach that follows your energy works fine. Until then, time blocking is how you keep your head above water.