Objectively, he could drop out whenever he wants, but choice isn't always that easy. People get accustomed to their lifestyle, whether it's forced or not, enjoyable or stressful. He's connected to people who have expectations, there's social pressure, internal pressure, pressure from his employees. Many people in positions like that do drop out, but do they always make a clean break? I think the point was that it isn't only the choice that matters, the power and freedom that comes with money doesn't trump everything else that goes into a person's life. While they might bring a lot of benefits, it's not all good, and the side effects of being in a position of power often make a person more powerless than ever. Once you're playing on a higher level, the competition is fierce and the expectations are sky high. That can trap a person into a certain path, even if they seem to have the resources to do whatever they want. It often seems like the people at the highest levels of power are the least free.