Most of the people don’t. They get stuck in an endless loop. The loop then slowly becomes expansive (an upgrade from a condo to a villa, a Ford to a Ferrari), but one keeps going.
One of the reasons that this happens is because of the economic system we live in (you need money for everything)— it is the fear that drives us to increase cash in bank for unfortunate situations (like a medical emergency). We start on the journey of building a secure future, we compromise on our present, and then we are caught in a loop.
For me, I have figured out that the way out of this is answering a simple question — “How much is enough” and “What is the right balance between playing it safe and taking enough risks”. If one can nail the calculation of risk taking, then one can get out of the cycle.