Getting your Trinity Audio player ready... Regardless of age, when I talk to people about their financial lives, the word retirement usually comes up. If they are over 50, the question is: “Can I retire?” But if they are younger, it becomes, “Will I ever retire?” The difference has a lot to do with the luck of a generation. For Baby Boomers (1946–1964) and older Gen X-ers (1965–1980), the economic system has generally (not universally) worked pretty well.