In his 50s, Michael Gates Gill had it all: a big house in the suburbs, a loving family, and a top job at an ad agency with a six-figure salary. By the time he turned 60, he had lost everything except his Ivy League education and his sense of entitlement. First, he was downsized at work. Next, an affair ended his 20-year marriage. Then, he was diagnosed with a slow-growing brain tumor, prognosis undetermined. Around the same time, his girlfriend gave birth to a son. Gill had no money, no health insurance, and no prospects.