In his fifties, 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 sixty, 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 twenty-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. One day as Gill sat in a Manhattan Starbucks with his last affordable luxury—a latté—brooding about his misfortune and quickly dwindling list of options, a 28-year-old Starbucks manager named Crystal Thompson approached him, half joking, to offer him a job.
