Travel for less by snapping up a stranger’s vacation – but flexibility is key

After Christmas in 1985, Janine O’Leary Cobb began typing away on a MacBook that she and her husband, Jack, had gifted their children, using it to write an eight-page letter about menopause. She printed it off, stapled the pages together and sent copies to about 10 friends in different parts of the country. At that time, menopause was rarely discussed, even among friends, nor was it well understood. It was the sheer lack of available resources, as well as her own difficult personal struggle with menopause and the resulting depression, that motivated Ms. O’Leary Cobb to research and write...