The anticipated retirement of tens of thousands of baby boomers will create an unprecedented opportunity to move significant numbers of people into career-track jobs at family-supporting incomes. Major industries, from health care and construction to automotive repair, will soon face deep shortages of workers as a result of projected growth and boomer retirements. Fortunately, many of these jobs have relatively low barriers to entry and could be filled by out-of-work young people. To achieve this result, the city government should convene employers and educators to determine how best to create paths of upward mobility in these fields.