Answer: Repeal the exclusionary zoning laws in this country's most overpriced real estate markets that are making it so difficult for young people to purchase their first homes. In fact, the regressive zoning laws are artificially inflating the price of many older folks' homes, which is precisely what is allowing them in many cases to pursue the more creative, higher risk career paths.
According to his Wikipedia page, Tyler Cowen is a committed free-market ideologue who still believes in the "meritocracy myth" (also formerly known as the "American Dream").
Got news for Cowen, this country's economy has long moved on since the days back when he earned that Harvard PhD!
As a next semester reading assignment for Cowen, I'd like to suggest Thomas Piketty's book Capital in the Twenty-First Century.