Editor’s Note: Besides helping boomers prepare for a financially safe retirement, Making Sen$e contributor Lew Mandell has served as one of our far-flung economics correspondents, reporting from Singapore last fall on how the government uses incentives to encourage and discourage certain behavior. Mandell returns in that role now, filing his observations from his recent trip to Cuba.

With a long interest in economies that have transitioned from a command to a market-based system, Mandell considers himself lucky to have made it to one of the last command economies traveling with the recently reinstated “person-to-person” program that allows Americans to travel to Cuba with groups approved by the U.S. Treasury Department. What he saw was an economy transitioning to a more market-based model after Raul Castro took the helm from his brother Fidel...

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