BOGOTA, Colombia — It’s been five months since the opposition lawmaker Juan Guaidó assumed the symbolic role of interim president of Venezuela, hoping to unseat the country’s strongman, Nicolás Maduro. Despite more than 50 countries recognizing Mr. Guaidó as Venezuela’s legitimate president, oil sanctions imposed by the United States, massive street protests, and the worst economic crisis in modern history, Mr. Maduro persists.

The staying power of Mr. Maduro’s embattled government has confounded the international community, academics, analysts and journalists. Call it a lack of negative imagination — the capacity to conceive of and prepare for worst-case scenarios. The inability to fathom the resilience of an authoritarian regime shows how politically naïve those in liberal democracies have become. Freedom and wealth give us strength, but it can also become a weakness. We become unprepared for the unthinkable and blindsided by events like the 9/11 terrorist attacks, the rise of Donald Trump, or the Brexit vote in Britain.

When the likelihood that Mr. Maduro could defy expectations and hold onto power for much longer is raised in meetings with p olicymakers in Washington or financiers in New York , it often incites anger or disbelief . I should know. In my work with Control Risks, a global risk management consultancy, we have raised the alarm for the last three and a half years that Mr. Maduro and his Chavista political movement can cling on to power longer than most people think. Mr. Maduro’s friends in Cuba, China, Russia and Turkey have helped him cling on. The West has consistently underestimated his determination and lack of scruples.

When I explain this to incredulous clients, I’m often met with uncomfortable silences or a battery of angry cou nterarguments. A journalist once wondered, half in jest, if my professional opinion was the result of being a closeted Chavista. People in democracies where logic, well-functioning institutions and strong civil societies prevail struggle to understand countries without those norms.