This chapter uses a quote by Barack Obama to outline how foreign relations in the twenty-first century, especially for great powers such as the United States, should be handled with deftness, caution, and prudence. It emphasizes the idea that people often take action without knowing the consequences. The authors highlight the need for wisdom, patience, and restraint in important political situations and argue that Obama’s diplomatic approach provides a good model when considering a new strategy to replace approaches that have proved ineffective, counterproductive, or disruptive to what remains of the international order Woodrow Wilson helped forge.