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As populism is on the rise (and, so it seems, here to stay), judges are especially vulnerable to public criticism and political pressure. Their constitutional mandate is harder than ever to fulfill, as they must carry out their interpretative task regardless of these potentially overwhelming external influences. In other words, judges must keep exercising their legal authority in a thoughtful way. What does thoughtfulness require from judges? In this short note, I start from Hannah Arendt’s and Stuart Hampshire’s accounts of thoughtfulness (I.), accounts which can be found in excerpts of their respective works Responsibility and Judgment (for Arendt) and Innocence and Experience (for Hampshire), and which remain highly relevant in our populist time. I analyze what these two pieces – which I consider to be convergent and complementary – entail for judicial decision-making. Based on these authors’ insights, I claim that judges, in order to be thoughtful, must adopt an approach to judicial interpretation that fosters case-by-case assessment, independence, impartiality, and an ongoing questioning of the legitimacy of existing legal norms (II.). They must also overcome the obstacles to thoughtfulness created by the legal system (III.).