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Cyberspace arrived with the promise of the availability of information without sufficient cautions regarding how this information might be managed or utilized. In the face of information overload, divisiveness prevails and ideology replaces reflectivity in guiding our ideas and behavior. Totalitarian, oppressive forces are on the rise, easily recognizable in our pressured, rigid, and unreflective political structures, but equally concerning in other institutions. Groups turn towards anxiety-reduction and lose touch with stated goals. Finding a common enemy can feel reassuring and discharges pent-up aggression but, as the reflective thought required for working through difficult problems recedes, anxiety increases, reflective capacities decrease, and the cycle continues. These difficulties are compounded in virtual forums, where pretense and obfuscation flourish even more easily than when we are confronted with the actualities of other persons. Reflectivity seems hard to come by, impeding the epistemic trust so crucial to making meaning together and solving mutual problems. How we encourage growth—and greater maturity and care—in those around us remains a challenge. A psychoanalytic lens may help us more effectively grapple with the complexities underlying ideological fervor and push back against totalitarianism in oppressive structures wherever we encounter it.