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In the early days of electronic computing, using a computer system involved navigating through the complexity of the system, keeping in mind its particularities while trying to access its potential. Much effort has gone into making that experience smoother and easier. In the era of time-sharing systems, a number of strategies were developed to accommodate the user in this new environment. One was the bundling of frequently occurring small sequences of commands under a short mnemonic that could be invoked; another was completion, the suggestion of possible completions of a command. Using the concept of "cognitive debt" (coined by J. Rohrhuber in the context of the PROGRAMme project led by L. De Mol), I will explore how both strategies manage and recalibrate cognitive debt in these timesharing systems, and follow how these strategies evolved later on in other systems, from GUIs to LLMs.