This article botanizes in the history of lexicography trying to connect the dots and get a deeper understanding of what is happening to the discipline in the framework of the Fourth Industrial Revolution. The objective is to suggest possible ways out of the present deadlock. History shows that a sudden change of the technological base, like the one we are now experiencing, suggests a total revolution of the discipline in all its major dimensions. In order to be successful, such a revolution requires a mental break with past traditions and habits. As a matter of example, the article focusses on a series of bilingual writing assistants developed by the Danish company Ordbogen A/S and the new challenges posed to lexicography by these and similar tools. It argues that these challenges cannot be solved by means of traditional user research which is retrospective as it unfolds in the framework of an old paradigm. As an alternative, and without excluding other types of user research, the article recommends disruptive thinking by means of brainstorm, immersion, and contemplation and provides some examples on how to proceed. Finally, it problematizes the incipient competition between human and artificial lexicographers and gives a brief account of a possible future redistribution of tasks.