Abstract: This article describes the path and milestones of the Ukrainian advertising and marketing industry from embracing a fanatic belief in the primacy of creativity with complete disregard for the consequences of promoting gender discrimination to creating and adopting a progressive state- and self-regulation framework. Those who started the journey did not know how far the road would take them, nor were the results fully foreseeable, though some were hoped for. The focus was on the careful analysis of stakeholders, including the advertising professional community and consumers, and tailored initiatives targeting every separate group. Thus, engagement with professional associations, NGOs, gender studies experts, marketing professors and students, judges, lawyers, MPs, executive state agencies, media, the general population, international partners and organizations allowed achieving the goal in a eleven-year timeframe (2011–2021). Separately we will discuss arguments and counterarguments about regulation as well as four criteria for distinguishing sexist advertising. Our experience might be of interest to those who work on similar initiatives or from the anthropological point of view with interest in the cultural peculiarities that determined approaches to Ukrainian stakeholders, as well as an overall discussion of the ethics vs profits dilemma.