In recent years, fire services in Mediterranean Europe have been overwhelmed by extreme wildfire behavior. As a consequence, fire management has moved to defensive strategies with a focus only on the known risks (the fear trap). In this region, wildfires can change rapidly, increasing the uncertainty and causing complex operational scenarios that impact society right from the initial hours. To address this challenge, proactive approaches are an alternative to defensive and reactive strategies. We propose a methodology that integrates the uncertainty of decisions and the cost of each opportunity into the strategic decision-making process. The methodology takes into account values such as fire-fighting safety, organizational resilience, landscape resilience, and social values. Details of the methods and principles used to develop and implement a creative decision-making process that empower the fireline are provided. A tool that segregates the landscape into polygons of fire potential and defines the connectivity between those polygons is used. Two examples of operational implementation of this methodology are presented (2014 Tivissa Fire and 2015 Odena Fire). These methods facilitate the analysis of possible scenarios of resolution and the costs of the opportunities that help build resilient emergency response systems and prevent their collapse. Moreover, they help explain the risk to society and involve citizens in the decision-making process. These methods are based on the experience and lessons learned by European incident commanders, managers, and researchers collected during the last decade.