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Explore the challenges and realities of working in information security through this thought-provoking conference talk. Gain insights into the pessimistic perspective often associated with the field, as Stefan Edwards shares his experiences and observations on being an "Eeyore" in the infosec industry. Delve into the reasons behind the cynical outlook prevalent among security professionals and learn how to navigate the complexities of the field while maintaining a balanced perspective. Discover strategies for addressing common frustrations, managing expectations, and finding motivation in a constantly evolving threat landscape. Whether you're a seasoned infosec professional or considering a career in the field, this talk offers valuable reflections on the mindset required to thrive in the challenging world of information security.