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Explore a candid and humorous conference talk that delves into one cybersecurity professional's unexpected journey from sysadmin to CSO. Discover how embracing weaknesses and leveraging opportunities can lead to career advancement in the cybersecurity field. Learn from Wes Sheppard's experiences as he shares his unconventional path through various roles, including sysadmin, engineer, architect, and infosec officer. Gain insights into managing imposter syndrome, adapting to new challenges, and finding success in cybersecurity leadership positions. Understand how recognizing limitations and seizing opportunities for growth can propel your career forward, even when feeling underqualified.