Working in Infosec is a fascinating and rewarding career like no other. However, despite news stating there is a shortage of skills in the industry, competition is high and gaining the skills and experience to succeed is challenging. This talk covers not only technical demonstrations which explore penetration testing, but questions the idea of red-teaming altogether. Follow along Dave's global journey about breaking into the infosec industry, with insights from taking down Russian criminals with the RIPE NCC, chasing a security internship at Google, and the countless challenges and considerations before finally landing a job as a Security Consultant.