For many infosec professionals, a logical career move is to an incident response role; managing security incidents as well as the people working on them. The transition to red tape, bureaucracy, and human chaos can be baffling and very frustrating to the hacker mentality. This can lead to us to burn out, or in the worst case, fail at the job. Instead of discussing incident response methodology, this talk will cover ten essential ‘lessons learned’ about bridging the infosec world with the business world. Topics include triage, communication skills, risk assessment, building business relationships, and presenting our ideas and problems in a way that interest an organization. The lessons are corroborated with funny, sad, and surreal IR horror stories.