Tom of Finland was a pioneering gay artist who also had a successful career in advertising. This document outlines five lessons modern creatives can learn from his career: 1) Pessimists don't win while pain and unhappiness can drive creative work; 2) Tom's artwork promoted safe sex during the AIDS crisis showing reason can outweigh passion; 3) Counter-culture respects the past while looking to the future; 4) Tom depicted masculine, powerful gay men which helped shape self-identity and soften stereotypes; 5) Changing how people see themselves can change how they are seen by society.