This episode explores the pitfalls of personal branding and advocates for building a reputation based on authentic contributions and character. Debbie Millman recalls the advent of personal branding and expresses her opposition to constructing oneself as a brand, arguing it leads to inauthenticity. Adam Grant supports this view, stating that personal branding prioritizes image over identity and can be perceived as self-absorbed, fake, or insecure. Mark Bolino's research reveals that while self-promotion might seem beneficial, it rarely translates to tangible career success and can backfire, especially for women and racial minorities. The discussion shifts to building a genuine reputation through a portfolio of work and sharing ideas rather than self-promotion. Chevy Cook's "failure resume" serves as an example of how honesty and vulnerability can foster trust and connection. The episode concludes by promoting the idea of "dual promotion," humor, and letting others speak on your behalf to build a strong reputation based on actions and values.