Failing Upwards: How to Rise in Cybersecurity by finding (and exploiting) your weaknesses

The talk starts from the observation that merit alone rarely earns a promotion into management, because managers have little incentive to move a strong performer out of a role they are good at. The speaker separates "failing upwards" from simply surviving setbacks and presents it as a deliberate career strategy that depends on contrast: showing the gap between where you are and where you want to be.

Much of the talk is a personal account. The speaker moves from a help desk job in Tokyo through cloud administration to a platform engineering role in the Netherlands, where, without being asked, they designed a security program from scratch. A new CISO later folded that work into an information security officer role, which became the first step into leadership. The speaker ties the pattern to social-influence ideas: counter-signaling, a bias for action, reciprocity, social proof and likeability. Trust inside a leadership circle is framed as a function of time and exposure, and the speaker argues that small, low-visibility contributions build that exposure.

The proposed method has three phases. First, ease off overachieving and immerse yourself in management culture through meetups and conferences. Second, quietly take on tasks that belong to the next role while still meeting current goals. Third, once accepted, join meetings you were not invited to and openly state your intent, accepting that the answer may be no and that you may need to look elsewhere. The speaker stresses that the approach takes months, suits in-house moves better than switching fields, and carries real risk to one's job. Practical takeaways include building comfort with awkward social moves gradually.