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

Wes Sheppard tells the story of his own climb through IT and security, starting from a request to handle a web application firewall and ending in a chief information and intelligence officer role. He presents the rise as a deliberate pattern rather than luck: he kept taking on work beyond his job, and each time that work earned him a move into a higher role. He frames this as "failing upwards," meaning an engineer who is only adequate in the current role can still advance by quietly doing the next job.

The middle of the talk covers the mechanics he credits. He names counter-signaling, a bias for action, and cronyism, which he treats as an exclusive circle that can be entered through time and exposure. He also draws on several principles of influence such as reciprocity, social proof and likability. His approach has four phases: become employable, quietly start doing the next role's tasks without asking permission, get known by the peer group and its management, then state the intent to move and update your public profile to match.

He closes by stressing that the method needs a concrete goal, some background in the target role, and a willingness to be less than excellent in the current one. He points to social engineering resources, persuasion research and body-language reading as ways to build the needed skills. The takeaway for practitioners is that the advice rests on one person's experience and is offered as a light, humorous look at career progression in security.