Sandberg describes a meeting where every woman besides herself sat at the side of the room rather than at the conference table. This moment woke Sandberg to the ways women choose to remain observers rather than participants at work—a decision Sandberg attributes to low self-esteem. On that note, she describes a speech she heard in college on imposter syndrome, or "feel[ing] undeserving and guilty" about earned recognition (28). The speech resonated with the women in the room, which Sandberg sees as a sign of a deeper problem:

We [women] consistently underestimate ourselves. Multiple studies in multiple industries show that women often judge their own performance as worse than it actually is, while men judge their own performance as better than it actually is…Even worse, when women evaluate themselves in front of other people or in stereotypically male domains, their underestimations can become even more pronounced(29–30).

Unfortunately, society as a whole tends to underestimate women as well; Sandberg notes, for instance, that the media often attributes women's success to external factors rather than their own skills or characteristics.

Sandberg explains that insecurity has affected her throughout her life, first in high school and then at Harvard, where she initially struggled to keep up. Even after settling in, however, she continued to feel out of place; she recounts a story about studying for a philosophy test with her roommate and her brother David, noting that while all three of them went on to earn As, David was the only one who correctly predicted he would in advance.