Monica and Taylor chat with Maya Hope, currently a Product Manager at Square, about feelings of imposter syndrome while leading a team. Taylor and Maya reminisce on their time together at a startup and discuss whether or not getting into a selective college at 17 says anything about you in your 30s. We discuss how the idea of “should” is a trap, and how imposter syndrome can be a negative feedback loop as you seek out evidence proving you aren’t good enough. Maya shares how her imposter feelings have evolved throughout her career and how she no longer feels the need to overcompensate by picking up every menial task around the office. We also talk about how growth mindset may not be for everyone. Lastly, we wonder if question marks and smiley faces in emails actually reduce the clarity, or can we all just write emails in the way that feels most natural to us?

Maya is a product manager at Square, where she leads a team that is responsible for moving millions of dollars a day, instantly.