Taking just one step too far

An engineering manager reflects on a recurring pattern in his career: pushing just one step too far in workplace situations. Through three personal anecdotes — criticizing a new CEO's responses, over-requesting access to vacationing engineers during a job interview, and fighting over a $75 team budget — he argues that deliberately testing limits, even when uncomfortable, is a valuable learning strategy. His core thesis: the discomfort of occasionally overstepping teaches you where real boundaries lie, and the outcomes of pushing tend to outweigh the costs of staying silent. He also shares a practical tactic of preemptively disclosing his tendency to overstep as a social buffer.