In terms of quitting and/or level of confidence in decision making, I'd recommend Annie Duke's "Thinking in Bets" and "Quit". Coincidentally (?), Duke's "Quit"

In terms of quitting and/or level of confidence in decision making, I'd recommend Annie Duke's "Thinking in Bets" and "Quit". Coincidentally (?), Duke's "Quit" discusses the importance of having a "board of directors" you can go to get objective and critical feedback from. Often, this could be peers / team, but in a work setting - which we often have little control - the quality is going to depend on culture. Truth Seeking > Group Thinking https://www.annieduke.com/books/ https://www.annieduke.com/books/ p.s. I recently picked up "How to Decide" but haven't read it yet. At this point I hesitate to recommend it, but given the other two I'm very optimistic.