In this episode, Dave and Jamison answer these questions: I seem to be very hot and cold about how I feel about my job. Some days I hate it and think about quitting, but other days, I feel it’s not that bad and can stick around a little longer. The reason for it seems to change depending on the day, but a lot of it seems to center around the people around me (i.e. developers who need me to Google for them, business people who don’t understand how to provide requirements), but sometimes I can’t tell whether it’s an attitude problem that will follow me anywhere or if it’s just time to leave. It’s a relatively small company, so I feel like I would be betraying my manager who has invested a lot in me if I decided to leave so suddenly. I’d like to give my manager a chance to address my concerns, but I’m afraid to sour our relationship if I come across as a complainer. I’m also not confident there’s any solutions to my current frustrations because it seems to be a company-wide issue. How do I make sense of all of what I’m feeling? I really like my company but their project management is atrocious, ad hoc, and “old school.” They’re not giving me privileges to configure Jira in ways that allow me to get stuff done. Is there an effective way to convince my CTO that I’m not going to screw up our secure systems or do I just need to find a new job?