In this episode, Dave and Jamison answer these questions: I was hired at a medium sized company as a staff level IC a few months back and a big reason I accepted the job was because I would be reporting directly to the CTO. I took a significant paycut in exchange for the opportunity to learn and grow directly under this leader, as this is a career path I am interested in. Three months later and without any heads up, I was reassigned to a different manger one rung lower in the org chart. One month after that, my new manager abruptly left the company. Still don’t know why. I was then reassigned to a leaf-node manager and I am now several hops removed from the CTO. So far I haven’t said much because rocking the boat too early in a new gig has gone poorly for me in the past. In hindsight this was probably a mistake but I’m afraid I missed the opportunity to say “hey now, wait a second…”. I don’t want to hurt this current manager’s feelings by telling them I don’t want to report to them, but also I am now both severely underpaid and reporting to someone who is technically at a lower career level than I am. What do? I’m a manager in a company which I joined after college. I’ve been here for 16 years. We have grown to 180 employees but still work like a startup in many senses, like talking multiple responsibilities. So although I manage a team I’m still hands in the code at least 50% of the time. I know most of tech stack and services but am jack of all master of none type. Recently, management has been pushing me to take more technical responsibility. I want to do that, but it is challenging and takes more time. My CTO is super fast and churns out CODE like a machine and I feel much slower than them. The work is pretty decent and challenging. I get to work on new stuff but have gotten comfortable here. When I think of looking for a change and look at the expectations from other companies they are technically challenging. I worry I have missed out on learning new things by staying so long at one place. What should I do, stay or move on? I haven’t interviewed for a new job in 11 years, so that’s another fear I have.