Why does reassurance about my work never make me feel better?

You ask colleagues and managers if the work is good, they say yes, and the relief lasts about a minute before you need to ask again. The reassurance never really lands. That is because you are trying to fill an inside need with an outside supply. The doubt is not really about this report or that project. It is a deeper question about whether you are enough, and no amount of "it's fine" from someone else can answer it for long. That is why the tank drains so fast. You are pouring water into a cup with no bottom. Try, just once, to sit with the uncertainty instead of chasing the reassurance. Finish the work, decide for yourself whether it meets your own honest standard, and let that be the answer. Building your own judgment is slow, but it is the only source that does not run dry.