Answer to: How do I push back on an impossible scope?

My question is: how can I communicate this effectively to my boss, who is also the more experienced developer on the project? He does not understand there is an issue with the timeline. How are your timeline expectations so different? I would assume the two of you are sitting in the same technical meetings, hearing the same feature requests, and thinking about the timelines together. I totally believe that you could have way too much on your plate, but what's causing him to think you don't? Is he simply an optimist? Does he know you have extra tools that will make the process quicker? Is the "must have" list in his mind smaller than in your mind? Does he view the deadline as a moving target, and if you're only able to replicate 2-3 of the big features by EoY that's enough for him to consider it a success? Does he know company management better and is aware that under delivering on new features is still going to be seen as a win instead of a failure? Figuring out what's causing him to be less stressed about the timeline is step 1. It could be he knows more than he's telling you (about technical matters, expectations, etc). Or it could be he's actually just a pie-in-the-sky optimist promising the world and is setting y'all up to underdeliver (a first in software development lol). Once you've figured out why your expectations are so misaligned, then I'd say following Hilmar's advice about how to manage scope and delivery would be useful.