I am a people people pleaser.

Especially when it comes to deadlines. I struggle heavily with them. For example:

My boss: 'Will the app be done by Friday?'

Me: 'well some features won't be ready but overall yes.'

The truth: "No even if I work on it 24/7 there are just so many things in the background that are too technical to explain to my boss that it will be impossible for me to hit that deadline. It will most likely take over a month to be ready for beta testing...."

I just don't know how to deal with those kinds of questions. I don't want to say 'most likely over a month' because it makes me look like a bad dev but at the same time I know that that is way more realistic than 'it will be done by Friday'

The truth is: even if it just looks like 3 buttons to you, in reality I need to change thousands of lines of code to accomplish the expected goals...

P.S:

I wanted to write this rant for a long time. Now I am drunk. There will be a sober more ordered version of this rant.

Not more accurately tracking my hours worked with estimates, then wondering why I feel like I've worked so hard for seemingly so little monetary gain.

Feeling the need to drop a client who always wants the "beer rate" for LOTS of work. Problem is, it's still income I wouldn't otherwise have, I'm a "people pleaser", I hate to cut people loose when I know I can be of help to them, and I hate seeming rude. Anybody got any tips for me?