I either underestimate or overestimate my deadlines...There hasn't been a single time when I have stated deadline in a standup for a feature and finished it on that day...It's either days before deadline or mostly few days or even weeks past it😓

This is the reason its called estimate :)

There are ways to get better and more accurate at them, but time estimations are very difficult 😋 Don't feel bad.

Guesses are not easy to get. Add some buffer period to your ballpark and be done with it

Deadlines are dumb.

If it's to gauge work effort, then fine, as long as everyone gets an update on said deadline after each workday understanding that it's completely fluid and that it will shift over and over again as more discoveries are made along the way. The problem is that too many people will take that first estimate as concrete gospel. That's when they become stupid.

Furthermore, if a deadline is allowed to shift and be fluid, why do we call them deadlines because that's not what a deadline is at all.

In conclusion: Deadlines are dumb.