That's the job but it can be one of the hardest parts of the job.
Then for the next project, you know the pushback you're going to receive so (perhaps unconsciously) you have this bias toward a lower estimate.
If you're not a regular employee the incentives are even worse. If one contractor tells you a week and the other tells you a month, which one will you hire? When you're billing for time and materials, and that's pretty normal, it hardly matters to the contractor if a deadline is missed because most clients know switching mid-project will only add to the delays.
Some really shit jobs would expect weekend work to make the difference but with this job market: f that!
I've given up on deadlines for projects; now we just have contributors work on small deliverables (that they usually define) that build toward the goal.
Not having deadlines makes learning about a new unknown unknown a lot less painful.