Why deadlines are usually stupid

Missing deadlines suck. However, I’ve never actually turned into a pumpkin when I’ve missed a deadline of any kind. Sure, I might get yelled at or feel badly about letting someone down. But usually, nothing worse ever happens. I say, “usually” because there are times when deadlines really do mean something — there’s a reason for the deadline and missing that deadline has defined and adverse consequences.
Most of the time, deadlines are date-driven. They are established through a calendar review and a “pin-the-tail-on-donkey” approach. Regardless of the domain in which the deadline is set, there’s usually no real rhyme or reason to a particular date being set as a deadline for something; it just usually “seems” like enough time for a particular action to be completed. Needless to say, I find that method of date-driven deadline setting to be stupid and, worse, arbitrary.
Deadlines should matter. The should be based upon a clear deliverable and an understanding if the roles and skills are available to satisfy the deliverable. If the roles and skills exist, then there should be some data available about the level of effort needed; that is, what are the tasks associated in meeting the deliverable and how long do those tasks take? Once all that data is collected, then and only then can a deadline be established. But, deadlines should have some impact, usually in the form of some adverse consequence for missing the deadline.
For example, when I work for someone, I do so with clear deliverables and deadlines to complete those deliverables. If I miss any deadline, the consequence is simple: I don’t get paid. It’s that simple; If I don’t meet the deliverable then I don’t get paid whatever the agreed price was for that deliverable. While things come up and there’s usually some allowance for slippage, the deadlines with which I typically agree are based upon my skills and knowledge about how long I take to accomplish associated tasks. I don’t put myself in a position to fail because I’m familiar with my capabilities and limitations.
When people/agencies just throw deadlines to a wall and hope they stick, they are creating a clear path of failure. So, the next time you agree to meet a deadline, ask yourself, “Is this deadline realistic based upon skills and history or is it stupid?” If it’s a stupid deadline, run like someone is trying to shoot you because in a very real way, you are being set up to fail.