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Does having an imaginary deadline really work for anyone ? All I've seen people do (myself included) is find a way to justify moving the deadline, questioning the authority of the deadline, the value in actually getting it done within the deadline and in the end stuff never happens, I'm not happy about having set a bad deadline and much worse missing it.

Unless its external, its more pain to ask it to be moved than to just slog it out and get it done, setting deadlines don't work.

For projects of personal interest, setting an imaginary deadline is the worst thing I did for my productivity and motivation. In a team setting, that has worked, but had very limited benefits and the drag on the team was really not worth it.

Is this a problem of having open ended side projects? At least for me, an open ended side projects are difficult to have a hard deadlines as there are no dependencies on the outcomes of your side projects.
I don't know how to interpret "open ended" in this context.

I see projects being in one of these 3 categories.

First, I know the end result, and I have done this before. I know what to focus on what not to, i have past experience to filter it out. I can predict how long it will take and slog it through to get stuff done with a deadline.

Second, I know the end result, just need to figure out how to get there. These tend to take longer than expected but they do get done. A deadline here would just mean, in most cases, me not being happy with the end result and dropping it or not having time enough to fit in the deadline.

Third, I don't know what the end result looks like. These are the stuff that just don't go anywhere. Setting a deadline here is just counter productive, expectations don't line up to reality, timelines are vague, direction is not clear. Deadlines only make this worse. Only thing I can imagine here is to set a timeout. Try to clarify and run small experiments. If nothing comes out of this in say 2 days, drop it.