Due to Poor Planning

How long should you pound away at a story before setting it aside?

I thought this new MS was going to be great. It had some great romantic scenes, some action, some coming-of-age, and, to be honest, I have some epic scenes planned for the sequels. If I ever get to the sequels. I can't make the first book - and we all know that if there is no first book, there is no sequel - work.

There are too many plot holes. Too many characters that won't cooperate. Too much of the world-building left unbuilt. All of it laughing at me because I can't form a coherent story around it. It's bothersome.

I feel like I have two choices:

1. Set it aside and work on something else. Anything else, to regain my sanity. Something I can enjoy.
2. Start writing...even though I don't have a plan. I told myself I wouldn't do it. I told myself that this time I would outline my face off before beginning.

But maybe that was my problem. I've outlined my heart out. Maybe I can't connect with a story until I write it, outline or no outline. With my other books - NaNo's excluded - I've reached the 2/3 marker before finding myself in a hopeless plot tangle that required weeks of reevaluation and outlining. Maybe that's just how I write. Maybe I can't find the story until I write it.

It scares me, the prospect of not being an outliner. I always thought I was. I'm a very analytical person, so I figured, "Of course I'm an outliner at heart! I'm just a panster due to poor planning!" But maybe I'm a panster after all. And as daunting as the prospect of the outlining agony 2/3 of the way through, anything is better than the outlining torture I'm putting myself through now. At least when I'm 2/3 of the way through, I'm emotionally connected to the story.

Seems I've talked myself into an answer. If I can find the guts to jump off the cliff of outlining into the unknown abyss.