We actually started last month. He finished his story before I did, and it took me 25 days to complete a 12k word story. (I did say I had a problem, didn't I?) I hated the story as I wrote it, and I hated the story when I finished. So, what was the point?
Glad to be done with the thing, I quickly retreated to my proper WIPs and basked in the sanity and coherency of the prose. Ah, the smooth narrative and the delightful dialogue were like soothing balms. Then it struck me:
When you see how bad your own writing can really be, you appreciate how well you write when you’re trying. You appreciate the trying.
The challenge is not about trying--trying to write a great, good, or even likeable story, or trying to come up with clever plots and indelible characters. I already know how to strive for precise words, better flow, coherent structure, strong voices, etc. I know how to endeavor to write well because I have, and after years of practice I know when I'm writing poorly.
The challenge is about doing. It is about setting aside inhibition. When I try my best, the final draft will be my best, to heck with how cringe-worthy it starts out. Right now, it's about writing now, and the more I do, the more I learn how best to approach it, how to work more efficiently and get better results. I second-guess a little less.