I still intend to finish up the second appendix and write an epilogue, and I have ideas ready for the sequel, but I need to get this out because I've been focusing on the flaws too much and hopefully a post mortem will be cathartic.
I think the biggest single problem with Shadows is that the main character, Dominic, is not compelling. Most of my other problems with it extend from that. In the original outline, Dominic was supposed to be the naive newcomer through whom some of the setting could be explored. He was going to slowly uncover the truth behind the other three principle characters (Vidre, Welexi, and Gaelwyn). Welexi would see him as an apprentice and later as a threat, Vidre would see him as a threat and annoyance and later an equal, while Gaelwyn would look to him for approval and eventually have to side with Welexi.
This all went more or less to plan and was basically fine. However, Dominic still wasn't interesting enough or compelling enough on his own.
Even now I have trouble articulating his story. He starts out as a street urchin, estranged from his family, and ... that's not enough. He doesn't have enough in the way of hopes and dreams, he has purposeless ambition, and though he displays agency it's just not enough because there's nothing behind it. It's not even that he's a shallow character really, it's that he's fumbling his way through this new realm of living, being dragged along behind it. His moments of actual action, like taking the lead on stepping in front of the duel with the Blood Bard, seem to happen because he thinks it's something he needs to do rather than because this comes from the core of his character.
If I had to rewrite it all, I would have made him a fanboy, a loyal adherent to Welexi who followed all of the news of the illustrati. I'd actually thought about that in the planning stages, but it felt too obvious and cloying. The character arc would have followed the same general path, but this time Dominic would have had his idealism stripped away from him. He would step up to the duel with the Blood Bard because he imagined that this was heroic. Welexi would still be threatened and we could still follow that arc. Perhaps that would have been too obvious, but I think it would have still been better. But that's not what I did.
I think Vidre worked well; she was complex and compelling, at least to me, and I didn't hear many complaints. I think of the four principle characters I understood her the best. She sat at a nice place in terms of proactivity and competence.
Welexi's reveal at the end of the second act was a little too fast and could have been foreshadowed better, but overall I don't have any other complaints. There was nothing structurally wrong with the character, he could have just been fleshed out a little better. I thought he was interesting despite that. The ambiguity of his character undercuts the end of the novel a bit. Maybe this is a case where ambiguity worked against making it compelling.
Gaelwyn was supposed to be a junkyard dog taken in and made presentable, which he did well enough. I think his relationship with Dominic could have been developed better, but Dominic could have been developed better, so maybe I should attribute it to that.
The plot gets a little muddled at the end of the second act (after the turn). It also gets a little muddled at the end of the Meriwall arc. It's entirely possible that there should have been an arc in between Meriwall and the Iron Kingdom, though I'm not sure what it would have been (and that's why it's not there). One comment that stuck with me was that they could have just sailed around the world, having adventures for ever and ever. I agree with that, and think that the period of stasis could have lasted longer.
I don't quite think that the introduction of the Harbingers was a mistake, but I'm not sure that they added much. If the conceit is that fame gives you power, then maybe the ability to bypass that undercuts what should have been a more full-throated meditation on what it means to be known by people, or the difference between stories and reality when people are motivated towards making a myth of themselves. If I'm going to toss a transformative artifact in there, it needs to have more of a point, more of a way of hitting at the central theme. Maybe I could argue that it's an extension of the thirst for becoming a legend? Again, it's something that I might not do if I had to do it over.
My other thought is that perhaps I should have started smaller. Dominic goes from unknown to being in the company of some of the most famous people in the world. But if I were starting smaller and ramping up more gradually, I would have needed Dominic to be compelling (see above) which he wasn't. And perhaps that wouldn't have worked in my favor either. In fact, it's entirely possible that the Corta subplot should have been cut from the beginning entirely. That subplot definitely should have had a better, more gripping resolution. (I think I was trying to mark the division between worlds, but I don't think it worked.)
The third act could also have been longer and more detailed. I'm not sure that would have improved anything as far as the larger points of the book.
Since I'm not trying to shit all over this thing that I spent six months working on, I thought the ending was satisfactory and pulled in enough elements from earlier that it closed some threads. The idea of winning by presenting a story still seems clever to me, which means that there's a good chance that it's actually clever.
It could have been better, more elaborate, more evocative. Some of the chapters didn't incubate long enough, especially at points where I was already feeling unhappy about the story.
I don't think that Shadows is the worst thing I'm written. I wish I could go back in time and do some things differently, but I wish that about most things I've written. I would actually go so far as to say that Shadows is good, though it would need serious work prior to publication. It's got issues, some of which I think I'll be able to avoid on future books or which I might have been able to see if I were more experienced. My biggest regret is definitely the character of Dominic, but that's also one of the hardest things to change in editing, short of rewriting the entire story.
I'll eventually get this novel edited into something that I'm more happy with, but it will probably take some time. Eventually my bad feelings about it will fade and I'll be able to take a more optimistic look at the work; right now my editing work is going slowly.