I don’t think anyone enjoys thinking about their failures, but that doesn’t mean we shouldn’t since one of the oldest clichés in the book that happens to be true is that we learn from our mistakes.
There’s two failures I’ve been thinking about lately, two failures where I’m not sure that I, as yet, have learned anything, other than that sometimes things just don’t work out the way you want them to.
The failures are linked in my mind because they’re both publishing-related, though at different ends of the continuum. I’m going to cover one here and one in the next post.
For a brief time form 2007-2008, I had a semi-eponymous publishing imprint, TOW (The Original Warner) Books. I’d had some success with a parody of writing advice for Writer’s Digest Books, and my editor there convinced the parent company, F+W Publications that it would be worth trying to establish an imprint of literate, LOL humor.
My job would be to select, propose, and then editorially oversee the line. All of the difficult/messy bits of the publishing business – production, marketing, promotion, distribution, etc… - would be handled by the professionals at F+W. I was so confident in my abilities to identify quality that I agreed to compensation that paid a relatively small amount for the editing work, but reasonably large bonuses when titles reached specific sales levels. I joked with my editor about shopping for summer homes.
I wasn’t necessarily joking.
So what happened? Not enough. The books were…are tremendous.  I can still pick them off my shelf and get a laugh within seconds. They were well-designed, decently distributed, but barely promoted, like 99% of all books published these days. Most publishers are trying to catch lightning, but have to settle for lightning bugs. After eighteen months of lightning bugs coupled with a rapidly contracting economy, the initial enthusiasm at F+W was reduced to a trickle, then whatever is less than a trickle.
I barely earned enough to buy a personal rowboat, let alone a summer home. They never even officially put an end to it.
So what went wrong? Mostly, I misjudged the market for humor books. Rather, I didn’t misjudge it so much as delude myself into thinking there was an additional market that didn’t yet exist, a market for humor books that ask to be read as opposed to “looked at,” a market that extended beyond Stuff on My Cat  or stuff like Awkward Family Photos .
As it turns out, the market for humor books that demand to be read, rather than looked at began with Nora Ephron and ended with David Sedaris. Now we just have Sedaris.
My failure in this case was another old book, hubris. I figured that if I thought it was funny, so would enough other people. I still believe in my LOL radar, but the TOW Books releases fell in a forest with nobody in it because they were all too busy at the forest filled with pictures of cats covered in Post-its . (Truth be told, the cat pictures are pretty hilarious.)
This is one of those “if only” failures in my life. “If only” any one of a thousand different things happened, it would’ve been different, I would've become a bona fide job creator and I’d be spending my weekend at a Romney fundraiser with my Hamptons neighbors , but none of those onlys came about.
But even today, I wouldn’t do much differently. The whole point of establishing the imprint was to provide an alternative to Stuff on My Cat. Sure, hubris was at play, but isn’t hubris a necessary ingredient for risk, and isn’t risk a necessary ingredient for reward?
It’s rare that failure comes without regrets, but I’m learning that this might be one of those rare cases. Some really good books (if I do say so myself) exist that might otherwise not have seen the day. The books put a little bit of money in the pockets of some writers that I think deserved it. The experience of working with these talented writers made me in turn a better writer and editor.
Maybe we didn’t wind up at the Hamptons, but the journey was a pretty good time.
Part 1 
Part 2 
On occasion, I'll tweet about my failures @biblioracle.