The first post if I started a weblog called 'Anonymous Writer'

Prologue: I can't come up with a better way to write this post. I started it with the title "feelings I'm ashamed to write about, because they make me sound like I don't understand how fortunate I am" but I can't spend the entire post apologizing for being in a really lucky position. This is what's been keeping me from writing more on here recently, I think. It's now been about two months where the full-time task hanging over my head is writing a novel based on the Anonymous Lawyer weblog I've been writing. I feel really fortunate to be able, for now, to write and not to have to go be a lawyer. But I've been scaring myself into feeling like that means I have no right to have any frustrations, or at least no right to write about them, because it'll seem like I'm ungrateful. But what that's meant is I don't write. And I miss not having the weblog as an outlet for me to sort out my feelings. The mere act of writing really does help make things clearer (and reader feedback helps sometimes too :), so I want you to pretend the rest of this post isn't really me. It's Anonymous Writer. Anonymous Writer is allowed to be honest even when Jeremy is afraid that being honest will get him a dozen e-mails that say he should be ashamed of himself for not realizing how fortunate he is.

Anonymous Writer

1. My boss needs to be fired. He lets me come in late, he lets me leave early, he doesn't stop me from spending hours doing things completely unrelated to work, and he gives me unlimited vacation days. He doesn't hold me to deadlines, he accepts lame excuses for why I don't get anything done, and he refuses to impose any sort of structure on the work day. He's pathetic. The problem is that I can't fire him because he's me. I'm a terrible boss. I came to the realization a few years ago that I'm consistently motivated more by trying to impress others than by anything inside of me, but didn't really believe that was completely true. It's completely true. To impress someone I respect and want to think highly of me, I will do anything, and I will do it quickly, and I will find the motivation somewhere. It'll just be there. It'll keep me up nights. It'll kick in, every time. Without that, it's like pulling teeth. I turn the Internet off and ten minutes later I turn it back on to check e-mail. I promise myself no food until I write another thousand words, and I eat anyway. I can't hold myself to anything. I need to get better at that, or get my editor to whip me with a belt or something. I'm a terrible boss. Two months and I still don't have a regular daily schedule. I make the excuse that writing is governed by the inspiration. I need to get over that crock of baloney, because I don't think it's really true. I'm just a bad boss. At least when I'm the employee. I suck at this part of being a writer, I really do.

2. What was awesome about law school, and gave me three years of weblog material, was that people cared. This was really something people cared about. There were emotions, there was drama, there were common experiences that actually mattered and had an impact on people. There was a seriousness of feeling. Things felt important. Same thing at the law firm as a summer associate, and probably even more so. Things really felt like they mattered, and there were people there who they mattered to. This made it easy to write stuff, frankly. It made it easy to find inspiration and see character and find stories. Things that seemed important were going on. There were reactions and confrontations and events. It felt relevant to write about it. It felt important. I had things I really wanted to say -- things I needed to say just to sort out the reality of the experience and figure out what was going on. What's really hard about this -- much much much more than I realized it would be -- is that when you're not in school and not at a job, it's really hard to find yourself around things that people are caring about, and to find things to write about. It's hard to even have things to say sometimes, because I'm not around people caring about things, I'm not seeing any drama or emotion or confrontation or even any experiences. I've been very, very, very deliberate about making enough plans with friends that I'm not lonely or bored. I've been good at that. Most days I have something to do with other people. Without that, I'd really be ready to shoot myself. But I thought that would be enough, and it hasn't been. Because while it's been really great to be able to hang out with people and go see shows and eat meals and do stuff like that, it hasn't put me in situations where people are really doing things that are important to them. And I know that most jobs aren't that important anyway, and that what a lot of my friends are doing all day while I'm trying to write is pretty boring and uninspiring. So it may not be any better. But it's something. There are other people. People with problems and stories. Things are happening. At the very least, it gives them stories to tell and things to think about. At best, it provides writing material. Nights like tonight, I convince myself that the best thing I could do would be to look for a part-time job -- any job where I'd be around people, probably -- for a couple of days a week, and the inspiration, the ideas, the new thoughts it would put in my head, it would all be more than worth the time it would take from the writing. And then I wake up the next morning and it feels like a stupid idea. But I know it's not, and I just need to do it. But then the boss part of me suddenly cares about my schedule and is like, "No, you're writing full-time, what the hell are you thinking about getting a stupid job for? Are you an idiot?" So I'm still trying to sort that out. But I need to do something, because it's really hard to write when there aren't new thoughts percolating through your head every day and new things to think about. I can only amuse myself for so long.

3. This relates to the previous point, but it's also hard to write when the feelings aren't fresh. What made Anonymous Lawyer resonate with people, I think -- and what made it compelling for me to write -- was that it was real. Not the stories necessarily, but the emotions behind them. The feelings were real. These were things I had to get out somewhere. That I felt compelled to write down. That I felt like I wanted to say. It was authentic. I really had something to say. But now that it's been a year since I was at a firm, it's hard to make it all seem so raw and fresh again. What I had to say, in a lot of ways I feel like I've said it. There are a lot of words on there. It's hard to make them seem fresh to me again, even though I know to a reader who hasn't read this stuff, it'll all seem fresh and new. It's hard to channel those emotions again, because it almost feels like a dream. How can anyone take the law firm so seriously? But people did. And it was scary. I felt real feelings. I had things to say. I worry a lot that I've lost that. That I no longer have anything to say. That I've written everything authentic that I have to write, and everything new I write is contrived and a little bit pointless, because it's just stuff in my head, motivated by the need to write this book instead of the need to say something. But then sometimes I wake up with a lot of inspiration and lots of new words to write, so then I forget about this worry. But not always.

4. Along those same lines, I worry about the transition from novel to weblog. The weblog has resonated with people and really works, I think. I worry I can't live up to that standard in the novel, and can't give the novel a reason to exist beyond the weblog. I'm trying very hard to make sure people who've read the weblog will like the novel -- it's not just a rehash of the same stuff. There's a plot, there are new characters, it's new words, there are things going on. But I also want people who haven't read the weblog to not be missing out on anything. I want to make sure everything about the weblog that's good is also good about the novel, plus more. Part of me is struggling with the question of what I'm trying to do with the novel. Is it just a novel, with a compelling story, interesting characters, and (hopefully) funny writing, or can it be more than that? Can it really say something about law firms and law school and what it all means and life and livelihoods and be something actually thought-provoking? Can I get people to read it not just for the story but for my voice? Can this be not just one of thousands of novels that come out every year but something really amazing? And I don't know if I can do that, or if that's too high a bar to set for what's basically the first novel-like thing I've written. I don't want to stop myself from writing a good novel because I'm trying to write a great one. But I also don't want to write merely an okay one if there's a chance to write something really extraordinary. And I don't really know what a great novel looks like, or what a bad novel looks like, or how to write a novel at all. So some days I feel like I'm faking it, sort of. Not really, but I've lived with this character and this material for so long that I sometimes forget what's good and what's shlock and what's actually going to make this a book worth writing, and a book worth reading.

5. Putting this in writing helps. If nothing else, just being able to write it reminds me I do have things to say, and thoughts going through my head, even if lately it's been hard to always remember that. I had my improv comedy class tonight and I felt profoundly uncreative. I start to worry sometimes that I'm losing whatever spark I might have had. That law school stole it, or that losing the pressure of trying to get a break, of trying to get my writing out there, of trying to get people to notice -- that losing that pressure took the spark with it, and I can't get it back. That I was funny and creative out of fear and out of anxiety about the future and out of this pressure to not end up at a job I hated, in a life I didn't want to live. And now that the fear is gone, maybe more is gone too. I haven't really convinced myself yet that I'm wrong about that, and it scares me. It scares me a lot. This is all really exciting, in the abstract, but sometimes a little bit frightening in the reality. Sometimes. Not always. Sometimes it's just really cool. :)