Shyster: Hardball

I've started a little writing project. This is the eleventh installment. Here's Part 1, Here's Part 2, Here's Part 3, Here's Part 4, Here's Part 5 , Here's Part 6, Here's Part 7 , Here's Part 8, Here's Part 9, and Here's Part 10.

My most optimistic plan for full-time writing had been to get something working by the fall of 2011. This was based just as much on the scarcity of opportunities -- there aren't a lot of full time baseball writing jobs out there -- as it was on the convenience of life.

Things like my legal career being stabilized enough to where, if I left it for something else, I could go back to it without having burned any bridges. Things like the kids finally being in school all day. Starting a part time writing job with NBC in April 2009 seemed like it would keep things squarely on that track.

In less than four months, however, I goosed it a little.

One night in late July, after a bit of bourbon, I wrote down all of the things I thought were working well with the NBC blog and all of the things I thought could be better. Then I slapped that into an email to multiple NBC people. At the end of it all I quite immodestly suggested that if I was working on the blog full time and wasn't distracted by my legal career, I could do more to make the good things happen.

I didn't hear anything for two days. I assumed during those two days that I had overstepped my bounds and pissed everyone off.  That's OK. Wouldn't have been the first time. Then I got this email from the guy in charge of everything:

From:
To:   Craig Calcaterra
Date:  Tue, Jul 28, 2009 at 7:48 PM
Subject: Re: Thoughts on CTB

They forwarded me the note you sent on Sunday.  I really agree with pretty much everything you said. What would it take to get you to do this full time? 

I want you to think about all that and see what it would take to make it work.

I tend not to notice the momentous moments in life as they're happening. I live them and carry on and only a little later do I realize that, hey, something pretty major happened back there. This was not one of those times.  My mind reeled. My heart raced. Adrenalin surged. I knew exactly what I had done. I knew exactly what the response meant. I knew that, at that moment, my life was about to change forever.

Everything I wanted to do at that moment -- respond immediately, scream from the tops of buildings -- crashed into everything I had learned about business and negotiation in the previous 14 years of my professional life. I almost had to handcuff myself to keep from writing back immediately and saying that they had me no matter what, pay me whatever they wanted.  I mean, how long had I been doing this for free? One cent more than whatever would keep me out of poverty was OK, right?

I calmed down.  After an appropriate time I responded and acted like a reasonable person, soberly weighing the risks of leaving my legal career against the rewards of living my dream.  It took a bit of time to get everything hammered out because that's just how that kind of stuff works, but we came to terms.  I worked my last day as a lawyer on November 27, 2009. When I left the building that day I didn't look back. Not even once.

On the morning of November 30 I woke up at 5:30 AM. I drank some coffee. I fed the children breakfast. I took a shower, shaved and got dressed.  I walked to the den and sat down in the same chair I'm sitting in as I type this, and I began to do the same thing I had been doing every morning for nearly three years: I read the baseball headlines. Then I wrote what I thought of them all.

But for the first time, it was my job to do so. For the first time since I was a teenager, I was doing exactly what I wanted to do with my life.  I was living the life I dreamed about over 20 years before.

And I'm still living it.


Head's up: there's gonna be an epilogue

Shyster: Circling the Bases

I've started a little writing project. This is the tenth installment. Here's Part 1, Here's Part 2, Here's Part 3, Here's Part 4, Here's Part 5 , Here's Part 6, Here's Part 7 , Here's Part 8 and Here's Part 9.

After a month of unemployment I interviewed with the Ohio Attorney General's office. The people there knew me from my law firm work, much of which brought my clients -- many of them unsavory -- into conflict with various state agencies.

My interviewers asked a lot of questions designed to determine if I was what, during those cases, I pretended to be, or if I was something else. Most of them seemed satisfied that circumstances and not character caused me to take unreasonable positions in contentious litigation. In this they gave me more benefit of the doubt than I had been willing to give myself.

One other topic came up in interviews: the baseball writing, which I had included as an item on my resume.  How serious was I, they asked? How much of a time commitment was it?  I wouldn't be doing it on company time which, at this job, would be taxpayer time, would I?  I downplayed the seriousness and commitment. Having never considered the idea that blogging from a state office computer would represent a misuse of public resources -- which is a misdemeanor in Ohio -- I paused and then said, no, I wouldn't be doing that. They offered me the job.

I began working in the AG's office in mid February. By late March, something strange was beginning to happen: I was beginning to like the law a little bit. Released from the billable hour and the need to manage insane clients, I actually started to warm back up to it. My colleagues and I sat around and discussed competing legal theories just like I imagined I would always be doing back when I was in law school but never really did in private practice. No one ever talked about the amount of attorney time being devoted to the case. Everyone wanted to win it and to win with their honor intact, but when the day was done, they went home to their families. Everyone was well-adjusted and had lives. It was almost enough to make a guy forget that he was making half of what he made back at the law firm.

I was still blogging, although my habits had changed. I made a point to write even more from home in the morning than I used to. Paranoid of breaking work rules and, by extension, laws, I never used a state computer or Internet connection to blog at the office. I brought my personal laptop and a mobile broadband card with me to work each day and would write a few posts during lunch. And, well, occasionally when I was supposed to be doing something else, but only when something fairly major was going on. It was a balance I could have maintained indefinitely if I had to.  But the balance was about to be thrown off.

In late March I got an email from Aaron Gleeman, who worked for the Rotoworld website which was owned by NBC. I had met Aaron once before and knew him in that way you know people on the Internet, but I didn't know him particularly well. NBC was launching a new baseball blog, he said. It was called Circling the Bases and would be part of a relaunch of NBCSports.com. Aaron and Matthew Pouliot of Rotoworld would be writing it, but they felt they needed a third person involved to round out the coverage. In Aaron's words:

It's funny, when we first started talking about the need/want to have a third person involved, the NBC folks told Matthew Pouliot and I to both come up with a short list once we got off the conference call with them. We hung up the phone and immediately IM'd each other with your name. It was like a moment from the world's most boring, least romantic comedy or something. Some of the higher-ups weren't familiar with you, but after reading your blog and doing some Googling several of them basically came back and said, "I think this Craig guy would be a good fit."

I began contributing a handful of posts each morning to the tune of a couple hundred bucks a week. Basically, taking what I would have written for ShysterBall anyway and putting it on the NBC site. It didn't alter my legal workflow any. It did, however, start to prey on my mind. I wasn't making a living, but I was writing professionally. For a major media company who was invested in smart, sharp baseball blogging. Everything I had ever wanted to do -- the dream I had as a kid but buried for years and which I thought would be the end of me when it resurfaced -- was within my grasp.

The only question was whether I could balance the legal career with the baseball writing long enough to where I could make the latter pay off before the former crashed to the ground.

Again.

Shyster: Reckoning

I've started a little writing project. This is the ninth installment. Here's Part 1, Here's Part 2, Here's Part 3, Here's Part 4, Here's Part 5 , Here's Part 6, Here's Part 7 and Here's Part 8.

On October 20, 2008 I was called to the managing partner's office. The conversation was quick.

Everyone likes you, Craig. You do good work when you're motivated, but you're not motivated. A law firm can afford to keep a nice guy like you around when things are going well, but things aren't going well. The firm needs to cut people. You're not going to make partner here, so you're one of the ones getting cut.You can have until the end of the year. We'll give a good recommendation to any potential employer. Your job between now and then is to hand off your cases and to find another job.

I knew on some level it was coming, so I didn't have much of a reaction. I think I even thanked my boss when he was done. I didn't feel much of anything for the rest of the day except maybe a small bit of relief if you can believe it. I had been worried for some time that I wasn't going to be able to reconcile my personal and professional lives. Now that had been taken care of for me. What lay ahead was harrowing, but I've always been better at dealing with adversity than anticipating it.

I left the office and got a drink. Then I drove up to the Ohio State campus, walked around for an hour or two and tried to remember how I perceived the world 17 years earlier when I first walked around the place. Nothing came of it so I went home.

After the kids were asleep I told my wife. I lied and told her that I was blindsided. I lied again and told her I knew that everything was going to be OK. How could I have any idea of that? The economy was in full collapse. People were being laid off by the thousands. Maybe I ruined us.

A sensible person would have taken that as a major wake up call. Would have realized that his pipe dream of being a writer derailed his legal career. Would have gladly traded any glimmer of hope that he could make a living doing what he loved for a steady paycheck doing what was necessary.  I've always been a sensible person, but in this case I made an exception.

In early November I was asked to move Shysterball to The Hardball Times website and did so at the end of the month.  I updated my resume and included the blogging on it alongside my other work experience. Maybe it would scare potential employers off, but I'd be damned if I was going to hide that part of my life any longer. I may have killed my legal career, but I wasn't going to kill the chance at having a writing career. Whoever took me next was going to take me for what I was, not something I pretended to be. Because we are what we pretend to be.

I didn't have a job yet when December 31st hit and began 2009 unemployed. I wrote my blog from home and hung out with the kids. When I was able to put the fear of being broke and maybe homeless out of my mind, I thought about how great it would be to do this all the time.

Shyster: ShysterBall

I've started a little writing project. This is the eighth installment. Here's Part 1, Here's Part 2, Here's Part 3, Here's Part 4, Here's Part 5 , Here's Part 6 and Here's Part 7.

It's the spring of 2007. I wake up at 5:30 AM. I never used to do this. I am not a morning person. But I am training myself to be one.  I just started drinking coffee at the age of 33.  I need it now. The baby wakes up by 6:30. Never any later. Sometimes earlier. It's my job to go to him when he wakes up, and it is a personal goal to have written three blog posts by the time he starts to stir.

I scan the baseball headlines. The games don't interest me as much as the stories around the games do.  The scandals. The human drama. The things that have enough of a connection to baseball to fit in what is nominally a baseball blog, but which have enough meat on their bones to where I can come up with an angle that justifies the exercise. There are hundreds of real baseball writers. I can't do what they do, because no one would care. But I can maybe do something that is different enough to where anyone who chooses to read my stuff will not have wasted their time.

There aren't many readers. Twenty. Then fifty one day. If I break 100 I am ecstatic, but I am happy with whoever shows up. Hmm. Half of today's readers were obviously looking for something else and quickly left. That's OK. Eventually more will show up.  Eventually they do.

They start coming in real numbers when Rob Neyer takes an interest. Does he remember that he liked what I had written for Bull five years earlier? Probably not. It wasn't very memorable. But I write something about racial politics in baseball that ESPN might not let him get away with, and he links it approvingly.  In an ESPN chat one day he says I'm his favorite baseball blogger. The traffic really starts pouring in then. I learn quickly to say what others can't or won't say for whatever reason. After all, I'm using a pseudonym -- Shyster -- so none of this can really hurt me. I want nothing more than to justify those readers' decision to give me their time. To keep them coming back.

By the summer I'm writing as many as six posts before the baby wakes up. Some are superficial. Some are deep. I'm learning, however, that the more you write, the more people want. It's not always about the unique takes, it's often about just being there and reliably updating so that readers always have something new. It's like working overnights back at the radio station: people just want a friendly voice sometimes. If you can make them laugh, all the better. If you can make them think occasionally you're way ahead of the game.

Soon those six posts before the baby wakes up turn into six before the baby wakes up and four at work before the day gets too busy. I'm still getting all my work done, though.  Surely this isn't going to turn into a distraction like Bull did. I'm smarter about things now. Writing shorter takes. And unlike then, I have a family now. Real responsibilities at work. I'm on the partnership track. I'm not going to blow all of that over writing, am I?

For the past four years I had gone out for drinks with coworkers several nights a week. I do it less now. I claim that it's because of family obligations, but it's usually because I have things I want to write. A book I want to read. I'm drifting away from my coworkers because of this. The esprit de corps of the gang is suffering because of it. I regret this a little because I like these people, but I can't do anything about it. Drinking and sharing legal war stories with my coworkers is important for a lot of reasons, but writing makes me happy. It's been a while since I've been happy.

It's September 2007. The head of the litigation department calls me in to his office. There is no real purpose for the conversation -- he says he just wants to talk -- but soon he begins talking about entropy. About how, if you don't add energy to a given system, it declines and degenerates. A legal career is that way, he says. How if you don't constantly work at it, everything eventually crumbles.  I know what he is telling me. I don't listen to him at all.

It's November 2007. I'm told that I'm not making partner this year. They just want to see one more year of solid production out of me. Which is what they said last year. They don't know that I'm writing a baseball blog every day. But they're not idiots either. They know my head is not in the game. They're giving me a chance. I know as soon as they give it to me that I'm not going to take it.  In the previous seven months I've found something I enjoy more. I have no pretensions that it could ever be a career. I just know that, unlike everything else in my life, it brings me joy.

It's early 2008.  I've dropped the pseudonym and blog under my own name. I'm not sure why. I won't get fired simply for having a blog, but I realize that I'm pushing it.

In June the Columbus Dispatch does a small story about me in a sidebar to an article about sabermetrics. They send a photographer to my office to take my picture. I'm sitting at my desk, legal books behind me, the glow of the laptop in front of me as I toss a baseball into the air.  Some partners in the firm thought it was great. No one said it was bad. Many, however, were silent. Silence among lawyers is unusual and ominous.

Later in the summer American Lawyer does a piece about me on their blog. "Lawyers with hobbies" or something like that. I realize that I've made a big mistake. I told the interviewer the truth about how much time the blog consumes. Anyone can read between the lines to see my priorities are out of whack.  I hear whispers that the firm brass is not pleased.

I know I should care. I know I should worry. I don't.  I'm getting several thousand page views a day now. I'm not making a dime, but for the first time I start to get a sense that I could make a career out of writing.  The only question is whether I can make that happen before I make a mess out of my career.