Shyster: Hardball

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

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

Craig Calcaterra

Craig is the author of the daily baseball (and other things) newsletter, Cup of Coffee. He writes about other things at He lives in New Albany, Ohio with his wife, two kids, and many cats.

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