Shyster: How I Went From Practicing Law to Living My Dream

I’m often asked how I got a job writing about baseball for a living.  How I managed to turn a legal career and life in an office tower to blogging in my pajamas.  The people who ask me that do so in the same way that they might ask a magician how he guessed the card they picked.  As if there were some simple trick to it all that, were I so moved, I’d be willing to divulge.

I don’t have an answer for them.  There was a lot of luck involved. Some of that luck was the residue of design.  It wasn’t good design.  Indeed, looking back I’m struck by how reckless I was to make many of the decisions I made while crossing over from the real working world to however you’d describe the world in which I’m more or less paid to argue with people on the Internet all day.

I write a daily recap of the previous night’s events in baseball called “And That Happened.”  It doesn’t seek to explain all that much.  It merely sets forth what occurred and tries its best to place those events into some kind of understandable context.  That’s the best I can do with my career path as well.

I wrote it all up in late 2011. This is it. It’s long.



I spent eleven years defending crooked politicians and embezzlers.  Amoral and sometimes immoral corporations.  The idle rich and – worst of all – the spoiled children of the idle rich.  My unhappiness with my clients was only exceeded by just how unpleasant it was to do battle with the lawyers on the other side of the table.  And as all of that played out my anxieties about making partner and providing for a growing family were ever-present.

I needed an outlet of some kind, and the closest one was at the bar around the corner from the office where I would spent late afternoons and early evenings with my similarly disaffected colleagues, engaged in a reality-obfuscating revelry.  I was drinking a lot, probably too much, and there is no question that it was the highlight of my day for a few years. In the office I was miserable.  A procrastinator by nature, I’d tend to put off work until the deadlines started to loom.

During the down time I’d ask myself how I got here.

In late 2006 I was 33-years-old.  I had been practicing law since I was 25, having taken no breaks between college and law school.  I had a two-year-old daughter, a one-year-old son, a wife who had quit her job to raise them, a mortgage and all of the other trappings of the early 21st Century burgher lifestyle.  At no time, however, had I consciously planned any of it. Things just sort of happened while I wasn’t paying attention.  Law school?  Seems like the thing to do.  Marriage? Well, it is about time.  Babies?  How nice!  A house in the suburbs?  Seems sensible.  A BMW? Allow me my one indulgence.  All of it was pleasant enough.  None of it was the result of a plan, let alone a dream.

But I had a dream once. Years before. What had happened to it? Where did it go?

When I was a teenager I truly wanted to be a sportswriter. The first time I ever thought I could write about baseball for a living was in the spring of 1988.  My dad had met a sports reporter for the Parkersburg Sentinel and told him that his 14 year-old kid knew a lot about baseball.  The reporter, seeking an angle for a preseason article, asked me to write up my predictions for the coming season to compare to his own.

I spent a ton of time on mine, predicting not only the outcome of the pennant races, but postseason awards, random statistical events, and everything else I could think of.  I typed it all out on the Speedscript word processor of my Commodore 64 – it was 15 single-spaced pages – and presented it to him.  He had about a page and a half of handwritten notes with off-the-wall predictions like “Sam Horn will hit 50 Homers!”  He ended up not writing the piece, but I kept the predictions.  It was only Parkersburg, West Virginia and for all I know that guy was more frustrated political writer than he was sports reporter, but my predictions were better – and better-written – than the pro’s were.  After that I knew I could be a baseball writer if I set my mind to it.

And for a while I did.  Rather than just perusing Sports Illustrated I’d study it.  I got baseball books by the armful from the library.  I’d watch ballgames with the sound off, pretending I was in the press box constructing game stories of my own.  I stopped merely following my own rooting interests and did my best to understand what was going on with every team in the game.  Late in the summer of 1988 I went on a family vacation to New York.  While there I made my dad take me all the way up to 116th Street so I could have my picture taken in front of the Columbia School of Journalism, believing full well that if I did so I’d somehow find my way back there again someday.

And then I lost my way.

As I progressed through high school, girls, music, theater, drink and drugs started to overtake baseball and writing on my to-do list.  None of these vices — if they were vices — derailed me personally, even as they crowded out my journalistic ambitions.  Indeed, dwarfing all but the girls were late 1980s dreams of material possession and status which did more damage to me than any drug could ever hope to do.

I recall a strange creative writing teacher my senior year who ambushed us all with a writing project that doubled as an exercise in psychological analysis.  We were given different starting sentences each day from which we were to craft a story.  I took my narrative in an intentionally sardonic direction, never pretending to take it seriously.  For a week I wrote of human excess and despair, infusing it all with as black a humor as I could muster.

When the story was finished the teacher read portions of it to the class and used the teaching/psychological aide which had launched the exercise to tell me that my future held a well-appointed urban home filled with mahogany furniture, cutting edge electronics and top shelf liquor, but the absence of love and warmth. And I thought that sounded sublime.

Neither my SAT scores nor my college fund were good enough for the Ivy League.  I applied to and was accepted to Ohio State and began my studies there with no particular plan.  I never once visited the journalism school or even gave it a second thought.  I took the classes that interested me – political theory, English and anthropology – with no care whatsoever about what kind of job I’d have some day.

I got good grades.  I toyed with the notion of going to grad school and becoming, oh, I don’t know, a political science professor?  A primatologist?  To the extent writing entered the picture it was because I fancied myself a novelist of some sort.  Of course that was a ridiculous exercise in image shopping and nothing more.  I was convinced that if I could carry on like F. Scott Fitzgerald, Norman Mailer or Hunter S. Thompson it would somehow will me into being a writer, but I never really gave much thought to actually writing anything beyond the papers that got me those good grades.  All of which led me to the same place it leads most people with my particular blend of talent, disposition and lack of ambition:  law school.  Training ground for those who love mahogany furniture, top shelf liquor and cutting edge electronics.

I drifted in college, but I simply went to sleep once I hit law school.  I would make it to class, but I studied far less than most students.  Probably because law school, like high school, is a place where peer pressure reigns supreme and I was fairly immune to law school peer pressure.  I got married the summer before I enrolled at George Washington and I lived in Virginia, not the District, and as a result I didn’t do much socializing or anxiety sharing with the 1L crowd.

I’d go to class until about 3PM most days, bum around DuPont Circle until my wife and her friends got off work and then have a drink or two.  Afterwards we’d get back to our apartment for a late dinner, watch a little TV and go to bed.  I treated law school as a job with very low expectations.  I was bright enough to get Bs without studying.  Knowing that the ultimate plan was to get back to some mid-sized firm in Ohio rather than compete for jobs at the white shoe law firms in New York and Washington, the grades didn’t really matter to me.

I had a job lined up by Christmas of my 2L year.  It was so … easy.  And then I really went to sleep. For the better part of a decade.

The early years of my legal career were superficially successful.  I had parlayed my middling grades at a slightly above-average law school into a job at a litigation boutique of decent local renown.  The work was fairly top-end as far as these things go, and I was more or less well thought-of.  After a time, however, I came to be thought of as more savvy than traditionally talented, and a pattern began in which I was trusted with sensitive and even personal matters more than I was trusted with complicated and sophisticated legal assignments.

While colleagues handled the class action lawsuit, I handled the sexual harassment case involving the senior partner’s fraternity brother.  While they defended the corporation, I defended the son of that corporation’s CEO from charges arising out a weekend bar fight.  This didn’t much bother me as I am a voyeur at heart, and I found the often sordid underlying facts of my cases far more interesting than the underlying facts of real litigation.  I took the fact that I was tasked with these matters as a sign that I was well-liked and was considered trustworthy.  Every law firm has a fixer, and I was well on my way to becoming just that.

For a time I reveled in my clients’ greed, avarice, frailty, absurdity and loathsomeness, viewing it all as great theater and job security.  I bought a house and filled it with nice furniture, top shelf liquor and cutting edge electronics and didn’t think twice about it.  I traveled and ate well and bought expensive suits.  When the dotcom boom created a ridiculous chain reaction in escalating legal salaries across the country, I jumped from my litigation boutique to a larger shop for money that was downright silly.  And I convinced myself that I deserved every penny of it.

I continued my old work habits at the new firm – about 60% fixer work and 40% real lawyering – but that proved unsustainable.  The same big business dynamics which had led to crazy salary escalation in a two-horse Midwestern town had also led to a mindset among management that the salacious, incestuous and petty legal/political problems of a two-horse Midwestern town were not the sort of thing upon which a valuable legal practice was based.  When a new matter ripe for my fixing talents came my way, it was not enough for me to say that the client was the wastrel younger brother of the bank president who would be very grateful if I got his sibling out of a jam.  No, I had to fight the business development committee to take the matter on and God help me if I couldn’t swear that it would lead to $100,000 in billable hours for fiscal 2001.

This dynamic led to some unpleasantness in the form of real legal work.  As in, reviewing warehouses full of documents in some far-flung suburban office park to the tune of $300 an hour.
It was soul-killing stuff for an easily-bored guy with a short attention span like me and it led me to look elsewhere for fulfillment.

By complete happenstance that fulfillment was found — at least for a short period — in my long-abandoned dream of writing about sports.

Late in 2001 my friend shot me a column a notable national sports writer had put together.  The point: Barry Bonds was about to break Mark McGwire’s single season home run record and the writer was not at all pleased with it. The Roger Maris card was played. A lot of nostalgia and “back in my day” was thrown on top and it ended up being something of a half-baked column. My friend ended the email with “good point, huh?”

I disagreed with the notion.  While I drifted fairly far from baseball through the 1990s, in the previous three years I had become reacquainted and actually once again obsessed with the game via my exposure to Bill James, ESPN’s Rob Neyer and the sabermetric world.  While no analyst myself, I shot back a sabermetrically-informed and profanity-laced tirade to my friend in which I outlined all of the reasons why the writer was wrong.  I went on about how you can compare the olden days to modern times and put the accomplishments of each in context. About how you could separate the wheat from the chaff and, dear lord, you could not simply say things were better when you were a boy, because brother, they were demonstrably not.

My friend forwarded my rant to a friend of his who was launching a webzine, called “Bull Magazine.” That guy asked me if I could clean up that rant for publication.  I did so.  And then I wrote some more.  By the spring of 2002 I had a weekly column up that started to gain a bit of notice.

I don’t know what kind of traffic the place did, but my little bits began to get linked by some of the websites I frequented while trying to kill time between document review jags.  Places like Baseball Think Factory (then known as Baseball Primer) chief among them.  The twin highlights of my run at “Bull” were receiving emails from Neyer and from Keith Law, who had just been plucked from Baseball Prospectus to help run the Toronto Blue Jays.  They seemed to like my stuff.  It made my year.  And it almost – almost – caused me to come to terms with the fact that I was finally, after all of these years, doing something that I wanted to be doing, even if it was then only a hobby.

But before I could do that, reality intruded.

In hindsight I would have crashed and burned at the document review law firm no matter what had happened, but at the time it seemed pretty clear that Bull had done me in.

It was March 2003 and I was called into the managing partner’s office.  He never mentioned the baseball writing – and I’m rather doubtful that he even knew about it – but he told me that I was obviously distracted and no longer productive. He said he wasn’t firing me as such, but it was clear that I had no future there. They’d give me a more than reasonable amount of time to find something and they’d tell anyone who asked that I was leaving on my own accord.  It was all very polite.

And really, given the good job market at the time, it wasn’t all that stressful.  I knew that with my experience – not so much to where a potential employer needed to decide if I was partnership material immediately but not so little that I’d need to be trained – I could find another job fairly easily. And within two weeks I did.  At a firm across the street.

The interview was a breeze.  Three years earlier while working at the fixer firm I had represented the hiring partner and his wife, handling some ugliness with a home contractor. It was a favor to my old boss who was the hiring partner’s golf buddy.  While that was going on the hiring partner — the man who was considering whether or not to give me a job — had been arrested for soliciting a prostitute in a grocery store parking lot at 9AM on a Tuesday morning and the wife had cried on my shoulder about it.  That I hadn’t blabbed about that all over town probably sealed the deal for me.  The hiring partner knew he could trust me.  And unlike the last place, the hiring partner worked for a firm where fixers were still highly valued. I got the job.

I took a month off before I started work there and took a cross-country road trip. While on that trip I found out that my wife was pregnant with our daughter. That obviously changed the game for me. It changed the trip too from one of aimlessness to one of self-discovery. By the time I got back I thought I had found some contentment and new resolve to make my legal career work.  And I worked at it for a while. A pretty good while, actually.

Motivated by fatherhood and the knowledge that this was my last shot to make something of myself as a lawyer, I worked hard. I shut down my baseball column at Bull. I worked long hours and worked difficult cases. I mentored law students and young lawyers and did my best to be reliable if not indispensable to the partners and the clients. I billed a ton of hours and settled in for what I thought would be a decade or two of keeping my head down and defining what middle age would look like.

But something happened as I delved back into the fixer work. Rather than experience a voyeuristic thrill from the foibles and scandals of my often noteworthy clients and their often newsworthy cases, I began to feel something else. Dread. Loathing. For my cases, my clients and eventually for myself. Maybe it was just because I was older or maybe fatherhood had changed me, but I couldn’t just sit back and laugh and mock like I had before. Bad people were doing bad things, quite often my job was to either defend or facilitate that, and I started to develop a pretty major problem with it.

Not that this led to some principled stand. I never made one. Instead, I internalized my discontent and dealt with it in other, less-than-healthy ways.  There are a million stories about this period in my life that I may tell one day — maybe here — but the upshot is that I began drinking more and began going out with coworkers too much, many of whom felt much the same way I did about our jobs and our place in the world. I’d unconsciously slow down work on cases I hated and overcompensate on cases I found acceptable. Which, however noble I wanted to pretend it was, was me not doing what I was paid to do.

All of this came to a head at the end of 2006. I had spent most of that year and the year before helping defend an embezzlement and public corruption case which was fairly big news here in Ohio.  I threw myself into it with abandon. I got close — maybe too close — to my client.  I lived it and breathed it.  At the end of it all I wasn’t sure who was right and who was wrong and whether my client deserved all that time in jail he got even though, in all honesty, the evidence required that he go there.  Despite all of that I still think to this very day that the people who led the mobs after my client were every bit as misguided and potentially corrupt as my client was himself. Though I myself never crossed any lines, I still feel like I suffered a complete loss of ethical and moral gravity as a result of the experience.

My client went to jail in November. Despite this outcome I received considerable praise from my firm about how hard I worked (i.e. how many hours I billed) and how dedicated I was (i.e. how many hours I billed).  I was told that if I had one more good year I’d make partner.  Despite this, I was basically numb through the end of March.

One Saturday in April of 2007 I decided that I needed something positive in my life. I needed to get back that feeling that I had five years previously when, on occasion, I wrote about baseball and, on occasion, someone said that they liked it and that it was good.  I sat down at my computer and opened up a Blogspot blog about legal issues that I had erratically maintained. It was called Shyster.

I deleted the legal posts, changed its name to Shysterball and put up a post about baseball. A few days later I put up another.  I thought it would great if a handful of people read it.  Anything else would be gravy.

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.

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.

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 is 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 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.

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:    Rick Cordella
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.

Ever since I began writing for a living, I’ve received emails from people offering me encouraging words. More common, however, are emails from people asking me if I have any advice for them. But even now I can’t quite say why it worked out the way it did. I can’t, as I am so often asked to do, give anyone any pointers. While it unfolded in somewhat orderly fashion in these posts I wrote over the past month or so, it felt like anything but orderly as it was happening. All I can say is that a writer writes, as the old expression goes, and I made a point to keep writing.

The key, though, is that at a couple of times in that process I stumbled over some good luck.  Better writers than I never get a chance to make a living writing and it’s not for lack of skill or lack of effort. It’s just for lack of the good fortune I happened upon. Maybe it’s silly, but I occasionally have something akin to survivor’s guilt over the fact that I’ve been able to make this my career while those better writers did not or, as of yet, have not.

I also sometimes wonder if I have cost myself something for going so hard after what I wanted.

My marriage ended in the fall of 2011.  I’m not going to suggest that my writing was the cause of that. Anyone who knows what actually happened knows that’s not the case.  But at the same time, every action has a reaction. People are creatures of habit and routine.  Who’s to say that my refusal to be content with my professional life as a lawyer didn’t upset the expectations of others? Who’s to say that in doing what I did with my life, I didn’t throw off my marriage’s equilibrium, even if that equilibrium was ultimately unhealthy and unsustainable? Maybe my soon-to-be-ex-wife had settled on a world view in which I would go downtown and fight with other lawyers all day for the next 30 years, and my short-circuiting that was something she simply couldn’t deal with anymore. Maybe my search for meaning and fulfillment spurred a corresponding one on her part and it simply wasn’t compatible with us staying together.  I have no idea. You have to ask her, I suppose.

The point of all of this is that, even though I laid all of this out as the straightforward narrative of a boy who made his childhood dream come true, nothing in life is so simple.  There are no definitive paths. There are no definitive beginnings. There are no definitive ends until the day we die. I’m doing this now. I wasn’t doing it before. I may be doing something else later. As all of that happens, other things happen. People come into your life and then leave. Others come into your life after that and, hopefully, stay. Those dreams you had once no longer hold currency. New ones crop up. No clear narrative of anyone’s life can be written until they’re dead and gone.

But what I’ve written over these past couple of months captures a chunk of it. An important chunk of it and one that will always be with me. And no matter where else life takes me, I will be able to draw on these experiences. To look back and say:

You once dreamed something big and made it happen.  You once had big problems and overcame them.  You once took risks that seemed unreasonable, but survived them.  There is nothing you put your mind to that, with time, effort, perseverance and a little luck, you can’t accomplish. And even if that luck doesn’t come, you will be able to look yourself in the mirror with pride for having made the effort.


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.

4 thoughts on “Shyster: How I Went From Practicing Law to Living My Dream

  1. I just read this again and went to reply……..and saw that I already had. Same sentiment.

  2. Thank you for taking the time to publish this information very useful!

  3. Just read this for the first time today after following you and reading your work for years. Hit me like a ton of bricks. I had the same dream as you. Even did it for a while in and right after college. Replace “legal industry” with “tech industry” and it felt like I was reading my own life story (albeit better written.) Thanks for the push, Craig.

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