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Back in 1995, I was underemployed. I’d graduated from USC, was living with my fiancee in Orange County, and doing part-time work for a New Jersey-based marketing company, work which had nothing at all to do with my journalism degree. Then I applied for, and was offered, a $22,500/year job as an assistant editor at a small publishing house. I took it because I-we-needed the money and the benefits the job provided, and because it was something in journalism.

After a few months doing layout and copyediting, an editor in the magazine department noticed me and offered me a job in his area. It was a tough call, because I really liked the people I was working with on the book side, because I was learning a lot, and because I tend to hate change. Nevertheless, I took the job, because the increase in salary and autonomy were significant, and the magazine side of the operation looked like a lot of fun.

Just shy of two years later, I left the position to work full-time on Baseball Prospectus 1998. Although the company, and my boss specifically, had been patient with me on the 1997 book, they were less interested in allowing me the time it would take to help write and fully edit and lay out the new edition. While that was the proximate reason for my departure, there were others, most notably including a strained office environment brought on by differences in work processes and my own boredom with the subject matter. It was time to go, even though I wasn’t quite sure where I was going.

After temping for a while, I caught on at the University of California, Irvine, as a data-entry specialist and, eventually, trainer for an in-house software package. I liked the people, they were flexible with me on time, and supportive of my burgeoning efforts to be a sportswriter. On the other hand, the work was even less appealing, and I found myself investing less and less of myself into it. At the same time, I’d moved into a more significant role with BP, helping to push the website to a daily content schedule. In late 2001, I elected to leave UCI with an eye towards working on BP, essentially for free, full-time. It was my opinion then that the only way BP could cross over and become a going concern was for the site to become a daily destination with regular features, and the only way that was going to happen was for the site to have a full-time managing editor.

Now, that’s a snapshot of four major career decisions by one man in a span of about six years. My experience isn’t unique. Every person, in managing their career, balances a host of concerns in deciding what job to take, or to not take. In the cases above I was thinking of money, health care, my upcoming marriage, my long-term goals, my daily satisfaction with the work, with the people in the office. The only person who might have grasped all of those factors and how they balanced, other than myself, was Sophia.

Over the next two months, we’re going to do a lot of writing about these types of decisions, except that these are ones being made by talented baseball players. We’re going to speculate that this guy will go here because he wants the most money he can get, or the other guy will sign there because he’s from that team’s area. We’ll assume that an agent, rather than a player, is making the decision. We’ll note that one team’s manager had a free-agent star in the minors, or that a slugger has always hit well in a particular park. There’s no end to the number of rationales you’ll see to explain why these marriages will or will not happen.

We have no idea what we’re talking about. I don’t say that just as an informed outsider; I mean, none of us, no talking head, no beatwriter, no columnist, no analyst will have more than a general read on where 100-odd free agents will sign, because the decision these players are making is an intensely personal one that considers factors we cannot know. Baseball players are just like the rest of us; they have wives and children and friends and family. They like specific places, big cities or small towns. They like warm weather or cold, surfing or skiing, the change of seasons or none at all. They have friends scattered about the country, and perhaps more important, their girlfriends or spouses have family and friends scattered about the country. I lived in and around LA for nearly half of my life for no real reason other than that my wife’s parents were there. You think there are free agents without concerns such as that, or a half-dozen others?

Even the players themselves may not know how they’re going to sort through all of these factors. Consider the top prize in the market, one Carsten Charles Sabathia. Sabathia is 28 years old, an age by which I’d made three of the transitions discussed above. For Sabathia, though, this is the first time in his life that he’ll have the opportunity to more than negotiate a salary. He was 17 when the Indians selected him with the 20th overall pick of the 1998 draft, and now, a decade later, he’ll be able to choose his employer, his organization, the city in which he’ll work and, presumably, live and raise his family. He’s never had this choice, or any one like it before, and as much as we’ll write about how he’s from Northern California, and how the Yankees are likely to meet or exceed any offer, or how he must want to play for a winning organization, and boy, did he seem to enjoy hitting… I mean, let’s face it, we’re all just guessing. How a man sorts through the various factors in making this decision, how he balances the concerns of his career, his family, his preferences and, of course, money, is impossible for others to know.

It’s hard to relate a decision like Sabathia’s to the ones we make in our own lives because his seems so much easier. Clearly, the amount of money in play make the choices that Sabathia, or Mark Teixeira, or Ryan Dempster have to make easier in some ways, but they also define the terms a bit more clearly. You or I might leave thousands of dollars on the table in exchange for something else, or trade off other things for that cash; these guys are dealing in the tens of millions, and as popular-no, populist-as it is to hand-wave away that money on the margins, it’s different when it’s yours. How can you turn down a million or two million dollars a year just to live in a certain place, or work for a certain person?

The difference is in scale, not in kind. The career decisions we make are intensely personal ones, and our reasoning is our own, perhaps shared with a loved one or an agent, but not beyond. What we see from the outside is a fraction of the factors, and at that, perhaps not the most important ones at all. So as we head into the latest free-agent season, and the speculation starts, sit back and realize that, as much as we try, no one knows anything.