Theo Epstein held a news conference this afternoon about why he's leaving the Red Sox. His answers were kind of cryptic, but, frankly, I was riveted, and have been riveted by this story for the past three days.

One of my friends put this best in an e-mail I hope he doesn't mind me posting:

I think what I just can't get by with this story is that he gave up his
dream job. A lot of people our age are struggling with finding a job/career that they actually like. At some point in life, most people give up on their dream, and make either small or large concessions.... Theo actually got to be GM of the team he grew up rooting for. Theo became the model of someone who actually accomplished his dream of becoming a GM.... Now, they've offered him $4.5 million to do his dream job over the next three years.

And he's walking away. It's pretty hard to believe. He must have his reasons. There must be something pretty unbearable about the working relationships there. Or maybe it's just a perfect example of someone of our generation expecting their job to be TOO perfect. There's always going to be some problems with your job.

Part of me admires Theo for having the courage to walk away from this amazing position without a concrete plan as to what his next step is. On the other hand, if he can't be happy with his job, what hope is there for the rest of us?

I think that very well captures the essence of why this is a fascinating story to me. It relates to a lot of the stuff I've been thinking about and writing about over the past year, about my struggle to decide whether or not to take the law firm job, about looking for something that's more fulfilling than that, for me. And about whether it's fair to expect that much from your job. On the face of it, Theo Epstein had a dream job. But, like Bill Simmons wrote in the column I linked to yesterday, which remains the best piece of writing I've seen on this thing, sometimes the reality can never quite live up to the dream.

Look, maybe it's easier than I'm making it out to be. Maybe after three years as a GM, Theo wants something more -- the next step, team President, CEO, whatever is next in the hierarchy, and didn't want to be trapped in this role forever. Maybe. But I doubt it's that simple. I wrote back to my friend that I don't know if I'd call what Epstein is doing courageous. It's not courageous to pass up $4.5 million over three years to be GM of the Red Sox. No matter his difficulties with the job, I'm fairly sure there are worse jobs out there. Being GM of the Red Sox, even if you can't trust the people you work with, even if their philosophy isn't quite the same as yours, even if they're trying to run a profitable business while you're trying to win baseball games and sometimes those goals conflict -- I'm sure Theo Epstein wouldn't argue the claim that there are lots of jobs that are a lot worse.

But he's in an enviable position. At 31, he's been the GM of a World Series winner. I think it's probably safe to assume he has all sorts of opportunities at this point. He could probably write a book and it would do pretty well and he would make enough to live. He could go on the lecture circuit. He has value in the business world -- his success as a GM probably makes him valuable in a variety of corporate roles. Within baseball, most teams would probably love to have him in their front office. He could start a foundation and do charitable work. Some of these things might be worse than being the GM of the Red Sox. Some of them might be better.

But I think most of us, in Theo's position, would instead be paralyzed by the fear that we'd never have it as good as we have it right now. That quitting this job -- that passing up $4.5 million over three years to do the job you've been doing, and that you've always wanted to do -- and that you've proven yourself to be good at, and that's gotten you all sorts of benefits in terms of name recognition, popularity, and the platform and opportunities that go along with that -- would end up being a mistake we'd regret for the rest of our lives. What my friend is calling courage I'd rather call presence of mind -- the presence of mind to realize that the fear is probably more imagined than real, and that he does have these other opportunities. And that if there are things about the Red Sox job that weren't working for him, maybe there is another position out there that'll make him happier, and maybe it's worth it to take that risk, because the reward could be so high.

I'm about to make a parallel here. I bet this isn't the first time Theo Epstein has done this. Theo Epstein went to law school. I'll admit this is a little bit contrived, because Theo Epstein went to law school part-time while he was working for the San Diego Padres. But let's imagine the Theo Epstein from a half-dozen years ago, in a low-level job with the Padres. Let's imagine him in law school. Let's imagine him passing up a law firm job to keep working for the Padres. Here's how the standard argument might go:

"Theo, you have a great job offer. An unbelievable job offer. How can you walk away from it? Most people would kill for this job, and you're just walking away, not even with any certain alternatives, but just because you can't put 100% into it. What do you expect? It's a job. Deal with it."

I'm squeezing for this parallel, but I really think it's there, and it's crystal clear in my head. The same criticism that people level on law students who don't go to firms is how people can react to Theo Epstein leaving the Red Sox. And it's an even stronger claim when the job in question is GM of the Sox, as opposed to a law firm.

So where am I going with this? If Theo Epstein isn't afraid to pass up the Red Sox job, why are you afraid to pass up a law firm job? :) Okay, maybe I'm forcing this, and I know I'm not being absolutely articulate here, but maybe this makes sense to someone, I don't know.

Anyway... the transcript of the Epstein press conference is here. It's not terribly revealing, and it's largely cryptic. But one thing stood out for me:

Q: Was there anything that could have been done at all to you to stay?

In the end, no. In the end, we had a lot of honest talks during that last week and reflecting on ourselves and the organization and the job and whether it was right. And again, the way I look at it you have to be all in. You have to believe in every aspect of the job and the organization and your ability to stay and do the job the right way, with your whole heart and your whole soul. And in the end, it just wasn’t the right fit. It wasn’t right.

Q: When you met with us after the season, it seemed like your heart and soul was in it. What happened (since then)?

There was a process, leading up to the decision, during which we really turned the microscope on ourselves and on the organization, on relationships and because to do this, we all felt that to do this, you had to be all in. You had to really believe. And that process was very difficult. I think a lot of good came from that process. There were a lot of difficult discussions that probably should have happened a long time ago, but in the end, you asked what changed, the process revealed that I could not put my whole heart and soul into the job at this time.

I'm reading too much into this, but I have a story I want to tell, so let me try to get there. Looking at this from the perspective of Epstein's bosses, Larry Lucchino and Sox owner John Henry, this past week must have been miserable. Here's your 31-year-old General Manager -- who's done a great job, and who you desperately want to retain. And he's forcing you into these long discussions about your business, and about the plan going forward, and about your relationships... this isn't how business works normally, is it... we don't usually have the ability -- or the desire -- or the idealism -- to get our bosses to do this. But when you want more than just a job out of something... when you're looking for that passion that it's fairly obvious Theo was looking for, and somehow in the past few weeks, lost, for whatever reason... I'm sure he found himself searching... searching for how to make this decision and how to justify what he was feeling... and making this whole thing out to be a lot more meaningful and serious and tortured than his bosses would have liked, I'm guessing.

As he was saying at the press conference what I quoted, I immediately thought back to my software job in Texas. It was about six weeks in. I'd been hired for the marketing department, but there was a couple of months of training at the beginning, everyone all together, programmers, consultants, business and marketing... and we did some projects and assignments... and one of the assignments was to learn the company's Insurance Commission software, and how to program commission formulas into it so that it would spit out the right calculations. It wasn't really programming so much as a bit of a logic puzzle. I found the exercise sort of fun, and I was good at it. At the time the company needed consultants more than it needed marketing people.

As I recall, my supervisor mentioned to me, based on this exercise, that maybe I could do a consulting rotation instead of marketing. Being a software company, there was certainly a sense that software consulting was a more important piece of the business than marketing. And I remember having a very awkward conversation with my supervisor, trying to get a sense of how much of this was my choice, versus something they really wanted me to do. And feeling confused, because this was a month out of college, my first job, and I didn't know... I didn't know what the dynamic was supposed to be, and whether by passing this up I would be hurting myself in a real way, or what the right answer was... and wanting to lean on my supervisor as a friend who would be able to give me advice, and tell me what the right answer was, given the kinds of things I wanted to do and was good at. And it felt so important at the time. Like a critical moment, and I didn't want to bungle it.

And what I'm remembering is a very awkward and uncomfortable conversation with my supervisor, in a supply closet/hallway thing, where I wanted so much to be accommodating, but also wanted so much not to be a software consultant... I recall feeling like I ended up seeming like I was eight years old and incapable of actually having a grown-up conversation about this. I ended up not doing the consulting rotation and staying in the marketing department. I also probably ended up making my supervisor think I was a baby unfit for the employed world. But, anyway, that's the moment I thought of when I heard Epstein say that, and I hope, for his sake, that his conversations went better than mine did.