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Dear Bill Simmons: Goodbye Forever

Dear Bill Simmons:

I’m not sure how much longer I can write these letters to you every week. I’m running out of stuff to talk about. In fact, that’s what I wrote about last week, that I was running out of ideas. That’s something you can’t get away with two weeks in a row. Maybe this isn’t going anywhere. You can only cover so much in an imaginary, one-sided relationship. I mean, I don’t really know you, not any better than anybody else on the Internet does. And while yeah, I know some stuff about some sports, mostly New York Islanders related hockey stuff, if I ever did get an interview with you, and you started asking me anything about the NBA, or the New York Rangers, or anybody besides David Wright on the Mets, you’d probably be pretty disappointed in the overall trajectory of the conversation.


Actually, that’s not true, I’m great at faking my way through most chit-chat, sports or otherwise. I know exactly when to say stuff like, “Yes,” and “Right,” and then I find the perfect moment to insert something cool that I read on Grantland. That’s how I found out about you, about the web site. It’s like, after so many years of standing at the periphery of group conversations, hoping that the topic of discussion might eventually turn to something other than sports, I found your writing, it drew me in, the way you can write about sports that doesn’t immediately cause me to lose consciousness.

That’s what I want to be a part of. Or, wanted to anyway. Like I was alluding to in the first paragraph, I don’t think it’s happening. I’ve been writing these letters to you every week on my blog for about two months now. And as the old saying goes, “If at first you don’t succeed, try, try again, for two months, and if after that you still don’t see any progress, just give up on it dude, because how long are you going to keep it up for? Three months? A year? Just cut your losses and get out while you still can.”

I guess this is goodbye, Bill. I feel like I just got to imagine what it would have been like to have just gotten to know you. But whatever, I mean, just because you have a dream, doesn’t mean that it’s going to come true, right? And it’s not like I have nothing. Sure, I’m not writing for Grantland, having a wide, far-reaching audience of people being exposed to my work. But I have this site right here, this little blog. That’s something. Chuck Klosterman doesn’t write for me, but that’s cool, I don’t need Chuck. I don’t need you Bill. I don’t need anybody.

OK, I apologize, I was getting a little emotional there. There’s no need for me to be a baby about this, I just get a little overwhelmed sometimes with farewells. You’ve got your life, I’ve got mine. I’ll get through this. Maybe some day we’ll be walking opposite directions through a crowded city street. Time might start to slow down for a second as we cross each other’s paths. For whatever reason, we’ll make brief eye contact. I’ll give you a really subtle nod, a casual smile. You … well, you have no idea who I am, so even if you reciprocate the gesture, it’ll be totally hollow on your part, leaving you with a weird sense of, “Why do people keep nodding at me? What’s wrong with that guy?”

I could go on and on forever Bill, it’s like, some part of me never wants this to end. But it has to. Don’t try to talk me out of it. Or, if you’re reading this for the first time, but it’s years from now, I guess you can still call me up and offer me a job. But I have be realistic. You’re just way too popular for me to be constantly begging you for work every week from my very tiny, almost imperceptibly small corner of the Internet.

But it’s cool. I wish you nothing but the best in the future. If, by some bizarre twist of fate, I ever wind up creating an insanely popular sports and pop culture web site, and you for some reason fall on really hard times, struggle to find your way back to the top, but can’t get out from languishing in obscurity, and you start your own very small web site, and you start writing open letters to me every week, asking me for a job, I’ll totally make something happen for you. Even if I already have a different Bill Simmons working for me, even if he’s not even a writer, like he’s just an accountant or something, I’ll make room for one more Bill Simmons. I’ll even give you the good BSimmons@ email address and I’ll make that other Bill switch to BISimmons@. Unless you don’t feel like inheriting the other Bill’s spam folder. In which case … you know what? Let’s just say that we’ll cross that bridge if we get there.

Goodbye forever,

Rob G.

Hey Bill, are you reading this?

Dear Bill Simmons:

Man, sometimes I feel like I’m never going to get a job at Grantland. Like, I’ll keep writing you these open letters every week, but that’s as far as my one-sided relationship with you is going to go. But I don’t know what else to do. Maybe a year or so ago, I wrote a real letter to you, to Grantland. I went to the web site and went to the “Contact Us” page and there was an email address to the editors. And I don’t remember what I wrote exactly, but it was all professional, like, “Dear editors: This is a very serious inquiry seriously inquiring about writing for Grantland,” blah blah blah.


And look, I know that you probably get way too much email to respond to, I get it. So I’m not mad or anything, it’s not like I take it as a personal snub. But it’s incredibly frustrating, to want something so bad, to want to be a professional writer, just throwing yourself out there on the Internet, over and over again, never getting any sort of response.

It’s like, even these letters, this whatever it is that I’m doing on my blog every week. Dear Bill Simmons: please give me a job. And then I go onto Twitter and tweet you a copy of the link, knowing that you get tons of tweets, that there’s no way you’re able to even view every tweet you receive, let alone consider a response.

But I don’t know what else to do. And it’s you, it’s Gawker, it’s all of these other professional high-trafficked web sites that publish all sorts of cool stories written by authors who, when I click on their profiles, they all look like they’re my age, like it shouldn’t be totally inconceivable that I could be doing what they’re doing.

It’s a tough job, getting a cool job, a job where you get to make stuff and write stuff and somehow earn money from it, enough money that you could theoretically support yourself. So far I think I’ve made about seventeen dollars from my writing. I don’t know how you do it, Bill, how you’ve built this media empire all based on your words, writing about sports, about pop culture, about stuff that you love.

Man, this is a pretty boring letter so far, I’m aware of that. I don’t know what it is, but I can’t think of anything to say right now. Last week I wrote about how I’d start from the bottom and work my way up. That was pretty cool, at least, it was cool in the way that I didn’t really have to think about it as I wrote it. The words just kind of flowed through me from somewhere else.

But right now, man, it’s really a struggle to get these sentences into paragraphs. You must be able to relate, right? I mean, you’ve done it, you’ve made it as a writer. What do you do when you can’t think of anything to write about? I’ve read all sorts of stuff on the topic, and most advice from professional writers always boils down to the inspiration/perspiration argument, that talent is cheap but work is hard.

And yeah, it’s hard to get this letter out there, I don’t know what to say, I’m feeling each week like I’m making a fool out of myself, desperately invoking your name on the Internet, like you’re magically going to swoop down from cyberspace and elevate my status from professional waiter to professional writer.

But isn’t that the kind of guy you want working for you at Grantland? Just think, I’m not afraid of my own self-imposed Internet writing deadlines. I need to write a letter to you every week. Why? I don’t know. I just made up a deadline and ran with it. Can you imagine what I’d do for you? For Grantland? Give me a deadline, and I’ll stick to it. I’ll get something out. I’ll perspire all over the place.

I guess that’s all I’ve got. Not very entertaining, I know, but sometimes you’ve just got to be willing to write something bad in hopes of eventually being able to maybe write something good. In the meantime, please read this letter from last week, the one I was telling you about just before. Also this letter, about a dream I had where you and I both went to space. That was a pretty cool one.

-Rob G.