During a particularly strange dinner conversation with my college friends, the words, "Kuwait, huh? How's that going to be?" came out of my mouth.  It was a strange conversation already, and then I made it stranger by opening my mouth and hearing Chandler Bing (circa "Friends", it was still the nineties) come out.

So, that's become a recurring phrase when I embark on something and have no idea what to expect, "How's that going to be?"  I didn't expect freelance to be so consuming.  Not time consuming out of necessity, but out of blind ambition that I haven't experienced in a while.  I'm in love with the opportunity.  And the opportunity appears to be everywhere!

Pinterest, google searches, the back pages of my shiny hard copy magazines all promise financial opportunities, just write, submit and cash the check.

Not so far.  I'm finding freelance to actually be far more like online dating.

When you're finally ready to admit to yourself that online dating is not a trendy pop culture phase, and you create an account, the first thing you're asked to do is describe yourself.

Sounds easy, I've known myself for thirty-four years. I know my self better than I know anyone else, how hard could it be to describe myself.  It's hard.  Both online dating and freelance submissions want to know something about who you are.  "Just a short bio" they all say.  So, in both instances, I have sat and stared at a blank box.  "I'm an attorney..." wait, no one really cares about that right? Does that seem like I'm bragging?  And anyway, who wants to be described by what they do.  I work out?  I have friends?  I watch too much TV and would rather read a book than talk to you? 

I thought about how my mother might describe me, "Single, but pretty;" "Sarcastic;" "Slightly autistic, but in a good way" (yes, that happens).

It's impossible! I cannot describe myself in 400 words, not because that's too few, but because it's too many!

If you survive writing a bio, you have to put yourself out there, both in freelance submissions and in online dating.  Initially, you're so overwhelmed with hope and opportunity and everyone promises it's going to be so easy!

Let me tell you, it's not.

You pull together your best work--photos for the online dating and writing for the freelancing--and you hit send. And then you wait.  And while you wait for a reply, you really start to question what is wrong with you.  Why isn't anyone emailing you?  What are they even doing?  Don't they read their emails as quickly as I do? 

Then you get a response.  Great! Someone wants to love me!  But not enough to pay me.  So I work for free because that's how you get exposure, and exposure is everything; or I buy my own dinner on an awkward first date, that's really just a redefined blind date, but I think I got experience. And that's what counts.

And it is.  It's great.  It's opportunity and that's what I'm looking for.

Until you get your first rejection. The "thanks but no thanks" from the guy you thought might be right for you, or the publisher really just isn't that in to the work you were once so proud of.  You're a great, independent, thirtysomething woman with all of her shit together.  Why wouldn't he/they want you?  That was your very best effort, your profile pic or your essay were the very best you could do.  If they don't want you based on your once in a lifetime best effort, no one is going to every date you or publish you.

So you quit, because that's easier.  It's easier to just tell yourself it's not meant to be.  You'll be alone, you always have and it's been fine.  And you'll just not be a writer.  It's okay, you have a day job.  Sure, it was your dream once, but so was love, and you've been fine without that.

But you can't quit.  Because being a writer is who you are, even on the days you don't want to be.  And that trash isn't going to take itself out and it sure would be nice to have a guy around to do things like that.

So you try again and expect things will be better.  That someone will love you, it both.

So freelance writing, huh? How's that going to be.  Don't quit your day job.