The Big Ask

When I was a kid, my dad was perpetually asking for things. He’s the kind of man of guy who asks if there’s free bread even if he’s eating at Burger King or Taco Bell. I was so self-conscious about my father’s utter lack of self-consciousness about asking for things that as a child and an adult, I’ve traveled in the opposite direction. I’m mortified by the idea of asking anyone for anything to the point where I have, over the course of my life, willingly done without solely to avoid asking for help. 

Christ, I had an apartment where the refrigerator and the oven both broke, but I figured that going without a working refrigerator and oven would be preferable to doing the unthinkable and asking my landlord for help. 

Asking for things makes me feel needy and vulnerable and dependent. It still does. It takes me right back to my childhood and the feelings of shame and embarrassment I experienced over my father’s lack of shame and embarrassment when it came to asking for things. 

I’ve discovered, however, that having to ask for things is a necessary evil in this world, particularly when you are born of modest means and the universe hasn’t exactly blessed you with incredible opportunities. As a freelance writer, I am continually asking potential outlets to believe in my ideas and me enough to pay me money for them and set aside space on their website for my creations. That might be why one of my least favorite aspects of freelancing, indeed, perhaps my least favorite element, involves pitching, with its constant exertion and rejection.

But there are moments in my life and my career when I desperately need help, when I cannot go without it. In these instances, it’s not a question of whether or not I want to ask for help. No, it’s a matter of necessity. I have to ask for help. When I was laid off from The Dissolve for example, I found myself in the unenviable position of having a six month old to feed and support and no clear path for providing for my family. So I was forced to reach out and ask for help, for gigs and assignments, but I was also profoundly blessed that a lot of people sought me out with offers of work.

Before I’ve launched books or big projects in the past I’ve done what I’ve called “The Big Ask.” I collect the forty or fifty emails of the most famous, influential people in my life and career I have a relationship with, and, in a group email, ask them to help me publicize or support my new project. As you might imagine, this makes me feel like a real asshole, and super-needy, and desperate, and vulnerable, and a bunch of emotions I try to avoid. 

And of the 40 or 50 people I contact, maybe three or four will respond to it at all, or help with a Tweet or a Facebook post or a podcast mention. I mean, I know damn well going in that Louie C.K or John Green aren’t going to use their enormous public soapbox to agitate loudly for the e-book of some semi-obscure writer they knew briefly ten years ago, but the possibility that they might has been enough to make the effort seem worthwhile in the past. 

I haven’t done that with Nathan Rabin’s Happy Place or Kanye & Trump however. It seems like a bit of a waste, and on the very off chance that Marc Maron ever thinks of me, I hope it’s not as the asshole who sometimes asks for favors via group texts. At the very least, I don’t want to be that guy. 

But I also don’t want to be some dude who’s too proud to ever ask for help. I’ve threaded asking for financial help via the Patreon into the fabric of the site in a way I hope is fairly organic and not too obnoxious for a very simple reason: I need this money to make a living and feed my family, and it’s been working, to the point where the site is only a few months old and I’m already halfway towards being able to support myself financially through it. 

And asking the cosmos online feels different than asking people directly. Heck, asking you beautiful people for help through crowd-funding has been one of the things that has allowed me to continue to work as a pop culture writer instead of doing something useful for society. 

As with everything, it comes down to finding a balance, and as this site grows and I get more comfortable running my own own weird little kingdom, hopefully I’ll get better at striking that balance between too proud to ever ask and too shameless not to constantly beg. 

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