Lake Merritt, Oakland. One of my happy places.

A Year Begins…

Why can’t I just freakin’ write something?!?!

This is how my forays into writing usually begin: me in front of a blank screen or blank page trying, generally in vain, to come up with something witty or profound or even just grammatically correct to say (gosh I hope that was grammatically correct…). Most of the time the scene ends with me closing my computer or throwing my journal across the room, letting out a huge sigh of exasperation and telling myself I’ll finish it just as soon as I clean the kitchen, walk the dog, sweep the sidewalk — you know where I’m going with this. I think most writers, even brilliant writers (which I’m not claiming to be) struggle with an oppressive sense of self-doubt and a mastery of procrastination that borders on mad genius. In fact, I am at this very moment simply refusing to walk away from this computer until I finish this draft. I’m actually pretending my wrists have fused with the keyboard and will only be released when I finally hit “publish.” Also, I’ve given myself a 30 minute time limit to get it completely done and I’m already at minute 13… Enter the Panic Monster! *

I guess this is where I should get to the point so I’m not forcing myself to publish something that is not only an unworthy piece of drivel but also makes absolutely no sense. What I’m doing here is embarking upon a new adventure/project/possibly migraine-inducing enterprise wherein I will be writing EVERY SINGLE DAY. And not just in my handy journal that no one ever sees but which allows me to say I write every day. No, I will actually be writing and publishing every day on this handy platform. Please be kind. At least in the beginning.

So now that I’ve rambled nonsensically for a bit you may (or may not) be wondering just what the hell this adventure/project/possibly migraine-inducing enterprise might be. Well here’s the short(ish) version: last week I was feeling like a special sort of failure at life when, while perusing Medium in search of some much needed inspiration, I came across a lovely piece by Jon Westenberg entitled “How trying to fail once every day changed my life.” He also gave it the catchy subtitle, “And helped me make a damn good burger,” which, truth be told, is what really made me read it. (What can I say? I really love good burgers.) About a week later he followed up with, “365 Ways to Win or Fail Trying,” and after reading both pieces I have to say I was actually feeling inspired. Inspired to do what was another question entirely.

Clearly I wanted to take a stab at failing 365 days a year but, let’s face it, I was already doing that. I did, however, think it would be fun/interesting/terrifying to try to come up with a year’s worth of challenges and see where they took me. I mulled over the idea for a while and shared it with Erik (my boyfriend, who often reminds me that he’s the most brilliant man he knows), who suggested part of the challenge for me could be not just journaling my experiences for my own benefit but writing about them on an open forum — out there for all of the world to see. My initial reaction was that this was, in fact, a brilliant idea. My second reaction was not visible to the untrained eye, but involved an inner-turmoil akin to that Red Spot on Jupiter: doesn’t look like much from here but I don’t want to land in the middle of it. Fast forward a week and a half and here I am, finally out of excuses and forcing the Instant Gratification Monkey (see asterisk below) to shut up for a minute and just let me get this done. It finally occurred to me that it’s unlikely that more than four, possibly five people will read this first installment anyway so if it’s total crap who really cares. Plus it’s supposed to be fun! I’m constantly telling people to not take themselves so damn seriously — do as I say, not as I do…

So here’s the challenge: I’m borrowing Jon’s idea (yes, I asked his permission and he very kindly gave it) and I will “set myself up for failure every single day.” AND write about it. (Did I mention every day? Did I also mention that red spot on Jupiter? Cause I think it just migrated to my insides). I’ve decided to call my forays into failure my “tasks” as some may be grand and some may seem silly or trite to those who don’t know me, but I’ll be doing my best to come up with scenarios that genuinely challenge me. It would be difficult, not to mention ill-advised, for me to commit to 365 grand tasks; two jobs and a dog just don’t allow a ton of free time. Nevertheless, I’m giving it a shot. So here goes.

Task #1: Come up with at least 30 days worth of tasks (per Jon’s suggestion). I’d prefer 60–90 but as this is my first task I’d like to try to win. It may be my only one.

That’s it. That’s the challenge and the purpose of this rather lengthy rant. Now I’m off to sling some whiskey and think of 30 things that will likely freak me out and make me want to hide in a cave… Wish me luck.

-I should note — that part where I said I was giving myself 30 minutes to finish? Epic fail. Huge. It’s been 60. At least you know I’ll be honest!

*The Panic Monster and Instant Gratification Monkey are not creatures of my creation. They are the brain children of Tim Urban, self-proclaimed Master Procrastinator and hilarious man/stick figure. Check him out at Wait But Why, and be sure to watch his TED Talk while you’re there. If you’re gonna waste some time, do it with Tim.

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