As a public service, I'm going to drop the Pasquin Rules for Job Seeking on you. But because I'm me, I'll do it in an extremely negative way. As in, please do the opposite of what I'm saying.
Please send it in an obscure file type. Or better yet, right in the email. Nothing says I-fail-at-technology like that. And why waste valuable time using the spell check that is in EVERY FUCKING program ever. Ignore it. I mean, what does grammar and punctuation have to do with office work anyway? Next you'll be saying my exposed tat of a blue fairy shitting rainbows might leave a bad impression.
Don't include one. Let the boss just guess at why there's a ten year gap in your employment history. Or why as a former rodeo clown you'd make a good accountant. But if you have to, make it full of buzzwords you don't actually understand. And don't tailor each cover letter to each individual job. Egh, that's work. I'm sure when the boss wakes up from reading it, he'll remember how impressed he was.
No phone number. That's so twentieth century, like when most of your potential bosses would have been born and be accostomed to. But if you have to, leave off a digit. Or area code. Oh, oh, oh, this is a good one: don't have voicemail. That $4 a month can go towards cigarettes and scratch tickets.
But maybe you're right, this is the twenty-first century and everybody does everything by email. Remember to send all replies to email@example.com. We're all adults here. Come on. And don't worry about file names. Nobody will notice that you called your resume 'fake as shit'. Nobody.
Write 'see resume.' The boss doesn't need to know why you left a job or who to contact for a reference. As with a scavenger hunt, he'll enjoy the hide and seek. Keep telling yourself, it's not laziness AT ALL.
Don't have interview clothes? No prob. Just show up in what you would for clubbing. Add glitter. That'll tell the interviewer you like people. And while we're on this subject, do most of the talking in the interview. That'll teach'em who's boss. And don't answer questions—they're a trap. And if you're wiley enough to avoid that, he'll agree he was outsmarted and HAVE TO give you the job.
Put ten points on the leader board. You've earned it.
All of the above has happened to me. Particulars have been changed to protect the clueless.