I recently applied for a job and ended up messing up my application email twice before finally getting it right. I was trying to send my application directly via email and mistakenly sent the first one from my personal Gmail account instead of my work email. For the second attempt, I completely forgot to attach my resume and cover letter. I finally got it correct on the third try, but by then, the first two emails had already been sent and I can't delete them. I'm really worried about the impression this might leave on the hiring manager. I know the first email was sent from my personal account, which some say is fine, but I can't shake the feeling that forgetting the attachments was a big mistake.