here's some general advice for writing a headline packet, stuff that works for me and may work for you, and stuff i've noticed reading friends' packets over the years:
1. write a ton of headlines. obvious, but you'd be surprised how many people send me 12 and ask me to pick the best 10. no. write like 40-50 headlines, then pick the best 10. then write another 30 just to make sure.
2. if a joke feels like it's perfect for an outlet and you can't believe they haven't done it yet...they probably have. use google, not the site's internal search feature, and the keywords to make sure it hasn't been done
3. your pun better be pretty fucking good if you're gonna submit it because it's not gonna sustain an article and you need a joke that can sustain a 200 word article
4. your headline may run without your byline, so if the joke is contingent on the reader knowing your specific deal (be it your race, orientation, etc) so it's not offensive, cut it or rewrite it
5. except on a very rare occasion, editors are probably not plagiarizing you, they probably got another version of the same joke from someone else and paid for it, because probably your joke is not that original or special. no offense. (this is more for after you submit)
6. it'll take them a few months to read all the packets, so unless your topical headline is HYSTERICAL, keep it evergreen so it's not stale by the time they get to it
7. "should i apply to this place that has rejected me so many times before????" well, ARE YOUR NEW HEADLINES BETTER THAN THE ONES THEY REJECTED LAST TIME? because if they are, yes! if you're just being a masochist, skip a round and come back when you're less crabby!
8. it's pretty unlikely that you will get rich or famous through headline writing so if it's not at least kinda fun, don't do it! not every person has to do every thing :)
9. this is just my personal opinion but i don't think it's advisable to post your rejected headlines even if it makes you feel better. rewrite them into funny tweets or something. i always feel weird reading someone's mediocre jokes that they have posted out of sadness :) :) :)
10. lists should always be 10 items long (lie, this is a lie, it doesn't matter, i just wanted a 10th thing, uh, stream evermore at midnight and wear a mask)
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