Freelancing is fantastic. It’s flexible and fulfilling and fun – and at its best, it empowers people to determine their own career paths.

That being said, it can also be demanding and unpredictable. It often takes only one or two incidents in a day to turn a perfectly reasonable, calm freelancer into a neurotic twitchy stressball. Freelancers are driven, hardworking creatures ping-ponging from project to project – which makes us excellent targets for pranks and tomfoolery.

Do you love freelancers? Do you love messing with freelancers? Do you wish to take terrible revenge on freelancers for centuries-old slights on your family’s honor? THEN TODAY IS YOUR LUCKY DAY, MY FRIENDS.

25 simple ways to make freelancers lose their minds

  1. Ask them their rates. As soon as they name them, laugh in disbelief and ask if they also mine gold BULLION at those rates, my GOD.
  2. Replace their Mac keystroke shortcuts with PC keystroke shortcuts – or vice versa. Enjoy the ensuing chaos.
  3. Switch out their coffee for decaf. Wait a couple of hours. Tell them to buck up, buttercup.
  4. Systematically replace every your in the final draft of their project with you’re. Send it back to them with a note asking if they’ve lost their minds.
  5. Dangle a lucrative project in front of them. Disappear.
  6. Visit their home office and sniff disapprovingly at every “time-waster.” Suggest they invest in fluorescent overhead lighting and cubicle walls.
  7. Inform them that in lieu of an invoice, you will now require a livestream video documenting every moment of their work. Tell them they will get a bonus if they cry.
  8. Comment on every blog post they write: “… but this does not relate to my life?1?11!!”
  9. Ask them if you can have a family discount – because aren’t we all part of the human family, really?
  10. Ask if they build “hazard pay” into their rates. When they ask why, refuse to answer.
  11. Repeat the following phrase liberally: “No pay, but great exposure!”
  12. Sneak up behind them and yell “YOUR QUARTERLY TAXES ARE OVERDUE!”
  13. Refer to their career as a hobby.
  14. Call them from an area with terrible phone reception. Leave them long, panicky voicemails about projects with tight deadlines. Make sure to include lots of details.
  15. Tell them they’ll need to get project approval from multiple supervisors in an undetermined order; bonus points if those supervisors are bad communicators with interpersonal tension.
  16. Call them at noon. When they answer, say: “Oh, hahaha, sorry, I’M SURE I MUST HAVE WOKEN YOU UP.”
  17. Offer to pay them in “treats.” Who doesn’t like treats?
  18. Give all edits in Comic Sans. Purple Comic Sans.
  19. Tell them that your preferred method of communication is via fax.
  20. Ask if they might have a job for your nephew, who’s a freelance… something or other. Wait, is he freelancing? You don’t remember. How about you just write down his email: bongmaster14@hotmail.com.
  21. Try to set them up on a date with said nephew – or worse, with yourself.
  22. Casually call them “sweetheart.”
  23. Assure them that the check is in the mail. Darkly hint about the unreliability of the postal service.
  24. Pair perfectionism with unclear expectations and a short temper.
  25. Advise them to get a “real job.”

Freelancers, do you have any advice on how to send your kindred to the loony bin? Does going to the loony bin, honestly, sound like a bit of a nice rest? Come gripe about it-- and then share your advice for witty retorts-- in the Best Lifestyle Practices Hive!