You can read all of the advice columns in the world. You can try to think before you speak. You can endeavor to be professional, courteous, and thoughtful in every interaction. Despite all of these precautions, you will occasionally – out of exhaustion or thoughtlessness or (in my case) a tendency to make inappropriate jokes – say the wrong thing at the wrong time.

Below is a list of my 20 biggest smack-my-forehead-what-did-I-just-say moments; these are just the ones I can remember. I share them with you now, my freelance brethren, in the hopes that you may avoid some of these slip-ups yourself. Go ahead, enjoy the delicious schadenfreude! I’ll be over here, supping on foot-in-mouth!

1. “Oh, whenever you want to send the check is fine.”

2. “I never, ever stop until my client is 100% happy.”

3. “Sorry, I couldn’t hear that - I’m in a public bathroom.**”

4. “I’m pretty flexible on rates!”

5. “It’s actually to WHOM shall I address this payment. Not to who.**”

6. “Whenever you want to call me is fine! I don’t really keep regular hours.”

7. “I almost failed out of high school. I mean, because of gym. I failed gym. I had no work ethic. Still true. I mean, but just in the gym. I mean…**”

8. “Oh, I basically forgot all about that.”

9. “I have a pretty good working knowledge of computer programming.***”

10. “I was operating on a LOT of cold medicine when I wrote that.**”


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11. “Haha, you can’t trust me for even one second.*”

12. “I’m just doing this until my trust fund kicks in.*”

13. “I’m in a completely different country right now, so I edited this at (the equivalent of) 3 AM.**”

14. “I’ll do this over as many times as you’d like me to.”

15. “I love edits and suggestions! Bring them on!”

16. “I’d use him as a reference but he’s dead.**”

17. [at 11:30 am] "Sorry, I just woke up.”

18. “I can guarantee that this will be successful.”

19. “I LOVE that [bad] idea!”

20. “I don’t think this is my best work.”

*Bad attempts at jokes

** True but ill-timed

***Poorly-planned spontaneous falsehoods

Kate Hamill is a freelance writer, playwright, and actor. She lives in New York City and consumes a truly frightening amount of Sriracha daily. Follow her on Twitter at @katerone.