Working as a freelancer is often interesting, and people are vaguely interested in your trade, which is always gratifying! It makes for easy dinner party conversation.

However, there are five deeply obnoxious questions that freelancers hear with some regularity – questions that should be weighted with 10,000 tons of rock salt and sunk to the bottom of the sea, never to rise again.

Here are the top 5 offenders – questions NEVER to ask a freelancer in a social setting!

1. When are you going to get a real job?

Word of advice: regardless of circumstance and situation, you will ALWAYS be the Jerk In The Room when asking this question. Unless you are playing a cantankerous old man in a bad sitcom, I don’t know why or how this should ever come flying out of your mouth.

If you ever, somehow, blurt this out, you really deserve nothing more than a cold stare and silence, and you DEFINITELY are going to be the subject of some ungenerous conversations later.

2. Ugh, how do you ever make enough money doing [X]?

What’s “enough money”, sucka? This is emphatically not your business. You have no idea how much money any freelancer makes – they may make more than you – and the answer to your inane question is probably “by working hard.”

3. How much do you make an hour?

Geez, buy a girl a drink first. How much do YOU make an hour/a year? Really? Can I see your tax return?

Phrased correctly, with lots of PREEMPTIVE APOLOGIES FOR IMPLICIT RUDENESS, you may gently inquire about general rates. But your freelance friend is under no obligation to answer.


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4. That seems hard. How do you stand it?

Any question that automatically equates freelance work with some inevitable calamity that must be withstood – like taxes, or death, or wasabi headaches - is probably a bad question. It forces your audience to assume a martyred expression, pretend toughness, or look desperately over your shoulder for a different conversational partner. Most freelancers don’t “stand” their work; they often like it and prefer it.

Let the freelancer be the first person to bring up difficulties; then, you can ask for grim details.

5. Any interest in doing work for free?

Listen, you may absolutely ask freelancers to work pro bono, especially for a good cause (your candle-making business may not count). Maybe you’ll get lucky, or maybe they can’t help you right now! BUT springing it spontaneously on someone puts you both in an awkward position. If you want to lure in a FREElancer (see what I did there?) shoot him/her a nice email explaining the project.

Asking about general “interest” in working for no money is unhelpful. For example, I WILL do passion projects for free. I will NOT, say, shovel your walk gratis.

If you happen to find yourself talking to a freelancer at a social function, ask about their take on the economy! Skincare! Zumba! Their guacamole recipe! Favorite email sign-offs! But avoid these 5 questions like the plague… unless you want to be the reason they order another drink.

Kate Hamill lives and works in New York City, where she consumes an inordinate amount of Sriracha daily. You can catch up with her on Twitter at @katerone.