1. "Have you tried [marketing, PR, or any other profession]?"
Have you tried astrophysics? Museum management? Professional snowboarding? Plenty of freelance writers have considered or tried out other jobs; choosing this one wasn't an accident.
2. "Don't you get lonely?"
Sure. I'm human. But there are plenty of ways to meet people besides working in an office with them. And one perk to freelancing is that the only people I have to see on a daily basis are the ones I consciously choose to have in my life, not the ones who just happen to sit in the next cubicle over.
3. "What do you do with all your free time?"
Do you mean the free time I have when I'm not working on something for one of the sixteen publications I write for?
4. "Want to run this errand for me?"
My work schedule may be flexible, but contrary to popular belief, I'm actually not just sitting on my couch all day, twiddling my thumbs while I wait for you to let me walk your dog!
5. "How do you stay motivated?"
I stay motivated the same way anyone stays motivated at their job: I have people expecting things from me, I have money to make, and I have work relationships to maintain.
6. "Do they pay you for that?"
Unfortunately, some publications do ask their writers to contribute for free or very little money. But lots of freelancers make a living through our writing, and we like to be recognized as working professionals who support ourselves.
7. "So what's your goal with this whole writing thing?"
I’m making a living by writing about things that matter to me! My goal is to keep doing what I'm doing right now.
8. "Can’t you just hand in the article later?"
I don't actually set my own deadlines. So please don’t take it personally if I can’t go to the movies with you on a Monday afternoon when I have three pieces due.
9. "Can you review my product/book/show?"
After you pitch me, I then have to go pitch an editor. It’s not as simple as “I feel like writing about this, so I will.”
10. "How can you afford to live in this city?"
Personal finances are...personal. Most freelancers may not make six figures (though I do know a business writer who does), but many of us nevertheless survive every day in New York, L.A., and other major cities by finding clients who pay us decently.
11. "It must be great not to have a boss."
I might not work in an office, but I certainly have people asking for and expecting work from me. I just have more than one!
12. "You should write about that!"
Saying this to me about anything mildly interesting discounts the thought and strategy that goes into determining what I write about. I think hard about which beats the publications I write for will cover, what's topical, and what makes for a compelling story.
13. "When are you going to get a real job?"
My work may not give me health benefits, and it may not be performed in an office, but my paycheck feels pretty real to me.
14. "It must be so nice to make your own schedule."
Freelancing doesn’t mean complete autonomy over my schedule; it does mean juggling deadlines and working odd hours. Believe me, it's not that nice when it’s 9am and I have four articles due by 3pm on the same day.
15. "Our contributors write in exchange for the byline."
Does your plumber fix your toilet in exchange for the recognition? If I were the only one benefiting from my writing, you wouldn't be asking me for it.
16. "But you’ll gain so much exposure!"
President Obama gets exposure. Sheryl Sandberg gets exposure. And people pay them, right?
17. "Wow, props to you, that must be a really hard life."
There's nothing wrong with trying to be sympathetic about the tough parts of my job. But the truth is that I have several clients I can rely on for consistent work, I never doubt my ability to pay the bills, and I keep doing this work because I love it.
