10 Sarcastic Comebacks for When People Question Your Freelance Life

To just about every adult in my life, freelancing is naturally very foreign to their way of being. These well-meaning, advice-laden folks don’t operate in the gig economy, yet many have made it their personal mission to help me find a “real job.”

These friends, apparently, want to save me from the cocktail party shame associated with having a job people believe is somehow fake.

They just don’t understand what it means to be a freelancer and actually enjoy it.

My neighbor, a partner in a respected law firm, told me how “A real job offers so much more in the way of security,” as we put our recycling bins on the curb. “Someone your age needs to think about the future.”

My future, I silently hope, includes Sunday mornings free of his sunrise lawn mowing and 500-decibel leaf blower.

My parents used to love seeing my byline, but my freelancing career still gnawed at them. My mother forever wondered when all my “freebie-work,” as she called it, was going to lead to a real job with benefits. This was despite me telling her I was paid for my writing, often handsomely, and that all-expense paid trips to the Caribbean and other exotic locale for my travel gigs was a very nice benefit indeed.

“That’s nice dear,” she’d say, rolling her eyes towards my father, who simply shook his head in bewilderment.

None of my fully-employed poker buddies can wrap their head around the fact that I don’t punch a clock.

“How in the hell are you going make it in this world without a nine-to-five job?” they wonder, all the while spouting about the greatness of full-time indentured servitude.

No matter how many times I hear these misconceptions, a part of me still hates them. Here, my fellow freelancers, are the most asinine of all their questions, plus some ready responses free of charge. Who said freelancing doesn’t come with benefits?

Ridiculous question 1:

Don’t you ever worry about where your next paycheck is coming from?

My response:

Actually, no. I worry incessantly about whether to use AP or Chicago Style and the merits of the serial comma.

Ridiculous question 2:

As a freelancer, don’t you pay out the nose for insurance?

My response:

Why, yes, I do. Especially for rhinoplasty, speaking of noses. Thank god for the Affordable Care Act and those good folks in Washington looking out for peeps like me—and employed folks like you for underwriting my every doctor visit.

Ridiculous question 3:

Doesn’t it suck that you’re always floating ideas for approval?

My response:

Not nearly as much as waiting for your boss’s boss’s boss to OK your $15 expenditure on paper clips.

Ridiculous question 4:

Isn’t working from home kind of lonely?

My response:

I’m never alone as long as “Oprah” and “The View” are on.

Ridiculous question 5:

What are you going to do when that magazine you write for goes out of business?

My response:

Gee, it never occurred to me that a thriving business could be mismanaged or find itself in the throes of shifting markets. How long have you been working for BlackBerry anyway?

Ridiculous question 6:

How are you ever going to meet that special someone when you don’t work in an office?

My response:

What? You guys don’t have Match.com at your office?

Ridiculous question 7:

Aren’t you tempted all day long by the fridge?

My response:

Yes, but also I’m never assaulted by aromas of my cubicle mate’s kimchi or reheated fish tacos.

Ridiculous question 8:

What is it like to not have a boss?

My response:

Are you crazy? I have 17 bosses and am trying to find more every day.

Ridiculous question 9:

Don’t you ever fantasize about what it would be like to have a real job?

My response:

Most all of my fantasies involve Penelope Cruz, deserted islands, and lots of rum. None involve work.

Ridiculous question 10:

Do you think I could make it as a freelancer?

My response:

You might want to check with your parents about the size of your inheritance first.