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It’s that time of year: The season of holiday cheer, itchy sweaters, and gatherings with relatives from the nether reaches of your family tree. And somehow, everyone shows up prepared with probing questions about each other’s lives.

If you’re a remote worker like me, and your job isn’t easy-to-understand, then you’re accustomed to a line of inquiry that, while well-meaning, veers on the ridiculous.

Here are six questions you may get asked, plus the perfect responses.


1. “How Does Your Boss Know That You’re Working?”

Grin. Bear it. Then answer the question.

I can promise you that the person asking it didn’t mean to take a stab at your work ethic. It’s just that the idea of nailing it on the job, without someone looking over your shoulder is new-fangled to your family. But with a little insight, they’ll get it.

So, give them some info about what you deliver every day and how you communicate with the people you work with. A story about video chatting or instant messaging makes things more clear.

Side note: This question usually comes coupled with the comment “I bet you get so much housework done!” I like to retort that my house is just as messy as my friends with 9-to-5 jobs, and sometimes it seems like I’m logging even more hours.


2. “Could You Get Your Cousin an Online Job?”

By working remotely, you’re officially your family’s ambassador for the internet and all things tech, period. You’ve probably “fixed” your share of Wi-Fi routers (by resetting them). Blew their minds by introducing them to Instagram. Performed miracles by defragmenting a PC.

Am I right?

Now in my case, I’m obligated to help with any and all questions career-related, because it’s kind of my thing. But my guess is that you don’t want to become your family’s digital career Sherpa, and that’s totally fair.

Pass the buck. Keep a grab bag of two to three job boards in your head for these moments. In addition to The Muse, I like Authentic Jobs, We Work Remotely, and Working Nomads.

This way you’re helpful, but not stuck helping anyone job hunt.


3. “How Do You Know You’ll Get Paid?”

Wow, Grandma is going there! But it’s only because she fears you could be working for flaky people—digital swindlers, dealing in snake oil. She just wants you to get paid, bless her heart.

This one’s pretty easy: Explain to her that you’ve done your homework.

Tell her about what you do to avoid all the creeps about there. About how you research the crap out of companies or clients that you consider working with. About the signatures, dotted lines, and terms you put into place to keep things above board.

She’ll smile and move on to your cousin’s “trendy” new hairstyle.


4. “Can You Come Visit Me Across the Country Since You Can Work From Anywhere?”

Pffft! Sure, you can work from anywhere. Coffee shops, your living room, or the occasional stint from a seat on a train, but not while you’re on vacation or when your aunt and uncle want to show you the sights in exchange for some free babysitting, so that you’d have oh, about an hour a day to sit at your computer.

Shoot straight and nip this one in the capital-B bud.

Tell them that you’d like to take the trip during actual down time, so you can focus on them. You know as well as I do that you won’t get any real work done from a guest room, even if they’ve got super-fast Wi-Fi. It’s a nice idea in theory, but it never works out that way.


5. “Do You Wear Pants?”

The answer here is “Maybe.” If leggings and pajama bottoms count as pants, then yes, I definitely wear pants.

In my opinion, this question says more about the person asking it than it does about what they think of me. Somewhere, in their heart of hearts, your loved one is pondering what it might be like to not have to give one thought to what he or she wears to work each day.

You know what? If they imagine that the day they start freelancing is the day they stop worrying about wearing pants, kudos to them.

Personally, I’m sticking to my home office uniform of athleisure casual. The alternative sounds chilly, frankly.


6. “Don’t You Just End Up Watching Cat Videos All Day?”

This question hits me where I live. I mean, who doesn’t love cat videos? The temptation to browse the depths of the internet all day is certainly there, but lucky for me (and my career) I channel my crazy cat lady tendencies into break time.

Mostly.

Let’s put it this way: I’ve never had to resort to site-blocking software. Anyway, you can circumvent this question with the magic of misdirection. Whip out your phone and stream your favorite cat video. Done and done.



Don’t get me wrong. I love the holidays, and deep down, I know that my family’s cringe-worthy questions come from a place of love. They’re just interested in what I do. So I strap on my jolliest smile and ask for a second helping of eggnog. I recommend that you do the same!