Holigay Gift Guide: What to Buy for Your Work-from-Home Pal


Illustration by Sophie Argetsinger

I have been a freelance writer for well over two years now. I wouldn’t say I’ve mastered the working-from-home/self-employed lifestyle yet, but I have it figured out for the most part. When I was first starting out, my mom, who owned her own business for my whole life, gave me a lot of tips and tricks of the trade. She worked in furniture sales and I’m a television critic, but our work lives have more in common than you might think.

People from all different industries are work-from-home freelancers, and we all tend to have a little bit in common. Unless we have a home office space, we’re regulars at every cafe within a one-mile radius of our home. We are very vocal about how stressful taxes are for freelancers. We always have too many pens and yet not enough pens. At any given point in time, someone owes us money for work we did.

Work-from-home freelancing isn’t for everyone, but for where I am in life at this very moment, it’s exactly where I want to be. If you have a friend who is long-term working from home, consider giving them one of the following gifts to make their lives a little easier.


This is an obvious one, but whenever a family member asks me what I want for Christmas, notebooks are at the top of my list. Non-writers seem to believe notebooks aren’t a very fun gift, but they’re wrong. I go through notebooks pretty quickly, and I like to keep at least one in every bag that I own just so I don’t even have to think about it before I head out the door. Moleskine is a popular brand, but they’re great because you can personalize them to cater to whatever your work-from-home friend needs. I recommend finding out what kind they prefer (I like having a mix of hardcover and softcover in all different sizes, but they all must be plain/unruled). Work-from-home artists and designers are likely to have specific needs.


Classic Moleskine // Creative Cloud Notebook // Padfolio // Evernote Business Notebook

Things to Help Turn Their Bedroom Into A Slightly More Professional Office

Some folks who work-from-home have their own office or study space in their home. Some rent office space. But a lot of us can’t afford that. I live in Brooklyn. I don’t know anyone with an office space in their actual apartment. I try to work in my kitchen as much as possible, but let’s be real, the allure of working from bed is irresistible. I’m sure there are psychologists who say you should keep your bed life separate from your work life, but whatever! It works for me, and one day I’ll have a fancy home office with floor-to-ceiling bookshelves, but for now, my bed makes a very comfy work station thank you very much.


Reading Pillow // Charging Station Task Lamp // Portable Laptop Table // Travel Light // Charging Caddy // Small Standing Desk

Organization Tools

Even the most organized freelancers could probably stand to be a little more organized. It wasn’t until very recently that I realized I should be carrying around a pencil case as if I’m still in middle school. But I started using a cute makeup bag to store pens, pencils, highlighters, etc., and it has changed my life. Most freelancers also do their own taxes (unless they can afford a CPA), and that requires being extremely on top of shit. Did you know we pay taxes four times a year instead of just on tax day? Please hug all your freelance friends today.


Trigon Bulletin Board // Electronics Accessories Bag // Moleskine Tool Belt // Taxes Organizer

Work Clothes

If you have a friend who works from home who SWEARS they TOTALLY wear “normal work clothes,” please introduce them to me so I can tell them to promptly fuck off. Okay, fine, I’m sure there are some people who have to change into regular person clothes in order to motivate themselves to work. Again, I bet it’s something psychologists recommend. But what’s the point of working from home (especially as an artist or writer) if you can’t keep it extremely casual at least a few days of the week? I’d reckon I’m not wearing pants for about half of the TV reviews I write. Sorry!


Pullover Fleece Sweatshirt // Soft Jersey Joggers // Spa Robe // Slipper Boots

Caffeine, Caffeine, Caffeine (and water)

Perhaps the only thing I miss about working in an office is the free coffee. When I’m not working literally from my home, I’m usually at a cafe. I’ve been to most of the cafes in my neighborhood in Brooklyn, but I like to go into Manhattan from time to time just for a change of scenery. But buying coffee in New York every day gets expensive quickly, so I try to make tea and coffee at home whenever possible. I’ve got a Nespresso, a french press, and a pourover. But if you’re going to support your freelance friend’s caffeine addiction, you should probably include a little postcard that says something along the lines of DRINK WATER TODAY that they can put on their desk.


Electric Kettle // Starbucks Gift Card // French Press // Chemex Glass Coffee Maker // Tea Variety Box // Insulated Thermos

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Kayla Kumari Upadhyaya

Kayla Kumari Upadhyaya is the managing editor of Autostraddle and a lesbian writer of essays, short stories, and pop culture criticism living in Orlando. She is the assistant managing editor of TriQuarterly, and her short stories appear or are forthcoming in McSweeney's Quarterly Concern, Joyland, Catapult, The Offing, and more. Some of her pop culture writing can be found at The A.V. Club, Vulture, The Cut, and others. You can follow her on Twitter or Instagram and learn more about her work on her website.

Kayla has written 814 articles for us.


  1. These are great. And it’s so true about the pants (or lack thereof). When my partner started working from home, I was all, um – I don’t know how I feel about you never getting dressed and working in your underwear all day. And then I got laid off and attempted freelancing, and now I get it.

  2. I get dressed! I wear denim vests or t-shirts I paid 50 cents for in the secondhand kids’ section somewhat more frequently than I would to an actual office, but I’m usually wearing something I’d at least wear to interview someone. (Unless it’s summer and hot, in which case my look can easily go from “office” to backyard beers 80% of the time.) Wearing pyjamas makes me not want to do anything and feel like I’m permanently sick in bed.

  3. I like work from home.So so wish to find one. Don’t think I would go for formal or serious outfit but would prefer very casual light wear. At the moment I’m busy making negotiations for work from home.

  4. I’m sure my roommate lowkey judges me for being in my PJs solidly 75% of the time. But come on – that’s pretty much the point of being a freelancer, isn’t it?

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