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The 12 Days of Cloud-Mas (Remote Work Edition)

Hey there!

In light of this unusual holiday season we’ve found ourselves in the midst of, the CloudApp team has put together a little Christicle (Christmas + Listicle?) to help our fellow work-from-homers get into the holiday spirit. So without further ado, we’re excited to introduce: “The 12 Days of Remote Work Christmas.” Feel free to sing along.

*Disclaimer: This read is best enjoyed with a Starbucks eggnog latte and a PTO day*

12. ”On the 12th day of Christmas, remote work gave to me:


If we’re being honest, in actuality most of us are probably on sleepless night 270. But whether it’s the crushing weight of being alive in the year 2020 or the lack of any concrete plans outside your home creating a new napping habit, just know that we feel for you, as our sleeping schedules are also suffering immensely.

We’d say that we can’t wait for this nightmare of a year to end, but then calling it a nightmare would imply that we’re sleeping, which as we’ve clearly just stated, isn’t happening. Tonight we’re popping 5mg of melatonin, putting on A Christmas Carol (the 1938 version), and hoping for the best. May visions of sugarplums dance in your head on this 12th night.

11. ”On the 11th day of Christmas, remote work gave to me:

This one doesn’t need much explaining. Much like our night 12, if you’re like me you’ve probably put on more than 11 pounds this year. Unfortunately, it’s not the 17 days of Christmas (really hoping I’m not projecting) so we’re making it work.

Some of us might’ve packed on a few from that fever dream of an April where we all started baking bread for some reason, and others may have let our workout regiment slide after gym closings.

To be honest I’ve been in the same extremely oversized sweatshirt for the past 8 months and don’t even really know what’s going on down there. Probably for the best. We have until January 1st to continue not caring about this so let’s just have fun with it. At least we know Santa doesn’t judge.

10. ”On the 10th day of Christmas, remote work gave to me:


This is no shade against Slack, it’s just as an inbox zero-er this is a tough one. I’m constantly craving the sweet relief of having zero notifications on all platforms, and yet most days it feels like ultimately a pretty vain pursuit.

The feeling of constantly needing to be so completely available at all times probably isn’t healthy, but that’s for a whole other blog post. Season 9 Episode 5 of Seinfeld warned us that “the mail never stops”- but the post office has nothing on the incessant Slack notifications. Let this lyric serve as a PSA to remind you to set yourself as “Away” and turn off all notifications on that first day of your holiday vacation. It’s what you deserve.

9. ”On the 9th day of Christmas, remote work gave to me:



Oh man, don’t even get me started on this one. At the risk of sounding callous, I’m just going to say it- I don’t want to go to these 99% of the time. I appreciate the effort of the people who plan them, and it genuinely isn’t personal.

Much like agreeing to after-work plans for Friday on Monday morning (remember having plans that required pants), these always sound like a good idea at the time, and then when they actually come around I resent former me for agreeing to it. And to make it even worse, it’s become dreadfully hard to get out of these because everyone knows you have nowhere to go.

You’re already probably drinking at home alone, so why not do it while staring at quasi-acquaintances on a screen? No thank you. Feel free to hit me up when we can go to real happy hours again, but this current trend is the stuff of a Black Mirror writer’s room.

8. ”On the 8th day of Christmas, remote work gave to me:


This is happening to even the most productive of us. And to be clear this goes for all streaming services- Hulu, Amazon Prime, Disney+ (I’ve been really into HBO Max lately)- pick your poison.

As far as vices go, there are definitely worse coping mechanisms, so try not to feel too bad about not leaving your bed all weekend (with the exception of the occasional DoorDash delivery) for a 3 season-episode binge. What else are you supposed to do? On the flip side, we have been pretty lucky to have some phenomenal content this quarantine.

From the Queen’s Gambit to Schitt’s Creek, there seems to be a little something for everyone. We encourage you to get through this holiday season with whatever t.v. guilty pleasure brings you comfort, unless, that is, you’re one of those Bachelor/Bachelorette people. You can do better.

7. “On the 7th day of Christmas, remote work gave to me:


If this applies to you, there’s absolutely nothing to be embarrassed about. We’re just happy you’re wearing pants at all. No one has time for anything with a zipper or a button in a pandemic.

The other day my brother came down the stairs wearing a pair of khakis and it was such a jarring image I thought the Queen must be coming over. I have definitely spent an actual 7 days in a row (probably more sometimes) in the same sweatpants this year. They’re comfy, practical for the daily walks from my bedroom to the living room, and forgiving to the waistline. I can only hope that 24/7 sweatpant-wearing remains socially acceptable in a post-quarantine world. It’ll be hard to go back after this.

6. “On the 6th day of Christmas, remote work gave to me:


Just a heads up, this blurb is basically going to be a not-so-subtle ad for CloudApp. You can’t blame us for sneaking 1 in out of 12. It’s also our blog post and we can do what we want.

Rescheduled meetings have always been a predicament that is to some extent inevitable, but this year it has become probable to occur at least once on just about every day that ends with a Y. But try not to be annoyed at your coworkers; life happens and many people are dealing with a wide set of new challenges this year that may be sabotaging their schedules, especially during the holiday season.

So instead of getting upset, get ahead of the problem by clearing your meetings, downloading CloudApp, and sending your colleagues a screen recording instead. They will thank you.

5. “On the 5th day of Christmas, remote work gave to me:


If you’ve attempted it more than 5 times, props to you. Honestly. I’m not a parent, but as a former child, I can honestly say that I do not in any way envy the parents or children attempting school from home.

If you are completely homeschooling your kids this year or even doing a weird in-person/remote school-hybrid while attempting to work from home, you are an absolute hero and you should be proud of even getting out of bed each day to face that. I can only imagine trying to get a 4-year-old to sit still long enough to endure a zoom call while trying to write a proposal or something. You’ve definitely made the nice list this year.

4. “On the 4th day of Christmas, remote work gave to me:


Be nice to your IT people, they are probably trying their best. But man, do I long for the days where you could just go down 2 floors to have a smiling face immediately fix your thing or give you the thing for you to fix your thing.

I don’t know about you, but for me, the greatest losses in the in-office to remote work transition has been the little things. The chit-chat at the coffeemaker about my weekend on a Monday morning, the way you can make eye contact with your friend in a meeting when another coworker says something completely insane, etc.

I know I’ll never again take for granted our brave IT people serving on the front lines of our coworking spaces to ensure we have an efficient and technologically literate environment. But do remember that if you’re in a pinch, there’s probably a YouTube video for that.

3. “On the 3rd day of Christmas remote work gave to me:


You get it.

2. “On the 2nd of Christmas remote gave to me:


If our eyes weren’t already destroyed from screen exposure pre-quarantine, they don’t stand a chance after the year we’ve had. Turns out having blue light blasting directly into your corneas for 17 hours a day doesn’t make your eyeballs feel too great. Go figure.

To make matters worse you have to worry about the judgmental Apple notification reminding you that you spent an extra 4% of your life last week staring at either a big screen or a little screen than the week before. I have recently been made aware that they make glasses that should help this. So that’s cool. Still, sometimes it’s probably best to just give your eyes the night off. Maybe go read a book or something.

1. “On the 1st day of Christmas, remote work gave to me:


If you’ve made it this far, props to you. With all that has happened this year, you’ve earned every second of this holiday vacation. This has been a rough one, but somehow so far we’ve all made it through together. All jokes aside, we really do hope you’re able to relax a bit, safely spend some time with your family and loved ones, and enjoy this holiday season as much as you can. From the bottom of our hearts, we would like to wish you a very Merry Christmas and a Healthy and Happy Holidays.

Best wishes,


Written by Kendall Pennington – Marketing at CloudApp