12 Awkward and Embarrassing Confessions About Working From Home with WordPress

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Being a freelancer can be great. I know it has given me the freedom to live life largely on my terms, which is awesome. But there are some drawbacks to this whole working from home thing that a lot of people don’t like to talk about.

I mean, you don’t want to sound ungrateful, right? You work for yourself in your house. You set your own hours and have control over your life in ways that people with an office 9-to-5 just don’t. At least, that’s how the mythology that surrounds working from home goes.

But anyone who has actually worked at home for any length of time knows, the mythology is just that—a story we tell that only highlights the best features of the experience. The reality of the freelance life is much darker. And hilarious. Often unintentionally so.

The reality of working from home is filled with mishaps, happenstance, and all manner of comical anecdotes that span the spectrum from mildly awkward to downright embarrassing. I’ve talked to several developers, designers, and generally WordPressy people about their most awkward moments and the results will either make you laugh out loud or utter a sympathetic, “You poor dear.” 

Let’s get to the embarrassment, shall we?

1. Clients Will See Your Pajamas

It’s inevitable, especially if you ever take video conference calls. So many work-at-home folks will get dressed up from the waist up but rock those PJ pants all day. And sometimes, the camera might catch a glimpse of your less-than-professional attire.

Sue Waters, the Support Manager for Edublogs and CampusPress, keeps her mobile devices in her bedroom. One night, she went to bed late. She’d nearly fallen asleep when the light came on her tablet. “It was a Google Hangout call coming in from friends attending a conference and I managed to accidentally answer the call,” she says. The result? “I ended up in a video call in my PJs discussing student blogging at 1 am.”

While no one got a real good look at her jammies, she did encounter some odd looks from other friends passing by at the conference as she struggled to wake up and form sentences that made sense.

2. You’re Always a Little Bit Scatterbrained

Allow your author here to make a bit of a confession. I work from home and my kids are in the next room, usually with their dad. But because little kids don’t understand boundaries—especially the concept that I’m “at” work when I’m really just in the next room—my three-year-old often barges into the office to ask me for something. Or if I hear my year-old son crying, my instinct is to go comfort him.

The lack of space between work and home life means I’m always thinking about both at the same time. And the end result is feeling pulled in all directions at once. Each interruption leaves me struggling to remember what I was doing last, and that can make for some odd client communication.

For instance, it seems like every time I send an email, I leave off an attachment. Or if I’m chatting with a client on Facebook Messenger, I’ll suddenly leave mid-convo and come back to the computer only to see a ton of messages that seem to employ a varying number of question marks. Or, I might just forget what I was doing and sit at my desk for 10 minutes clicking at social media until I remember again. Then cue the office door swinging open and my child charging in and…

3. Your Social Skills Take a Nosedive

When I posted this topic in a social network group for WordPress developers, one member immediately posted a link to a comic at The Oatmeal. And yeah, even a quick glance through it will show you just how accurate it is at portraying the struggles (and sometimes disorientation) of working from home. One panel was highlighted as particularly apt:

The Oatmeal comic captures the work from home life perfectly.
The Oatmeal comic captures the work from home life perfectly.

I know this doesn’t apply to every freelancer but without external structure imposed on you by a 9-to-5 job, things tend to…slip. Including your ability to communicate with real live humans.

Lucas Stark, a senior web developer, admitted he pays inside the gas station just to have a few moments of human interaction. Another member of the group added, “Every day I go to the grocery store because that is the only time I talk with folks I’m not related to.”

Freelancing can be isolating and it often requires a formal effort to get out and amongst people. Which, if we’re being honest, doesn’t happen every day.

4. You Ask Yourself, Did I Take a Shower Recently?

When you’re cooped up in your house all the time, personal hygiene takes some effort. If you don’t have to be around other people every day, the impulse to clean up to look and smell nice isn’t so compulsory.

One developer I spoke with (who wished to remain anonymous) admitted to letting the “pit sniff” test be his guide, which he admits is totally gross. But “It’s just one part of the real story of the work-at-home life no one wants to talk about,” he says.

5. You Eat Weird Stuff. Like, Really Weird Stuff

Working from home means you can delight in homemade breakfast, lunch, and dinner, right? Because you totally have a ton of free-time on your hands. Well, actually no. Many people who work from home actually work longer hours than those with office jobs because there is no defined line between work and home. And because of that, skipping meals can be a regular occurrence.

Also, common is the six o’clock panic that you haven’t planned for dinner and need to throw something together quick before you yield to the siren song of delivery yet again (see #7).

Because of these factors, putting together truly strange dishes happens all too often. When you’re a freelancer, a frozen corn dog, a leftover slice of pizza and a steamer bag of green beans totally counts as dinner. Hey, a least I got a serving of veggies in!

6. Sometimes You Miss the Office Camaraderie

When you’re working an office job, it’s hard to believe you’d ever miss the banal and mundane water cooler chatter. In fact, you might welcome a break from it. But after spending a few months at home without anyone to socialize with during the day, you’ll start to miss those small talk conversations.

Were they mostly pointless? Of course. But they did offer a chance to communicate with other real live humans in three-dimensional space. Which you won’t even realize you’d miss until you’re cooped up in your house for the three days straight.

7. Food Delivery Services Know You By Name

You’d think that working from home would mean you have all the time in the world to prepare home-cooked meals but more often than not it doesn’t turn out that way. When you’re not compiling weird concoctions from what’s leftover in your fridge, you’re ordering delivery.

There was a point where I ordered pizza so often, the delivery guy knew my name. It filled me with sadness whenever he greeted me at the door with, “Having pizza again, Mrs. Barron?” But I’d just nod and smile and pay for my order as quickly as possible.

Lucas Stark is quick to point out that delivery does offer a brief chance for addition social interaction, however. It could even be considered “lunch with friends,” he says.

8. Conference Calls Are the Bane of Your Existence

“Huh?” That’s what I’m usually thinking to myself whenever I’m pulled out of my cocoon into a conference call. And it’s not just the fact that I hate being on the phone. No, it has everything to do with the fact that I can’t understand what people are saying on conference calls.

I vividly remember being on a conference call once with an in-house team at a marketing company. I was the only freelancer on the call and it was the first time I’d ever heard any of these people on the phone before. They all were sitting next to each other, on speaker phone, and I was using every muscle in my body to try to hear what they were saying in their obviously echo-filled meeting room.

I literally didn’t hear a single word they said. I somehow got through the entire conversation with a strategic combination of “uh-huh” and “sounds good” and didn’t lose the client in the process. Most uncomfortable 20 minutes ever.

9. Kids Like to Insert Themselves Into Your Schedule

Speaking of client calls, web dev Louise Treadwell had a funny experience recently on video chat all thanks to her five-year-old son. While chatting with an agency client, her son was behind her making faces. “Then he took off his shirt and started flexing his skinny little muscles.”

Her team was “turning red” in an attempt to hold in laughter all while she was “totally oblivious.”

“Finally, they couldn’t take it anymore and everyone was howling laughing,” she says. The situation was helped by the fact the agency is made up of a team of stay at home moms. But still. Sometimes there’s no hiding the fact that you’re definitely not in an office environment when you work from home.

10. But Babies Look At Your To-Do List and Laugh

Working from home with a baby around is a unique challenge. Just ask Sarah DaSilva, Owner of SuperPowered Web and mother to two children, one of which who is a year-old. “Working from home with a baby is choosing between listening to whining or letting your baby sit on your lap and knock over your coffee,” she says.

The silver lining? “At least now my desk is clean and smells of coffee.”

11. The Lines Between Work and Life Blur

Sometimes, to embarrassing effect. A writer I’m familiar with (certainly no one you know…) once sent an email to her husband asking for his assistance on a project. She might have signed off the message with a promise to provide thanks for said assistance with sexual favors.

But you see, this writer (that you definitely don’t know) thought she had her husband’s email address memorized. It turns out, however, she did not. And the approximation she input in the “To” field was the address of a stranger. One who promptly responded with a message that began with “I don’t think I am who you think I am” and ended with “whoever you sent this to is a lucky man.”

This writer you totally have never heard of before turned untold shades of red and promptly buried herself in pillows. Because, holy embarrassment, Batman!

12. Sometimes Clients Don’t Comprehend Boundaries

One developer I spoke to had a recent run-in with a client who apparently had no sense of boundaries when it comes to conducting business with those who work from home.

“My most recent horrified moment was when a client who I’d never met before decided to drop by my house unannounced on a Saturday morning,” she says. She was of course in her pajamas and her three kids were running around wild. She could’ve just not answered the door, but you see this particular client was a cop. And he thought he was funny.

When he knocked, he said, “This is the police,” she says, so she opened the door, “PJs and all,” only to see the client standing there. “I think I must have given him the coldest look ever,” she says. Understandably so, don’t you think?

Wrapping Up

Working from home is great. But that doesn’t mean it’s not without its challenges. Or that the at-home work environment doesn’t lend itself to some awkward and embarrassing situations. As you’ve seen here, sometimes working from home is the very thing that creates a whole mess of awkward.

Did you enjoy these real-life stories? What’s the most embarrassing or awkward thing that’s ever happened to you while working from home? Feel free to share below. 

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