12 Awkward and Embarrassing Confessions About Working From Home with WordPress

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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33 Responses


    My home office is in the bird room (small house, and they don’t scream as much if they can see me). I tell clients that I cannot do phone calls too early in the morning or around sunset when my birds are loudly singing the wakeup and bedtime calls of their people. Misha, my big Moluccan cockatoo, I have personally measured at more than 105 decibels. Get all 3 going at the same time, and it’s like a loud rock concert.

    Really, an hour before or after sunset or after breakfast and they’re quiet enough for me to talk on the phone. Otherwise, risk getting your ears blown out.

    Clients who have tested this by no-phone times have realized that phone calls can wait, and sworn never to get a cockatoo as a pet.

    Neil Savage

    I disagree with most of this. I feel like it all comes down to your work ethic as you should be working from home like you work in the office. Sure you can dress differently at home and you have different distractions at home then you do at the office, but ultimately you should have relatively the same experience.

    I’ve been working from home over a year now and I still have a healthy relationship with the same employees I worked in the office with, I’m working less because I don’t have to commute anymore saving at least an hour a day and I stop working when everyone else does transitioning instantly into my social life once that office door shuts.

    Sure working from home isn’t for everyone, but I think it really comes down to self control and discipline – the same traits that you should have in a office working environment. You don’t need to take shortcuts or become lazy just because others don’t directly interact with you in person.


    I had a stint where I worked from home, for over 2 years. ALL of these items applied – especially where just the mere mentioning of conference calls began to cause a headache. ugggggghhhhhh.

    One item that I experienced – not sure if anyone else did – dealt with friends and family. All of a sudden, when they know you work at home, they want to call you at all hours of the day. And sometimes they get upset that you didn’t reply to them until lunch or after 5. It’s like they think that you aren’t really doing anything at ‘work’ and would be able to just pick up the cell phone any ole time.


      Joshua, count yourself lucky. Yours call, mine show up. Sister, cousins, friends, all wanting my help with something.
      In the last 24 hours I had to stop what I was doing to welcome: one niece sleeping over, one cousin wanting to talk, buy plane tickets for my husband, help someone with invoices, pay mom’s bills online and my own kids keep coming in every 40min (I counted).
      The funny thing is people actually support you, but they don’t seem to understand that when they keep you away from the computer, they are getting in your way.
      It is really, really, soooooo really frustrating. I tried explaining, but no use.

    Umesh Kumar

    I can totally relate, WFH has pros and enough cons, Food is sorted for me, but the social life sucks a bit.

    I meet very few people in a month as compared to the time I was working at a regular Job.

    Good that we don’t have Video Calls over here ;), and I do feel like going office ( once in a while ;) ) but then I get to travel more which is a good thing.

    So basically yeah, it boils down to how you manage it, staying home all the time, or taking benefit out of it and doing things or travelling to places


    Lol, thanks for this Brenda! I’ve been working for myself mostly from home for 10 years (wow, how time flies) & done pretty well adjusting: I have a virtual office plan which gives me office space to meet with clients when we need to meet in person. I’m very private about where I live, which has been for personal reasons, although now I realize it also helps prevent clients from dropping by (eek, who needs that?!) I have a cat, dog & bird, whose company I love more than office co-workers, and my dog makes sure to get me outside for a walk every day. Although, while I do my best to schedule calls when my bird is likely to be quiet, there have been times he participates in the conversation, or my cat decides she needs my attention & gets talkative. I also go to networking events frequently enough to help me balance time working alone and time in the world with people when I’m dressed professionally :)


    I can relate to some of this, and much more when you throw in working from anywhere via satellite internet…ya see, I’m part of a growing subculture of location independent entrepreneurs (aka: full-time RVers who call the home office wherever they park it).

    It *might* be embarrassing if clients knew I was dumping my black tank during the conference call. Or that the reason I didn’t call in last time was I didn’t want to waste my bandwidth.

    Currently reporting in from somewhere along the Mexican border—no cell service, no people, just a few javelina and plenty of solitude to hunker down and git er done for a while!


    You’re talkin’ about myths, but spreading a lot of myths about freelancing life by yourself. And if you think , there are no myths or awkward, embarrassing and hilarious moments/situations in the life of a 9-to-5 worker, think twice. As the saying goes: The door swings both ways.

    But let’s take it step by step…

    1.) I’ve never worked in my pajamas. Why should I? I know 9-to5 Jobbers lookin’ hilarious in their suits or their casual clothes, so what’s the deal?

    2.) I know a lot of 9-to5 jobbers, who are scatterbrained the whole day, the whole week, the whole month, the whole year, by making dumb decisions all over the place, or simply fail big time.

    3.) There are several studies floating aroud, that 9-to-5 jobbers like to check out their so called ‘social life’ on facebook, twitter and such while they have to work and some companies try to spy on their employees and try to control them, due to this circumstance. What’s your opinon about that?

    The degredation of social skills can also take place at your company, in your 9-to-5 job. Why? Because either way, your job consumes your social life up to the max, so their’s no time for family, friends, girlfriend/boyfriend, partner etc. – even no time for your work colleagues.

    Besides that: If you have to work from 9 to 5 in a building, you will see not much daylight per se. Some of the offices in companies remind me of dark chambers by the way. In my home office, I have the freedom to go work outside, on my balcony, on the terrace etc..

    5.): Since I’m a freelancer, I have much more time for cooking at home, which means fresh food that I want and enjoy to eat. I have not to deal with the junk food some companies are offering. Talkin’ about food delievery services, I know a lot of companies, who are dealing with it. Why? Because some of them have no lunchroom, no kitchen, no time to take care of good and fresh food.

    9.) Kids(and other family members) can always insert them into your schedule. If your kid(or family member) gets sick, had and accident or similar issues, your 9-to-5 schedule flies out the window anyway.

    11.) This is a common illusion, misconception or trap, because there is no such thing as separation between work and life. You never work outside of your life, that’s a simple fact. There’s always a blur between life and work.

    12.) I know a lot of companies, who had no sense of boundaries whatsoever. They let you work like a slave 10, 12 or even more hours, regardless of your private or social life, because they simply don’t care about it. If you’re a freelancer it boils down to discipline and you should always know by yourself, when boundaries are crossed. Simply put, you have to learn to say stop and no.

    Wrap up: Freelance work is not a mess, as you claim, as long as your disciplined and/or able to structure and manage your own life. To me, the regular, unflexible and rigid 9-to-5 job is a mess, a waste of time, a waste of social and/or family life. You always pay a price.

    I would never ever go back again to a 9-to-5 job. It’s simply a worn out model, that doesn’t fly anymore…, or you want to cling on the 9-to-5 dogma your whole life, to all eternity. I’m definitely not that type of guy. I want to go further, I want to think outside the box…


    Brilliant post Brenda. As I am sitting in my home office, in track pants, sweatshirt and my comfy dressing gown. Personally the only way to dress for work :)
    My personal favourite is the “oh my god I have 10 mins till that skype call”, find a shirt and maybe a jacket, quick shave and 30 seconds to go, phew made it :D
    Nice to know I am not the only one who enjoys some of the silly perks of home working, my kids are all grown up so I only get my Labrador looking for a biscuit cause it’s been like 10 mins since the last one dad and I’m starving. And I totally get the friends that ring you in the middle of the day, cause your at home and can’t possibly actually be busy. Thanks for the Smiles and the LOL’s Brenda.


    Lol you tell me the exact problem. Now please tell me the solution as well ? how to make friends ? I am working as a freelancer since 2014 jan. Now am totally friend less. Friend less means no friends at all. I am frustrated with this is daily stupid routine. waking up from bed on you computer go to Bathroom, sit on your computer to check email, go to kitchen for breakfast and come back to computer to work. blah blah I am totally ruin.


    The lack of social interaction really got to me. I joined a co-working office space (CoCo in Minneapolis) There I found a group of WP freelance developers all with the same idea. WordPress Wednesdays was born. Everyone shares a big desk once a week, currently a dozen of us, we get out of the house, we enlist each others help, we do lunch, go for walks, we meet people in other lines of work at CoCo which not only expands our horizons but also often leads to work! This also gives us a slick professional environment to meet clients in, access to conference rooms and a even a classroom. $70 a month for 5 days a month.Most cities have co-working spaces available now.

    I encourage anyone to see if they can put something similar together. Maybe you already have enough friends freelancing in your town. Maybe there is a user group in town and you could put the word out for interested parties there. One day of human contact a week makes all the difference. The office space gives you a much more professional interface to clients who are actually in your town. Even simply a child free environment to take a skype video call.


    Thanks for the laugh this morning. There’s so much here that resonates with me…as I realize I’m still in my PJs & robe, with a chatty 7 year old & 2 needy dogs running around & hubby still out of town (I THINK it’s been 3 weeks?). Stolen moments of peace and quiet are when the house is still and “the sun don’t shine”.