We Asked People Who Work From Home The Questions You Are Too Embarrassed To Ask

Photographed by Beth Sacca.
The number of people who work from home is on the rise – but it's still far, far from the norm. Which is why these non-office workers can hold so much allure for the rest of us. Are they productivity machines, who get to do laundry while they work, or are they lonely recluses, missing human interaction and never donning a bra? The answer is sometimes both at the same time. But, like with all jobs, there are ups and downs and highs and lows. Just like no two people or companies are the same, no two workers will have the same work-from-home experience. But if you’ve ever daydreamed of ditching your commuting flats and work tote for good, you’re not alone. We asked people who are making things work without ever setting foot into an office. Read on- it may make you feel grateful for your cube mate, or be the push you need to start applying to the remote gig of your dreams.
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Do you just wear pajamas all day?

“Absolutely not. If I don’t get dressed and put a bra on I get nothing done. I used to not get dressed or brush my teeth or wash my face until I made my deadline on deadline days but that made me feel disgusting. Now I am up and nice before 9am - one hour after I start work at 8.” –Field Researcher, 27
“No! I may have a meeting at some point in the day, or need to go outside for a break/lunch, etc. Now do I wear a bra less? Definitely." – Founder and CEO, 30
“Pretty much! Leggings and a baggy t-shirt make me much more productive because I’m not constantly adjusting my uncomfortable bra or fixing my pants.” – Marketing and Data Base Coordinator, 27
“Yes” – 30, Claims Adjuster

Doesn’t it get lonely?

“I’m a very social person, so I really thought this would happen – but it hasn’t! I prioritize going to the gym around lunch a couple times a week or having lunch with a friend. Getting out of the house regularly is key.” – Director of Product Management, 30
“100% That was the biggest thing I was not prepared for. It was great for about a month, to not be constantly interrupted by coworkers with questions or just idle chitchat, but then I realized I was extremely lonely and not really enjoying working in complete isolation.” – CEO and Founder, 37
“No, since I spend a lot of time responding to e-mails and being in conference calls all day.” –Manager, 28
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Are you crazy productive, or are you streaming Hulu all day?

“About the same. Less distractions, but it’s also easier to put a load of laundry in, start the dishwasher, etc.” – Marketing and Database Coordinator, 27
“More productive, the quiet lets me focus more on tasks, and the flexibility in my day lets me balance chores in the downtown vs. when it used to be spent going to coffee shops for work.” –Freelance Writer, 28
“It varies day to day. There are certainly days where I'll sit at my computer and pop in a movie, but there are other days where I have a steady flow of work to do” – Unknown

Do you travel more because you can work from anywhere?

“Yes! Gives me flexibility to be around family and friends away from home more.” – Experience Manager, 31
“Not really. I do feel like it’s harder to shut off when traveling because I can “work from anywhere.”’ – Freelance writer and editor, 36
“Nope! I am a homebody through-and-through. “ – Marketing and Database Coordinator, 27

You must work for a start-up if you get to work from home, right?

Yes… and no. The people we surveyed work for major corporations and smaller companies, as well as digital-first companies where everyone is comfortable being on a computer all day. Many are self-employed, or do work that requires a lot of time out of the office with clients so a normal office isn’t tenable. Many are self-employed.
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Do you actually work from home all day or are you one of those people sitting in coffee shops in the middle of the day?

“I have an at home office. I work from coffee shops and with friends when I have a light day and can mostly be done offline. “ – Experience Manager, 30
“I move around the house all day. I have a home office but I hate it. I work part of the day at my kitchen counter, part from my couch. Sometimes if it’s a bad day I work in bed." – Field Researcher, 27
“I try to keep my coffee shop days to a minimum, but I need at least a few to get out of the house and get a change of scenery. The only problem is the one that is closest to my house will top off their very good coffee if you are sitting at a table working. If I don’t have the self-restraint to reject a refill, I’ll eventually have to leave because I’m over-caffeinated.” – Writer, 30

So it must be pretty amazing to work from home, right?

“A thousand times, HELL YES” – Freelance writer, 28
“Sometimes” – Data Analytics Manager, 28
“Wouldn't trade the freedom for anything." – Content Creator, 21

What advice do you have for people who want to work from home?

“There are trade-offs, and it won’t always be perfect. You have to take the bad with the good, and make sure you remember the why of why you wanted to do this. For me, and in the position I’m in, its the flexibility to do everything from take a Monday morning off because I’m tired, to visiting family last minute because I miss them.” – Writer, 30
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“Be Disciplined. Make sure you set rules and boundaries for yourself. Listen to music, but do not let yourself be distracted.” – CEO, 30
“Communication with your team/colleagues is key. Answer the phone calls, & respond to emails quickly. You never want anyone to feel like they can’t get in touch with you” – Director of Property Management, 30
“Make sure you see some daylight." – CEO, 30
“Create a routine that works best for you. Keep a work space that allows you to be your most productive and get your thoughts flowing.” – Freelance writer, 28
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