Working From Home and Being Self-Employed: Frequently Asked Questions

I've been self-employed and working from home since 2014 (ummm, how has it been four years already since I finished university?!) mostly out of the sheer will of avoiding an office job because that is my nightmare. I know, I know, there are other jobs in between working from home and working in an office. But working from home has always felt right for me, and especially since getting sick in 2016, I couldn't imagine doing anything else!

As much as I love working from home (I'm a freelance writer and social media manager), it also comes with several challenges. But so does any job!

I recently posted on Instagram about planning to write this post and asked people to send me their questions, and I got a few about what's tough about working from home, so I'll definitely talk more about that.

Here are some frequently asked questions about working from home:

"Do you work in your pajamas? I would"

More like, do I ever NOT work in my pajamas? "They" say you're supposed to get dressed like you're going to work every day, but that just means more laundry so working in my pajamas basically means I'm helping the environment...riiight? But yeah, most days I stay in my pajamas until I work out, and after I work out I work in my workout clothes! And the cycle repeats...

"What hours do you work?"

This is kinda tough to answer because it varies so much. But, I never work typical 9-5 hours. I do work for several hours a day, but I usually start later in the day (around noon), but I take breaks to cook or workout or whatever and often don't finish until 11 at night. I really love the freedom of getting to work whenever I want!

"Do you work in a home office?"

It pains me to answer this because I so badly want to say yes. But NO! I actually HAVE a home office with a beautiful desk and all sorts of cute stationery from Indigo I spent a bunch of money on and never use, but I never sit at my desk! I hate the feeling of sitting in a chair for a long time (always have!). So, most days I work sitting sideways on my couch with the dogs under my knees. If I'm feeling crazy, I'll sit at the kitchen table or work from my bed for a bit. But yeah, most days, couch city.

"What about health insurance?"

One of the greatest advantages of being employed by a company and working a more "regular" job is the benefits that come with it. I do not have insurance, so I pay out of pocket for prescriptions and dental and eye care, etc. But the amazing thing about living in Canada is I was able to have a surgery that would have cost about $130,000 USD in the United States be entirely covered without insurance! Pretty incredible. There are definitely times I wish I had coverage because dental care is insanely expensive, so I plan on getting some soon and just paying for it myself.

"Do you get lonely?"

Not really, no! But that will depend on your personality. I enjoy being alone, AND I enjoy being with friends. There have been a few times where I'm like, "Wow, I haven't seen another human in person for three days...perhaps I should go outside!" But generally, seeing people in my free time fills my cup up enough that I don't feel lonely when I'm working. I also don't think being alone equals being lonely, so it really will just depend on your personality type. I think if you want to work from home but you are the type to get really lonely when you're alone, you'll have to plan your weeks well to make sure you're seeing other people or doing whatever you need to do to feel balanced.

"How do you stay motivated?"

Truthfully, there are lots of days when I'm NOT motivated. But when you're self-employed you rely entirely on yourself to make dat money, so as much as I want to just "take a day" or not work, I can't if I want to get paid, so that kinda forces you to be motivated, if that makes sense? I also find being really organized helps and clearly tracking my tasks and goals also helps. It feels really good to cross things off, and I think that encourages you to do more. Setting a timer is also a beneficial tool. If you're reeeeeally dragging your feet one day, set a timer for 30 minutes and promise yourself you'll work hard for that time, and by the end of it, you usually want to keep going!

"What's the best/worst part of working from home?"

It's hard to pick just one best thing, but at the top of the list would definitely be getting to be with my dogs all day. I love having them there with me, and I always hate leaving them at home when I go out so being around all day is fantastic. I also love that I can make my own hours. This has been absolutely essential for me since being sick. Not every work from home job gives you this flexibility, but since I'm self-employed, I have a lot more freedom. It's also preeeeetty awesome in the winter when your car is buried under three feet of snow and you can just stay inside all day!

The worst part for me, and this is not the same for everyone who works from home, is not having the benefits and job security you get from working for a big company. This has more to do with being self-employed than actually working from home though!

"What do people misunderstand about working from home?"

One thing that's been frustrating for me is that some people assume I'm free whenever. Like, they'll be like let's hang out on Tuesday afternoon! Whereas you wouldn't ask someone who works a 9-5 office job to do that because you respect their work hours. It doesn't make me mad, because I understand why people would ask, but I do just wish people understood that a bit better. To be fair, often times I CAN hang out on Tuesday afternoon if I plan my week right, but I'm not just free to do anything anytime because I'm self-employed, you know?

Phewf, that was a long one!

Until next time!

xo - C