If You Want to Work from Home, Ask Yourself the Right Questions

Yep, it’s been a hot minute since I’ve updated the blog portion of the site. It’s been quite busy on the business front. I’m not complaining. I’m generally busy working on other people’s sites and content. I still keep the work from home writing and editing jobs list updated as often as I can. I wish it were daily, but between virtual schooling, work, and, you know, my own introverted life pursuits…I do it as often as I can.
Anyhoo, I had another conversation with someone I’ve known for over a decade. It is a recent conversation. This person is well-read and educated. It centered around getting started working from home…mostly as a side-hustle. And, if a side-hustle is what you want to do because you have a dream job / business in mind, that’s totally fine. However, if you want to work from home, you must ask yourself the right questions. If you don’t ask yourself the right questions, no one can help you. Not even me and I’ve been doing this for a really long time. Not only did I write the book on it, I rewrote certification classes on working from home in different industries for a college I won’t name because I cuss a lot. While they routinely leave glowing feedback for me on my Upwork profile, I am well aware that I can be rough around the edges. Of course, I do NOT interact with my clients in such a manner…and, yes, many of my clients have read my blog. Some even follow me on social media. Hell, some fucking met me on social media. Anyway…so, what are the right questions you need to ask yourself to work from home?
What Do You Want to Do While Working from Home?
Be specific. Be very specific. Don’t just say that you want to be a virtual assistant or a writer. Sure, it’s okay to be broad in some sense of the word. I write about a lot of topics. I also handle search engine optimization both in writing and on websites. I also handle social media. My clients know I am a good person to bounce things off of if they need ideas. I am an excellent researcher not just for writing my own articles, but just for whatever my clients may need.
So, what do you want to do while working from home? Are there certain types of things you really enjoy doing? I love analytical tasks. Yes, I love writing…but in addition to that, I love the SEO aspect of it because it’s a game for me.
By the way, the wrong answers to this question include:
- Anything
- I just want to spend more time with my family
- I just want to quit my job
- Variations of those answers
Here’s why those are the wrong answers. The “anything” answer will land you with freelance work or clients who make you fucking miserable. You’ll end up with lousy pay. You’ll decide that working from home just isn’t possible.
Related: Freelancing Isn’t Free – Don’t Get Fucked Over
The “I just want to spend more time with my family” ends up smothering you even if you’re as introverted as I am. And I really love my family. One of the reasons I started doing what I do was to make sure I am here for them. So, wanting to be with your family is 100% valid. Here’s the real catch. When you’re working, you’ll feel like a dick for not spending that time with them. If you’re not working because you’re spending more time with the family, you’re not making money. It takes time to figure out that happy medium…especially in a global pandemic.
Oh, and if you work from home and you have friends and family who do not, they will likely think you don’t work and are a babysitter. You must be prepared to stand your ground about many things. Learn to say no to protect your time.
The “I just want to quit my job” is valid to some degree. I’ve worked plenty of jobs that sucked. I’m sure we all have. Poor management, shitty coworkers…pay that didn’t cover the bills…whatever. I get it. I worked two jobs when I started this business. I taught college. I worked part time in a law firm. This magnificent little beast was very part time. So, I do understand. Again, though, desperation can put you into a dangerous spot. Free cheese in a mousetrap is often free cheese in a mousetrap. Don’t take shittier wages than you’re getting now. I’m not saying don’t quit. You do what is best for you. I’m saying be mindful and know what you want to do.
I knew I wanted to write and edit. I knew I’d be happy if it had something to do with law since I taught Paralegal Studies and all the supporting legal courses, history, and a ton of other classes. I wasn’t quite sure how I’d make it happen. It was kind of a build the plane while it was flying…
What Don’t You Want to Do?
If there is one thing I know for sure, it is that you do not want to be miserable working from home.

You really don’t. Make a list of the shit you absolutely do not want to do. What do you hate? I recognize this seems so basic, but it always seems like people take jobs they fucking hate when they start working from home…like those are all that exists.
I knew when I first started that I’d take paralegal work from lawyers if necessary and I’d talk to lawyers on the phone, sure. I would not be their receptionist. I also would be a virtual assistant who answers the phone. I would not do customer service (except for taking care of my own clients). I. Fucking. Hate. Being. A. Receptionist. I’m good with people. I just hate being on the phone. I also hate being in meetings. I take as few as possible. Same with Slack because many people just abuse the shit out of it. I’ve quit gigs over it. I don’t have four hours a day for “meetings” that should have been a one paragraph email and that I probably didn’t need to know. Frankly, being added to everyone’s Trello, BaseCamp, or ClickUp is getting just as bad.
What do you hate? Make a list. Avoid those things. Why would you want to be in your own home while working and doing what you hate? It would be prison.
So, the question isn’t:
How do I start working from home?
The right questions should be:
What do I want to do from home?
What don’t I want to do from home?
Maybe even:
What would make me drink bleach if I had to do it from home? (Please don’t drink bleach…you will die.)
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