Do You REALLY Want to Work From Home?


When you hang out in the personal finance blogosphere, you never run out of articles to read about self-employment, passive income, and making money online. It seems that everyone is either earning a full-time living from home, quitting a job, contemplating quitting a job, or starting a new enterprise in hopes of striking it rich. After 4 years of economic turmoil, more and more people (not just bloggers) are desperate for a way to quit the rat race. And ever since I quit my job last December, I’ve become the sounding board for all the people in my life who long for a self-employed lifestyle.

I wish I could do what you do. Can you teach me?

I’d love to work from home, so I’m thinking about quitting my job like you did.

What do you think of this business idea? I could replace my salary easily with this, right?

Few people understand the awkward position I was in (and the total insane leap I took) when I left my career. I was NOT financially prepared. I wasn’t even dying to become self-employed. If I could have found another job in my field, there’s no way I would be self-employed right now. But a lot of things happened and I made the best decision I could at the time. Through some miracle - knock on wood - it has worked out so far and I’m very happy. That doesn’t mean everyone can (or should) work from home.

Working? Or Hanging Out?

A lot of the friends who are so eager to follow my lead don’t seem to realize that I actually do work. A LOT. Like 15+ hours a day, 7 days a week. People have this vision of me sitting down at the computer for an hour or two, cranking out a few blog posts and website logos, then spending the rest of the day lounging around. I’ve invited a few people to come sit at my house and watch what I really do all day, but for some reason none of them have taken me up on it.

Sure, there are a ton of advantages in working from home. I can wear my pajamas all day. I can work from my backyard or my sister’s house or any other location I choose. If I’m sick and need to lie down, I can do that without asking permission. But all of those advantages come with caveats.

  • Working in pajamas: Some people have to get up and get dressed every morning, even at home, to be productive. Not me. But the disadvantage there is that I look like a bum all the time. Even when I bother getting dressed, I stick to jeans and t-shirts because decent clothes feel uncomfortable now.
  • Working from anywhere: I could get in my car tomorrow and drive to the lake for a week. But would I actually get any work done while I was there? I doubt it. If I’m going somewhere fun, of course I want to enjoy it like anyone else! So I’m usually tethered to my desk if I’m actually working.
  • Unlimited sick days: It’s great to take a nap when I’m sick or exhausted. But that also comes with the knowledge that I’m not getting paid while I’m sick or exhausted. Every hour I spend doing something else means I get to spend more than an hour making it up later.

People seem shocked that I work so many hours and take so little time off. But that’s because their idea of self-employment is an extended vacation. If I want to pay my bills, I have to work. And if I want to save money for the inevitable dry spells that come up, I have to keep working even after the bills are paid.

At some point, I’m sure my emergency fund will recover enough for me to feel comfortable taking breaks. Right now, though, I live in a state of complete paranoia where money is concerned. My income is more than adequate (knock on wood again), but I can never decide what to do when I get paid. Do I pay my bills ahead of time in case I don’t make any more money this month? Do I stock up on groceries now? Should I put this money in savings, or am I going to need it next week?

The Truth About Working From Home

Self-employment is great for a lot of reasons. I don’t blame anyone for wanting to escape a 9-5 and find opportunities to work from home - a lot of workplaces are toxic, or maybe your chosen career (like mine) is just a poor fit. But it’s important to realize that working from home is still working.

When you’re self-employed, you can’t always set certain hours (well you can, but you may not be able to stick to them). You can’t depend on a paycheck every two weeks. You may find yourself constantly revising your business strategy - or sometimes starting over nearly from scratch - as you learn what’s successful and what isn’t. You will work longer and harder than you’ve ever worked at a “real” job.

Working from home can give you lots more time to spend with your family. But it can also be difficult to actually find time to get work done. Someone is forever inviting you to lunch or asking you to drive Grandma to the doctor or dropping off their kids “just for an hour since you’re home during the day now.” You have to be assertive and set firm boundaries or you’ll never make a dime.

Oh, and I didn’t even mention the drama that comes with self-employment taxes and health insurance. But that’s a whole other post. Just know that there’s a reason people get to excited about benefits when they work for someone else - that’s probably the hardest thing to give up.

One More Thing

The most important consideration to make regarding self-employment isn’t about money or even the exact methods you’ll use to earn your living. The one thing you should spend time thinking about before any of that? Your personality and temperament.

Some people are simply not motivated enough to get up every day and spend a ton of time working. Some get bored without the social interaction that comes with a “real” job. Others need to know that a paycheck is coming on a set schedule with taxes already witheld and no surprises.

There’s nothing wrong with any of those qualities, but if you know you don’t work well independently (or if you can’t handle the uncertainty of “feast or famine” when it comes to income), working from home may not be the best choice for you. Despite what many people think, it’s far from easy, though self-employment can be a great experience if you’re adequately prepared.

35 Responses to “Do You REALLY Want to Work From Home?”

  1. Debt and the Girl says:

    Very nice post. I for one actually hate working from home. I don't like the lack of structure and the temptation to not do anything is too great for me. I like being able to go to a work place ever day and then crash at home when it is done. The idea of working in PJ's sounds good, though.

    • Andrea says:

      I have to admit, I love being able to wear what I want. I'm pretty good about staying on task - the panic of, "If I don't get this done, I won't be able to pay the bills next month" is pretty motivating - but it's really hard to escape when I want a break.

  2. callmewhatyouwantevencheap says:

    Great advice and your right about having a certain type of personality and temperament. It's not for everyone!

    • Don says:

      This is what I was going to say. I couldn't work from home - I'd be too distracted. But my girlfriend on the other hand thrives when she gets to work from home. To each their own.

  3. Lance@MoneyLife&More says:

    Definitely all very valid points that most people don't consider. Working from home comes with a lot of distractions so you have to be disciplined to be able to make it.

  4. mysti1031 says:

    I don't think I would want to be self-employed…but I could work from home. I would get dressed (comfy, but not jammies), with shoes (left over FlyLady habit). I don't think I would have the TV on…too distracting. But radio, yes. But to be able to do the laundry while I work….that would be great. Not having to take time off to wait for the repair guy.

    I am not in a position right now that any of this would work….but it is nice in theory.

    • Andrea says:

      I'm not a big TV watcher, but there's no way I could get any work done if I was. I do like to play music in the background.

      I love being able to get things done around the house. Unfortunately, though, I don't have as much time as I thought I would. I had this image in my head of a spotless, Martha Stewart kind of house… But it's really hard to stop when I'm in the middle of something! Luckily I have a lot less laundry now that I don't have to wear separate work clothes!

  5. @EmpoweredDollar says:

    "But the disadvantage there is that I look like a bum all the time…" I hear ya! I have a regular 9-5 but get to work from home on Fridays. I just FEEL slobby, even if I'm only on a conference call and no one can see me

    • Andrea says:

      I really should make a better effort, even if it was only a day or two a week. But it's so hard to convince myself to put on jeans or dress pants when my yoga pants are RIGHT THERE! I've definitely lowered my standard for what is acceptable to wear when I leave the house.

  6. cestarr says:

    Great questions and a very helpful perspective on self-employment. For me, the perfect balance is working part-time outside of my home and writing part-time from home. It gives me enough of a schedule to keep me disciplined but gives me enough flexibility to enjoy quality family time. It isn't always perfect, but it's a good balance for me. Thanks for your honest reflection Andrea!

    • Andrea says:

      If my web design business wasn't so busy, I'd definitely consider a part-time job. I think that would provide a good balance. I think the transition would hurt me, though - when I worked outside the house, I always needed some time to switch gears once I got home.

  7. Budget & the Beach says:

    OH I know all of this too well. People often glamorize working for yourself but I think it's even harder than full time. You wear SO many hats. I never realized how important security was to me until I started freelancing (which I was kind of forced in to by being laid off). I think, for me, the only way I'd ever enjoy it is if I was in a steady relationship/married where they had a good, steady job and I was on their benefits. But since I know I can't rely on that, I really want to get back to full time.

  8. DebtsnTaxes says:

    I've never really thought that working from home would mean working less hours. Maybe because I know a lot of people that are self employed and I know they are working a minimum of 12+ hours a day. I don't think it would be easy. I think the priority for me, if I was self employed, would be that whatever I chose to do I would want it to be something I really enjoy.

    • Andrea says:

      That's a great point. If you don't love it, you'll be just as frustrated as you are in a regular workplace. I feel very fortunate that I love what I do! I definitely still get frustrated, but I enjoy it enough to make up for those moments.

  9. Financial Samurai says:

    I hear you on the power hours of non stop working!

    How much is fear of not making money driving you to work?

    Part of the reason why I decided not to sell my house in a post on Yakezie.com is b/c I would be spending more at my house by 60% when I finally leave work.

    I'm finishing up my book on how to profitably leave work now. Hope you check it out!

  10. krantcents says:

    Working from home sounds easier, but I know it isn't. Having your own business is work. It is just a more convenient location.

  11. Donna Freedman says:

    Agreed, agreed, agreed.
    And here's another point for freelance writers: Unless you luck into a contract situation, you will always, always be chasing the next assignment. No real down time per se.
    That said, I enjoy the upside of freelancing/working at home more than I dislike the downside. For me, it works. If I had to do this with small kids in the home? I couldn't.

  12. @ElPesoNuestro says:


    I quit my job six weeks ago.
    Before doing it a built a comfortable financial cushion, signed a commercial agreement to work from home for a company, had a blog with decent traffic and a couple of paid writing gigs. Still every day I hustle to make sure I will have income on the future.

    I started writing a Diary of the Self Employed (http://www.elpesonuestro.com , sorry only in Spanish ) to share my experiences with all the readers , to show them the truth about what it means to be freelance.

    Great…great post!

  13. Canadianbudgetbinder says:

    You’ve posted alot of great information that anyone who wants to work from home should consider. It’s not as easy as it sounds and just because you are at home doesn’t make that better than going to work. Yes you get all the perks like working in your pj’s but you put your time in. I don’t even earn money from my blog and it’s alot of work but I know when the time comes loving what you do is more important. When you love your work others will see that and the rest will follow.

    I can’t imagine how many hours you work in front of your computer. It takes a special disciplined person to do what you do so congrats. This only tells me you have confidence in your ability to get the job done with pristine quality. Sometimes relying on word of mouth marketing about the skills you have to offer is one of the best marketing adverts you can have.

    Keep up the hard work Andrea! Cheers Mr.CBB

  14. maria@moneyprinciple says:

    I am just finishing a year sabbatical - which in effect meant working from home. I have never worked so hard, achieved so much and felt so utterly wipes out. Working from home is not for the obssesive types: it is for controlled people who can pace themselves. Oh, and I missed the social aspects of being out of the house and my students of course.

  15. Janice says:

    Agreed. I watched my mother work from home freelance most of my life. She was a nervous wreck when she opted to choose that instead of working for one company. There were definitely perks but she also had the same issues as you - where she was constantly working and others thought she wasn’t.

    She also had the issues of health insurance and taxes. She was the main bread winner so she had to get health insurance for all of us. Crazy.

    I’m glad you wrote up this post - it’s great to hear another side of this.

  16. Teinegurl says:

    I feel i could do the same thing you did or still have my part time job and do blogging on the side and make money too , I would do it if i knew how. It's good to know the reality of things before jumping into something so thanks andrea

  17. bogofdebt says:

    Excellent post. I wish I could show this to a friend who has moved away. He went from working for someone to working for himself and the store he owned was going downhill. Most people thought the place was closed because he kept such odd hours. I work from home sometimes and that's hard enough. I don't have a desk so it's so easy to sit on my bed and watch Netflix…I mean work on my projects.

  18. Jerome says:

    Since 5 years my wife and me work from home, each in our own business. After 5 years experience, the main thing we miss, compared to when we worked in a company, is the direct contact with colleagues. You know, the nice chat over a cup of coffee. And I, but not my wife, miss the travel which I used to do a lot. But that is it.
    Yes, our income is varies a lot but that has nothing to do with working from home. And yes it is difficult to find new work, but that also has nothing to do with working from home. That is related to having a small business. Working from home saves money and time, and requires a bit more discipline (we have 5 small children…). Especially the low overhead is a tremendous advantage. We both have overhead cost below 5% of turnover. And that includes everything: insurance, office supplies, etc. These low overhead costs make a huge difference for our pricing. And it reduces stress when things are slow for a couple of months.

  19. Save Big Live Better says:

    Thanks so much! This is all so true and I'm glad someone finally put it into perspective! I run my website, an at home business, and of course take care of the assumed duties of someone that works from home of the cooking and cleaning and so on, and then do it all again as my 1 year old runs around after me and UN-does it! LOL, at the end of my 36 hours days I'm exhausted even more so than when I worked out of the house full time!
    Its definitely a choice that should be thought about in detail before being made, but can be very rewarding, if you're prepared to put the work in to get there:)

  20. Jai Catalano says:

    I actually like working from home. I actually get to work outside of home from time to time so being home to work or pay bills is cool by me. You say one gets to spend more time with the family. Well not when you live in NYC. My kids are in my office because my office doubles as a living room/dining room. If I had a house maybe it would be better or at least different but the fact is when they get home I pretty much have to quit for the day or pick back up after they fall asleep.

  21. Tammy says:

    Before I left the rat race I was working from home. People look at me crazy now when I saw that I gave it up. I learned that maybe working from home a few days a week and in the office a few days would be a better fit for me. I got to the point that I didn't leave the house for days at a time and didn't want to. I turned into a complete anti-social hermit. That was when I knew I needed a change.

  22. americandebtproject says:

    I love this. I think the point that you get (and I finally got) was that we have to work very hard to be successful/financially independent. I used to love the idea of a work from home job because I had no intentions of actually working. I just wanted some kind of BS job where I could still live by the beach and live a complete life of leisure. OK, that's still kind of my dream, but now that I found work I really love, I want to have work, at home or in an office. I like the idea of partial working from home with a healthy dose of getting out of the house. At my firm we are allowed to work one day from home, and we have a 9/80 schedule. That one day a week always feels like a luxury and so far I've had to attend a meeting every "work from home" day so I only get to spend about 4-5 hours working from home. When it's like that, I am VERY productive at home. I love it! I focus, take quick snack breaks (nutella sandwich!!), and don't get interrupted by coworkers or even email, because I realize which emails truly are urgent (usually none of them) when I work from home. At the office, I am always doing the most urgent task or responding to the latest email. At home, I KNOW what has to get done and it's usually more important, non-urgent stuff. I think a 3/2 or 2/3 work from home/work in office/on-site balance of the week would be perfect.

  23. Allison @Insomniac Lab Rat says:

    I think I would really struggle to work from home. I’m too easily distracted.

    I’m going to have to work on my at-home productivity when I have a paper to write, or a grant, or my thesis…

    I tried to do a lot of my qualifying exam writing from home, since when I’m in lab I’m either distracted by all the people, or feel like I should really be doing lab work. At home, I had a hard time buckling down and writing. Of course, that was during the time when we were buying our condo, which was one of the most time-consuming, horrible, soul-sucking things I’ve ever done…so I’m hoping things will go better next time I have a really big writing project!

  24. BalancingMoney&Life says:

    There are lots of benefits to working from home, but I know I'd have a hard time with it - depending what I was doing. When I ran my eBay business, I was BUSY - writing ads, answering emails, packing, shipping, buying new product, taking pictures.

    When I did some consulting, writing presentations, etc., I had a hard time staying focused. Not for me!

  25. socarr says:

    Awesome post! You are so talented it is great to see your income bar increase every week! I think a lot of us would be interested in a post about taxes and insurance for the self-employed! I am sure there is a lot that only you could put into funny and educational words. keep up the great work!

  26. fugalportland says:

    I'm not sure I could do it. I need human interaction. If I had an outside sales job, then maybe I'd be able to do it, because at least I'd be talking to people when pitching! But right now, over the phone? Nah, not for more than a few days here and there.

    Also, how do you NOT snack all the time from home? That was my problem when I worked remotely for a week. I wanted to eat everything all the time.

  27. Charlotte @ GoBeRich says:

    All good points. I get to work from home for my employer two days a week. It used to be 4 but due to too many new people at the office, I have to go in 3 days. I too have found that I can't work with the TV on but I can with music. I do like the fact that I can get up and put in a load of landry before work and be able to move it once the cycle completes. My husband works close to home, so we get to have lunch todether those two days.

  28. stacyverb says:

    My husband works from home and it is definitely a mixed blessing. Yes, it's great to be able to just roll out of bed and start working without having to get dressed or commute. But he tends to go stir crazy being in the house that much, with no one to talk to but the cats. Also, he never really feels like he's OFF work, because even when he's not working, he's still AT work.

  29. Brilliant Finances says:

    Yes, working from home is not easy. It's also a huge risk to take to go out on your own.

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