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Unsent Letters: Self Employed Still Means Working Edition


Dear Real Life Friends,

I feel like my verbal explanations of what I do all day haven’t been effective, so maybe a letter will help you understand a few things.

Yes, my work clothes are pajamas and a bathrobe most days. I traded in my flat iron and commute for bedhead and dogs on my lap. Sometimes I take naps after Jay goes to school. I’m not worried about what restaurant I’ll go to for lunch because it requires too much time and energy to get ready. All of those things are true.

However, some of you seem to be under the impression that I just do whatever I want all day and money magically appears in my bank account. While I would LOVE for that to be the case, self-employment doesn’t really work that way. At least not for me.

Please don’t be offended when I don’t answer the phone. And don’t call 11 times, then text, “Call me when u get a chance,” all because you want to tell me what your boyfriend said that pissed you off. I promise, if I could talk to you, I would. But just like when I had a “real” job, your problems are going to have to wait. And when I do answer and you ask what I’m doing, don’t laugh like it’s funny when I say, “Working.”

Of course there are perks to being my own boss. But I also deal with crap that you don’t have to think about. Like taking out my own taxes every single time I get a little bit of money in my hands. Wondering if I’ll make enough to pay this week’s bills or whether it’s time to go back to a career I hate. Working 12-18 hours a day because there’s no clocking out and going home. Getting in a really good writing groove, only to be interrupted by the dogs barking or my stomach growling or picking Jay up from school or YOU calling my effing phone multiple times back to back.

You may be shocked to hear this, but freelance writing means I have to write things. Like daily. It takes hard work to create content that people may actually want to read. And the most time-sucking tasks don’t directly result in money, yet I have to do them anyway.

The fact is, talking to you doesn’t help me get paid. While I’ll gladly call you back when I can, don’t expect me to feel sorry for you when you’re earning a salary while talking on the phone all day. And DON’T do that wistful “must be nice to stay home” thing because it makes me want to hug you. You know, because a hug is a strangle you haven’t finished yet.

If someone dies, please call me as many times as you need to until I answer the other phone. Otherwise, time to STFU and GTFO. I have work to do.



About Andrea Whitmer

Andrea is a freelance web developer and mom trying to maintain a sense of humor in an otherwise chaotic world. She blogs in hopes of helping others avoid the same mistakes she made in the past. Join in the discussion here on So Over This, or connect on Twitter, Pinterest, Instagram, or Google Plus. You can also subscribe to new posts via RSS so you never miss out!


  1. You sounds as though being self employed is making you awful grumpy. Would working in a normal office be better for you?
    Best wishes

    • Hi! You must be new around here. I say that because I'm ranty and bitchy all the time, not just since becoming self-employed. Actually I think it has improved quite a bit. Thanks for your comment!

  2. Edward - Entry Level says:

    This has a lot to do with while I've resisted full-time entrepreneurship since college.

    I would never tell somebody who was self-employed that "being able to stay home" is "nice." I was unemployed for 17 months, staying at home is NOT nice. Maybe for the first week or so, but after a month, your own home starts to feel like a prison.

    • I think it's a matter of perspective. If I was sitting here trying to find work and stressing constantly, I'd hate it. But since I get to spend time doing what I love, it doesn't feel restrictive to be at home. It's just hard to get things done when people think I watch soap operas and hang out all day!

      • Edward - Entry Level says:

        A valid point. Although, even now that I'm employed again, I get antsy if I stay home too much. If I were self-employed, I would probably have to get a co-working space.

  3. LOL. This is awesome. I think some people still believe that self employment means you never have to work, when in fact, you usually have to work harder, you just don't have somebody breathing down your neck (and usually, you actually do – your clients – just not a boss). 

  4. You make a lot of valid points Andrea.  Being an entrepreneur is much different than being an employee.  A lot of people have a hard time wrapping their heads around this as a lot of people haven't been on both sides of the fence.  You are doing great though.  Keep it up!

  5. LOL. I'm not self employed but I get to work from home quite a bit and people always think I am in my jammies all day 🙂  It's actually not true for me.  In order to feel productive I have to be fully dressed.  I don't even like working in my socks or slippers!

    • I've heard a lot of people say they get dressed every morning. I think it depends on the person, as well as what they're doing. Since my posts were written in pajamas before I quit my job (at night or early in the morning before work), this feels like my uniform. 🙂

  6. hehehe. One of the most honest post anyone can read 😀 It is good to know that you are well focused and cannot be disrupted by external influences that easily.

    good luck.

  7. So would any of your friends respond better if you gave them a window of time to call during?  If you normally take a break from writing around 5pm for example, and took an hour for personal stuff? Most of my work- from- home friends do this, so everyone knows they are working during the rest of the time. Good luck.

    • What a good idea! Maybe it would help if I said, "You can call me at 6 and I'll be able to talk." That's usually the time I stop to eat dinner and straighten up the house, so I could talk during that time. For some friends, though, that's the time their significant others are home and they don't want to talk – they would rather keep bugging me during the day. I'm going to try that out and see how it goes. Thanks for the suggestion!

  8. The best part about this post is that you could rewrite it 5 years from now and it will be just as true then as it is now.

    I wish my life were even half of what people tend to think it is because of my particular employment situation. I think people tend to have an idea of self-employment being a lot like a James Bond lifestyle where you spend an hour each day doing some super-critical task before spending the other 23 hours putting on a tuxedo and hanging out with hotties at an upscale bar.  If only that were true.

  9. Andrea, this topic is dead on. As a home-based entrepreneur approaching her 11th year in business, I recently started working out earlier in my day to improve my health and clear writer's block. Consequently, someone said, "Well, those of us who work can't exercise during the day." I chalk up such small thinking to a small mind.

    • Oh wow, I probably would have smacked that person in the face! I'm really sensitive to those kind of comments; hopefully it gets better with time. I feel a real need to defend my choice even though it really shouldn't matter what people think.

  10. LOL.    I once worked from home (although in a salaried job). I loved it (because I worked in shorts, did laundry, fed the dogs etc) but also hated it because the phone would start ringing at 5am(East Coast clients) and wouldn't end until 8pm(Hawaii based clients).

    I know exactly how you feel. Friends do call expecting that I had nothing to do all day.Some called cuz they were at the golf course and wanted me to drop everything to play.

     I think for all of us that do work from home, setting our own hours(even if it sometimes meant 15 hour days) has it's own rewards.

    • Very true. I have hours in my head that I plan to keep, but it never works out that way. I think I need a program that will shut down my computer during my "off" hours to prevent me from working!

  11. CultOfMoney .Com says:

    Even when I was working from home I always tried to make time for the socializing, otherwise you kind of just disappear.  This is especially true of co-workers, you need to spend some time chatting.  In an office, if you ever run into those folks who just work-work-work, you'll notice that many people just don't care, because no one knows them.  It may be different as a work from home writer/blogger, but I think you really do need to schedule social time, as people like to work with people they like (and boss/managers/clients reward those they like best.)

    • I do spend time chatting online with other bloggers throughout the day, but that's much different than friends calling to talk about the weather or random gossip. Interrupting what I'm doing when the conversation has nothing to do with writing or blogging doesn't seem productive. In a normal workplace things were much different – like you said, if I didn't socialize, none of my coworkers knew me.

  12. "A hug is a strangle you haven’t finished yet."  Best. Line. Ever!  Thanks for the Monday morning laugh. 

  13. I completely sympathize with you, Andrea.  It's funny to see the reactions, and struggle, as people learn what I do now and they try and make the connections in their heads.  For so many, "working" means going to an office and working for someone.  Crazy what they're missing out on!

    • I agree! If I have it my way, I'll never work for someone else again. Having true control – knowing someone can never call me into an office and tell me I don't have a job anymore – is absolutely priceless. A lot of my friends try to tell me about job openings, and I ask them, "Why would I want to get dressed when I can make more money at home in my PJs?" So far no one has a good answer for that; just a lot of "But it's steady income!" Is it REALLY? It wasn't for me.

  14. Anonymous says:

    Loved the reference to Copernicus the Homicidal Monkey!

  15. Gotta love these letters that you write.  It is why you are one of my favorite reads.

  16. Enjoyed the rant!

  17. LOVE!!!!! I'm still working towards actually making real (liveable) money at my freelance writing/coaching/illustrating/designing gig but that doesn't mean I'm not working hard at trying (albeit, often in my pjs) xx

    • Exactly! It's a different ball game when you have to hustle for every dollar you get. I'm actually dressed today and I'm shocked how uncomfortable jeans are. Can't wait to get home and back to my pajama pants!

  18. Andrea – I work at home as a full-time web design freelancer, so I feel your pain.  Because my paycheck isn't guaranteed, I work a hell of a lot harder and longer hours to make sure that I'm successful and able to take care of my family.  I also have friends that don't "get" why I can't have 2+ hour lunches every day. I could, but I choose not to because I feel like I function better if I have certain expectations for my work day, like working during a core set of hours.  It can definitely leave you feeling frustrated and demeaned when dealing with family/friends constantly questioning your work ethic.  Just because you're at home doesn't mean you aren't busting your hump! Best of luck to you – just from reading your blog I can see that you're driven enough to make it!

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