Confessions of a Late Sleeping, Bunny Slipper Wearing Freelance Writer

I'm getting kinda tired of reading all these posts about the right and wrong way to behave as a full time writer (and apparently, I'm not the only one). I'm also curious about all these myths that we are supposed to be worried about that ultimately (in my experience anyway) do not matter.

For the past two weeks I've seen a great number of posts on various writing blogs about how freelancers must fight against stereotypes and adopt certain conventional behaviors in order to "make it." As a freelance writer who personifies many of the freelance writing stereotypes we are supposed to be fighting against and who, apparently, embraces no conventional behaviors but who does manage to make a living, I'd like to set the record straight about how little each of these points have mattered in my career--and I'd like to get your feedback about how they do (or don't) affect you.

So here are my favorites:

Freelancers are people who don't work well in a corporate environment. When I first read about this myth that freelancers are people who were (or are) unable to “make it” in the corporate world I disagreed violently. I mean, just because we are freelancers doesn’t mean we have not or would not make it in the corporate world. After all, I left a successful career in order to freelance so I already had made it.

But then, when I really thought about it, I remembered that I was never really happy in that environment. I hate dress codes, meetings, restrictive schedules, commutes, seminars, speaking engagements, working with other people—all the things that a corporate life entails. So how did I succeed there? I sucked it up and faked it for years and you know what? I would not have been able to do that for another 30 years until retirement. Nope, not at all. So for me, this myth is true... and I don't care. Does that mean my freelance writing career is doomed? Does that mean I have to pretend that this myth isn't true for me? Um... really this doesn't generally come up in conversation nor does it affect how well I do my work so I don't think it really matters.

You can't be a successful freelancer if you hate working with people. I don’t hate people. I like people. I’m fun, easy to get along with, and I sometimes enjoy hanging out with people. But I hate working with people, so I don't. That doesn’t mean I can throw all my interpersonal skills out the window though, because I do have to occasionally talk to people on the phone and through email—but come on. That is so not the same as working with people. You don’t have to go into an office, listen to someone's boring stories about their weekend or look at their vacation pictures and pretend to care, you don't have to collaborate, consult, or do any other partnering exercise if you don’t want to. As a ghostwriter you need to interview people and be comfortable with a back and forth--but if you have ever worked in the corporate world then you know this is not the same thing as a team environment--something I avoid like the plague.

Freelancers who want to make it cannot wear bunny slippers all day while writing and simply must get dressed and, if necessary, put on a bra. Okay, I don’t actually have bunny slippers but I do wear my memory foam slippers a lot and I often stay in my pajamas all day.  There is just no reason for me to get dressed if I don't feel like it. If getting dressed helps you become more motivated or focused then by all means have at it. But if you are better off working in a comfy flannel PJ set, sans brassiere, with slippers that make you feel like you are walking on a cloud, what’s the difference? Sure, my boobs are going to sag earlier than my corporate equivalents--but does that really have anything to do with my ability to write and communicate for clients? This myth that you have to wear clothes and (gasp) real shoes is crazy. No one but you knows what you are wearing. Unless you have an in-person meeting. I would totally put on a bra for one of those.

Freelancers who want a real money-making career as writers cannot sleep until noon on weekdays and must work some sort of traditional daylight-hour-based schedule. The best argument for working a traditional 9-5 schedule that I read is that freelancers want to be available to their clients—and I totally get that... but I do it a little differently. In each of my contracts I have a guarantee that I will respond to all emails within 1 business day unless there is a holiday. This comforts potential clients but also leaves me uncommitted schedule-wise and means I don't spend all day waiting for an email or phone call that may or may not come. I have clients all over the globe so it is really impractical to try to be available for them all during their normal work schedule. But also, I don’t work for my clients. I work for me. I need to be available for my boss… which is me. I have to work the schedule that allows me to be at my best—not the schedule that someone else works.

Since this is one of the most popular myths about successful freelancing, I have a little theory about it. I think a lot of freelancers work a rigid schedule because they are afraid that they might not work otherwise--and they could be right. They may also be concerned that their friends and family will lose respect for what they do if they do it at all hours. But remember, it is YOUR career. YOU define it, not anyone else. You may have to be available for the occasional scheduled client phone call, but that doesn't mean you have to work 9-5. Think of all the successful WAHPs out there who have to work nights and weekends--are they less successful than freelancers working 9-5? Are they worse freelancers? What about people in school, caring for a loved one or doing anything that requires them to work a modified schedule? Even if you are like me and just sleep late because you prefer writing at night or you like to spend time at the beach between 9-5, it really does not matter. No one even knows you are doing it. Just do your work, do it well, and get it done before the deadline.

So the way I see it, you don’t need to worry about whether or not I wore clothes and a bra as I typed this (hint: I didn’t), you don’t  need to worry about being available 24/7 based on someone else’s schedule (hint: if you set guidelines at the start, you don’t have to), you don’t need to worry about being a corporate failure (hint: you’re a leader not a follower; an independent thinker not a conformist), and you don’t need to worry about your hatred of collaborative environments (hint: some of us just work better alone). Worry about putting out quality work to your clients by the deadline while fitting in a little marketing and networking. If you are in the early stages of your career, you might be a little less flexible and may have to put in some more hours, but you can still do that the way YOU want to. When I decide how to run my business, I think of Mr. Wizard from Tooter Turtle, “Be just vhat you is, not vhat you is not. Folks vhat do zis are ze happiest lot.


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24 thoughts on “Confessions of a Late Sleeping, Bunny Slipper Wearing Freelance Writer”

  1. Yes, Yo, yes. In my Slaying the Email Dragon post here at AFW, I touch on the once per 24 hour period email response time I have. I also like to start work around 4 pm or sometimes like… 11 pm and I’m damn sick of hearing that I can’t do that.

    I can also wear what I want.

    And I’m pretty sure that once my baby’s born I’ll be working even stranger hours to raise said child.

    You did a really good job with this post. My whole world is the Internet so I scan instead of read, but I read every word of this post.

    This bodes well with the re-launching / re-opening / startup of my new freelance writing business. Thanks for being the best kick in the pants ever.

    Now if you’ll excuse me, it is 7:32 am here and I’m going to bed now.

  2. Oh, and sorry for the double comment, but would you give us an example of your contract…like quote extractions or a template? You seem to have it all figured out 🙂

  3. Fuzzy slippers all the way!

    I have a rigid schedule. I just don’t always choose to stick to it. 🙂 When I need a day or two off (like now b/c I stupidly hurt myself), I take it. If I feel a rush of energy in the evening and want to knock out a project I do (but rather than letting me overwork myself, I take that time out of the next day’s workday and sleep in if I want to, or finish early).

    But yeah, anyone who says you can’t wear fuzzy slippers and PJs to work and still be a successful freelancer is just jealous that they couldn’t and plenty of us can. 😛

  4. Yolander,

    You are so describing me! I’ve owned my own business or freelanced for most of my very long career and can’t imagine working for anyone else. I work at night and sleep during the day unless I have a meeting or phone call (which is rare). Most of my clients love my schedule because they can send me something at the end of their workday and have it back by the beginning of the next day. I plan time every day for these short-turn-around projects as well as long-term projects. I dress very comfortably and wear socks, no shoes. As you say, it’s my business and I’m in control.

  5. I wear slippers. And though I don’t wear PJs every day, I do put on clean sweat pants.

    And why not? That’s how I’m comfortable.

  6. I’m usually in pajamas and a robe during the first half of my day (which ends at 8am, so it’s probably not that unusual). Then the other half till noon I’m often in jeans or sweats (only way to convince myself to workout afterwards is to already be dressed for it).

  7. My freelance writing and editing uniform is pretty much a pair of Hollister sweats and a tshirt. I put on jeans at 3 when I have to pick the kids up from school. If its winter, I don’t bother to change out of my tshirt, ’cause I have a super cute wool coat. Please don’t tell my clients 😉

    When I meet locally, I dress up, of course!

  8. Quote: “In each of my contracts I have a guarantee that I will respond to all emails within 1 business day unless there is a holiday.”

    Nice! I’d like to borrow that concept, please.

  9. Yup, I agree completely. Just sitting here on the couch, rocking the pink Snuggie, pajama pants and t-shirt. Did a day’s work from 8pm – 11pm just like every other night, and I don’t think I’ve put on a bra all day – even to go out. Big sweatshirts FTW!

    For those stressed about working “normal” hours, just let your clients know upfront that you’ll be delivering work before midnight rather than just saying “at the end of the day” which might be considered 5pm. Letting them know you’re free to chat or call in the evenings only is easy as well, In five years of freelancing, I’ve only have one client not conducive to that schedule and I didn’t like him anyhow. 🙂

    And I deal with emails with style and grace thanks to the iPhone. I answer then at red lights, between classes and while chatting with other teachers at lunch. No sleeping until noon over here, but plenty of off-the-wall solutions to freelance writing.

  10. Great post, Yo. I’m a night owl by nature. If I didn’t need to function during daylight hours (e.g. taking and picking kids up from school, watching the 3yr old), I’d work all night and sleep during the day for sure.

  11. So it looks like the schedule and the dress code struck a big chord–which makes sense since those are the most important benefits of freelancing. What about working with others and corporate failure? Any thoughts?

  12. I definitely like working alone. That’s not to say I dislike collaboration. Love it (why I partner with you chica). But I like to physically work alone — not be surrounded by incessant babbling, others’ phone calls, etc. I had my own office at my last “real job,” and that was okay. Having a door to close makes a big difference. But there were still a lot of calls interrupting projects, people popping in, etc. With freelancing I probably cut out 98% of that. Love it.

  13. While not corporate per se, I teach and I love it. I left the corporate world, took a huge pay cut, and started teaching because I love it about eight years ago. I’ve made more writing than I have teaching for about four years now, but I still do both because I don’t want to give up either. Duel income is nice, too.

    As far as being a failure, I’m afraid I’m most certainly not. I’ve been up for promotions multiple times and am one of the leaders in every school I’ve been in. But, as I’ve noted everywhere I’ve worked, I tend to be an exception, not a rule, so I’m not sure if my testimony is worthwhile or not. LOL

  14. Well, although it looks like my writing career could be close to over, I can say that my schedule was waking between 9:30 and 10 in the morning so I’d be ready to start writing by 10:45 at the latest. And though I didn’t write all day, I had my goals for the day and I never stopped writing until I had finished my articles for the day. If that meant staying up until 3AM to write, I did it, mainly because I tend to stay up until 4AM anyway.

    And I wore sweats all day unless I had a networking event to go to; as you said, what’s the point in getting all dressed up with nowhere to go and waste clean clothes?

  15. LOL Nice way of thinking about it Mitch – wasting clean clothes. I suppose we could say it’s another way to increase our productivity, because we slash laundry time. 😉 (I hate laundry days.)

    I’m sorry to hear your writing career might be coming to an end! I hope that means you found some other work you’ll be happy with at least.

  16. Not quite, unfortunately. Last week my main writing client lost clients of his own, and that means I lost most of my writing assignments as well. I hate the scrambling these days, as does my wife, so it might be time to look for something more secure for awhile. I love the freedom, but what’s freedom without the money to spend on it, right?

  17. My background is in healthcare finance, leadership/management and SEO issues, but I’ve been writing about the housing industry, green issues, wedding stuff (tons of that), legal issues and financial stuff in general. Thanks for asking.

  18. I’m sorry to hear that Mitch. It can take a little bit of time to build up that diversified client base and, for me at least, it always seems like there are a good deal of “unknowns.” After all, any of your clients could stop ordering at any time, so I can understand the desire to move on to something more predictable. It might be a good idea for you to continue writing part time as a way of building up that base and then going full time again once you’ve got a strong network.

  19. Thanks. I’m going to continue trying to get writing clients as I’m searching for something else, as I enjoy doing this. That, plus I still have to get paid in some fashion until I land something, right? 🙂

  20. Yes, I certainly hated the corporate environment. The irony is, though, that if you freelance, get successful, hire people and so on, you end up creating your own corporate environment. Still, writing the company newsletter is going to be a doddle!

  21. Ben, that’s why I make it a point to be as laid back as possible when I hire contractors. I don’t want to get so caught up in managing that I’m no longer technically a freelancer. That’s why I do this. I hire other people when I don’t want to do something or don’t have time to do something, and the rest I do myself. Fortunately it’s possible to keep things balanced and still maintain the freelance lifestyle.


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