Freelance Writing Week: Is Freelance Writing For You?

Welcome to Freelance Writing Week at Bleeding Espresso!

A new pen online by Squonk11 on FlickrIf you’re interested in freelance writing, even as a part-time gig, this is the place for you.

All this week I’m going to share what I’ve learned about freelance writing over the past six years. I’m basing the posts on questions I remember having when I was starting out and also those asked in my Questions post a little while back. If you’ve thought of more questions on freelance writing, please share them in the comments!

OK, so as I see it, the first step in pursuing a freelance writing career is figuring out whether freelance writing is really for you.

Just like not everyone was cut out to be a doctor or lawyer, not everyone is meant to be a freelance writer. I personally love the freedom of researching and writing from home on assignments that interest me, but not everyone enjoys such work, a lack of structure, and a solitary working environment.

Here are:

Five Characteristics Every Freelance Writer Should Have
(Or Be Willing to Work On):

1. Good writing and grammar skills. You don’t need to know everything right now, but it certainly helps to know the basics. If you’re not sure whether your writing is effective and more or less grammatically correct, ask someone whose writing you like to read and critique it.

The Elements of Style Also, I always keep two books handy: a good dictionary and The Elements of Style by William Strunk, Jr. and E.B. White.

2. Self-motivated. No one will know if you show up for work except you (and your bank account), so you really have to be able to push yourself to work when you’d rather be flipping through magazines or, ahem, out walking the dogs (or baby goat).

My best advice is to keep a regular work schedule just as you would if you had an office job, and if you want extra time off here and there, work ahead to earn it.

Some people also suggest you dress for work as you normally would as well, but I personally work much better in comfy track suits and also spend zero time getting ready for work in the morning, which leaves me more time to write, take walks, and read magazines. But if you feel and, most importantly, work better in a suit, have at it!

3. Determined and not easily discouraged. Rejection is a part of the freelance writing business for *everyone.* Don’t take it personally.

You’ll apply for far more jobs than you’ll secure, and you’ll send out far more query letters than assignments received. That’s normal. Just keep pushing ahead and building a name for yourself and eventually the work will come to you. Really!

I know, I didn’t believe that either when I started out–until I received some job offers based on writing I’d done elsewhere. Your reputation does precede you, so be sure to always put your best effort out there.

4. Reliable and responsible. Show your clients that you deliver quality work on-time, and you’ll quickly build a good reputation among editors.

Yes, sometimes life happens and you’ll need an extension; most clients will understand that–so long as it only happens once in a while. Simply contact your client and let them know ahead of time, and they’ll appreciate your professional attitude.

Computer & screen by thewind on Flickr5. Organized. As a self-employed person, you have to keep track of everything including assignments, due dates, research, invoices, tax information, and more, so if you’re naturally scatterbrained and not willing to work on being organized, freelance writing may not be the best career choice for you.

I keep an editorial calendar for each month to keep assignments straight and often work in blocks of time, e.g., research for a half hour on one assignment, invoicing for ten minutes, email for fifteen minutes, write another assignment for a half hour, etc. It not only keeps me organized, it also allows me to reward myself for good behavior throughout the day and keeps me motivated.

Be sure to come back tomorrow for Great Freelance Writing Resources to Get You Started!

If you haven’t already, be sure to subscribe through an RSS feed so you don’t miss a single Freelance Writing Week post.

Also free free to bookmark, Stumble, and share these posts with friends via email, your blog, and Twitter. The more people we have reading them, the more ideas and suggestions we can come up with in the comments. We freelance writers have to stick together!

What do you think are the most important qualities freelance writers should have?

34 Beans of Wisdom to “Freelance Writing Week: Is Freelance Writing For You?”
  1. Gil

    A good mind, motivation and organization. Maybe, that is why I became a “bean counter”!

    Well I think you need all those things to count beans too…at least I would 😉

  2. Ooooohhhhhhhh! I am SO freaking excited that you’re writing about this!!! It’s such good timing.

    What I’d really love to see is a sample query letter – maybe one to a magazine. I have seen them in books, etc. but I’d love to see a real live sample of a letter written by someone I actualy KNOW. (well, you know…kinda know….in the sense of blogger “knowing.”)

    Can’t wait to follow the rest of this little series!


    Salena of The Daily Rant’s last blog post..Eddie Is He Wearing Trousers?? Friday

    Query letters forthcoming 🙂

  3. 03.23.2009

    I’ll be following this week with great interest!

    poppy fields’s last blog post..Photo Hunt: Yellow

    Thanks! If you think of any questions, please share!

  4. 03.23.2009

    Michelle, great topic to expore! I think sustainable enthusiasm is important. It is easy to be all motivated one day, write like crazy, and then the next day to think, eh, I’ll probably never get published. (how do I know this?? hmmmmm). I think it is part of discipline, maybe, but also a positive mental outlook.

    Diana Strinati Baur’s last blog post..Daytripping in the Monferrato: Agliano Terme and Costigliole d’Asti

    Very true, Diana. This is why tomorrow I’ll be sharing one freelance writing book that keeps motivating me each and every time I flip through it 🙂

  5. Ciao Michelle! Oooh… I will be glued to Bleeding Espresso all week! Thank you in advance for sharing your wealth of experiences and insight. It really helps those of us trying to get started with freelance writing! This post is a great start. You have given me 5 important things to focus on now. Sometimes it really is hard just to know where to start!

    I second Salena’s request… I don’t know much at all about writing query letters. Do you have any tips for that? Also, is it customary to include a resume? What if you are just getting started? Thanks again Michelle!

    Laura at Ciao Amalfi’s last blog post..Sunday Shout-out: 2 Baci in a Pinon Tree

    Great questions, Laura, thanks! And thank you for your excitement 🙂

  6. Ciao Michelle! Spreading the word!

    Laura at Ciao Amalfi’s last blog post..Freelance Writing Week @ Bleeding Espresso!

    Grazie mille Laura!

  7. Richard

    Hmmmm, I would say the most important asset in freelance writing would be imagination…

    Everything I have ever written has came first as an imagination…

    For example; “I imagine I can still taste “kid al forno” I used to eat in Greece and Ethiopia”….mmmm Now this is worthy of writing about….

    Ciao, Ricardo, aka ezduzit777

    Lalalalala I can’t hear you…. 😉

  8. 03.23.2009

    Thank you, Michelle – the Bleeding Espresso freelance writing seminar couldn’t have been more timely. I’m sure we’ll all benefit from your generosity, expertise and tremendous insight. I second Salena and Laura’s question, adding my own appendage, what is the best solution as far as submission letters: short and coldly to the point, or a luring essay?
    I think the following tool freelance writer wannabes need – after your introductory and inspiring tips – is practical examples. The “cv or not cv” debate, some query letter templates, tone and intention expressed in each, etc.
    Grazie, lovely muse. Ciao

    Lola’s last blog post..Cute cutlery

    Looks like lots of people want to know about queries…I think I may have to extend Freelance Writing Week!

  9. 03.23.2009


    Since I really don’t want to be a FT Freelance Writer- for me it is important to be choosey about what I write. I really only want to write about the things I am passionate about and have a working knowledge of- this way the work is interesting to me- and therefore the finished product will be better.

    But, since I am interested in Italy, France, food, wine, travel and antiques- I guess I have a pretty big pool to pull from 🙂

    And I would say another another important trait of freelancers would be the ability to network well. This way jobs could come to you…as well as the other way around!

    I’ll be tuning in all week for info!

    My Melange’s last blog post..Women’s Italy Retreat

    Networking is definitely a part of it, but I kind of hate that word since it sounds a bit schmoozy…rest assured you *don’t* have to be schmoozy to make connections, thank goodness 🙂

  10. Perfect timing sognatrice mia, as I’ve finally got the novel nearing second draft, waking the blog from its winter hibernation, and got my nice new 2009 Writer’s Market in the mail.

    I’ll be looking forward to query letters, job resources, and clues on how to use one’s blog when you don’t have a published portfolio. And recipes! And more goat pictures!

    No pressure, right? By the by, you’re stealing my thunder on tomorrow’s post about freelance writing resources….

  11. 03.23.2009

    Great idea Michelle. I’ve got you on my subscription list. I’m really looking forward to this week!

    deeba’s last blog post..ROASTED RED BELL PEPPER & LAMB PASTA…HHDD & CLICK

    Excellent! Thanks for being such a loyal reader, Deeba 🙂

  12. I am very excited about this week! All your tips are dead on especially being organized and a self-starter.

    Also get used to people thinking you don’t really “work” for a living. grrrr.

    nyc/caribbean ragazza’s last blog post..Ocean Views + Spaghetti Con Vongole (with clams) = An Amazing Lunch

    Hah, that is *definitely* true. I could include that under “determined” in a way…you need to have a pretty thick skin to not let sly comments about how you don’t “really” work get to you 😉

  13. Great points, Michelle. I can’t wait for your other posts.

    I’d also like to add to what you said about being reliable, etc. etc. and about “life happening.” I emailed all of my clients when I had to go to TX last month for Dad and I think maybe because I was always on time (or early) with assignments they were that much more willing to give me time. I also have to say that I have great clients. 🙂 One of them even paid me without an invoice because he knew what I was going through.

    Cherrye at My Bella Vita’s last blog post..Seven Wonders of the World in Bella Calabria

    That’s great, Cherrye; it is nice when you can build relationships with your editors rather than just one and done deals 🙂

  14. 03.23.2009

    Ciao Michelle,

    Thanks for this post, I can’t wait to read the next ones. I’ve been dabbling in freelance work (mostly travel writing) for the past month, and its definately something I plan on pursuing further. Thanks for all the tips 🙂


    Anait’s last blog post..Chuckle, Chuckle

    Great! I hope you enjoy the series!

  15. 03.23.2009

    Thanks so much Michelle-I really appreciate that you are willing to share your expertise!

    I hope you enjoy Janie!

  16. 03.23.2009

    This is wonderful Michelle! And I had to laugh, because, I have the Strunk & White book right next to my computer. ; )

    Anali’s last blog post..Hello Spring!

    It’s seriously one of *the* books I’ve had with me (in various editions) since high school…can’t beat it!

  17. 03.24.2009

    I’ve been freelancing the last five years, ever since I stopped working full time when I had my daughter. But the last few months it hasn’t been such an easy task. The magazine I’d been regularly writing for just doesn’t have the budget for freelance and to be completely honest, I haven’t made that great an effort to find more freelance work. I think I’ve got to get back into the field though. Look forward to reading up on your pointers.

    maria’s last blog post..Synagrida me Estragon sto Fourno — Red Snapper Baked with Tarragon

    It’s so easy to get comfortable where you are; I had a similar thing happen to me around last summer when my three main gigs suddenly dried up in the same month! Yikes! Definitely a good reminder to always be on the lookout for opportunities….

  18. Diane Monroe

    Thank you so much for sharing your insights! I am a full-time Mom and student right now and freelancing is my dream… I will keep your suggestions handy. Thanks again!

    Ooh sounds like you have some built-in niches…I’ll talk more about those on Wednesday 🙂

  19. 03.24.2009

    Thanks for the feedback, Michelle! Looking forward to your other posts!

    Rosa’s last blog post..BloggerAid: Working Towards a Worthwhile Cause

    Thanks Rosa!

  20. 03.24.2009

    This is definitely great timing. I can always use the extra tips, advice, and motivation to get going on a freelance career. I’d be interested to hear what you have to say about clips when you are just getting started.

    Alison’s last blog post..the ego is happy

    I think that was probably my most pressing issue as well when I was starting out…I’ll be addressing it at least in part on Wednesday 🙂

  21. JT

    This is a great opportunity that you are offering, Michelle. I will not miss a post. Thank you so much! JT

    My pleasure 🙂

  22. 03.24.2009

    I am sooooo excited about this week….and more if you do decide to extend it. I agree with Diana’s comment that self doubt can stop us in our tracks, assisted with a full dose of daily life. Worse yet, I think creative people tend to be more melancholy so we really have to beef up when it comes to rejection.
    Looking eagerly forward to your series Michelle!!!

    Romancing Italy’s last blog post..Italia on the Road with Motocard

    Absolutely! That’s where that determination comes in…it can be *very* discouraging when you’re just starting out and don’t even receive responses–believe me, I know. I swear if I ever hire writers, I’ll be sure to at least respond to all applicants 😉

  23. Ciao Carissima!
    A friend is looking for a freelance travel – events writer based in Naples for a very nice project…if you have anyone in mind, please contact him directly:
    Jeffrey Kennedy
    jjeffrey followed by kennedy located at

    Francesca Maggi, Rome’s last blog post..Excess Baggage

    Have gotten in touch with someone I know who’s qualified; hope it works out for them!

  24. 03.30.2009

    Well that’s done it. I’m a new subscriber who is currently in limbo professionally. Have tossed the idea of freelancing around but had no idea how to get started. Am looking forward to the rest of this week now. Thank you for that 🙂 !

    Hope you found all the week’s posts OK–just go to the category Freelance Writing Week!

  25. 04.08.2009

    Your list of traits is so true, but for some freelance writers like me it seems that we need to add one more to the list- patience. I have some buyers that take ages to pay. =p

    *Very* true! Thanks for coming by 🙂

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Michelle FabioMichelle Fabio is an American attorney-turned-freelance writer living in her family's ancestral village in Calabria, Italy and savoring simplicity one sip at a time. 

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