Want The Writer’s Life? Here’s My Week…

English: Scout at Ship's Wheel by Norman Rockw...
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So you want to be a freelance writer?

For many people, it’s a cherished dream: work at home, no commute, wear PJs til noon, no crazy boss or office politics!

I’ve been writing for a living for 30+ years, and have been freelancing, this time, since 2006. Here’s what my week this week — typical in some ways, very unusual in a few others — looks like:


I normally don’t work on weekends but I’m facing multiple deadlines and have to interview people this afternoon — including boys ages 8 to 11 for a story for Boys’ Life, the magazine of the Boy Scouts, for whom I’ve been happily writing for years. With no kids of my own or nephews, I need some great quotes from these boys, one of whom has a shrieking sibling in the background during our conversation. I email several clients to track down late payments and invoice a few others.

I check in with the Hollywood scriptwriter who’s been writing a pilot script for “Malled” for CBS for months. It’s now, finally, with the network executives who can give it a green light — or not. How weird it might be to have a television character based on…me.


Eight hours at the hospital getting every bit of my body tested for upcoming hip surgery.

I’m home by 4:00 p.m., worn out from listening carefully to so much complex information. Terms like “blood loss” don’t help my nerves.

I still have to finish up my Boy Scout story; invoice Reuters.com for an op-ed I wrote last week; try to find out the status of two stories I pitched to The New York Times (for whom I’ve been writing since 1990.)

Working freelance means wearing a dozen hats at once: marketing, coming up with ideas, finding editors to buy them (at the right price!), billing, pitching, researching, interviewing, reading, writing, finding sources and — the worst! — chasing down late payments. One client screwed up so badly I still haven’t been paid for a story that ran in November.

So, like every freelancer I know, I hustle for work constantly — and use a line of credit to pay every bill promptly. My bank charges 19 % APR (!) and $12 every time I use the overdraft protection, which these late payments force me into.

I can only afford, finally, to get this surgery because I’ve saved enough to take 4-6 weeks off entirely for my recovery. Freelancers have no paid sick days!

The anesthesiologists’ office warn me that a typical bill for my two-hour operation is $3,800, of which our health insurance will pay, at most, $1,000. I’m in no mood to wake up facing a $2,800 bill. One more thing to try not to worry about.


Into New York City for a haircut. Next week my husband, (a professional photographer and editor), will take my new headshot, which I need for my websites, blog, book events, speaking engagements and other professional gigs. I get asked for it a lot, and everyone who runs their own business should have a good, recent, flattering one.

I’ve tried to clear the decks of work almost completely, so I can go into this major operation without worrying I will disappoint someone or miss a deadline. I still have two paid blog posts left and five days to get them done. I’ve been trying to sell a story about the surgery, but no one has bitten. (Yet!)


I fly to New Orleans, where I’ll attend a cocktail party at a conference of retail business owners. I’m excited but nervous. I hate turbulence and my last flight (home from Chicago in November) was horrible. I enjoy doing public speaking, but writers generally like to have our words speak for us, and giving a great speech isn’t a natural or obvious talent. Last year I hired a terrific speaking coach whose advice and tips made me much more confident.


At 1pm eastern time, I join an hour-long conference call of 15 fellow writers all across the U.S. who serve on the board of the American Society of Journalists And Authors, a 1,400-member group that advocates for writers’ rights, improved working conditions and pay. I’ve served on the board for five years and am leaving it in July. I’ve enjoyed it, but I’m pooped. At 3:30, I’m speaking on the topic of how to hire, manage and motivate low-wage employees, something I learned firsthand when I worked for 27 months as an associate at The North Face, an outdoor clothing company, and which formed the basis of my latest book, “Malled: My Unintentional Career in Retail.”


Play day! New Orleans is one of my favorite cities to visit. I’ve been there twice before, once in the spring of 2002 to interview men and women for my first book, about American women and guns. It makes a city a very different place when you’re there to work and try to get to know even a little of the political and economic structure and whose opinions matter most there.

21 thoughts on “Want The Writer’s Life? Here’s My Week…

  1. It’s always great to read about someone else’s “charmed” life – at least as we perceive it. One of my closest friends is a best-selling novelist, but she juggled a teaching career with raising a family and writing two novels each year for a few years before she was able to just write for a living. Still, like yourself, she juggles marketing, appearances, blogs, tweeting – things that many aspiring writers don’t consider as part of the job. Best of luck with your surgery. Here’s hoping your recovery is swift. Looking forward to reading your book. I suffered through a few years of retail management when I was young – and could still stand on my feet, in heels no less, for eight hours a day – and sales associates are definitely unappreciated by the public as a whole.

    1. I normally wouldn’t part the curtain, so to speak, but I think it’s useful for people to know how much bloody stress is involved! I’m sure there are people who think I’m very successful (which is better than the opposite) but after 3 decades doing this, not nearly as successful as I expected and in no way related to my efforts as far as I’m concerned…

      Every aspiring writer needs to learn as much as possible about the realities of this life or can end up terribly bitter (and broke.)

  2. Hi Caitlin. Coincidentally, I’ve just posted on my own blog about the woes of authors trying to make an income. My biggest problem – like yours – has been chasing tardy payments from my freelance work. It’s diabolical in New Zealand where all papers and magazines are held between a duopoly, who seem to be competing for the most incompetent payment system in the universe. Or maybe it’s just Evil Corporate Trick #967, you know, the one where small creditors can be ignored.

    I find a curious expectation among non-writers that writers’ main motive is a quest for celebrity fame and fortune. Of course it isn’t, and people who write on that basis are in it for the wrong reasons. But even so, writers need to eat – house and clothe themselves and their dependents, and so forth. Not in a spectacular way. Just modestly in the sense of being able to pay the bills. As we know, most full-time authors do not make the equivalent even of a ‘day job’ from their royalties and have to either find part-time work elsewhere, or spin their skills into related areas – tuition, talks, editing, contract writing and so forth. It’s hard, it’s not lucrative – but it’s what we have to do to answer that passion, that calling.

    Would that things were different, of course.

    I suspect a good deal flows from the general mind-set of a couple of centuries back when writing was the play hobby of the idle rich (d@mn you, Mr and Mrs Shelley!). The royalty structures we work under now came from that era. And I do wonder about what is going to happen to writing incomes given the flood of “free” books being self-published around the web into this coming century. Will we go back to writing being a hobby or available only to those with independent incomes? I suspect so. But we’ll see.

    Hope your surgery goes well & all the best for a speedy recovery.

    Matthew Wright

    1. Part of the problem you face in NZ — which I faced when I lived in Canada — is a smaller market dominated by fewer media owners. Not only are there fewer competitors, the pay is also abysmal, stuck for decades at the same low rates because they can get away with it. In the U.S. there are, of course, many more people competing for the same work but there is much more OF it and some of these places pay very well indeed. I tend to find a few clients and stick with them for as long as possible.

      Every writer has to balance the PITA factor (pain in the ass) when taking on work…one of these new clients proved to be a lot more work and hassle (and low pay) and I may not work for them again because of it. The smart editors know they have to balance low pay with few demands. My Boy Scout stories don’t pay a lot but they are fun and quick and they even (!) pay me royalties once in a while, which is classy.

      The book-writing is never about lots of $$$ but about consolidating my rep and other good opportunities (the TV deal, paid speaking gigs) and the chance to work on something much longer and more satisfying intellectually. The income is certainly part of my revenue stream though. I cannot get any sort of teaching position because I only have a B.A., not a Master’s.

      Thanks for the surgery good wishes…

  3. Wow! It seems that writing is actually the least of the things you need to do to be a freelance writer! If only the hustling and hassling were minimised…!

    I have done consulting work and gave it up because of the hassle and hustle involved. I somehow thought freelance writing would be different (and it’s something I still aspire to do), but maybe not!

    Good luck with your surgery, Caitlin. Hope it all goes well.

    1. I know of very few freelance writers who do not spend at least 20-30 percent (or more) of their time marketing…i.e. hustling. A lucky few are simply handed assignment after assignment and I have never, sadly, been one of them. They tend to be people who are very skilled at schmoozing and self-promotion and that’s not my strength. I do pitch a lot — usually 2-6 story ideas every week (which isn’t that much really, probably should be 10+ a week) but also tend to focus narrowly on editors and markets whose taste I know…One editor recently said yes to 2/4 pitches and loved the 3rd, which was good. But it is a constant, wearying hustle. If you don’t like that part of the game, it’s just not worth doing.

      Thanks for the good wishes. I am pitching (of course!) a piece about the surgery as well…

    1. I HAVE to blog. I enjoy it but was literally ordered to do so by my agent long before we sold “Malled”….any writer (at least author) who does not have a growing on-line and social media following (and can prove it to a publisher) is not in a good position to compete with those who do. It’s one more thing they expect (unpaid!) from us. I hope to write (and sell) more books, so am also hoping that some of my blog readers will also evangelize for/buy my books.

  4. Great job. I freelanced for several years and failed at it. I thought talent was enough and that publishers should be fawning over me and beating down my door. Not quite like that, is it? If you haven’t already, you might blog about talent not being enough. Timing is more important and that takes hustle and hard work. Again, great job. HF

    1. Talent? As if! I see some stunningly mediocre people who make multiples of my income…but they are VERY good at mixing it up with editors and I’m not very good at that no matter how much I try. I’m OK hustling but prefer to find a few good, reliable, smart and decisive editors (usually male, usually NOT women’s magazines) and go from there.

      Thanks for the post idea. I guess it seemed obvious to me (!?) but maybe others think the way you did…I know very few writers who are not hustling, even very experienced ones, but I am not in the stratosphere of the elite (Vogue, NYT Mag. etc) yet and who knows if the air is different there? I doubt it.

    1. Thanks! 🙂

      I also don’t have to face the many needs of kids, old parents or pets which most people do. (Hm. Now I sound heartless!) I have a lot of energy and like to live well….that also tends to motivate me! I know that living in NY tends to up one’s game as so many people are SOOOOOOOO successful you can always feel like some lazy slug compared to them.

  5. A TV show based on Malled? AND it’s scripted? I’d watch that. I’m sick of non-scripted reality TV. Freelancing sounds like a lot of fun but I don’t think I could live without a regular pay check. It’d very difficult and I’d have no savings ever. But here’s a question – if you could do it all over again, would you pick freelance writing again?

    (Ps. I posted my Malled review and recommended that North Face make you their CEO: http://brokenpenguins.wordpress.com/2012/01/08/malled-by-caitlin-kelly-explains-why-store-associates-are-so-surly/ )

    1. Freelancing CAN be fun but stressing about income is not! You can absolutely live without a paycheck but you have to be super thoughtful about the difference between wants and needs…you need food/shelter/insurance/savings/clothing/dental and medical care. Everything else is gravy. You need a low overhead and the self-discipline to live below your means. I think that’s harder for some people than anything else.

      CEO? Wow. Cool! Thanks…I can’t wait to read your post. 🙂

  6. Trying not to worry about bills and how to pay for them. One of the least talked about parts about being a freelance writer. Not to mention the constant interruptions and how often you think: If I could only have eight uninterrupted hours.

    1. The only way to not worry about paying bills: 1) make enough you always have savings; 2) and/or have access to a line of credit to cover your needs. Mine is $15,000 and I’ve used a lot of it when I needed to, always with the income on its way but late; 3) live LOW.

      I wish I had interruptions! It’s crickets at my place….gets lonely and dull.

    1. I’ll be posting tomorrow, more generally, on some helpful tips. But “real publisher”? By which you mean commercial houses? If so, you have to go through an agent. No house touches un-agented material.

  7. Pingback: Freelancing: 3-Month Gig « The World Writ Small

  8. Pingback: Where the road leads if you’re serious about writing « M J Wright

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