A week in the life of a freelance writer

By Caitlin Kelly


It’s not what you might think, or expect.

I’ve been working full-time freelance, alone at home, since 2006.  You’ll notice how little time I actually spend writing –– compared to marketing, follow-up, networking and admin.

I sure don’t sit around awaiting my muse — the UPS guy, maybe.


To the post office, sending off, sometimes via snail mail, LOIs, aka letters of introduction. Their goal is to introduce me to a new-to-me editor or client, enticing them into working with me.

The return rate, i.e. paid work, isn’t terrific, but it must be done. I sometimes enclose a copy of my latest book, along with my resume, letter and business card. Sending one package from New York to London (I sent two), would have cost me $22 (!) each. I argued with the postal clerk and got it reduced to $10.

That’s a business deduction.

I write for money. Pleasure, too, but mostly for money.


I have a new ghostwriting client, for whom I produce two blog posts a month. Staying on top of invoicing is key, since some clients take forever to pay, even “losing” your invoice. Working carefully, I now avoid most deadbeats, and have used lawyer’s letters when needed to successfully get the payment I was owed.


I teach writing classes here to professional designers — I attended school here in the 90s


The necessity of freelance journalism, for all but the fortunate few, is pitching — i.e. coming up with ideas and finding markets to pay you (well) for producing them. That also means sifting through dozens of email pitches from PR firms, most of them completely useless and of zero interest to me.

Total time-suck!

Pitched two ideas to a university alumni magazine, one of which piqued their interest, but hasn’t yet produced an assignment.

I find most of my ideas through pattern recognition — noticing cultural, social and economic trends and offering an idea when it’s timely and in the news. Stories without any time hook are called “evergreens”, and are harder to sell.

Pitching also means plenty of rejection. A health magazine said no to three ideas, (asking for more.) A psychology magazine ignored my pitch for a shorter essay and asked if I’d write it at twice the length — but insisted I show clips (published work) just like it, which I don’t have. An editor I’ve already worked with hasn’t replied to two more pitches.

Pitching also means following up, dancing the razor’s edge between being annoying (too soon, too often), and being ignored.

We rely fully on my income as well, so I can’t just sit around hoping for weeks on end.

malled china cover
The Chinese edition of my 2011 book, Malled: My Unintentional Career in Retail


Offered a brief, easy assignment, into the city to cover an event for a trade magazine in another state. They offered one fee. I negotiated it 30 percent higher.

Negotiation is always nerve-wracking, but it’s essential. Many women writers fail to ask for more, and end up broke and annoyed because we don’t.


Have a phone meeting next week with a new-to-me editor in Canada, so need to read her website’s work carefully to make sure my ideas are a potential fit.

I’m heading to Europe in June for four to six weeks, and already have several feature ideas I want to pitch, so I can write off some of the expenses, dig deeper into that country’s culture in so doing and earn some income to offset the costs of the trip.

Without some solid data and proven contacts, it’s harder to sell a story, at least one worth $5,000 or more, a very rare bird to catch these days.

I’ve already found an interpreter in Budapest, so that’s a start.


Hate this.

Have been chasing a PR official in Europe on a story for more than three weeks, my deadline long past. The editor is easy-going so we can wait, but the income I relied on for a finished/accepted/invoiced story? That’s now weeks away.


My favorite activity. A new blogger hired me to coach him, and we worked via Skype from my apartment in suburban New York to his European home, a seven hour time difference.

I also worked with a four-person team at a local art film house to help them better shape their pitches and press releases to journalists.

The late David Carr, NYT media columnist — much missed. Brilliant, no bullshit.


Two newspapers every day. Twitter newsfeed. Social media. Books. Magazines. Websites. (Plus NPR, BBC radio.)

If I’m not reading constantly, I don’t know what’s going on and could miss something crucial I need to know to pitch and write intelligently.


The least of it!

Blogging keeps me writing between assignments.


Without which, nothing happens.

Connected with an editor in Canada (thanks to a referral.)

Connected with a Toronto entrepreneur (we met through Twitter) with whom I hope to do some long-distance coaching for his clients.

Connected with a fellow writer I met last spring at an event of fellow writers who all belong to the same on-line group — she might have assignments to offer.

Spoke to a freelance photographer in California about writing and editing her new website.

Spoke to a PR exec in Seattle about possible blog writing and a white paper.


Two new assignments from a new-to-me editor at The New York Times, a place for whom I’ve been freelancing steadily since 1990; here’s my most recent, about the odd things people find when they renovate a home.

16 thoughts on “A week in the life of a freelance writer

  1. you put in the time, the work, the patience, the brains and the talent into the process. it’s clear that a freelancer must adapt and grow with the market, and that is a skill in itself. i wonder how many can and will be able and willing to do this. i admire you and your work ethic. congrats on the the new nyt assignments )

    1. Thanks…all pretty fundamental. 🙂

      It has been a lot of pivoting to add coaching and media strategy. Teaching is often fun (teaching adults, especially) — and as long as we have monthly 4-figure bills, work is still on the table!

      I don’t make nearly as much as I want to, but I still enjoy what I do, and for that I am fortunate.

      1. Isn’t that what is most important? We all define success differently, and for most it is money. For the people in the 1% category of the world, happiness falls high on the charts. Money will come if you keep growing and becoming better at what you do and helping people along the way.

    2. I couldn’t agree more. This post summarizes a lot of concepts I’ve read about recently. I’m excited for all of the above and more because I know what I am enthusiastic about in my life and writing is at the core of that. Great post and thanks for sharing the great insight.

  2. I always enjoy reading your insights into the freelance writing life. It sounds like you have to be incredibly proactive and enterprising.

    As an aside, with my interest in linguistics and language differences across the pond, I’ve often noticed that Americans and Canadians refer to Europe as a single entity (e.g. the reference to “that country’s culture” in your post). In the UK, I’ve never heard someone say that they were going to Europe. Instead, they’d say they were going to Spain/France/Portugal/wherever.

    Do you think it’s because whenever North Americans travel to Europe, they generally visit quite a few countries during the same trip as it’s such a long way? So, maybe it’s become common parlance to refer to “Europe” as a collective rather than naming the individual countries. Language differences fascinate me. 🙂

    Looking forward to your European features. Which countries are you planning to visit?

    1. Thanks!

      Freelancing means mustering the energy to hustle EVERY day — and I’m one of the few people I know who refuses to work on weekends.

      That might have been a sloppy edit on my part — I AM aware that Europe (people do this with Africa as well!) is composed of many different nations. 🙂 In my fellowship year, 8 months, I was Paris-based and traveled to: Italy, Germany, Denmark, Romania, Bulgaria, Turkey, Yugoslavia (then its name), Holland. I know some bits of Europe (France, Spain, Portugal, England, Ireland, Italy) better than others.

      I think some people here say “going to Europe” as a quick shorthand…they may well be visiting multiple countries (like on a river boat tour, for example) and, frankly, maybe because so many Americans (even those with $$$$$) don’t even take vacations, so they downplay it. It’s like (which I hate) when you ask someone here where they went college and they may say (please)…Providence, RI (Brown) or New Haven (Yale.) in some bizarre humblebrag.

      Many Americans have no notion of geography; “Europe” they get — it’s across the Atlantic for us. Individual countries, if they have never been to them or even heard of them (Montenegro?), don’t register. I can trade notes on specifics of Paris and London, for example, because I’ve been fortunate enough to visit each of them many times, and lived in each. But that’s not typical of many Americans. They get much less paid vacation and wealthy ones never seem to take time off, but just keep making $$$$$$ instead. So a much less wealthy resident of a European nation may well have visited many other nations there (and more affordably and quickly — a $200 airfare rt/t , not $800 to $1,200, for example) and know it much better as a result.

      Right now, I’m planning to visit England, France, Hungary…for sure. Possibly Czech Republic, Poland, Scotland, Finland. It will depend entirely on whether I can get several well-paid assignments to report when I’m there to get some help with my costs.

  3. Great insight for someone like myself who was unaware of the intricate culture of being a freelance writer. I get the sense one must be a bit of renegade not only to navigate this domain but to also thrive it it! BRAVO!

    1. Thanks…

      It’s slightly different, of course, for each of us, as we are all independent businessmen/women and run our business accordingly. Some lucky folk have weekly or monthly paid columns so they are not chasing income nearly as hard, and some have much higher expenses than we do, (student debt and/or the costs of raising multiple children — neither of which we faced.)

      Renegade, for sure! Renegade enough to crave autonomy — but also corporate/docile enough to speak the languages of sales and business. It’s an odd mix. 🙂

  4. Pingback: [BLOG] Some Sunday links | A Bit More Detail

  5. Whew… the work behind the words left me winded (see what I did there).

    As a rookie and humble blogger, I’m beginning to understand the effort that goes into bringing a simple post to life and in front of viewers willing to engage. The leg work has quickly taken up even more of my time than the “good stuff” (writing and sketching).

    Prior to reading your post, I would have said, I can only imagine how much more work is involved in paid free lance work. Now that I have a better idea, I can confidently say…

    ignorance is bliss

    1. Yup. 🙂

      In an era when people think “yeah, I can do that — dead easy”, my posts about the writing life (I post them every few months), are meant to be something of a corrective.

      Just because hitting “publish” is easy and quick doesn’t guarantee that what is actually being published is compelling, copy-edited and cogent. In a sea of words and arguments on the web, how do we make what we say interesting?! That takes thought, work, reflection and revision.

      WORK?!!!!! Unpaid work???!!!

      Why, yes. 🙂

  6. This is great insight into the business side of writing. I’m assuming that it takes up at least 50% of your time and you’ve learned to become very efficient it to leave you enough time to write. Or maybe you’re also became a very efficient and disciplined writer too?

    1. I write extremely fast…I have to, given how much time the rest of this takes! Having worked as a daily newspaper reporter helps, certainly. I don’t agonize for days or weeks over what to say; once my research and reporting is done, it doesn’t take me long to write the final product.

      1. I think this business has its rules as any think else . Once you get the skills take of and go. Other thing is , it does matter to have a degree to be a good writer as long as you know how to do the job.Anyway, i have enjoyed reading this intersting post. thank you

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