10 must-dos for freelance writers

By Caitlin Kelly
I've been writing for them since 1990
I’ve been writing for them since 1990: sports, business, real estate, you name it!
A few thoughts — I have been fulltime freelance, (this time, have done it many times before for years on end), since 2006; I live in the spendy NYC suburbs. I write for a wide range of publications, from The New York Times to Cosmopolitan, Marie Claire, More and websites like Quartz.com and Investopedia. (I also teach freelancing, writing and blogging, privately to individuals.) Samples and rates here.
I won’t talk here about your need to be a great writer or boost your “brand” but the array of other skills you also need to succeed in a highly competitive business.
A few thoughts:
1) If you’re simply not making enough money to meet all your costs, (and save money as well), take on part-time work and make sure you remain solvent by so doing. Babysit, tutor, dogwalk, retail — do whatever it takes to keep your credit score stellar and your bills paid, always, on time.
I took a part-time retail job in Sept. 2007 when the recession hit hard and stayed in it for 2.5 years until I had replaced that income and doubled it (monthly); people (i.e. ego-threatened writers) kept saying to me (since my previous job had been as a NY Daily News reporter)…”Oooooh, I could never do that.” Oh, yes you could. Get over yourself and make the money you need. Your landlord or mortgage company couldn’t care less if their payment money comes from the NYT or from….anything else. And, oh yeah, that grueling, low-status, low-wage job experience became my well-reviewed NF book , “Malled: My Unintentional Career in Retail” and won me a TV option from CBS for a sitcom.
malled cover HIGH
2) See point one — you never know what will happen if you dare to step off the well-trodden and safe/comfy path of: “I’m a freelance writer.” Detach your ego and status anxiety from your income, always. Yes, of course, be excellent, but do whatever work you take on to the best of your ability. Excellence shows and people appreciate that.
3) Do everything you can to separate yourself from the pack. There are thousands of us; one “secret” women’s writing group I belong to online has — (yes, really) — almost 2,000 people who self-identify as freelance writers. So figure out what you do better than anyone or more quickly or more efficiently (not more cheaply!) and seek out clients who really value those skills and will pay you well for them.
I speak two fluent foreign languages, have published my photos in major media, and have no kids or pets and have been to 39 countries, often alone — so I can travel easily and work in other languages. Many people can’t or have never done so. That wins me good work.
4) Be a human being. When possible, get to know your clients/editors as people — they, too, have pets and kids and birthdays and illnesses and surgeries. Send them nice cards and/or flowers. Check in with them every few months, and just ask “How’s life for you these days?” I did that for one editor facing very serious illness, someone who had not assigned me work for several years and I wondered if she ever would again. She did. I would have done this anyway. Your clients are just as human as we are; in other words, create and nurture your professional relationships with care and sincere thoughtfulness.
5) Don’t expect (too) much too soon. By which I mean, get a very clear sense of your current and true market value and work from there. Just because you want to be in a Big Name Magazine right now doesn’t mean you’re ready or the editor agrees. Ambition matters, but realism and a little healthy humility also have value, (says this native Canadian.)
6) Be positive, upbeat, friendly and confident. The economy is still shitty and shaky for many people and working with someone smart, capable and who will not let them down — no matter what! — is appealing to clients, some of whom may, realistically, fear losing their jobs if you screw up.
7) Live as low/cheaply as you possibly can. The less overhead you carry, the more creative freedom you have to take on and do interesting work more slowly — i.e. work of serious long-term value, not just buying this week’s groceries.
I learned how to canoe at camp -- useful when we went to Nicaragua
On assignment this year in rural Nicaragua
8) Reach out for new non-journalism opportunities, every day: online, by phone, through social media, at events. Two of the most life-changing, fun, challenging and well-paid opportunities for me in 2014 came because I simply took a chance and reached out (i.e. cold-called) two major organizations I never thought might welcome my skills. They did and I’ve never been happier as a result. Just because we’re “freelance writers” doesn’t mean we only have to work for really crappy pay from struggling/cheap media companies.
9)  If you keep comparing your income to the Big Stars making Big Bucks, you’ll die. Just focus on what you can do, well and consistently. There is always going to be someone making a lot more $$$$ — and crowing loudly and tediously about it. Just do great work!
10) Have fun and take very good care of yourself — go for long walks, alone or with your dog or a good friend. Get plenty of deep sleep, including naps. Go see a movie or spend an afternoon at a gallery or museum. Eat your vegetables! Being a freelance writer can be terrific, but also lonely, isolating and wearying, leading to burnout. This is a sort of job that requires mental, physical and emotional stamina. Rejection is normal. Get over it!
Want to learn more? Want to boost your your freelance income?


25 thoughts on “10 must-dos for freelance writers

  1. I love all of this advice. I really like this: “Detach your ego and status anxiety from your income, always.” I think it works the other way as well–that you can identify yourself as a writer, even if the bigger pay check comes from the “day job.” The source of income and source of fulfillment don’t have to be one and the same. But paying the bills is always a reality!

    1. Thanks, Jean.

      I see far too many people freaking out about whether they’re a Writer or not. Just get on with it and pay your bills on time. Very few people will ever care as deeply the source of your income, simply that you are fiscally responsible.

  2. Thanks for sharing this, Caitlin! I’ll definitely keep these tips in mind for future writing work 🙂 On a side note, I read ‘Malled’ this week and thoroughly enjoyed it. It was really interesting to see behind the scenes of the retail world in the States – and a little bit frightening too. I was surprised at the treatment of associates and the lack of benefits, especially in comparison to here in the UK. An excellent read though!

    1. It might not be easy to say “better”….but differently?

      I have no children — and 80% of women do. That reduces my competition to 20% of the women who do not; i.e. who, like me, have a very different perspective on life.

      I use all my “difference” when possible as a strategic advantage.

  3. I work part-time, and not only has that paid the bills, but it’s given me time to actually spread my mind out and get inspired. I’ve come up with so many ideas at work just sitting at the computer and doing my job! It’s great. And in the job search I’m doing now, I’m looking for work in a number of fields, a lot related to writing but others like politics or entertainment or office jobs. These jobs will not only (hopefully) allow me to stay afloat, but may also give me great ideas for stories. You never know what might come up.

  4. Great post, Caitlin! Freelance writing is all about…freedom. Most writers who run after money forget that. The life of writers and editors who work online is hectic but you should never forget that you can stop at any moment, just to enjoy life.

  5. Sigh, you have captured it all, thank you for reminding us to take care ourselves :)… I am an Independent curator, having changed careers at 38, its not been easy, with money, with finding work and with adjusting to realities of being ‘Independent’, still struggling to find work, in a the culture sector.

  6. Such great wisdom in this list. Love how you are able to throw the ego aside and just help others see it’s ok to just do what you need to do to get by. It’s awesome how you used that experience to write “Malled” –I thought it was fascinating to read and it really made me wonder how I’d feel going back to that, and what kind of perspective I would have now vs. when I was a teen/or college age. And also I liked “be a person”. It’s really so true about building relationships, in whatever industry you are in. If you make an impression you never know where people will pop up in your life over the years.

    1. Thanks! Good to hear from you again! 🙂

      I think people attach wayyyyyy too much importance to their job title or status and freak out if they have to step off that path, even briefly. I was still writing while working retail and it remained, I admit, my primary identity and source of income, but it was one of the best decisions of my life to go work for $11/hour…I realized what grindingly hard work it is and how millions of Americans are screwed doing it with no quick escape from it.

      I’m glad Malled resulted from it, but I was also very relieved to be able to leave that world, and work behind. I loved some aspects (as you know from reading the book) but by the end was worn out…

      I am still Facebook friends with my very first editor from the mid 1970s! It means a lot to me (and to her) to have her “like” my posts and my blog.

  7. Just read most of this out to my artist husband, because it definitely applies to visual folk too. Probably to all forms of being self employed. great post and thank you for the inspiration and insight.

  8. Excellent piece, Caitlin. I especially like what you say about not letting a particular job designation define you and keep you from meeting your financial obligations. We are who we are regardless of the type of work we do. I take a great deal of pride in remaining independent, doing my best in whatever I have to take on. The main takeaway here, I think, is that attitude matters–not only to those around us, but to our own state of mind and happiness.

  9. Some trenchant observations, here. Well done, and inspirational without being cloying in a Lifehack kind of way. For food, I suggest: Use coupons to stock up on six months worth of staples (rice, pasta, beans, can veggies/fruit). Shop at produce stores near the end of the day, ditto for meat and fish shops. Freeze stuff. Buy in bulk, but not so that it kills your budget (there’s a fine line between overconsumption and ‘paying full price.’ I’d add some freelance tips but other than ‘marry rich’ the rest are trade secrets.

  10. Great advice for freelancers! I started cooking once a month for a large church group and I am really enjoying the people and the experience. I was just thinking about teaching at a community college, too. I don’t have a Masters, but I have experience and skills — why not?

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