10 must-dos for freelance writers

By Caitlin Kelly

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.

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.

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?

Check out my classes and webinars — now offered at your convenience, scheduled around your needs, not on fixed dates.