10 Lessons From a Resurrected Freelance Writing Career

10 Lessons From a Resurrected Freelance Writing Career

I’ve learned a lot in my sixteen-year freelance writing career, especially because it is technically two freelance writing careers, bifurcated by the Great Recession of 2008, which coincided with the birth of my son. And yes, it turns out that old chestnut is true: hindsight does indeed sharpen the vision.

When I got my start as a freelance journalist in 2000, print journalism was still at its zenith. Most of us only used the Internet for chat rooms and odd hobbies.

I wrote predominantly for local and regional print publications, doing boots-on-the-ground reporting and attending every local pub crawl, garden society open house, and coffee with the local politician.


I was successful enough to have steady work, but my bills were low and I owned no major assets. I took very few risks to push myself outside my comfort zone and thus failed to aim for better paying and bigger name publications.

When I finally began to stumble back toward my half-abandoned freelance career around 2014, I found it harder to break into print publications, but web-based publications were hungry for content from capable writers.

With persistence, collaboration, and dedication, I’ve pushed past the boundaries of my comfort zone to break into goal publications, both web and print and make a living wage.

Here are 10 hard-won lessons from my two-part freelance writing career.

1. Print is Not Dead, but Digital is Key.

Print has not disappeared into obscurity in the face of the digital revolution the way fear-mongers predicted, but when it comes to freelance journalism, there’s no doubt that digital media is here to stay.

The savvy freelancer can’t ignore web-based publications, and would do well to break in their chops on the way up to what remains of print journalism. It’s true there are fewer print magazines than ever before, owned by even fewer parent companies, but there are still assignments to be had.

Build your clips by writing for online content with an eye to the land of the glossy. For an annual fee, companies like MediaBistro offer a “how to pitch” section with information on a plethora of publications, in addition to a wide range of free resources on the web that’ll teach you how to get published in your dream publications.

2. Your Ideas Are Probably Better Than You Think.

I’m sure it’s happened to you: an idea strikes you with that effervescence of something great. Yet by the time you actually write it down or draft an email to an editor, fear has stormed in and kicked your poor idea to the floor and you give up on it. If you need more writing ideas, check out this list of 43+ ways to find writing inspiration.

Freelance Writing Lessons

If you’re like me, then a few days, or a week later, that idea you didn’t pitch is a published story… written by someone else who went for it while you balked.

Editors weigh in that writers who are persistent and convincing in their pitching often get the story, even if the first time is not a charm. And really, what do you have to lose? Don’t get hung up on perfectionism. A gentle, “not for us” is far better than missing an opportunity that someone else is more than happy to take.

Check out The Guardian editor Jessica Reed’s pitch clinic, where she critiques pitches to tell you why she did or didn’t accept it.

3. Rejection isn’t Personal.

Rejection is nobody’s favorite part of freelancing, and I’m not about to tell you that you should start to like it; however it is an important part of the process.

Working freelancers quickly learn that editors reject pitches for dozens of reasons. It’s rarely personal, often a matter of taste, and sometimes as simple as that they have a story already in progress. (Hint: if an editor says: “We are about to run something like this… you’re onto something; re-pitch).

Not only that, but an editor who has taken the time to send you a rejection is likely to be open to future pitches from you (See #4 and #5 below). Instead of lamenting your failure, take it as a tool for learning. Revise the pitch, spin it off into a new idea, or take it elsewhere.

4. Re-Pitch.

So there you are, stung by the rejection you were hoping would bring you fruit instead.

There are now only two things for you to do: revise that pitch, and then pitch and pitch and pitch again. In my first freelance incarnation, I would simply give up after a single rejection.

Now, most of my failed pitches have become successful, eventually. One pitch took me a year to place, and others have gone through as many as a dozen rejections. Every time I’m rejected, I tweak a pitch a little more. Especially persist in those pitches that are important to you; sometimes it’s just the right idea at the wrong time. But times change.

5. Trust an Editor’s Invitation.

When an editor says “Please pitch me again,” they mean it; they’re not just being nice.

Don’t hesitate; pitch again. You now have a direct line to someone who’s interested in your work, and likes what they’ve seen.


6. Network.

Don’t live in the vacuum of your own mind. Perhaps the biggest lesson I learned in my freelance two-fer is that collaboration with other freelancers is better for all involved.

Of course, it has to go both ways: you can’t just be a taker and must be wiling to share your tips and resources, too. Social media now offers nearly unlimited forms of such groups that you can join, or create one of your own. I belong to several that have been invaluable not just for practical tips and editor contacts, but for moral support and commiseration.

7. Don’t Play it Safe.

My biggest mistake in the first half of my freelance career was always playing it safe. If you don’t pitch the big leagues because your imposter syndrome is louder than your confidence, you’ll never crack that market or make more money.

Many of my biggest successes have come from acting “as if” I’m good enough and going for it, rising to the occasion (yes, often through sweat, tears, and excessive coffee). Often times this means I do research in advance, secure interviews before I have an assignment, and anything that will make me sound like I know my stuff when it comes time to pitch. Here’s how to overcome imposter syndrome as a freelancer.

8. Ask Questions.

Freelance Writing Tips

Whenever you have the chance to ask a professional a question about your field, do it.

And rather than a generic question like, “How’d you get so successful,” try for something more specific, like: “What’s some advice you wish you’d been given?” or “What’s a pitfall you wish you knew about sooner?” And if you’re baffled to try and find a particular editor contact or writer’s guidelines, turn to Twitter.

Any publication worth its salt (and plenty others) have a twitter feed, and you can send a direct tweet to an editor; it hasn’t failed me yet.

9. The Best Stories Are About People.

My most commonly failed pitches are those that try to sell an idea or concept, rather than the people behind them.

It doesn’t matter if you’re writing about finance or fitness, there are always people involved, and if not a specific person, the impact of your topic on human lives.

10. Stretch Yourself.

My college degrees are in the arts and humanities, yet somehow, over the past two years, my strongest beat as a freelance writer has become science.

I would never, ever have imagined myself interviewing scientists about neurology and cancer research, yet here I am, and it is both exhilarating and exciting, depending on the day. Every so often, take on a story that feels a little bigger than you’re used to, a little more daring.

If you have a niche, creep out of it. There are benefits to specializing and generalizing, but it’s worth shaking it up. If you’re used to writing only essays, take on a reported piece, or vice versa. Branch out to a new topic because it gets you excited. Take a personal cause and try to find a story in it.

The bottom line is: the freelancers who succeed are the ones that keep getting back up, again and again.

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Jordan Rosenfeld is a freelancer writer whose work has appeared in Mom.me, The New York Times, The Rumpus, The Washington Post, Writer's Digest, and more.