August 16, 2020

I always knew I wanted to be a freelance journalist.

While my classmates were looking at internships and dreaming of large newsrooms in cities across the country, I was poring over magazines, reading bios to see which sections were written by freelancers, which editors had reputations for being gracious with emerging journalists, and creating stacks of SASEs (self-address, stamped envelopes) in which to mail my clips, which in those days, consisted mostly of articles in my student newspaper, and the occasional reader submission to my local paper.

Over the years, I’ve had many people reach out to me for advice on freelancing. Some have been journalists who were transitioning from staff jobs and already had the credentials to make such a leap. Others were people who had never worked independently, in media or elsewhere.

In one notable case, an acquaintance reached out on behalf of his friend whose Taekwondo studio had just gone bankrupt, and was, “looking for a quick and easy way to support his family.” That he thought freelance writing was a way to do that showed his complete lack of preparation for jumping into the field.

For the past decade, I’ve supported myself as a full-time freelance journalist, sans trust fund or wealthy spouse, and time and time again, I’ve watched talented journalists who envisioned freelancing as a means of practicing journalism unfettered by corporate constraints make their way back into traditional newsrooms.

I’ve watched journalism organizations, publications and conferences host workshops or write articles about freelancing that begin and end with “landing the perfect pitch,” often taught by editors who have never been freelancers themselves.

And I’ve watched great pitches land, and fall apart, or articles be killed, or payments never come, and I’ve told anyone who would listen, and many who would not: Freelancing is more than a pitch. It’s a business.

Being a good journalist is not the same as being a good freelancer

The difference between being a journalist and being a freelance journalist is the difference between doing your taxes online and opening up an accounting firm. It’s the difference between taking a flight and running an airline, or between making the world’s best cupcake in your kitchen and starting a food truck.

I’m a journalist and editor, yes, but in order to do that on a freelance basis, I’m also a salesperson, a strategic planner, a communications specialist, a grants manager, and a bounty hunter.

Once, when a change in accountants at a client resulted in confusion over whether or not I had been paid (I had not), I brought a box of cookies to the office, introduced myself to the new accountant, and very politely refused to leave until he cut me a check. (He did.)

After years of working day jobs and freelancing on the side, when I was ready to take the leap, I spent a year transitioning into full-time freelance work, much of that time, building the necessary connections, contracts, and credentials to do so. While it’s incredibly challenging, I enjoy running my own business, which is fortunate, because the business side of freelancing on a full-time basis takes more of my day-to-day than being a journalist and editor.

Freelancing is more than a pitch. It’s a business.

Because I knew I wanted to be freelance, I devoted as much time, if not more, to learning the business of the freelance industry, as I did to learning how to become a journalist.

My degrees, in English literature and communications, were helpful, but most of the pragmatic lessons had to be self-taught; even among my friends who went to journalism school, drafting query letters, cold pitching an editor, putting in a grant application, and chasing down late payments, aren’t skills that are typically taught. They’re skills that can be learned on the job, but have a steep learning curve, and will take time away from the journalism work itself.

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In my article about how COVID-19 has impacted freelancers, I pointed out several instances where I had landed a pitch, and the article never materialized. In some cases, because the outlet folded, in others, because an editor ghosted me. In two instances, I’ve pulled articles from publication because the edits rendered them inaccurate and in one notable case, disrespectful to my sources.

Had I been counting solely on the publication of those articles to keep a roof over my head, I would have quite literally been homeless. Instead, I had built a diverse revenue stream that included freelance articles, speaking engagements, contract communications work, and more.

Don’t quit your day job.

If you’re steadily employed right now, whether in a media job or not, absolutely do not quit your day job. Under any circumstances.

I quit my stable corner office job with benefits at the height of the last recession to turn full-time freelance, and it was a mistake. While it’s impossible to say for sure, I suspect one more year at that job, while continuing to freelance part-time, would have helped me tremendously. Given our current economic climate, anyone who willingly quits a full-time job to take on the risky endeavor of starting a freelance business from scratch really had better have spent a significant amount of time and research preparing to do so.

If you are recently laid off, put in as many applications for jobs as you can now, even when people aren’t hiring, so you’ll be in the queue when they are. Apply at temp firms, become a delivery driver, any sort of work you can. If you are new to freelancing right now, the sad reality is, without other means of support, it is going to be incredibly difficult to build a lucrative, self-supporting business.

After my COVID article was published, many people wrote to me to share their own frustrations with freelancing. But more alarming were the people who wrote to me to ask for my advice in starting their own freelance career. One even wanted to quit a staff job to do so. But quickly within our correspondence, it was clear they weren’t ready. Why? They had no concept of the basic tenets of freelancing, from how to write a query letter, to how to establish a workflow, to understanding the current marketplace, to how much work to do on a story before actually getting an assignment.

More importantly, they hadn’t thought about their pipeline.

Build a pipeline.

One of my largest frustrations as a freelancer, and one of the biggest shocks to people just entering the freelance industry, is simply how long everything takes. From idea to payment on a story can quite literally take years. Even shorter assignments, with outlets who pay on time, can typically have a two-month cycle.

Over the years, I’ve standardized my workflow into a pipeline. It’s required a fair amount of tweaking in the past few months, and I’ve had to regularly update my strategic plans, as work and our industry looks more uncertain. But in normal times, it goes something like this:

Research → Pitch → (Follow-up pitch as needed) → Pitch elsewhere → (repeat as needed) → Get assignment → Negotiate contract → Submit assignment → Wait on editors → Do edits → (repeat as needed) → Publish → Do social outreach → Invoice → Get paid.

The key, of course, is to have multiple projects moving along this process at any given time, so that something is always being pitched, always being written, always waiting on a payment, or being paid. I took a year to begin filling this pipeline with various projects, and they were in various stages when I finally quit my day job. (And I’ve had to take on various day job contracts over the years as freelance projects have ebbed and flowed.)

Start small.

If you find you have some time on your hands, or are stuck in a job you hate and are dreaming of a day when you might break free, channel that energy into creating the resources for your freelance business when the time is right.

Build an online portfolio at a free site like Contently.

Read one of the original freelancing bibles, Lisa Collier Cool’s “How to Write Irresistible Query Letters” or the Writers’ Market. Avoid any books with titles that include “easy” or “quick” or promise a certain amount of income in a specific period of time. Those days are done.

RELATED TRAINING: Building a Scalable Personal Brand 

Join online freelance communities, check out podcasts on freelancing, follow successful freelancers on Twitter to see who they’re writing for and how they’re managing their business.

Take free massive open online courses designed for startups and small business owners and salespeople.

And, when you feel like you’re ready, or you must, take the leap.

Molly McCluskey is an award-winning freelance foreign correspondent and investigative journalist whose work has appeared in The Atlantic, The Washington Post, National Geographic, Rolling Stone, and many more. Follow her on Twitter at @MollyEMcCluskey.

This article was originally published on August 11, 2020.

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Molly McCluskey is an award-winning freelance foreign correspondent and investigative journalist whose work has appeared in The Atlantic, The Washington Post, National Geographic, Rolling Stone,…
Molly McCluskey

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