Five sure-fire ways to make more money as a freelance journalist

By way of verbal throat clearing: Notice how I didn’t use the word “secrets” in the headline? Like Mr. Ping, the lanky bird dude in “Kung Fu Panda” with the mysterious noodle soup, I’m gonna level with you: There is no secret recipe. At least when it comes to getting the inside on client opportunities by which freelance writers live and breathe.

Now on to the careerist meat and potatoes. In 2009, I was laid off from the Chicago Tribune—with the added insult of becoming a national joke as the door slapped my ass on the way out. You see, I was writing a Trib syndicated column called “The Recession Diaries.” I went from covering the news to making it … and from spoiled full-time staffer to hapless freelance journalist.

It all happened in the blink of a byline. Just like that. Wow. Bam. Shit.

I’d like to say I played out my smarts; maybe in the end I grew some brain cells. Regardless, there’s nothing a deadline journalist knows better than a gun to the head. Assignment: Make money fast. Deadline: Yesterday. Word count: Speechless.

But pressure can cook up tasty results. To paraphrase acclaimed Chicago TV journalist Phil Ponce, you can’t cook up noodle soup without heat. These five strategies made me stand out and allowed me to double my income from my Chicago Tribune job in roughly two years.   

1) Add to your skill sets. I’m much better at moping and eating a tub of ice cream than this. But in the weeks after my layoff, I began to hack away at graphic design, video editing and advanced audio production. Then I went back to school for a master’s degree in communication. Looking back—now with the M.S. and bedrock skills in all these areas—I contend this approach created advantages in my quest for freelance work other candidates simply didn’t have.

Make it work for you:

“I would love to write this column for you on Dumpster diving…”

versus…

“I’d love to write this column for you on Dumpster diving and produce a new podcast for you that I’ll host, record and post myself as a value add.” (Feel free to use my catchy title, “The Dumpster Diaries.”)

2) Put on your “Mike Nesmith hat.” That is: Stand out. Make yourself unforgettable. When Hollywood held auditions for The Monkees cast, Nesmith grabbed a wool hat on the way out of his apartment, supposedly because his hair was mussed up. Dozens of might fine young men mugged for the camera that day but the show’s producers remembered the Texan with the winter headgear in sunny L.A. As the final four were picked, one producer actually asked: “What about that guy with the hat?” That 90-second decision to don the hat put Nesmith heads above, you might say. It changed the course of his career and his life.

Make it work for you:

“I’d love to write this story about Black Friday…”

versus…

Write a song about Black Friday that touches on current events. I did this at AOL (with the invaluable help of editor Beth Pinsker) and got promoted from freelancer to full-time employee at AOL within a week. The song, which I wrote and performed, is attached to this story.

3) Always out-deliver. OK, so you’re in the hunt for a good freelance gig but have to complete one of those dreaded, dumbass writing tests. Welcome to the cattle shoot, mooing away with all the other wannabes. Let’s break that spell and turn you back into a human writer.

Make it work for you:

The test says to turn in an 1000-word story by Friday on vacuum cleaners that cites three sources, so that’s what you do…

versus…

Write two stories, each citing five sources, and turn them in on Wednesday.

4) Always go through “who you know.” Again, this is about busting out of the cattle shoot. In a quarter century of doing this journo/writer thing, better than 90 percent of my best opportunities came through introductions and networking. So if you apply cold for a job, remember that many HR people are overwhelmed (or in some cases, dumber than a box of rocks). Your best intentioned inquiry will hit the round bin in less than 90 seconds.

So many freelancers overlook the Power of Weak Ties. You may have a first-level connection on LinkedIn whom frankly you don’t know well. But these people will oft be more comfortable setting up an intro or passing you on to the right person. It’s lower risk for them. With a close friend, it can be quite opposite. They may hold back because if you fail it will spoil two relationships: with you and their contact.

5) Make it warm and personal. Everybody wants something. Writers want work. Thus that editor is not a real person, but an automaton that spits out assignments if you enter the right pitch-letter password.

Yes, some editors solicit cold pitches. But how about warm ones? Once you embrace that editors and such have lives outside of work—with kids, hobbies, passions and sick relatives on their minds—you begin to relate to them on an entirely different level that connects instead of repels.

Make it work for you:

You really want that job writing about investment and in essence pester the editor for work.

versus…

You wish an investment editor “Happy Birthday” via LinkedIn, asking about their birthday plans … and casually inquire “by the way” about whether you can do anything for them. (Note the language: Do not beg for a gig here!) One one occasion, after I asked this in a birthday note, the editor in turn inquired as to whether I knew any investment writers. Swift came the reply: “Me!” This turned in to a six-year gig that conservatively earned me $150k.

Parting shot: pluck, persistence and letting go of what you can’t control

OK, thou cynical readers in the congregation: All of the above could net you bupkis. That said, this is a game of batting averages: More persistence equals more results. Meanwhile, do everything in your power to have faith in yourself. Writing is by nature lonely and the chances to beat up on yourself abundant. I still do it a few times a month. Then, to quote Frank Sinatra, “I pick myself up and get back in the race.”

That’s life—at least the freelance journalist’s life. Now let’s go live it.

Have questions, comments or of course freelance writing gigs? lou@qwoted.com.

Lou Carlozo is Qwoted’s editor in chief. 

This week on Lou Carlozo’s “Bankadelic”: a thought-provoking podcast featuring four women leaders in financial services, “Women, Banking and the Path to Success.”