On the hustle of freelancing - David Silverberg

A question I often get is: How do you hustle to get those freelance gigs? Isn’t it nerve-wracking to not know where your next cheque is coming from?

My short answer is often a variation of, “It’s only frustrating when I don’t come up with ideas or have the energy to reach out to potential clients. Otherwise, the hustle is exhilarating.”

The long answer is, well, this blog post. What I mean by “exhilarating” is the thrill of the hunt, the internal high-five of Yes! Got the gig I wanted! With the hunt, though, comes the pain of rejection, but I’ve developed a thicker skin than ever before thanks to the dozens of pitches I send each year. With the good comes the sting of the stiff-arm.

Note that I wrote “sting” because it feels more like a momentary prick than a sustained bruising. I’ve learned to pick myself up after a round of dejection and realize I just have to hone a pitch better, find a more alluring story idea, select a more appropriate outlet for the idea. Often a rejection can energize a freelancer to be better than he was yesterday.

The hustle of freelance writing is a 24/7 exercise. So when I read an article in a magazine, there might be a quote from someone who isn’t central to the story but whom I find intriguing. That person might form the basis of my next pitch, once I learn more about what they do. Or I might be a tech conference or a cannabis expo like Lift for kicks but my journalistic Spidey-sense will be tingling when I come across someone or something that could be my next pitch. To paraphrase Glengarry Glen Ross: Always Be Closely Watching.

As to the nervy bit of business of not knowing if I’ll be getting a hefty cheque this month, that’s the game I decided to play so I have to go with the flow. Some months are more lucrative than others, sure, but lately I don’t get out of bed for anything less than my minimum rate and such discipline has invigorated me. I realize I’m beyond the $150/article rate of 30-year-old me. I realize I’m only interested in writing about topics that tingle me in that can’t-wait-to-tackle-this-article kind of way.

I’ll end with a quote from one of my favourite thinkers on freelancing and productivity, Seth Godin. He was once asked about the notion that “Freelancer” was “mostly considered a second class citizen.”

Godin swiftly refuted that prejudice: “Think about the people who are truly great. The programmer who can save you months. The cartoonist who draws life-changing images on the backs of business cards. The guitar player who can sit in on a recording session and change everything…These people are first class. They’re in charge. Top of their game. The best of the best. That’s the freelancer each of us is capable of being.”

David Silverberg

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