🌐 How to break into freelance writing

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“They found a badly decomposed young woman bloated from being submerged in water. All she had on was a pair of earrings.” 

It’s 2019, and I’m listening to Crime Junkies while packing CDs at my BMG Music internship. The majority of my days here are spent either pulling data from Nielsen into Excel, eating lunch alone, or holed up in the shipping room.

I was not a good intern. Despite fighting tooth and nail for the position, once it started I felt antsy and useless. Upset that “Nobody would give me anything to do,” I filled my spare minutes with podcasts on decapitated women or running to the Chipotle on Park Avenue. 

Four years later, I realize the problem wasn’t them. It was me (shocker). 

Here’s the thing: No one wants to be responsible for you. I was waiting for the BMG supervisors to give me something to do, anything. But they all had plump to-do lists and the absolute last thing they wanted to pile onto it was, “Educate the intern.” 

For them to find me indispensable, I shouldn’t have waited around for orders. I should have created my own orders. But I didn’t, and in April, they let me go.

Had I developed a sense of initiative, things would have likely turned out differently. Initiative transforms you from a burden to an asset — from a “Ugh, what should I tell them?” to “Woah, they handled it.”

The freelance writing world is no exception. 

To break in, you can’t dilly dally waiting for someone to tell you what to do — you must create your own experience. Here are three examples of initiative in the wild: 

• Example 1) 

In 2020, I was a baby freelance writer. To get noticed, I created a free guide of Mathew Kobach’s and David Perell’s “How to Crush It On Twitter.” This led to thousands of Twitter followers and (paid!) writing piece for Jack Butcher. 

Action Item → Create a guide, article, or other resource to showcase your writing experience. Bonus if it’s a remix from a popular author or creator (if they report you, it’s instant credibility).

• Example 2) 

Imagine you’re a content director at a Very Big Important Firm. Your to-do list? Atrocious. Then, you get a cold email from a freelance writer along the lines of, “Give me something to do.” 

So now on top of everything, you have to find work for this random person? 

No thank you. 

But what if the freelance writer emailed instead saying, “Hey, I was on your website. I noticed [lack of this]. So, here are [proposed ideas] to help you with this. I can deliver a full draft by Tuesday if you need.” 

Boom. Initiative. Here’s an example cold email I sent back in 2020 to a remote work startup. This email led to a $3.3K a month deal! 

Action Item → Come up with several article ideas when cold pitching a client. Bonus if you can link the CTA to their current offer (to show how the content would lead to sales).

• Example 3) 

Freelancer Chris Bibey wanted to pivot from writing about the gaming industry to personal finance. 

Did he sit around and complain that his clients wouldn’t give him anything about the S&P 500 or Bitcoin to write about? 

Of course not. Here’s what he did instead: 

Action Item → Write a review, first-person essay, or blog post about the industry you’d like to break into.

Whenever you feel like “there’s nothing to do,” I promise you — there is. Start looking for areas where you can contribute and get after it. 🏃‍♀️

✍️ Quick Freelancing Tip

^{This section is usually a writing tip, but we’re turning this into a freelancing tip (for now). Enjoy!}  

Aim to have up 4-6 months of living expenses. This gives you leverage, letting you decline (or negotiate) projects that don’t pay enough. The thing about leverage is it’s magical as leverage begets profit.

Here’s what I mean: 

Earlier this month, a new client came into my orbit. They requested a test assignment but there was no mention of it being paid. I told them I didn’t do unpaid test assignments, knowing I could afford to lose a potential client.

“We’re happy to pay your hourly rate for this test,” they responded. This leverage resulted in me getting paid for my time.

A few days later, they’d told me I’d passed. “Unfortunately, you’re out of our budget,” they said. “We do have a one-off assignment available, but it’s at [$X] rate. Can you do it?” 

I responded that my rate for this type of assignment was almost double. “That works with us,” they finalized. 

What! This is the power of leverage. Operate from a place of calm and confidence, and that energy will reflect in your business – usually through profit.

 🥒 Content Diet

👩‍💻 Cold Pitch Tracking Template (Notion) by Me — In 2020, I created a Notion spreadsheet that tracked all the clients I’d pitched, the dates I would need to follow up, and cold pitches. Here’s that template (totally free!).

Bonus: It includes the exact cold pitches I used with clients.

🎙️ Nastygal Founder Sophia Amorouso on Diary of a CEO — Sophia is a badass. I loved her interview with Steven Bartlett, where she recounts her story from 18-year-old stripper and serial shoplifter to owner of a $100M company.

📖 Feel Good Productivity by Ali Abdaal — I’m drinking the Ali Abdaal kool-aid – sue me. I do like his message that productivity is just a matter of play and fun. Who said hard work had to be torturous?

Thanks for being here! 

Today is my second to last day in NYC before leaving for Bali with a one-way ticket. I’m very nervous but also so, so excited.

See you on the other side,

Alice 💌