How Ship 30 Helped Me Become a Better Freelance Writer

Alice Lemee

Ultimate Guide Table of Contents

I first took Ship 30 for 30 in January 2021. It was my third month as a freelance writer, and I had made a whopping total of $4,562. Averaging out to about $1,550 a month, it was barely enough to keep up with NYC’s exorbitant prices. 

But, it was a start. 

I’d published 13 articles on Medium, had two retainer clients and had around 1,000 Twitter followers. My embryonic reputation as an online writer was budding. 

I was looking for a way to level up as a freelance writer, and I knew the key lay in writing online. Publishing articles would maximize serendipity, accelerating my progress. But I wasn’t publishing. Caught in the illusion of busyness, I convinced myself “I didn’t have the time.” 

So when I stumbled upon Ship 30 for 30, I knew it was in my best interest to hop aboard. 

Those 30 days in January altered the entire course of my career trajectory. I walked away with brazen confidence, lifelong connections, and a robust portfolio of writing samples. 

Now, almost a year later, I made around $6,000 from freelance writing this November. 

Here’s how Ship 30 helped me get there. 

You Learn the Fundamentals of Digital Writing 

There is a vast difference between how school taught you to write versus how you should write online. 

Academia instructs us writing is formal. There is a word count to hit and flowery language scores bonus points. 

But digital writing isn’t your AP English class. 

When you’re a freelancer, untangling your institutionalized knowledge from your writing is the first step. Because clients won’t want to hire you if you write like this: 

“Family vlogging is a subdivision within this industry where families allow viewers to have access to their domestic life by posting videos about everything from their morning routines to announcing exciting life changes, such as buying a new home or revealing a pregnancy.” 

Good lord. For context, this is from one of the first articles I ever posted on Medium. 

Ship 30 for 30 begins the cohort by running through the rules of digital writing. Think cadence, tone, rate of revelation. As a newbie freelance writer, these lessons will build your entire foundation. 

I learned how to: 

• Kill your darlings. Eliminate every word, sentence, or character that doesn’t do anything for your story. The best content writers are able to communicate ideas in as few words as possible. 

• Make your writing scannable. Online readers skim before diving deep. Learn to divide your writing into H2, H3, and H4 headers. 

• Craft delectable headlines. Your headlines get you through the door because when you pitch new clients, you’ll want to present them with 3-5 strong article headline ideas. 

• Reduce your writing time. As a freelance writer, time is money. The faster you write, the more articles you can submit. Before Ship 30, it took me around 90 minutes to publish 300 words. By February, the same word count took me half an hour. 

You Discover What Clients You Should Work With 

You might be scratching your head. But Alice, I know what clients I want to work with! 

Do you? 

Have you actually worked with a client in a similar industry or do you just like the idea of writing for them? 

In the first few months of freelance writing, you probably won’t land dream clients. 

It’s not because you’ll get rejected. It’s because you won’t know they’re a dream client unless you start working together. Trust me, you don’t want to sign a 3-month retainer writing about a subject you end up despising. 

For example, when I first began my career as a freelance writer, here’s what I thought I’d like to write about: 

• Internet Trends 

• Digital Media 

• Future of Work 

• Consumer Technology 

Halfway through Ship 30, I plopped down and spent my morning writing an article about remote work. It sucked. Extracting inspiration was like squeezing water out of a rock. I didn’t have a good time writing it, and readers could tell. The essay didn’t do well. 

The bright side was it taught me I shouldn’t write about the future of work. I stopped pitching remote-first companies the same day, and it’s saved me from a lot of future headaches. 

You Have a Portfolio of Work to Show Potential Clients 

The resume is dying. Employers would rather check out the quality of your thinking online than read a one-dimensional cover letter. As Penny Queller, SVP of Monster once said

“There’s nothing on a resume that demonstrates the individual’s aspirational self. It’s a primitive artifact and a static presentation of who you are.” 

And if you’re a freelance writer, your writing samples are what will make or break you as a potential candidate. 

Don’t believe me? In late January, Mikael Cho, the founder of Unsplash popped into my DMs. At the time, I didn’t have a website or portfolio, which meant he’d checked out my Twitter to assess my competence. 

And as you could probably guess, my Twitter page was sprinkled with Ship 30 for 30 essays.

Not even five months ago, I was spending my free time on the dumpster fire that is LinkedIn, shooting job applications in the abyss. My inbox looked like this: 

Mikael’s message was a result of my Ship 30 essays maximizing the surface area of serendipity. If you’re a freelance writer, clicking “publish” is the best way to uncover unexpected writing opportunities. 

The craziest part of all of this isn’t even how these atomic essays build up your portfolio. It’s the fact that by showing up, you immediately become someone worth paying attention to because you’re doing something 90% of people don’t

You Grow Your Twitter Social Media Following 

“Grow your following.” Ugh, I know. It sounds vapid and uninspiring. And let me be clear -- it is not integral to your success as a freelance writer. 

But if you’re a freelance writer, it’s advantageous to hang out on Twitter. It’s the watering hole for editors, founders, entrepreneurs, and social media managers. They’ll post job opportunities, tips, and resources. 

If you can build a solid following, it gets easier to slide in people’s DMs and inquire about writing opportunities or connect with other freelance writers. 

When joining Ship 30, there’s a guarantee you’ll see some kind of boost. However, nothing could prepare me for what was about to happen. 

Julian Shapiro, a growth marketer with over 220K followers, gave me a shoutout on Twitter. This resulted in 3,000+ new followers overnight. When I first saw that I had gained 256 followers in a single minute, I thought Twitter was glitching. 

You Prove to Yourself You Can Do Hard Things 

A good chunk of my Ship 30 peers didn’t make it through the full month. As the weeks elapsed they would drop like fruit flies, deflated by the challenge. 

Their abandonment was fuel to keep me going. I saw Ship 30 as a way to prove that I was serious about becoming an online writer. It was a testament that I could do hard things. And when I published my final essay, I felt ecstatic. 

This accomplishment was more than an ego boost. It was a reminder that I could keep going when things got tough, which they do when you’re a freelance writer. Trust, you’ll run into moments where you think, “Maybe I’m in over my head.” 

When I had moments of reckoning, I remembered how I’d shown up before, and could show up again. Ship 30 was a reminder to be grateful for hard work because anything worth doing is difficult.

As Sam Altman once said, 

​​”Hard work compounds like interest, and the earlier you do it, the more time you have for the benefits to pay off.” 

Doing Ship 30 three months into my freelance career was how I was able to catapult to the next level. It gave me a newfound confidence in my grit, writing capabilities, and taught me everything is a question of prioritization—not time. 

Looking to level-up as a freelance writer? Sign up for Ship 30 for 30 today. And if you have any questions about freelance writing, you can always shoot me a message. 

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