How to Become a Freelance Writer: A 10-Year Pro’s Real-World Guide

When people ask me how to become a freelance writer, I often take a moment to reframe the question. The truth is I don’t have all the answers. Anyone promising a guaranteed path into freelance writing should probably be taken with a grain of salt. 

My journey started long before I ever called myself a freelance writer. It involved following creative instincts, surviving bad jobs, taking chances on strange opportunities, and slowly figuring out how writing could turn into a real career.

Here’s how it happened.

 

Becoming a Freelance Writer

1. Writing Was Always My Thing

As a kid, I was that student who actually loved writing assignments. Outside of school, I took on bigger challenges, like attempting long screenplays in high school and college.

Looking back, those screenplays were terrible. But they taught me I could sit with a creative project for hours, keep going when it got difficult, and actually finish the thing.

That matters more than people think. A lot of aspiring writers like the idea of writing. Fewer people like the repetition, the doubt, the revision, and the discipline it takes to finish something. Freelance writing rewards the second group.

2. College: Finding My Voice

In 2004, during my first semester at Montclair State University, I realized I wasn’t passionate about my major, broadcasting. So I switched to English/Creative Writing. That decision felt risky but the experience opened doors and educated me along the way. 

One of those doors was studying with Dr. Ross Gay in 2005. He encouraged students to take risks with poetry, writing, and even your profession. He taught me that you can bend the rules once you learn them, which is something that stayed with me long after college and well into freelancing. He also taught me to stand up to employers when they do wrong by you and not fold just because they have more power than you do. 

In the one year he was there, Dr. Gay did more than any educator in my life, teaching me that knowing your worth is crucial in life and especially creative professions. We never stayed in touch but I hope he sees this one day. Thank you, Dr. Gay.

3. Post-Graduation Reality Check

I graduated in 2008, right during the recession. The comments I got from countless people all boiled down to the same discouraging message:

“Your English degree is worthless.”

I believed it, and like so many others, I took jobs to survive. I worked at countless restaurants and bars. My first “real job” was at Enterprise Rent-A-Car in Brooklyn. Then, I bounced around some startups.

Those years weren’t glamorous, but they taught me how to handle rejection, adapt quickly, and communicate with all kinds of people. At the time, none of that felt connected to writing. Looking back, it was all useful. Freelancing is basically a constant exercise in rejection, adaptation, and dealing with people from all kinds of backgrounds.

4. Taking the Leap in 2014

By 2014, I was ready for something new. Back in New York City after a short stint away, I decided this was my last shot to prove people wrong about my degree and career prospects. But after months of lackluster results, I almost resigned to the typical path I didn’t want any part of.

Then, I found a Craigslist ad for a writing role at a sketchy-sounding EDM news site. I knew it was a red flag from the start, probably several of them, but I went for it anyway. At that point, I was less concerned with whether it was ideal and more concerned with whether it was real. If nobody else was going to hand me an opportunity, I was willing to see what I could build from a bad one.

That leap paid off in unexpected ways even if it came with plenty of chaos.

What was billed as a contributor role morphed into an Editor-in-Chief position by the time I took the job. It turns out nobody was on staff. This wouldn’t be a writing gig. It was a resurrection project. Today, I’d run for the hills at that offer. But not then. Not when I knew that this would likely be my only shot to show people that I could not only write, but that I could run the show myself. And I did just that for about six months:

I took over a dying online publication with no budget and, over time, built a team of over 40 writers and photographers across three countries. We covered major events, festivals, and interviewed artists until the owner decided to rebrand into a platform for his parties.

While far from ideal, this experience taught me two things:

Even the most random gigs can lead to invaluable experience.

You can build something real out of a bad setup if you are stubborn enough and learn fast enough

It also taught me something else that matters for anyone trying to become a freelance writer. Early opportunities are not always impressive on paper. Sometimes the value is not in the brand name or paycheck. Sometimes it is in the reps, the clips, the confidence, and the proof that you can do more than you thought you could.

5. Finding My Niche in Cannabis Writing

Fast-forward to 2017. After a stint at AOL and various startup roles, I was ready to return to freelancing. I remembered a quote I’d once heard:

“Find something you love to do and get someone to pay you to do it.”

That stuck with me, and I decided to focus on cannabis writing because it was the subject I kept coming back to and actually cared enough about to keep digging into. Using just one AOL article I’d written about cannabis, I started cold-pitching clients, using the article as a small proof of concept. I offered cut-rate services to prove my value. Within weeks, I landed my first cannabis client: PurePressure. From there, I built my portfolio and established myself as a go-to cannabis writer.

That part matters. I did not wait until I had the perfect site, the perfect niche page, or ten polished samples. I used what I had. One article was enough to get started. A lot of writers stall out because they think they need a bigger portfolio before pitching. Usually they just need to start pitching.

6. Building a Sustainable Career

Freelancing in the cannabis space wasn’t easy. It required in-person and online networking at industry events, cold outreach, and constant self-promotion. But slowly, I built a steady stream of clients, balancing media work with copywriting gigs. Coupled with word of mouth referrals, and I’d fully transitioned into cannabis content by 2019.

To get there, I worked on all sorts of copy and content projects. My work ranged from cannabis website copy and blogs to email marketing cannabis campaigns, and even diving into topics like local SEO for cannabis brands. I also learned the value of cannabis branding and consulting, helping companies craft their identity in a competitive market. Some of that foundation came from my time at the online reputation management firm BrandYourself, where I got a closer look at how SEO, visibility, and online reputation actually work.

As I navigated the industry, I contributed to some of the best cannabis websites and discovered how essential dispensary SEO tips are for cannabis businesses. These projects opened doors to collaborations with cannabis marketing firms and even cannabis branding agencies.

This was also the point where I stopped thinking about writing as just writing. A good article is one thing. A good article that matches search intent, targets the right SEO keywords, and earns clicks is another. Once I started paying closer attention to how content performs in search, the work opened up.

That does not mean every freelance writer needs to become a full-on SEO strategist. But if the goal is to get paid well and stay useful, understanding the basics matters. Businesses are not just paying for words. They are paying for content that helps them show up, compete, and convert.

7. The Pivot to Full-time Copywriting

After working in both news and media for seven years, it was time to pick a path rather than split time between two avenues. By 2023, I realized that media writing alone wasn’t fulfilling or sustainable for me.

The constant grind of deadlines and low pay made it clear that I needed to focus on work that paid fairly and allowed me to use my skills strategically. So, I shifted to full-time copywriting, SEO consulting, and digital marketing for dispensaries and cannabis brands.

And thus, AWARD was officially born.

This pivot has been transformative. Today, I help cannabis companies with cannabis email marketing services, dispensary branding plans, and cannabis SEO services. From crafting engaging copy to optimizing dispensary website design, I’ve found work that aligns with my skills and goals.

It also gave me a clearer answer to the question at the center of this post. Becoming a freelance writer is not just about getting published somewhere or landing a few clients. It is about building enough skill, range, and resilience to keep adapting as the work changes.

And thus, AWARD was officially born. 

The AI Factor: Writing in a Very Different Era

When I started freelancing, AI writing tools simply were not part of the conversation. Writers either did the work themselves or they did not. The idea that a machine could generate blog posts, marketing copy, or long-form content in seconds was not something most people were thinking about.

Today that landscape looks very different.

AI writing tools are everywhere, and they are not going away. They can help with research, brainstorming, outlines, and even early drafts. Used carefully, they can speed up parts of the writing process that used to take hours.

At the same time, they create new problems for writers. Overreliance on AI can flatten someone’s voice, weaken writing skills, and flood the internet with generic content. They also raise real questions about the future of certain writing jobs, especially lower-tier content work that companies may now try to automate.

Because of that, writers entering the field today have to make a decision that simply did not exist when I started. How should AI fit into their process, if at all?

Some writers avoid it completely. Others use it as a productivity tool. Most people will likely land somewhere in the middle.

Even writers who choose to stay fully human still need to understand how AI is changing the search landscape. SEO has long been part of digital copywriting, but now it is being joined by newer ideas like Answer Engine Optimization (AEO) and Generative Engine Optimization (GEO). These approaches focus on how content appears inside AI-driven search experiences, not just traditional search results.

In other words, writers today are not just competing for rankings on Google anymore. They are competing for visibility inside AI-generated answers as well.

Whether someone embraces AI tools or rejects them entirely, it is something every writer now has to think about.

How to Become a Writer in 2026

Anyone looking to become a writer today has more opportunities than ever. Freelance writing, journalism, copywriting, and content marketing all offer viable career paths depending on skills and interests.

Freelance writing rarely follows a predictable path. Mine started with a general interest in writing and eventually grew into a career focused on cannabis branding, dispensary SEO, and digital marketing in the cannabis industry.

Most people who end up freelancing arrive there differently. Some come from journalism. Others start in marketing, blogging, or completely unrelated jobs. The path usually develops over time as opportunities appear, skills improve, and writers figure out where they fit.

The things that helped me most also changed over the years. What worked in 2017 would probably look different in 2026. The fundamentals of good writing still matter, but the environment around writing has shifted. SEO has long been part of digital copywriting, and now newer ideas like AEO and GEO are entering the conversation as AI-driven search continues to evolve.

Still, a few things have stayed consistent. Look for opportunities where you can find them. Advocate for yourself. And when you finally get your chance, show people why you belong there.

Hopefully sharing my experience helps other writers who are trying to figure out how this career actually works. There is a lot more to freelancing than writing itself, from finding clients to managing taxes and running your work like a business.

More Writer Insights

Liked this article from AWARD? Be sure to check out more detailing Andrew’s first-hand experiences working in cannabis news and freelance writing:

• The Best Cannabis Websites for News + Info 
• Top Search Engines in America: How to Rank
• Fighting Back Against Digital Plagiarism: Lessons from My Experience
• LinkedIn: Still the Best Cannabis Business Social Network

Want to learn more about how to become a freelance writer? Contact us today to learn more about the process and how we can help you along the way.