Is Freelance Writing on Upwork Still Worth It in 2026? Four Writers Explain How the Industry Has Changed

Spend five minutes online and you’ll find countless writers asking whether freelance writing still has a future. Reddit threads, LinkedIn posts, and YouTube videos routinely declare the profession dead.

The concern isn’t irrational. A survey by SideHustles.com found that 57% of writers and content creators reported losing work to AI.

However, not all types of writing are easily automated. The writers we spoke with argued that, while AI excels at spitting out generic, low-value content, it still struggles when it comes to nuanced or technical topics.

That means that the bigger shift is not that freelance writing disappeared. Instead, the path to becoming a successful freelance writer has become more specialized. If you can develop knowledge in a specific industry and demonstrate that expertise to clients, you can still compete—even in a marketplace filled with AI tools.

The hardest part is getting established (and the wait before you “take off”)

For new writers, the biggest challenge is building the reputation needed to compete for the writing jobs that do exist.

So, how long does it actually take for an Upwork profile to take off?

“It is always hard to say how long it will take,” said Elizabeth Lumpkin, MD, founder of the medical writing and content strategy agency Road Warrior Ink and a veteran medical writer who transitioned to freelancing after more than 20 years in clinical medicine.

“You will read stories about it taking one or two months,” said Lumpkin, “but my experience is that it takes about a year to get to where you have regular business.”

Gabrielle Seunagal, an expert content writer and AI specialist who has earned more than $300,000 on Upwork, agrees that the biggest frustrations come early in your career when you are establishing credibility.

When she was starting out in 2017, Seunagal had to spend more time applying for jobs, earning reviews, and proving herself to clients in order to build her profile “brick by brick.”

Today, things are very different.

Rather than constantly submitting proposals, Seunagal now receives a steady stream of client invitations on Upwork (requests that arrive directly in her inbox and don’t require her to send proposals).

“A profile with consistently positive client reviews goes a long way on Upwork,” she said. “It demonstrates to clients reliability and a track record of high-quality deliverables.”

How do you actually get clients in the beginning?

Securing your first contracts requires a heavy upfront time investment.

Lumpkin advises beginners to expect a 20- to 30-hour weekly commitment at the start, primarily dedicated to writing proposals. She also stresses the importance of creating your own opportunities to prove your expertise.

When Lumpkin first started, she used an “any port in a storm” tactic. She took whatever work she could get just to build a track record, even though those initial pieces don’t reflect her highly specialized medical portfolio today.

“If a new writer has anyone in their circle willing to ‘hire’ them, pay them, and post a review, it is incredibly helpful,” she said. “This is not the time to be shy about asking for help; there is a lot of noise on the platform, so you have to make some of your own noise and network.”

Beyond networking, Lumpkin added that new freelancers need to pull every lever available to them to land those first few 5-star reviews. That includes:

• Setting entry-level rates initially to build your job success score.
• Offering paid test projects to lower the risk for hesitant clients.
• Optimizing your profile with a professional headshot and a niche-specific title (e.g., Lumpkin uses “Medical Content Writer Physician with SEO and B2B Expertise” rather than just “Writer”).

You also need a portfolio, even if you don’t have past clients yet. “Keep writing, even if no one is paying for it,” she advised. “I wrote a white paper for my website that has gotten a lot of attention. I didn’t make any money upfront, but it has generated a lot of interest.”

If you are unsure what to write about for your Upwork portfolio samples, she suggests leaning on the very tools you are competing against: ask AI to generate practice topics for you.

Lumpkin also believes that taking a freelance-specific writing class to get early critiques—and eventually getting picky about early clients to avoid low-paying headaches—can protect your rating while you build momentum.

Ultimately, it’s about building trust and being persistent. Even with regular business and Top Rated Plus status, Lumpkin says she still writes about four to five proposals a week just to keep the pipeline healthy.

If freelance writing has changed, Upwork is where those changes are most visible. The platform was already competitive before AI entered the mainstream, with thousands of writers competing for the same projects.

AI has made things even tougher. Today, freelancers are competing not only against other writers but also against a marketplace flooded with AI-generated proposals and low-cost AI content.

To succeed, you have to know (and prove) your value.

AI spam has made it harder to stand out

Most writing jobs on Upwork are awarded through a bidding system. Freelancers search for open listings, spend platform credits called Connects to submit proposals, and compete against dozens of other applicants for each project.

While this bidding system has always made competition on Upwork intense, AI has increased the volume of proposals that clients receive. Freelancers can now generate customized pitches in seconds, which leaves clients to sort through dozens—sometimes hundreds—of applications that often sound eerily similar.

Brandi Marcene, a veteran copywriter who has earned over $2 million on Upwork and runs her own agency at BrandiCopywriter.com, identifies this as her biggest platform frustration.

“This makes the process more difficult for both freelancers and clients,” she said. “Qualified professionals must work harder to differentiate themselves … while clients spend more time filtering through responses that fail to address their actual needs.”

Ironically—and interestingly—that creates an opportunity for you to stand out.

If you’re applying for jobs today, a proposal that asks thoughtful questions about the project, references the client’s instructions, and explains specific steps you’d take when approaching the work can help you stand out from a flood of AI-generated pitches.

But even if you can still land work, clients aren’t paying for the same thing they were four years ago.

Clients now pay for expertise, not just words

Proposal spam isn’t the only shift AI has created. Since anyone can generate basic text in seconds, client expectations have fundamentally shifted.

“Clients now expect considerably faster turnaround than in previous years, while simultaneously holding higher expectations around quality,” Marcene said. “They understand that content can be generated quickly by anyone, and are therefore paying specifically for insight, strategic thinking, accuracy, and effective communication.”

Marcene says that means you sometimes need to contribute before the writing even begins.

For one client launching two commercial construction brands, she started not by drafting website copy but by conducting competitor analysis, keyword research, SERP analysis, and audience research.

That work uncovered an opportunity to position both companies around their project coordination and operational reliability rather than simply showcasing their completed projects.

The resulting strategy then shaped the websites’ layout, messaging, and SEO content before a single page was written.

It’s work that goes well beyond producing polished copy and exactly the kind of strategic contribution that experienced freelancers say clients are increasingly willing to pay for. As Marcene puts it, your proposals and profile now need to demonstrate that you’re offering more than polished prose.

Applying for jobs has become more expensive

The financial mechanics of applying for jobs on Upwork have also changed. Specialized defense and firearms writer Trent Gander, who says roughly 90% of his work comes through his Upwork profile, is particularly critical of the platform’s proposal boosting system.

In this boosting system, you can spend additional Connects to raise your proposals higher in a client’s inbox.

“I encounter a lot of people spending the equivalent of like $5 … in order to be at the front of the list for a particular project,” Gander told us. “It’s people essentially gambling to see if they will get the job.”

For lower-paying projects, he argued, the math simply doesn’t work. “I don’t want to spend an extra $5 to $10 just to get a job that may pay me $50 or $60.”

Because Connects currently cost around $0.15 each and are rarely refunded if you don’t get the job (and some jobs can require tens of them to apply), bidding on every project where you might be a fit can quickly become unviable. 1

If you’re just starting out, it’s worth being selective. Rather than submitting dozens of proposals, focus on projects where your experience is an especially strong match.

If all goes well, you may build a base of repeat clients who invite you directly to new projects so that you can avoid the bidding process entirely—like our featured writers all do at this point.

Upwork’s algorithm can be obscure and frustrating

Getting to the top of Upwork requires platform gamesmanship and a high tolerance for algorithmic quirks.

When you first start, it’s common to get outbid by the sheer volume of competitors, which causes a lot of freelancers to give up in their first year. But even after you’ve established a successful profile, the platform keeps you on your toes, Lumpkin said.

She noted that her biggest current frustration is the lack of transparency in Upwork’s ranking algorithm.

“Overnight, my [Job Success] score once dropped from 100% to 85% with almost all five-star reviews and no complaints from any clients,” she recalled. Customer service offered no explanation, and a few weeks later, the score bounced back to 100% on its own.

Surviving on Upwork means learning not to panic over these algorithmic hiccups.

Ask different freelance writers how they survive in the AI era and you’ll hear very different philosophies.

Some writers see AI as an essential tool that helps them work faster and compete more effectively. Others have built their brands around offering completely human-created work.

The right approach depends on your niche and how you intend to market yourself.

You can fully embrace AI as part of your competitive strategy

In Seunagal’s view, resisting AI is a mistake. Along with SEO blog posts and marketing emails, she also produces Answer Engine Optimization (AEO) content—writing crafted specifically to be cited by AI search tools like Google’s AI Overviews—for clients in niches ranging from elder care and politics to e-commerce brands.

She now uses AI throughout her workflow for research, outlining, fact-checking, and editing.

This aligns with findings from a recent Side Hustles survey, which showed that 73% of independent workers who use AI use it primarily for research or search assistance (rather than letting the software generate actual creative output).

In a recent blog post on her website, Seunagal argued that avoiding AI leaves workers at a disadvantage.

“Failure to learn and leverage AI means self-isolating from opportunities to compete in the workforce,” she wrote. “It’s just making you poorer and more expendable in the long term.”

This belief doesn’t just stem from anecdotal evidence. Upwork reports that demand for skills explicitly referencing AI grew 109% year over year, which suggests that clients increasingly expect freelancers to understand AI workflows.2

Is anti-AI sentiment detrimental to women in the writing space?

Seunagal argues that her proactive AI integration is a gender-conscious career strategy to avoid self-sabotage.

“Women should embrace AI in our careers. The men are doing it and are increasingly in the rooms where decisions get made about it,” she wrote on her blog.

Her observations are mirrored by the Side Hustles survey data, which highlights a stark gender gap in how male and female freelancers approach the technology:

• Men are more likely than women (51% to 42%) to declare that learning to use AI is an absolute necessity in 2026.
• Men are nearly twice as willing (30% vs. 17%) to use AI to lower their rates and actively undercut competitors.
• Twice as many men as women (26% vs. 13%) are comfortable completely outsourcing their workflows to AI.

For Seunagal, this means that total rejection of AI is a severe competitive liability.

“Anti-AI absolutists won’t necessarily get phased out by robots, but they’ll be succeeded by fellow humans who study and optimize AI accordingly,” she argued. “Moving forward, I predict the sweet spot for freelancers is learning and integrating AI … while also maintaining our innate human value as creatives.”

You can also compete by staying fully human

On the opposite end of the spectrum, Marcene explicitly writes “no AI means no AI” on her Upwork profile.

As an agency founder, she produces conversion-focused website copy, landing pages, and long-form ghostwritten eBooks. Her clients often come from highly regulated or high-trust fields like fintech, real estate, healthcare, and finance, where confidentiality, factual accuracy, and a distinct human voice are paramount.

She says she doesn’t use AI for drafting, rewriting, or even research.

“This approach resonates strongly with a particular segment of clients,” she said, pointing to concerns around originality, confidentiality, and maintaining a distinctive brand voice.

Trent Gander follows a similar philosophy. He revealed that he knows of a successful writer who trains AI tools on their own writing style to work more efficiently, but personally steers clear of that practice.

He describes his work as cruelty-free copy, arguing that he prefers not to rely on language models trained on potentially unlicensed creative work. “I like the process of writing, so I don’t want a machine to do the thing that I love to do,” he said.

However, Gander does not ignore the technology entirely. He uses AI notetakers to transcribe client interviews and occasionally takes flat-rate editing jobs to fix poorly written AI drafts.

“I come in, I clean up what AI has already done,” he added. “I literally fix it in like 30 minutes or less.”

The takeaway from these different approaches to AI is that the technology itself is less of a deciding factor in your success than whether you can provide something beyond the first draft, such as AI skills or expertise in a specific niche.

If you’re hoping to build a freelance writing business today, the days of getting paid to simply write are over. AI has reshaped the writing industry, especially when it comes to generic content. Having subject-matter expertise may be the answer.

Trent Gander’s career demonstrates why specialization has become so valuable. He produces technical copy, defense-industry articles, and physical security breakdowns for manufacturing clients, specialized security firms, and niche publications. His workflow relies heavily on real-world military and law enforcement expertise.

Gander has found that AI tools are structurally incapable of handling his niche.

“I have actually found that ChatGPT is not allowed to talk about the subject,” Gander said, citing safety filters built into many mainstream LLMs that restrict discussions around weapons and subjects that can cause harm.

Even when AI tools do write about firearms, Gander said, the output is frequently inaccurate or relies on outdated myths. “A lot of this is just snake oil and myth from the 1970s on. ChatGPT will talk about them, but it will not be accurate.”

Gander views himself as a translator between dense industry terminology and consumer-friendly English, a skill that requires real-world experience and is much harder to automate.

If you’re considering a niche, Gander recommends choosing an industry you’ve worked in or know firsthand as a customer.

One of the biggest questions modern freelancers ask is what to charge.

AI has lowered the cost of producing basic content, but according to the writers we interviewed, that doesn’t necessarily mean you should lower your rates—once you have your foot in the door, at any rate.

Instead, they argue that your pricing should depend on the value you bring.

Different writers price their work in different ways

The four freelancers we spoke with all charge differently because they sell different kinds of expertise.

Gabrielle Seunagal lists her baseline rates at $60 per hour or $0.10 per word. By using AI tools to handle initial research and outlining, she is able to produce high-quality, human-polished drafts much faster.

Brandi Marcene’s agency offers a wider array of writing services and charges $35 per 500 words and up, depending on the project.

Trent Gander charges a flat rate of $30 to refine AI articles and leverages his specialized industry background to charge an hourly fee of $60.

Meanwhile, thanks to her medical expertise, Lumpkin charges $125 per hour.

Although their pricing models differ, these four writers are all charging for something more valuable than words alone.

What is “too high” in the age of AI?

Where the writers differ is in how they define “too expensive.”

For Gander, the answer depends on the complexity of the work. He argues that for simple AI-assisted articles, anything over $0.05 per word is too high.

Seunagal, on the other hand, believes that writers with technical AI expertise (e.g., AEO knowledge) who understand how to structure content for modern search landscapes should charge premium rates. “Writers deserve fair compensation for our work.”

Gander agrees that specialized niches should enjoy a higher pay ceiling, but notes that clients ultimately pay for commercial impact.

“Someone who is technically not proficient but consistently brings in 20% higher revenue will fetch a higher price than a technically proficient individual who does not bring in any additional revenue.”

How do you justify your prices to clients?

For a client who argues they can get drafts from an AI for free, Marcene suggests reframing the comparison entirely:

“AI can produce text quickly, but it can’t replace strategic thinking, original research, nuanced messaging, brand judgment, or accountability. The cheapest content is often the most expensive if it fails to perform or needs to be rewritten later.”

If a client pushes back on a rate as unjustifiable, Seunagal suggests that it is usually a sign to walk away rather than enter a race to the bottom.

“I think if a client believes a human freelancer’s pricing is ‘unjustifiable,’ they are better served by working with a different freelancer,” Seunagal said. “As for my own rates, I always ensure they align with my skill sets, my industry knowledge, and my almost decade of experience as a freelance writer.”

The consensus among all four writers is that Upwork is still worth it, but with a few caveats.

“It is still the largest platform out there,” Lumpkin said. “Unless you already have a bank of contacts and referrals, I think it still makes sense to use Upwork. You do need to understand the frustrations that are common to almost everyone who uses Upwork.”

Seunagal agreed. “If I had to start again on Upwork from square one, no clients or reputation, building a successful operation would take more effort compared to nearly a decade in, but the effort would still be worthwhile,” she told us.

She added that thanks to Upwork, she has been able to build and grow her writing career while staying updated on freelance trends, understanding changing client demands, and adjusting her marketing strategies to match.

Marcene also believes that Upwork remains one of the most effective platforms for establishing initial credibility, but she cautions against putting all of one’s eggs in a single basket. She recommends building an independent website, maintaining a strong LinkedIn presence, and investing in content marketing alongside marketplace work.

Doing so, she told us, provides far greater long-term stability.

New writers should be patient

If you’re new to freelancing, Gander’s advice is: don’t quit your day job right away.

“Once you start to get traction and start to be equal to or greater than your current job, then you can transition,” he said.

Four years after ChatGPT reshaped the writing industry, freelance writing hasn’t disappeared, but it has become harder to succeed as an “average” writer.

Generic blog posts, SEO filler, and low-value copy have been handed to AI. If you want to thrive, you need to build expertise that machines struggle to replicate.

Whether you embrace AI like Gabrielle Seunagal and Lumpkin, reject it entirely like Brandi Marcene, or carve out a specialized niche like Trent Gander, you’ll need to figure out what your competitive advantage is so that you can compete on something more meaningful than word count and pricing.