Can Legal Professionals Still Thrive on Upwork in the Age of AI?

A decade ago, after a 30-year career as a solo practitioner and litigator, Brian Cadwallader made a difficult decision. A prolonged illness forced him to step away from the courtroom and give up his active law license.

To supplement his disability pension, he needed a flexible, part-time income stream. He turned to the website Upwork, which is a popular marketplace that freelancers can use to find jobs.

Cadwallader drew on his decades of expertise to offer litigation consultation, do legal ghostwriting, and draft pleadings for pro se litigants (people who represent themselves in court).

It turned out to be the right call. Working just four to five hours a week, Cadwallader built a sustainable practice from the comfort of his home, and now pulls in around $20,000 to $25,000 per year.

How realistic is repeating Cadwallader’s success as a beginner?

Unfortunately, in 2026, the freelance landscape Cadwallader operates in looks very different from the one he encountered when he started.

“It was easier to land a job then,” he admitted. “Not as much competition.”

The economics on platforms like Upwork have shifted, and the specter of generative AI is looming over both the legal profession and the wider knowledge economy.

Many clients are turning to AI for legal work, and increasingly, even lawyers are, too. Some have even been caught and sanctioned because their submitted documents contained erroneous legal citations or other AI-generated errors.

For instance, one recent case covered by The Guardian involved a New Mexico attorney who was fined $5,000 for using ChatGPT to draft an appeal that turned out to have fabricated police testimony and ⁠witnesses.1

Cases like this reflect a broader problem with so-called “hallucinations” in generative AI, where systems produce incorrect or fabricated information while presenting it as factual.

Recent research points to the scale of this issue. The 2026 Stanford AI Index found that hallucination rates across 26 leading AI models ranged from 22% to 94% on a factual accuracy benchmark, which evaluated reliability across 6,000 questions in six domains, including law.2

This is why, although some budget-conscious clients on freelance platforms may want to substitute AI for human expertise, the technology has not eliminated the need for qualified attorneys.

The market for legal expertise remains relatively strong, in contrast to other white-collar fields like marketing, which have been hurt more by AI.

That tendency to hallucinate is also partly why, in Cadwallader’s opinion, AI isn’t capable of performing at the level of even a junior attorney yet.

“At its heart, AI is still Garbage In, Garbage Out,” he said. “I don’t rely on it.”

The rise of AI has changed his workflow, but he mostly hasn’t found the changes threatening or damaging. He said that many clients like to check his output against AI, which he isn’t afraid of.

He also told us that his best long-term clients now use AI to refine their own questions before turning to him, which he welcomes because it makes their paid consultations more efficient.

How legal professionals should use AI in their work

Cadwallader views his bespoke (fully human) writing as one of his strongest selling points, but he does leverage AI tools like Microsoft Copilot to quickly handle preliminary research, such as finding a statute of limitations in an unfamiliar state.

“Copilot pointed me to Texas Civil Practice & Remedies Code § 16.003 and described the major exceptions to the rule,” he said about a recent project. “I then copied and pasted the citation into a browser, found the statute, and read it for myself.”

While AI might not be ruining the legal freelance market, newcomers should still be aware of certain wrinkles when using platforms like Upwork.

First, platform fees can get high. Upwork handles the financial logistics, which is a plus for freelancers, but the platform’s variable freelancer service fee, which can range from 0% to 15%, “gets a little old” over time, Cadwallader told us.3

Another factor is the platform’s bidding system, which requires you to purchase digital tokens called Connects to send out proposals (i.e., job applications). Each Connect costs $0.15, and the number of Connects required varies by job.4 A proposal can cost a few dollars, with no guarantee of winning the contract.

While this is a major point of contention for many freelancers, Cadwallader, who joined the platform before the May 2019 rollout of the bidding system, told us he takes it in stride. He scans listings daily but only submits proposals 4 to 5 times per month, spending around $45–$60 a year on Connects.

Because he charges a rate of $100 per hour, he doesn’t need to win every job. “If the ad asks for something too cheaply, I usually don’t bother replying,” he told us. “I have the luxury of being retired and not having to count on my Upwork earnings to live. For me, Upwork is an avocation, not a vocation.”

Platform pitfalls for legal professionals

That flexibility doesn’t mean the platform is without its headaches. For legal professionals looking to transition to Upwork, Cadwallader pointed to two major systemic frustrations:

• The dispute resolution process is biased: Cadwallader told us that Upwork often sides with clients by default. “Upwork treats its freelancers rudely when clients complain,” he said. Even if you have a near 100% Job Success Score and dozens of 5-star reviews, a single client complaint can result in an automated termination warning from Upwork without the platform ever asking for your side of the story.
• The platform’s time tracker is flawed: Legal work requires immense amounts of reading and research, but Upwork’s hourly payment protection monitoring software requires a certain number of keystrokes and mouse clicks to guarantee payment. “Upwork won’t pay for anything that doesn’t generate plenty of keystrokes,” Cadwallader said. “I’ve learned just to accept what I am told I will get and just move on. The fee guarantee is not 100%.”

Despite those frustrations, Cadwallader says the platform can still be a viable source of supplemental income.

During a typical three-month period, he earns between $5,000 and $8,000, and occasionally, a highly lucrative client—what he calls a “whale”—comes along. At the time of our interview, he was finishing up a project for one that netted him $6,000 in just two weeks.

If you’re a newly licensed attorney, Cadwallader’s advice is to not expect your earnings on the site to replace a full-time salary right out of the gate, but to recognize its value as an independent income stream.

“I wouldn’t start Upwork to make a living at it, but as a side gig, it is worth about $10,000 in the first six months,” he told us.

When you have zero platform reviews, pitching clients at a premium rate can be intimidating. Cadwallader’s advice for standing out in a sea of applicants is to be conversational, offer upfront value, and prove your real-world chops.

How to write your proposals

“Stand out by being chatty in your proposal” was his advice to newbies. “Hook them in with a free estimate.”

When he pitches a client, he starts out by highlighting his decades of litigation experience and his 80+ five-star reviews on the platform. He invites prospective clients to verify his real-world credentials and prompts them to Google a famous case he took to the Louisiana Supreme Court (Cadwallader v. Allstate).

He also addresses his client’s potential fears head-on. In a typical proposal, he guarantees that he will not farm the work out internationally or use AI.

An example job proposal for lawyers on Upwork

Cadwallader sent us an example proposal to demonstrate how he addresses clients in the beginning:

It’s worth noting that Cadwallader mentioned sharing his contact information after a contract has been established. Doing so before a contract begins constitutes circumvention, which is against Upwork’s terms of service and may result in your Upwork account being banned.5

Setting your rates

As mentioned, Cadwallader charges $100 per hour for consultations, ghostwriting, and pleading drafting based on his years of experience.

You’ll need to take into account your own background and research your industry’s standard rates to determine what to charge (as well as the nature of the service you plan on offering, since there are many different kinds of freelance legal work).

For example, the Editorial Freelancers Association’s 2026 rate chart, based on survey data from its members, lists $75–$126 per hour for legal ghostwriting.6

Once you’ve settled on a fair rate, consider how flexible you’re truly willing to be. Cadwallader doesn’t cut his rates and doesn’t advise you to either. He said that a client should be willing to pay for your specialized education.

“Don’t cut your rates,” he warned, “or you will resent taking slave labor cases.”

When a client’s budget is too low, he doesn’t back down. As in the example proposal he showed us, he addresses it directly by saying, “Your budget is low for this work … I believe my rate is fair to both of us.”

He also told us that sometimes, he’ll add a humorous reminder that his hourly rate is essentially the same as an automobile mechanic’s.

While human freelancers like Cadwallader continue to succeed by relying on bespoke writing and hard-earned legal experience and intuition, AI technology is advancing at breakneck speed.

In September 2026, OpenAI introduced Astra for Law, a legal-focused version of GPT-6 Astra that uses a dedicated legal search index covering US case law, statutes, regulations, court rules, and administrative decisions.7

Google also recently expanded its Gemini Enterprise offerings for legal professionals, and Thomson Reuters launched its own AI model trained on its vast, proprietary Westlaw database.

These new tools may eventually trickle down to solo practitioners, law firms, and eventually savvy clients.

Navigating Upwork in 2027 and beyond will likely require leaning on your human communication skills—in other words, your ability to build trust and manage your clients’ anxieties in ways AI cannot.

As Cadwallader has proven, clients are still willing to pay for the peace of mind that comes from years of experience, which is something you can’t prompt an AI to generate.