Workers are already polyworking, but the employee handbook hasn't caught up

9.3 million Americans held multiple jobs in November 2025, the highest number in 25 years, per the Bureau of Labor Statistics. The Society for Human Resource Management named polyworking a defining work trend for 2026.

Workers have been restructuring their professional lives around multiple income streams for years, but most HR handbooks still classify outside employment as a moonlighting violation.

The portfolio career economy

Juggling multiple jobs has often been seen as a survival strategy for low-wage workers. However, research from the Federal Reserve Bank of St. Louis found the opposite. The more educated the worker, the more likely they are to hold multiple jobs. 31% of managers hold at least one additional job, per Owl Labs' 2025 State of Hybrid Work Report. So, it's happening at every level of the organization, shifting from what was once just a second job into something more deliberate: a purposely crafted portfolio career.

Aaron Cruikshank runs CTRS, a market intelligence agency he built to $1 million in annual revenue, teaches market research at the graduate level in Vancouver, and coaches consultants on building their practices. Three professional identities, all scaffolded off each other, running simultaneously.

For Cruikshank, financial pressure started his portfolio career. "I live in an area with a high cost of living, and I have three kids," he says. "My wife works as well, but [...] a family in my area needs to be grossing $250k a year to keep their heads above water, and most families can't do that with only two jobs between two people."

51% of polyworkers say the extra income is "absolutely essential" to cover basic monthly expenses, according to Monster's 2025 Polyworking Poll. Salary increase budgets are averaging 3.5% in 2026, as found in Willis Towers Watson's July 2025 Salary Budget Planning Report, while inflation is running at 3.8%, per the BLS. Workers are losing ground even when they get a raise.

But financial pressure tells only part of the story. Laura Podesta spent 12 years in television news, the last five as a CBS News correspondent on a 1AM wake-up. She left in April 2022 when her sons were one and three. Today, she runs her own media training practice, consults for a PR agency and a content studio, and does voiceover work. She and her husband take a month every year to travel.

"I started to envy people who were building their own businesses," Podesta says. "Once I experienced that emotion, I knew it was an indicator of what I really wanted: the freedom to choose when I worked, and how I worked." That choice came with a cost. "I make about $10k less than when I was a full-time news correspondent, but this flexibility is well worth the $10k difference," she says.

The disclosure gap

Workers stay quiet out of fear for how their employer will respond, per SHRM. The result is a transparency gap that only surfaces when something goes wrong.

Cruikshank doesn't only polywork. He runs a fully remote team and extends the same flexibility to his employees. His model came with its own lessons. "A team member came to me with a project," he says. "The budget was too thin, so I passed and gave my blessing to pursue it independently." What happened next was not what he expected.

"They created a whole new company with a website and team members that were not from my company, scraped a bunch of the service offerings from my website almost verbatim, and started marketing themselves as a competitor," Cruikshank says. "That was explicitly against [our] contract. They seemed shocked that I had a problem with them setting up a competing business while working for me and using my employee health benefits."

Cruikshank thought the contract language was clear, but it wasn't. "If you're going to allow polywork, you need to be super clear with people what's on side and what's not," he says. "But apparently I wasn't explicit enough."

The policy that isn't there

The risk for companies isn't just operational. Matthew Crook, General Manager at UK-based PeopleHR Evo, points to security as a real concern. "Polyworking poses a major data security risk to large organizations that could see leakages or IP theft rise as a result," he says.

Crook is less worried about malicious intent than about how easily polyworking employees move information across employers. They're more likely to repurpose their experiences and share past examples of their work An innocent portfolio share can compromise data without the employee ever realizing it. Institutional knowledge moves across professional contexts in ways that are harder to track than a deliberate breach.

Marcus Denning, a senior lawyer and principal at MK Law in Melbourne who handles commercial litigation and employment disputes, says the outside-employment policies most companies have on the books were never built to hold up under pressure. "The clause that fails first in any outside employment policy is the conflict of interest language," he says. "Vague wording has never held up when an employee disputes it."

"Most policies stop at requiring disclosure and say nothing after that," Denning says. "That is exactly where they fall apart under pressure." When that gap reaches a courtroom, the policy has no teeth. A workable policy needs a specific disclosure trigger, a deadline, a named recipient, and a written process for what follows, he adds.

For a smaller firm, Cruikshank's framework has three simple conditions. Disclose the outside role. No competing work. Deliver the output. If something relevant lands in a team member's lap while working for him, he gets the first right of refusal. “Beyond that, it's the worker's business,” he says.

Time is the wrong metric

Disclosure policies only work if the performance infrastructure underneath them shifts, too. Most organizations still measure employees the traditional way: hours logged, time spent, and asset utilization. A worker who completes a project in three hours and spends the rest of the afternoon on a second role looks identical to an underperformer on a traditional timesheet.

The reason larger organizations struggle to move away from time-based measurement is structural, Crook says. Traditional HR practice treats employees as assets measured by utilization. A worker who is highly efficient and finishes their work in less time registers as underutilized in that model rather than as a high performer. "If an employee doesn't have enough work to do, that model sees a problem."

That’s why Cruikshank runs his company on outcome-based performance. Every assignment his team takes on comes with what he calls an "effort budget." "I will pay you up to 20 hours to do task X by date Y," he says, "and as long as they deliver, I'm good to let them manage their time day to day."

The resistance, he says, isn't really about productivity. "I suspect [HR leaders] are worried about loss of control and accountability. If time-based metrics are a big contributor to your performance metrics and you give that up, it might feel like giving up control." Time theft already exists as a policy violation, he says. Polyworking just requires a different framework, not a harder one.

The shift is necessary but harder than it sounds, Crook says. "If performance was judged by outcomes alone, the need for those time-based metrics [goes] away. I think in order to embrace polyworkers, you need to be able to let go of [the idea that] time spent equals performance. That's a hard shift for some organizations, largely because outcomes are harder to turn into a metric than hours logged on a timesheet."

Building around portfolio careers

Sam Gardner is the founder of The Continuity Co., a firm that steps in to run operations for startups when founders need to step away. As a mother of three managing multiple professional engagements herself, she built the company deliberately around people who work the same way.

The best talent, Gardner says, has structured their lives around flexibility and the work they want to do. "Time affluence," the ability to control when and how you work, she says, has become as important as financial compensation for experienced professionals. "The sharpest people I know are not really available in that full-time, permanent, all-consuming format anymore."

Portfolio career professionals bring something a full-time employee can't, Gardner says. Someone working across multiple organizations is inside the day-to-day operations of several companies simultaneously, building expertise and networks that a single-employer hire never accumulates. "That's basically a whole sales force that people are giving up because they want the full commitment."

Access is one side of the argument. Retention is the other. Companies that embrace polyworking report higher employee retention, per Owl Labs. "As people go through personal growth over years of time, it makes sense that what you need ebbs and flows in your professional career," says Sierra Alea, COO of The Continuity Co. and Executive Director of VC Backed Moms. "You don't leave, you just dial your capacity up and down."

The control problem

Organizations already understand the value of polyworking, Crook says. They hire fractional executives to access senior talent without the commitment, and they let them go when priorities change. The model is flexible by design. But those same organizations tell other full-time employees the opposite: commit exclusively or not at all. "It's about having your cake and eating it when it comes to fractional workers," he says.

That double standard has legal consequences. "I've seen a company terminate an employee for outside employment while their own procurement records showed external workers contracting for comparable roles in the same period," Denning says. "HR and procurement had never aligned their policies, and that gap became very difficult to defend once it was in front of a third party."

Cruikshank says most companies are operating from the wrong assumption: treating professional identity as something the employer owns, not just the work produced during hours paid. "I think it's a little sick to assume as an employer that you own a worker's professional identity," he says. "The employer only owns how that worker represents themselves when they are working for you. Anything beyond that, with the exception of doing competing work, is none of your business."