Should You Be Working Two Jobs?

Why work two jobs?

Financial necessity remains the most immediate catalyst for this trend. Rebecca Croucher, SVP of Marketing & Sales Enablement at ManpowerGroup NA, observes that “many report that as the cost of living has increased, they began living from paycheck to paycheck and taking a second job, which provides some comfort” [2]. The numbers substantiate this claim. Analysis from the Federal Reserve Bank of St. Louis shows the percentage of college-educated multiple jobholders rose from 45.1% in 2019 to 50.2% in 2024 [3], dispelling the notion that this is solely a low-wage worker phenomenon. Additionally, the average number of hours worked per week is on a downward trend. As ZipRecruiter’s chief economist Julia Pollak notes, “If employers are seeing soft demand for labor and cutting hours, that’s another reason why people are taking on additional jobs to fill the week and their bank accounts.” [4]

Yet economic pressures only partially explain the proliferation of polywork. The digital revolution has fundamentally altered the employment equation. Platforms like Uber, Fiverr, and Airbnb have dramatically lowered barriers to supplemental income, while remote work technologies have dissolved geographical constraints [5]. Professionals can now maintain a corporate position in London while freelancing for clients in Singapore, all from a home office in Dublin. The technological liberation of “digital nomadism” enables today’s workers to construct patchwork careers that would have been logistically impossible a decade ago.

It should be noted that there is a difference between polywork and a side hustle. Polywork is being employed in multiple full-time jobs, while side hustles are your efforts in an auxiliary role — rather than in another full-time role. Meanwhile, for a growing number of people, multiple jobholding represents not economic desperation but strategic career design. Writing in Forbes, Jennifer Jay Palumbo highlights the emergence of “portfolio careers,” where professionals intentionally combine roles across industries to build diverse skills and income streams [6]. David Nebinski, host of the Portfolio Career podcast, frames this as accumulating “career capital” — transferable competencies that enhance long-term employability [7]. The example of Serena Kern-Libera, who balances singing, a policy role at HM Treasury, and running a record label, exemplifies this approach [8]. As April Rhine writes in Harvard Business Review, “It’s a new way to think about, talk about, and –– most importantly –– craft your professional future to navigate our ever-changing world of work with purpose, clarity, and flexibility.” [9]

The downsides

The psychological and physical toll of sustained polywork should not be underestimated. Croucher warns that conflicting schedules and relentless demands can lead to “fatigue and burnout, which can affect your performance at both jobs” [10]. Research from Paychex paints a concerning picture: polyworkers report higher levels of burnout and stress, while being less likely to feel inspired or satisfied with their work [11]. The cognitive load of maintaining multiple professional identities — what psychologists term “attention residue” — erodes mental resilience over time.

Performance metrics reveal tangible consequences. Polyworkers demonstrate poorer organisational skills, frequent tardiness/absence, and difficulty integrating into company culture  compared to single-job counterparts [12]. These findings have not escaped employer notice. Anthony Klotz, the academic who coined the term “The Great Resignation”, reports that concerns about secretly overemployed remote workers now rank among the top three questions he receives from corporate managers [13].

Is it allowed?

The clandestine nature of much polywork creates complex ethical dilemmas. Websites like Overemployed explicitly advise users to conceal multiple roles, with their first rule being “don’t tell anyone”, while their website admits it exists to “give the man, aka Corporate America, the middle finger for always trying to screw the little people over” [14]. McKinsey estimates 5% of the workforce engages in this “double-dipping,” often under significant stress [15]. The case of Bryan Roque, who simultaneously held positions at IBM, Meta, and Tinder before collapsing under the strain, illustrates the psychological toll of such secrecy [16]. It’s not a surprise, the stakes are high –– a Gallup poll found that 50% of the HR bosses said their business had punitive policies for workers who flouted hybrid rules, a big jump from the 16% who said this in September 2022. [17]

Yet the moral equation isn’t straightforward. In an era of eroded job security and stagnant wages, is it unreasonable for workers to diversify their income streams? Author of The Secrets to Happiness at Work, Tracy Brower PhD, suggests transparency with employers to avoid conflicts of interest [18], but as Forbes contributor Caroline Castrillon notes, many organisations remain unaware of employees’ additional commitments [19]. This disconnect fuels an uneasy tension between worker autonomy and employer expectations.

Ireland

Ireland presents a compelling case study in polywork dynamics. Central Statistics Office data indicates 4.6% of Irish workers hold multiple jobs, with concentrations among younger demographics and urban residents [20]. The tech sector — a cornerstone of Ireland’s economy — has seen particular growth in undisclosed remote roles, facilitated by multinational corporations’ flexible arrangements.

However, Ireland’s employment law remains ambiguous regarding undisclosed multiple jobs, creating legal grey areas. Culturally, where American workers might celebrate side hustles, Irish professional norms have traditionally viewed polywork with suspicion — though this stigma is eroding among younger generations facing Dublin’s housing crisis, where average rents consume 57% of take-home pay [21].

Finding the balance

For those committed to multiple roles, experts propose several strategies for sustainability. Croucher emphasises boundary-setting and self-care [22], while Tiffany Cruz of Power Writers USA advocates visual time mapping to identify inefficiencies [23]. The Overemployed community paradoxically recommends mediocrity — “be average”, they say, to avoid detection [24]. Such a strategy raises questions about job satisfaction and professional growth, something that Croucher addresses. “Overall, it’s important to carefully consider the pros and cons of working two jobs before making a decision,” she says, “since working multiple jobs may not provide the opportunity for career advancement and can make it difficult to pursue additional education or training.” [25]

Should you be working two jobs?

As polywork evolves from outlier to mainstream practice, its long-term implications remain uncertain. But its rise reflects deeper societal transformations — the gig economy’s erosion of traditional employment, technology’s enabling of borderless work, and generational shifts in professional expectations. As Castrillon observes, “Combining skills and pursuing multiple career paths provides more security and is an effective way of staying agile” [26]. In an unstable economic climate, the ability to diversify one’s professional portfolio may transition from advantage to necessity.

Yet the human costs cannot be ignored. Between financial pressures and personal wellbeing, workers are navigating uncharted territory. The challenge for individuals and organisations alike will be developing frameworks that harness polywork’s opportunities while mitigating its risks — creating sustainable models for the future of professional life.

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