How different side-hustles should trigger distinct employer responses

The job market has been in an eternal flux since the gradual disappearance of the job-for-life concept since the 1990s. Globalisation and the flexible employment models that enabled it have fundamentally reshaped the relationship between employers and employees ever since.
The pandemic marked another turning point: the mass shift to remote work made the traditional nine-to-five office routine for knowledge workers increasingly obsolete.
Remote – and to a smaller extent, hybrid – work means that an employee’s presence in the office ceases to be a major criterion for assessment, and their value is primarily judged on their output.
But this shift also makes it harder to define what constitutes a reasonable workload – an issue that has grown even more complex with the rise of generative AI over the past three years.
This environment has blurred the boundaries of a full-time job and has given rise to a new phenomenon: overemployment. Depending on whom you ask, the individuals who juggle multiple full-time jobs are either the heroes of efficiency or the new con-artists of the digital era.
One oft-cited example is a software engineer in India who managed to work for multiple US start-ups simultaneously without his employers being aware of his “moonlighting”.
He was handed dismissals from most of his positions – one of which ultimately stemmed not from poor performance but from the tangled web of lies he spun to hide the fact that he was operating from India.
Some extra income on the side
These headline-grabbing cases, however, only represent a broader trend. The technological advancements of the past decade have made it easier for employees to earn additional income alongside full-time work.
Supported by online marketplaces that provide built-in payment systems, invoicing tools, marketing packages and subscription management, a full-time employee can easily find the time to craft jewellery or artisan goods and sell them. Online course platforms enable people to monetise their expertise as lecturers, mentors, reviewers or webinar hosts. Side-hustlers can also take advantage of freelance marketplaces that match clients’ business need, project details and budget with the right talent.
Most of these sites feature client-rating capabilities and job success scores, while others operate more as online recruiters, inviting applications and selecting candidates through technical challenges, test projects or even oral interviews. For a subscription fee or commission, freelancers can also access file-sharing tools, video meeting features and escrow protection, or generate invoices using platform templates.
Typical jobs advertised on freelance marketplaces include web and app development, remote tech support and quality assurance testing, and fresh additions from the gen AI era – prompt engineering and content generation – have further broadened the choice.
And while many people design websites or create graphics as hobbies, these skills are increasingly being monetised by experts filling multiple full-time roles simultaneously. There is even a Reddit community, r/overemployed, where individuals share tips on how to juggle two or more full-time remote jobs.
Employers, meanwhile, must walk a tightrope of trying to strike a balance between allowing flexibility and protecting employee wellbeing while still safeguarding their own business interests.
Incorporating safeguards into employee contracts
The case of the Indian job collector offered lessons – especially for start-ups that put growth ahead of robust processes.
One immediate safeguard is the use of IP address monitoring for roles where physical location matters. Another is resisting the temptation to skip thorough vetting simply because a candidate performs brilliantly in interviews.
Employment contracts should also be explicit about the employer’s stance on secondary work. While a total ban is the simplest option, it is not realistic in sectors struggling with talent shortages, where employers need to compromise.
In such cases, the employment contract should clearly define the process for requesting approval, specify which types of side-hustles are permitted, establish the boundaries around confidentiality and set out the rules governing the use of company equipment.
The trickiest part is specifying how a side-hustle must not interfere with an employee’s primary responsibilities.
The pragmatic approach, where the employer doesn’t mind how many hours the employee spends working for them as long as their performance isn’t affected, clashes with working-time regulations that set a 48-hour limit across all jobs.
The only way for employers to remain compliant when their employee holds multiple full-time posts is asking the employee to willingly sign an opt-out agreement.
Although employers can refuse to opt out, without it, juggling several full-time roles becomes legally problematic.
Yet another game of catch-up
Employment law is far from the only field struggling to keep pace with new forms of work made possible by advanced technology.
There are 168 hours in a week, and no combination of AI tools and anti-fatigue medication can stretch that into enough time to hold three or more full-time roles within an eight-hour-day framework.
The anomalies surrounding overemployment, however, highlight the inconsistencies at the convergence of remote work, shadow AI use and the global battle for digital talent.
To restore balance, employers of remote digital workers must revisit the basics: what counts as full-time in a world no longer governed by an eight-hour working day? What constitutes “delivered” work in a home office setting? And how should responsibilities be shared between employers when an individual splits their primary labour across multiple organisations?
The problem of multiple full-time employment clearly looms much larger than the freelance gigs unrelated to the core job. While the former raises existential questions for organisations about trust, loyalty and confidentiality and calls for recalibration of the terms of employment, the latter tend to enrich employees’ professional and personal lives without necessarily having any harmful implications for the employer.
They can provide creative fulfilment and variety, as well as a welcome additional income stream. With employees’ mental and physical wellbeing being front and centre, these side hustles should be talked about, perhaps even promoted and celebrated at workplaces.

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