As more companies begin trials of four-day work weeks for their employees, the question needs to be asked – what will people do with their extra day of freedom?
For many people, this could be a great opportunity to spend more time with family, get into the great outdoors, or simply kick back at home.
Many people will devote this extra time exploring their passions, and we would undoubtedly see an uptick in short-term courses – but a lot of workers will choose to pursue side hustles and start freelancing in the areas they eventually want to transition into.
Let’s take a look at the impact of a four-day work week on side hustling.
Key Takeaways
- Four-day week adoption is still small. Gallup puts it at 8% of employees, though roughly 90% of companies that run a structured trial keep the model.
- Side hustling is now mainstream and increasingly driven by necessity.
- Employers should never put a non-compete in an independent contractor agreement. It undermines contractor classification rather than protecting the business.
- Engaging your own W-2 employee as a 1099 contractor for extra work is almost always misclassification, and paying the same person on both forms in one year is a known audit trigger.
The Growth of Side Hustling
Employees often begin side hustles as a way to generate more income. But many people find that side hustles also give them a much needed creative outlet and let them explore their personal interests outside of the 9 to 5 grind.
A rising number of employees are realizing the potential of combining their existing jobs with freelancing or side hustles – either to help them upskill, get in touch with their entrepreneurial side, or to earn extra cash from skills they might already have. This number will continue to grow once employees have an extra day of free time on their hands.
For example, your full time designer might also be a good copywriter, and decide to take up some freelance writing work on the side now they have a four day work week. Or, you might have a staff photographer that also makes handcrafts – and their shortened work week now gives them a great opportunity to build and grow an ecommerce store to sell their products on the side.
Side hustle participation is now large enough that it shows up in federal data. The Bureau of Labor Statistics counted 8.55 million Americans holding two or more jobs in June 2026, about 5.3% of everyone employed, and that figure only captures people whose second job pays a wage from an employer. Freelancers and self-employed sellers fall outside it entirely.
Survey data puts the real number considerably higher, though estimates vary widely because each survey measures something different. Intuit QuickBooks found 47% of US adults earned side hustle income in the twelve months to December 2025. Bankrate recorded 27% with an active side hustle in mid-2025.
If the extra day is going toward income rather than rest, the wellbeing case for the shorter week gets complicated.
Popular Side Hustles for Employees
Most employees will begin their side hustle journey at one of these common starting points.
Freelancing
If your employees have a variety of skills in their resume, it makes sense for them to earn extra money and pursue their passions – if it doesn’t conflict with their full time job in any way.
Freelancers can start with zero skills or experience and work their way up to well paid gigs quite quickly. Roughly 43% of Americans with side hustles report earning more while working fewer hours than they would in a traditional salaried role, which is part of why the path from side project to full-time independence stays well-traveled.
So with the growth of the freelance industry comes the opportunity for more employees to explore the possibility of freelancing full time if they can realize the potential of this side hustle.
Blogging
Blogging can of course be done on a freelance basis, simply writing articles for other companies. But many employees might opt to start their own blog writing about something they’re passionate about.
The blogging industry is huge. The potential to make thousands of dollars a month is definitely a drawcard here. All you need is a laptop, some basic website building skills, and a sprinkling of SEO knowledge.
A four day work week would enable employees to write more posts for their blog each month, monetize them with ads or affiliate marketing, and start earning some relatively passive income on the side of their full time job.
Ecommerce
Dropshipping, Shopify stores, Etsy, Amazon FBA, print on demand, digital products – the amount of opportunities for side hustlers to start selling things online is huge, and it’s an attractive option for people who have just discovered the joys of a four day work week.
It’s cheap to get started, and often doesn’t even require any outlay to start selling things and making more money every week.
Side Sustling Pitfalls to Avoid
Whether you’re a freelancer or an employer, it pays to be aware of the potential problems that could arise from side hustling.
Employment contracts need to be taken into account in case any of the clauses affect an employee’s side hustle endeavors. These might include aspects such as:
Tax Requirements
From the employee side, this can be easily overlooked if you’ve always had your employer handling taxes.
The money earned from a side hustle can feel a lot like “free” money, but the tax man will definitely come for a cut of these earnings at some point. It’s advisable for any new side-hustlers to get professional tax advice before they start out.
Restrictive Covenants
Non-compete and non-solicitation clauses are common in employment contracts, and an employee's side hustle can run into them. Enforceability varies significantly by state, and what holds up in one jurisdiction may not in another. Employees should read their agreement closely, and employers should be clear about what their clauses restrict.
Employers should put a non-compete into an independent contractor agreement. Restricting a contractor from working for other clients is one of the clearest signals that the relationship is really employment. It works against the IRS common law test and fails outright under Prong C of California's ABC test, which requires that the worker be customarily engaged in an independently established trade. A non-compete in an IC agreement doesn't protect you. It hands a regulator evidence.
Protect the business with confidentiality terms, IP assignment, and clearly scoped deliverables instead. Those hold up without undermining the classification.
Non-Disclosure Agreement
Similarly, if a non-disclosure agreement has been signed between an employer and employee, this needs to be finely combed through in case a side hustle breaches any elements of the document.
Depending on the employee’s new side hustle, they could risk accidentally running into complicated legal problems – resulting in expensive fines, the loss of their job, and an untimely end to their new business.
Intellectual Property Agreement
If there’s a contract clause or separate agreement that relates to intellectual property, this could have an impact on potential side hustles – especially if an employee intends to use something they’ve created while in their full time role. Protecting your company’s data and other sensitive data is paramount when you’re working with freelance contractors.
Carefully checking what’s been agreed to in terms of IP between an employer and employee can prevent future problems, and enable employees to confidently grow their side hustle.
Combining Full-Time Work with Freelancing
The greatest pitfall when it comes to side hustling is the time and energy it takes from employees. Even with a four day work week, growing a new side project isn’t easy – there are always a million things to do and problems to overcome.
For employees, it can be difficult to leave the side hustle “at home” while they’re at work. It’s exciting, it’s challenging – and, it’s potentially a way for them to transition to freelancing on the full time basis.
It’s super important that employees don’t try to juggle their working hours with growing a new side hustle at the same time. But with the rise in four day work weeks around the globe, it will become even easier for employees to have the best of both worlds.
As employers, it’s in your best interests to embrace the rise of side hustling. With four day work weeks, it’s inevitable that your employees will pursue other opportunities in their spare time – whether it’s for passion or for economic reasons.
Rather than trying to prevent this happening with strict employment contracts, there’s an amazing opportunity to create internal marketplaces and offer freelance opportunities for full time employees that might like to take up extra contract gigs in their spare time.
How Worksuite Fits into the Conversation
Worksuite manages the external side of a blended workforce, which is where the compliance weight sits.
Every contractor engagement runs through classification before work starts, evaluated against the applicable federal, state, and local tests across all 50 US states and 190+ countries, with the outcome documented on the worker's record. Onboarding, contracts, and tax documentation are automated and configured by worker type and jurisdiction. Payments process in 190+ countries and 120+ currencies with 1099 filing handled at year-end.
For organizations building an internal marketplace or a preferred contractor bench, Worksuite's private talent pool keeps skills, rates, availability, and past project history searchable, so filling a short-term gap starts with people you already know rather than a cold search.
Book a live demo to see how Worksuite manages contractor classification, onboarding, and payments in one platform.
FAQ
Can I pay my own employee as a 1099 contractor for extra work?
Almost never. The IRS treats the relationship as a single employment relationship, and issuing the same person a W-2 and a 1099 in one tax year is a recognized audit trigger. Additional work performed by an existing employee is generally wages and belongs on their W-2, subject to overtime rules where they apply. Narrow exceptions exist where the second engagement is a genuinely separate business providing an unrelated service, but they're fact-specific and worth confirming with counsel.
Should an independent contractor agreement include a non-compete?
No. Restricting a contractor from working for other clients is one of the strongest indicators that the relationship is really employment. It works against the IRS common law test and fails Prong C of California's ABC test outright. Protect the business with confidentiality terms, IP assignment, and clearly scoped deliverables instead. Worksuite's contract templates are built to hold up under classification scrutiny rather than against it.
Can employers stop employees from having a side hustle?
It depends on the employment agreement and the jurisdiction. Confidentiality terms, IP assignment clauses, and conflict-of-interest policies commonly restrict specific activity, while blanket bans on outside work are harder to enforce and vary by state. Many employers now find it more productive to channel that energy into internal project work rather than police it.
How do companies manage a workforce that mixes employees and contractors?
The two groups need separate systems, because the requirements genuinely differ. Employees need payroll, benefits, and I-9 verification. Contractors need classification, IC agreements, W-9 or W-8BEN collection, and payment through AP rather than payroll. Worksuite handles the contractor side, including classification across all 50 US states and 190+ countries, automated onboarding, and global payments, so the contingent half of a blended workforce is managed as rigorously as the employee half.
