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Side-hustles aren鈥檛 one-size-fits-all, and that鈥檚 exactly why the conversation around them keeps evolving. Some entrepreneurs swear by them as a way to stretch skills and explore untapped opportunities. Others see them as a potential minefield of distraction and stress.

So, why do opinions differ so wildly, and how does context, personality and goals shape whether a side-hustle is a boost or a burden?

This isn鈥檛 just about productivity hacks or work-life balance – it鈥檚 about the nuanced ways founders experience and interpret side projects, and why the same approach can feel liberating to one person and limiting to another.

 

Perspective Matters: Why Do Founders See Side-Hustles So Differently?

 

One of the most surprising things we found when speaking to experts is just how polarised views are.

For some, side-hustles are mini playgrounds for experimentation, letting founders test ideas, expand networks and explore industries without fear. They talk about side projects as 鈥渟andbox environments鈥� where creativity flows and lessons are learned quickly.

Others, however, caution that the impact isn鈥檛 universal. What works brilliantly for one founder can feel like a constant drain for another. Factors like personality, current workload and business stage heavily influence the outcome. A highly structured founder may thrive juggling multiple ventures, while someone who thrives on deep immersion may find side projects fragment their energy.

Even among seasoned mentors, advice differs.

Some encourage side-hustles as a safe way to explore new revenue streams or product ideas, while others argue that splitting focus early can slow progress and dilute the leadership vision. At the end of the day, it鈥檚 not about right or wrong; it鈥檚 about fit. A side-hustle that energises one founder could exhaust another.鈥�

This diversity of opinion underscores a key point – that is, the value of a side-hustle isn鈥檛 fixed. It鈥檚 shaped by context, intention and the individual鈥檚 capacity to manage multiple creative and business streams. Understanding that nuance is essential for founders trying to make an informed choice.

 

 

Here’s What The Experts Have To Say:

 

• Judit Mora: CEO and Co-Founder of Nuumad
• Olivia Parks: Owner and Lead Organiser at Professional Organiser New Orleans
• Lindsey Mignano: Venture Financing Attorney at SSM
• Darian Shimy: CEO of FutureFund
• Liz Benditt: Founder and CEO at The Balm Box
• Ross Buhrdorf: CEO and founder of ZenBusiness
• Thomas Fighter: Founder and Criminal Trial Attorney at Fighter Law
• Elle Farrell-Kingsley: Founder and Strategic AI Advisor at PsyberVision
• Hans Scheffer: CEO of HelloPrint
• JM Ryerson: CEO at Let鈥檚 Go Win
• Vishal Kumar: CEO and Co-Founder of Camera Intelligence
• Gary Ross: Founder and CEO at Blip Insurance
• Lee Holmes: CEO of INFINOX

 

Judit Mora,聽CEO and Co-Founder of Nuumad

 

 

“Having a side hustle can be really helpful for founder development. When I was building Nuumad, I was also working two other jobs, and those early side hours were where we could experiment, test ideas, and shape the company in a thoughtful, user centred way. Of course, it鈥檚 important to manage your time, but a side hustle can give aspiring founders space to grow, build confidence, and gain experience before going all in. For me, it was an invaluable stepping stone that made taking the leap to Nuumad feel much more manageable.”

 

Olivia Parks, Owner and Lead Organiser at Professional Organiser New Orleans

 

 

“I definitely believe that side hustles can be incredibly valuable for founders. Side hustles enable you to try a variety of different things, exposing you to what you actually enjoy and are naturally good at.

“When I graduated from college, I started nannying and working as a household assistant for families while applying for full-time jobs. I was trying so hard to find a job that 鈥渇it鈥�, but nothing felt right, and I honestly had no idea what direction I wanted to go in.

“What I didn鈥檛 realize at the time was that the side hustle I was doing was the direction. By being inside families’ homes, helping with daily routines, and keeping families on track and organized, I discovered my true calling, which ultimately led to the six-figure home organizing company I own today.

“In my opinion, side hustles are great because they force you to try things, pay attention to what comes naturally for you, and help you figure out what you like and don鈥檛 like. That鈥檚 how you figure out what direction and path you鈥檙e actually meant to go in.

“For some people, side hustles are a distraction, sure. However, for aspiring founders, they can be a clear path to understanding your ‘why’ and what you are meant to do with your life and career. I鈥檇 recommend side hustles to anyone trying to figure out their career or entrepreneurial path, especially those who feel lost or stuck.”

 

Lindsey Mignano, Venture Financing Attorney at SSM

 

 

“A side-hustle can help or hinder founder development – and the effect depends on why you鈥檙e doing it, how you structure it, and what stage your startup is in.

“From a skills perspective, a founder doing contract work for small businesses that are the key customer base of his startup may sharpen customer empathy and GTM instincts.

“Second, reducing founder personal financial pressure can extend the founder鈥檚 personal runway and prevent them raising prematurely. On the other hand, a side hustle can take away from the founder’s focus on building his startup and there can be legal trouble if the ownership of the IP (startup versus side hustle) is not clear.

“Furthermore, if the side hustle in any way competes with the founders’ main business (the startup), the founder could be liable for breach of his fiduciary duties as an officer and/or director of his startup.

“Finally, investor optics may sour as an investor of a startup may see the founder’s time spent on his side hustle as a lack of dedication to building the startup at hand.”

 

Darian Shimy,聽CEO of FutureFund

 

 

“Based on my experience, a side hustle can either be a very valuable asset or a serious liability. The differences tend to come down to intent. When a founder uses a side project as a legit way to experiment, learn, or explore unique ideas they can’t pursue at their main company, it tends to be a great way to strengthen and broaden their way of thinking. From personal experience I have found that stepping into a different context can reveal blind spots and spark solutions I wouldn鈥檛 have arrived at otherwise.

Saying all of that, the second a side hustle becomes an escape from the hard problems that you should be solving, it works against you. I have always operated where founders owe the team clarity, consistency, and presence. If a side project take away from that, its no longer serving growth.”

 

Liz Benditt,聽Founder and CEO at The Balm Box

 

 

“For me, teaching as an adjunct professor has been an invaluable strategic side hustle while building The Balm Box. It provides access to world-class academic research, which continually sharpens my thinking as a founder and fuels innovation that directly benefits my business. The modest income also created financial breathing room in those early years, allowing me to support my family without pulling precious capital out of a young company.

“Perhaps the most unexpected benefit is talent: I even hired one of my former students, whose fresh perspective and digital fluency have been a tremendous asset.

“A side hustle shouldn鈥檛 be a distraction – it should be a multiplier. When chosen intentionally, it keeps founders mentally stimulated, connected, and resourced in ways that accelerate – not hinder – startup success.”

 

Ross Buhrdorf, CEO and Founder of ZenBusiness

 

 

“A side hustle can be one of the best training grounds for entrepreneurship. I know that personally because every business I鈥檝e ever started was originally a side hustle, including ZenBusiness. I鈥檝e watched hundreds of thousands of people use a small project to build the muscle memory they need to eventually run a full business.

“A side hustle can help an entrepreneur test ideas, understand customer needs, and build time management skills without a 9鈥�5 structure. Intentionality is key, and the founders who benefit most treat their side hustle as a place to experiment and learn, not just earn. It gives them real-world insights without the pressure or risk of going all-in too soon.”

 

Thomas Fighter,聽Founder and Criminal Trial Attorney at Fighter Law

 

 

“A side hustle can be good if it provides you with鈥俛nother MENTAL SPACE to think, learn and reset. When I did take on occasional鈥俿mall teaching or consulting projects outside of my main practice, they helped me see problems from fresh angles. Those moments helped sharpen my communication skills and think of鈥俬ow I would manage my team later on. That kind of clarity can come from a side project, but鈥俹nly if it serves the main mission rather than distracts from it.

“A side hustle can also be a鈥俤istraction. I found myself at one point in鈥俶y career undertaking too many obligations all at once 鈥� legal writing assignments, volunteer commitments and firm duties. Though everything鈥倃as meaningful, it stretched me. I did a less effective job because I was splitting my focus. I assessed if the extra project adds any value at all or is simply another obligation. The balance matters, especially when clients hire you to represent cases where they鈥俬ave had their safety and rights violated.

“Be STRATEGIC about the side hustle. If what the project builds is a skill that you really need 鈥� if it鈥檚 leadership, communication or financial discipline 鈥� it鈥俢an enhance your founder work. A side hustle should have CLEAR BOUNDERIES –you鈥檙e safeguarding your focus 鈥� and sparing yourself a burnout. It鈥檚 an asset, not a distraction when tuned with the right structure.”

 

Elle Farrell-Kingsley, Founder and Strategic AI Advisor at PsyberVision

 

 

“I’ve noticed people often assume I鈥檓 a disciple of the grind and hustle culture because I鈥檝e balanced full-time roles with freelancing and a growing portfolio of passion projects. But my view is far more nuanced. I鈥檓 fully for people exploring new ideas, taking on small adventures, and holding onto the stability and safety of a salaried position while they test or transition into something of their own. A side project can spark curiosity, creativity, and even clearer thinking for the main venture.

“But what I find troubling and frankly abhorrent is when a side hustle becomes something someone needs just to stay afloat. That signals a society slipping, a social contract cracking. It reminds me of Melville鈥檚 Bartleby, quietly resisting the machinery of meaningless labour. When the 9-5 demands a 5-9 simply to survive, the system, not the worker, is the problem. A creative or exploratory outlet shouldn鈥檛 become compulsory overtime.”

 

Hans Scheffer, CEO of HelloPrint

 

 

“I believe side hustles help founders more often than they hurt them, but only when they鈥檙e aligned with your bigger mission. A small project on the side can help keep you creative and give you a space to test ideas you鈥檙e not ready to roll into the main business. In my own experience, those experiments sometimes lead to the breakthroughs you bring back later.

“But there鈥檚 a line. If the side hustle pulls your energy away from the core team or stops you from thinking long-term, then it’s more of a distraction than a value. The idea is staying honest with yourself. Keep it if it fuels you and cut it if you’re feeling drained.”

 

JM Ryerson,聽CEO at Let鈥檚 Go Win

 

 

“In my experience, the most successful founders are rarely building just one thing. Every high performer I know has a side project that keeps their mind sharp and their creativity alive. When all your energy is locked inside a single company, pressure narrows your thinking and every setback feels bigger than it is. A side hustle breaks that pattern. It gives you a separate arena to test ideas, fail cheaply, and stay innovative without risking the core business.

“The mistake founders make is assuming a side hustle dilutes focus. It only becomes a distraction when you treat it like a second full time job. When you approach it strategically, it becomes a release valve and a perspective builder. Side hustles don鈥檛 pull founders off course. More often, they expand the vision and resilience needed to build something that actually lasts.”

 

Vishal Kumar,聽CEO and Co-Founder of Camera Intelligence

 

 

“For me a “side-hustle” is only a distraction if it’s unrelated to your primary mission. If it’s strategically aligned, it鈥檚 not a side-hustle – it’s a distribution channel.

“My journey is a perfect example. I was a cultural data scientist at Sotheby’s and started creating content about my role. That “side-hustle” helped me build a community of 30,000 followers.

“As a founder, now that community – as well as the other creators I’ve met – is our initial adopter base for Caira, our intelligent camera. My side hustle helped me build a pre-vetted customer list, which significantly lowered our customer acquisition cost.

“So, does it help or hinder? For me, it was the single most valuable asset I built. The right “side-hustle” is an unfair advantage.”

 

Gary Ross, Founder and CEO, Blip Insurance聽

 

 

“As someone who works with entrepreneurs, I believe side hustles can be one of the most effective training grounds for founder development. It forces you to test your skills on two fronts, sharpening your judgement.

“But the benefits are not automatic. The biggest risks I have seen are burnout and being under-resourced. When a side hustle feels personal, founders often treat it more casually, potentially overlooking the financial and operational risk they would never ignore in their primary business.

“This is exactly why at blip, we created a Five Step Financial Guide for side hustlers. With the right structure, a side hustle can become a genuine accelerator for founder growth. It gives people the space to experiment and build confidence without risking their main venture. Far from being a distraction, a well-managed side hustle can improve skill sets and ultimately make them more capable when leading businesses.”

 

Lee Holmes,聽CEO of INFINOX

 

 

鈥淧eople often talk about side-hustles as if they鈥檙e a guilty pleasure, as if they are something you should sneak around with after hours. I鈥檝e never subscribed to that. In my experience, side-hustles usually come from one of two places: passion or spotting a gap in a market. And frankly, I want people in my company who have that sort of spark. It shows spirit, creativity, curiosity, a willingness to engage with the world and try to make it better. That鈥檚 exactly the mindset that drives innovation.

“Of course, there鈥檚 always the argument that a side-hustle might dilute focus. But good leaders don鈥檛 fear that, they channel it. If someone has the energy and drive to build something on the side, then as a CEO my job is to harness that attitude for the benefit of their current role. A person who鈥檚 learning, experimenting and growing outside the office tends to bring more to the table inside it.

“And if, one day, their side-hustle becomes so successful that they leave to grow it full-time? Good for them. The world needs more people building things, creating value and challenging the status quo – that鈥檚 how resilient economies are built. There鈥檚 no downside to having alumni who go on to launch great companies.

“So yes, I think side-hustles help founder development, and talent development more broadly. They keep you stimulated, they keep you sharp, and they remind you why you got into business in the first place. As long as the day job is done well, I鈥檒l always back people who back themselves.鈥�