Does Having A Side-Hustle Help Or Hinder Entrepreneur And Founder Development? The Experts Weigh In

Side-hustles have become a defining feature of today’s entrepreneurial landscape. For some underestimate the cognitive load their primary company requires – from crisis management to strategic direction and even the emotional labour of leading a team. When attention is divided, the main business often absorbs the consequences – slower response times, weaker decision-making and a loss of the intensity needed to achieve early traction.

There’s also the question of identity. Side-hustles marketed as “freedom” can sometimes create pressure to constantly produce, monetise and “perform”, turning what should be a source of inspiration into yet another workstream. Without boundaries, the side-hustle risks becoming a second job rather than a creative outlet.

Ultimately, a side project only becomes beneficial when it enhances the founder’s development – not when it drains time, energy or strategic clarity.

Matthieu Rouif: CEO at Photoroom Rich Pleeth: CEO and Co-Founder of Finmile Jan Hendrik Von Ahlen: Managing Director and Co-Founder at JobLeads Crawford Warnock: Founding Director at Firstname Communications Estelle Keeber: Founder at Immortal Monkey, PR and Marketing Strategist Fiona Harrold: Owner of Fiona Harrold Agency Claire Crompton: Co-Founder and Commercial Director of TAL Agency

“More and more people are turning to entrepreneurship and side hustles to achieve financial freedom. The interesting shift isn’t side hustle versus start up, it’s access. With AI tools, you can design a brand, create product images and test ideas from your phone, without big budgets or technical skills.

What excites me most about the future of AI is the potential to facilitate new and make creative and financial freedom available. In that context, a side project can be a very practical way to experiment and learn what customers actually value, before deciding whether to commit full-time.”

Ri ch Pleeth, CEO and Co-Founder of Finmile

“At the very early stage, a side hustle can be a useful way to stay afloat financially but once your main business gains traction, it becomes a liability. Building a company demands complete focus. You can’t expect to build something meaningful if half your brain is somewhere else.

“Founders who try to juggle too much end up doing neither well. After the survival phase, the best thing you can do for your growth and your business is to go all in, every ounce of attention, energy, and conviction. That’s when real momentum starts.”

Jan Hendrik Von Ahlen, Managing Director and Co-Founder at JobLeads

“ , having a side hustle can go either way. It can help you focus more, or it can fully steal your focus. Before you actually embark on a side hustle, I would recommend asking yourself one question: will this sharpen my main thing?

“If your project can give you customer insight, lets you test some cool and unconventional marketing ideas, or helps you build new skills that would help your main business, I think that’s a really great thing for your personal development. However, if it just drains your energy, steals your precious time without giving you anything back, or competes with your users, it’s just a distraction.

“If you do want to work on a side hustle, it’s a good idea to have some boundaries in place. For example, you can time-box it. For instance, you say that you will be working on it on Friday from 2 to 5 PM. Write some purpose that you could tie to your main company and also think about a potential kill date. If it hasn’t taught you something or earned you some money by this date, you should stop.

“Next, be transparent with your co-founders and investors and tell them about your new project, as well as set clear conflict boundaries. When it comes to me, I would favor some small, fast, shippable side hustles like newsletters, tiny tools, micro-courses, and stuff like this. They could create value without adding any extra operational drag.”

Crawford Warnock,  Founding Director at Firstname Communications

“I am not a fan of the word ‘hustle’ in ‘side-hustle’. It makes it seem like the value of doing something outside of work is defined by the money it makes – which just makes it ‘more work’. The whole point of a side hustle is that that ‘side’ is what sets your soul on fire. The money needs to be a bonus, otherwise all those other benefits – creativity, energy, focus and passion, won’t turn up: which means they won’t turn up in your day job either.

“And make no mistake, side hustles need to be driven by huge amounts of passion: it SHOULD be the sort of thing you would do for free, because in my experience, many side-hustles take a lot of time and effort to get to the point of paying anything decent. From what I have seen, it is the case that people investigate a lot to assess that there is a gap in the market, but then make huge assumptions about the market in the gap and then get caught out by that.

“This is not to either dump on side-hustles, or say people should just be all about the day job: my day job is in the office and on Zoom and the phone, but it is trips into the mountains for three days at a time that has made the most contribution to my personal growth – I just don’t think that the current framing [of] side-hustles is that helpful.”

Estelle Keeber, Founder at Immortal Monkey, PR and Marketing Strategist

“After nine years , I have seen both sides of the side hustle debate. Creativity is important but so is focus and energy. Most founders underestimate how much mental and emotional load their main business already carries.

“When you split that attention in two you slow your own progress without realising it. Growth comes from consistency, clarity and having the space to actually execute.

“If you want innovation, you get more of it by going all in on the business you are building instead of scattering your efforts. The best results in my career have always come when I poured everything into one direction. For most founders a side hustle is not freedom. It is a distraction.”

Fiona Harrold, Owner of Fiona Harrold Agency

“A side hustle is invaluable for building your skills and you never know where it could lead. I worked on a local newspaper on top of a full time job after university and got incredible experience in writing attention-grabbing headlines and pitching ideas to the editor.

“That experience has proved invaluable today running a PR agency pitching ideas and coming up with attention-grabbing headlines!

“Whether you need the extra income or not, you could make connections that could be so valuable.

“Follow your passion, build your expertise and you’ll make yourself what Jim Rohn calls ‘an attractive person’ – one who draws opportunities to them.

“You don’t know where that side hustle could take you!”

Claire Crompton, Co-Founder and Commercial Director of TAL Agency

“People love to say, ‘do what you love and you’ll never work a day in your life,’ but as a founder, I know it’s not that simple. I still have bills to pay, and like everyone else, I’ve felt the squeeze of the cost-of-living crisis. I love what I’ve built, but I’m not pretending this is the only thing I ever want to do. My own dream projects don’t always align perfectly with what pays the bills – and that’s exactly why I don’t expect anyone else to give up theirs either.

“Having a side hustle gives me a sense of purpose outside the day-to-day of running a company. It keeps me motivated, curious, and – funnily enough – far less likely to burn out – and the same is true for the people who work with me. When you’re building something you genuinely enjoy, you bring a different kind of focus and resilience back into your “main” role.

“What I’ve found is that a side hustle isn’t a distraction for me; it’s more like a catalyst. It pushes you to be more innovative, more creative, and a better problem-solver. Those are skills you can’t learn from a webinar or a training session – they’re shaped through real experience. Creativity can be hard to tap into on demand, but when you’re going after something that genuinely excites you, ideas flow more freely. You learn to think differently, to stretch your abilities, and to approach challenges with fresh perspective. And all of that feeds straight back into the work I do as a founder.”

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Based on reporting by techround.co.uk.