Side Hustle Or All In: Analyzing The Entrepreneur's Dilemma

It’s a question that fills hundreds of Quora and Reddit pages, and no one seems to agree.  

What is the best way to start a new business? Do you keep it on the side until it’s viable, or do you just jump in and go for it? 

The reason the question is so pressing is that the number of people either considering or actually having a side hustle is increasing. In fact, according to the Harvard Business Review, 50 percent of Gen Z want to become their own boss, mostly because they are disillusioned with the corporate world. Meanwhile, another study found that 36 percent of Generation X and 22 percent of baby boomers said the same. So, it’s certainly front and center when it comes to the younger generation of workers. 

But making this dream a reality is complicated. So that’s what we will look at in this article—whether it’s better to make the leap, or to stay on the sidelines for as long as possible. We will weigh the two arguments, and you can then decide which route to take.  

The Case For Side Hustles  

The number of new businesses that fail within their first year stands at roughly 20 percent—on top of that, over 50 percent don’t make it to five years. It’s a sobering thought, but for those who are passionate about what they do, no statistic is going to stop them. Whether you are going all-in or keeping it on the side, the attraction of starting your own business will always remain attractive to many people. The question is, how best to approach it?  

Entrepreneur Mark Cuban—a regular on the popular television show, Shark Tank—is in favor of side hustles. He argues that it’s important to save your money, and not make the move until you’re entirely sure what you’re doing. In other words, use the side hustle to validate your concept before committing fully. Cuban notes that while there are certainly many success stories (and we see them all the time on social media), most people who leave the corporate world to pursue their own ideas either struggle a great deal, or fall completely flat. That’s Cuban’s view, at least. 

His advice is in line with that of most financial experts: if you’re going to make the leap, you should ensure you have at least one year’s worth of money put aside to cover your living and business expenses before you make the all-in move. 

So, what are the key advantages of side hustles? To start, they allow you to test ideas and develop new skills. If it brings in some extra income on top of your salaried job, then great, but if not, you are still afloat. Keep in mind that even the social giant Instagram was once a side project. 

People who are most successful with side hustles ask themselves whether their passion project is purely about passion, or whether it has genuine market value. Giving yourself deadlines and generating that sense of urgency is also important. If you’re too “safe” (i.e., having your career working in parallel), the drive to build and to market as fast as possible isn’t always there. So, it’s about avoiding endless tinkering, and ensuring that you’re making something you’ll introduce to the market at a set date, rather than letting it drag on for years and years. Get it out there, then iterate as you go along. 

It’s also important to be consistent. You can’t work on your side hustle only when you feel like it. It requires discipline and a steady approach to the work. 

The Problem With Side Hustles 

Side hustles have limitations. No one has endless energy, and splitting time between a full-time job and a growing business can lead to burnout. Then progress slows down, and your side hustle never reaches its full potential. 

It’s also important to recognize that certain industries demand a level of commitment that a part-time effort cannot provide, no matter how disciplined you are. Some startups require an all-consuming approach that’s difficult to balance with another job. 

We have already discussed generating a sense of urgency, but if you’re unable to do that, the project will languish. The problem is that there is a real sense of urgency with many ideas because the market moves so quickly. Your revolutionary tech idea suddenly becomes outdated as new developments arise. You can easily fall into the trap of brand-building without ever creating or releasing a product. 

The Case For Going All-In 

At the other end of the spectrum is the all-or-nothing approach. This means quitting your job to focus entirely on your new business. The method requires full commitment, allowing for faster growth, deeper industry immersion, and the ability to seize opportunities that you might miss if the project is only a side hustle. You won’t be alone in this approach—the likes of Jeff Bezos and Elon Musk both took this route. 

An all-or-nothing approach allows you to invest more time—every available hour, in fact. The more you put in, the faster you can get your offering out there. You can also control your schedule, and you no longer have to work around your day job. You also get back some of your positive work-life balance. 

The point of starting a business is to get a product or service out there. Going all-in speeds up that process: you are motivated, the urgency is there, and you’re fully focusing on this one thing. You also feel more free to tell the world about your venture, rather than hiding it in case the manager at your day job finds out. 

The Problem With Going All-In 

There’s no denying that this approach carries significant risks. Without a financial safety net, failure can have severe consequences. It’s also easy to say that you need to build up a year’s worth of savings ahead of time, but actually doing that is not easy. And even if you do get all that cash saved up, the stress associated with seeing your money run out—and no new income coming in from your new business—should not be underestimated.  

Ultimately, not everyone has the resources or tolerance for that level of risk to go all-in. The kind of pressure it can produce can negatively affect decision-making and creativity, leading the business to stall. 

So, Which Approach Is Best? 

There are examples of both sides working. Ultimately, you must choose what suits your bank balance and your temperament. For some, the idea of quitting their day jobs produces such shivers of panic that they are unable to think straight and focus on the new business. For others, the idea of splitting time between a side hustle and a day job is unimaginable, and nothing will stop them from going all-in. 

The right choice depends on your circumstances, your industry, and how you view risk. If you have a lot of financial obligations, or you’re not completely certain about your idea, then a side hustle offers a safer way to start your journey. On the other hand, those in fast-moving industries or those with strong financial backing may benefit from full commitment. 

In all cases, success comes from a great idea and great execution, whether you’re doing that part-time or full-time. The best approach is the one that aligns with your personal situation and your long-term vision. 

About The Author 

As founder and managing partner of UAE-based Trade License Zone, Karl Hougaard ensures that the company lives up to its brand values and delivers an exceptional customer experience that sets it apart from business setup operators in the region.