The 3 Major Pain Points That Most Small Business Owners Deal With

Running a business is hard work. An article from Entrepreneur magazine highlighted something that new entrepreneurs know too well: the lack of sleep. After speaking to 500 small business owners, 61% felt stressed out, and 56% of those owners were losing an average of 7 hours of sleep every week.
What do you see when you think of a new business owner? Probably someone on the phone with suppliers, scheduling meetings with VC agents, while being responsible for their team. All this while running on four hours of sleep and an increasingly severe coffee addiction.
With how much competition exists in almost every niche, new entrepreneurs have to constantly deal with a host of stress and major pain points. However, as the age-old idiom goes, knowledge is power. If you have a heads up on some likely challenges, it’s possible to prepare and save yourself the headaches that keep you up at night.

In this article, let’s explore three key pain points that often cause a disproportionate amount of stress to owners and how to fight them.

#1. Birth Pains from Employee Logistics When You Eventually Grow

When you’re still in the early stages of growth, it makes perfect sense to do everything on your own. However, no business dreams of staying ‘small’ for eternity. Every quarterly and annual goal is growth-focused, which means eventually, you’re a medium-sized business and one day, a large one.

Thankfully, Remote, a global HR and payroll platform, helps answer the classic question of “Should I outsource payroll or do it in-house?” They explain that if your team is small, local, and full-time, it makes sense to do things in-house.

You can continue in-house, even up to a mix of full-time and contractor workers, with caution. It is only when you step into large contractor work, international full-time employees, and international contractors that outsourcing your payroll with a global employer of record EOR becomes critical.

It makes logical sense to slowly scale up logistics like payroll once you get bigger, but it rarely happens in a structured manner. If you haven’t anticipated changes and growth, you might still be running things in-house and bleeding a lot of time and energy.

Let’s look at an example. You run a small design agency, and things are going great. For the first two years, you manage everything from salaries to contracts manually using spreadsheets. However, you are steadily growing and decide to onboard three freelancers from different time zones.

Before you know it, your simple system has collapsed, and you’re missing invoices, running into tax issues, and getting super burned out. It’s a predictable tale that is easily avoidable.

#2. Cash Flow, Cash Flow, Cash Flow

Cash flow issues are among the major pain points that can quietly cripple a small business. It is essentially what helps you keep your operation running and allows you to pay recurring bills and expenses. Some believe that cash flow is a critical metric of a business’s financial health.

As Remote notes, cash flow is arguably one of the biggest problems that small businesses tend to face. The fact is that a business can be profitable on paper but still suffer if cash isn’t available to meet daily expenses. This is something that countless new founders realize too late.

Data from the Small Business Index from Q2 of 2025 shines light on this. When compared with manufacturing, professional services, and retail, small businesses had the lowest levels of comfort with regard to their cash flow. For perspective, manufacturing was the most confident in their cash flow (83%), while small businesses were at 58%.

That said, it’s possible to prevent cash flow issues before they even occur. In fact, Investopedia points out several strategies a business can use to minimize cash flow troubles. We believe their most potent recommendation is to encourage and incentivize customers to pay early.

Other good strategies that they recommend are to cut better deals with your suppliers so you’re paying them less. Likewise, it also makes sense to conduct an inventory overhaul so that stagnant goods do not hurt your cash flow.

A Few Quick Tips on Spotting Cash Flow Problems Early

Naturally, applying good strategy is only half the battle. The other half involves spotting the red flags that most founders miss. These tend to show up very quietly in daily operations, much before cash flow issues become obvious in your balance sheets.

The biggest indicator tends to be small delays when you need to make a vendor payment. To be honest, this is such an obvious sign, and it’s insane that entrepreneurs fail to see the implications. If you are asking for extensions from suppliers more than once or twice, it’s rarely just the fault of logistics.

Similarly, do you avoid looking at your bookkeeping software because you don’t like what it shows, but are partially confident that things will work out? If so, that’s another classic sign of escalating cash flow problems.

Lastly, take a look at your sales and discounts. If you find that you are resorting to flash sales and massive discounts frequently, it shows a need for quick money. If you notice even one of these three signs, it should be enough to give you the wake-up call you need.

#3. Knowledge Gaps That Need to Be Filled

A lack of experience and knowledge is one of the most overlooked major pain points for new entrepreneurs. There are so many lessons you learn from messing up that it’s hard to simply follow an online guide that solves everything.

Thus, in an indirect manner, one major pain point is the lack of real-world business knowledge that affects you every day. This can manifest in the form of errors when filling out forms or even in the opportunities you miss.

For instance, so many new entrepreneurs may be unaware of the incentives that their small business size can avail. These include ones like the federal Work Opportunity Tax Credit (WOTC) that you get from hiring certain target groups. What is the exact benefit of doing so, you ask? You can claim up to $2,400 credit under WOTC for each employee hired.

Other times, your knowledge gaps manifest by simply doing things the long way. The fact is that small business owners are often focused on survival, and these knowledge gaps keep compounding. Talk to any experienced entrepreneur, and they’ll tell you how important it is to shift to a growth mindset. If you don’t know where to start, focus on gaining experience, deliberately upskilling yourself, and hiring veteran employees. Just these few steps should help turn things around.

Ultimately, if there’s one key takeaway from all of this, it’s that pain points are inevitable. If it’s not these three, there will be another set that you need to overcome. That said, the ones mentioned in this article are some of the most common major pain points affecting new entrepreneurs today.

The bad news is that it’s going to be tough. Making a business run like a well-oiled machine is not a cake walk. That said, the good news is that help is available in vast quantities on the internet. So, seek it out, apply new insights, and the biggest pain points will soon scab over.