Sales tax is one of the few areas of compliance that many small business owners find genuinely stressful.
Not because they are reckless. Not because they are trying to avoid tax. But because the rules are fragmented, the consequences can feel outsized, and it is often hard to know with confidence whether you are doing things “right.”
This came up repeatedly in the research I conducted for my Master’s dissertation, which focused on the sales tax compliance burden small businesses face, particularly after remote seller rules expanded. What stood out was not panic or indifference, but uncertainty.
In that research, 75 percent of small remote sellers said they either currently worry or have previously worried about sales tax audits. More than a third said it is something they think about regularly. That kind of background worry is not common across other tax types.
Most business owners accept income tax, payroll tax, and even property tax as manageable parts of running a business. The rules are not perfect, but the expectations are generally clear. Sales tax tends to feel different.
Sales tax compliance asks businesses to navigate state-specific rules, keep an eye on thresholds that change over time, and make judgment calls with incomplete information. Many sellers are not ignoring their obligations. They are actively trying to understand them while also running a business.
The structure of sales tax enforcement adds to the mental load. Sales tax is a fiduciary tax, which means accuracy matters. For businesses that have not yet registered, potential exposure can also build over time, which makes timing decisions feel heavier than they probably need to be.
What is worth saying, though, is that this stress often eases with structure.
Several business owners I spoke with said their anxiety dropped significantly once they had better tracking in place, clearer documentation, or outside support. The rules did not suddenly become simple. They just became visible.
The system is more complex than it needs to be, but it is the system businesses have to operate within. Spending energy wishing it were different rarely helps. Understanding it well enough to make calm, informed decisions does.
This is why sales tax has a habit of stealing a bit of sleep. It is not the work itself, but the not knowing that tends to follow people home at the end of the day. Once there is clarity around what actually matters, that background noise tends to quiet down.
