Tax Season Dos and Don’ts for Businesses Most business owners consider tax season to be one of the most stressful and “taxing” period. This is generally due to the fact that business owners tend to wait until the wee hours to file rather that prepare throughout the year for tax season. These do’s and don’ts for tax season will assist in reducing your stress while saving time and money. Do: Know deadlines and changes It is imperative to be knowledgeable of filing deadlines and whether or not there have been any changes. Small business owners who fail to meet the deadlines will be required to request an extra time from the IRS and pay over estimated taxes if they anticipate any outstanding. Monies that are owed to the IRS are still due on tax day irrespective of an extension being granted.