W-2 vs 1099: how worker classification really works (and why the IRS cares) One of the most common and costly mistakes we see in small businesses is worker misclassification. Many business owners assume that if they pay someone as a contractor and issue a 1099, that settles it. Unfortunately, the IRS does not see it that way. Whether a worker should be treated as a W-2 employee or a 1099 contractor depends on how the work relationship actually functions, not what you call it.

Cash Flow vs. Tax Liability: Why Profitable Businesses Still Get Caught Short at Tax Time One of the most common (and frustrating) conversations I have with business owners goes something like this: “We had a good year. The business made money. So why do we suddenly owe so much in taxes?” On paper, the numbers look strong. In reality, cash feels tight. This disconnect usually comes down to a misunderstanding of cash flow versus tax liability. Profit does not mean cash in the

Every year, many taxpayers measure the success of their return by one number: the refund. A big refund feels like a win. A small refund, or worse, a balance due, feels like a loss. But in reality, your tax refund is not a bonus, a reward, or a gift from the IRS. It’s simply your own money being returned to you, and understanding that distinction can help you make better financial decisions year-round. A tax refund happens when more money was withheld from your paycheck, or pa

Why Married Filing Jointly Is Almost Always the Better Choice (and the Rare Times It Isn’t) When couples get married, one of the first tax questions that comes up is how to file. While there are two options available, Married Filing Jointly and Married Filing Separately, the reality is that filing jointly is almost always the better financial move. In our experience working with families in Green Bay and De Pere, joint filing wins out in the vast majority of situations. The b