02/01/2026
If the phrase “chasing down W-9s in January” makes you cringe, you’re not alone. Most 1099 problems don’t start at filing time—they start months earlier when contractors are paid without a plan. Here’s why thinking about 1099s all year can save you time, money, and frustration.
Why 1099 Compliance Matters (and Why It Shouldn’t Be a January Fire Drill) Every year, many business owners find themselves scrambling in January—tracking down contractors, requesting missing paperwork, and racing to meet 1099 deadlines. This last-minute stress is almost always avoidable with a ...
