This is a real-life account of an IT specialist who may have been too astute about taxes , almost leading to a devastating financial blow from the tax authorities. Story Background: The "Perfect" Plan That Almost Exploded During an economic downturn, contract IT work was booming. Our protagonist, let's call him Jason, landed a lucrative contract with a major bank. His income was excellent. He heard from friends: "Starting your own company as a contractor saves a ton on taxes!