I did this as a 1099-contractor, since that’s about the only way to do it as a contractor. Paying estimated quarterly taxes four times a year wasn’t bad. I cal

I did this as a 1099-contractor, since that’s about the only way to do it as a contractor. Paying estimated quarterly taxes four times a year wasn’t bad. I calculated my withholdings, remitted my tax payment through EFTPS, and was never surprised at tax time. I don’t think I ever got a refund or owed when I was doing it myself. I learned that many people who have never contracted before are shocked they have to do this, lost on how it works, and had (then) no good place to go for actionable advice. I found that surprising and kind of sad in a way. We could be doing so much better with financial literacy.