Can't say I've made the jump, but I've been 1099 for 20 years; I haven't worked a full-time W2. The extra Social Security and Medicare Taxes kind of suck. I'd recommend doing your own taxes; it helps you learn the tax system to make sure you are taking advantage of any credits and deductions available. I'd also recommend when it comes to health insurance, pick one of the HSA-eligible plans and deposit the maximum allowable into your HSA account. An SEP retirement plan allows you to put up to 25% of your income (max $66k), which is a nice benefit. Honestly, let me know if you have questions in the future, I'd be available.