Most people I know who are successful contractors got their start by being ex-coworkers with middle/senior management at the company who hires them for their fi

Most people I know who are successful contractors got their start by being ex-coworkers with middle/senior management at the company who hires them for their first gig. It's a kind of mafia. Good luck. There's a lot of surprises. More complex taxes, issues with liability, marketing (not an engineer's strong suit typically), extracting cash from clients, the cost of health insurance/SS, the need to appear to be self-employed from a tax standpoint. Small companies don't know why it's so expensive, large ones push the payment out in time, entrepreneurs will trade you .1% of the company for a ton of work because their idea is so darn good. OTOH, self-employed IRAs are pretty sweet.