Wow, everyone talks about the freedom but forgets the brutal cost of health insurance! My freelancer friend pays over $700 a month for a bad plan. That's a huge hidden pay cut. OscarRoberts is right about losing the steady backup, but the safety net you lose is way bigger than just help on projects. A single medical issue without good company insurance can wipe out a year's freelance income. That constant money stress would kill the flexibility joy for me.