It is easiest for a lot of people. I know someone who did this a lot and ended up with an extremely high salary just a few years after dropping out of school. He would look for different companies after 1-2 years of working at his current one, apply, and try to get a better salary. It got to the point once where the companies he was working for were bidding for the person with the companies he applied to. This wasn't at Silicon Valley, and wasn't with startups, and he never quit his current job unless he had secured a better job.