This whole dialogue shows a very laborer-centric view of the world. What is missing from this entire conversation is the concept of being an employer/founder or independent consultant. If you want to bootstrap a startup, the Bay Area cost basis is going to destroy your nest egg until you can raise capital. Also, this conversation implies that you are employed 100% of the time, ignoring any cases where you quit, are fired, or the "rocketship" startup you joined doesn't work out.