I say again: if all of that is true of the people you know, even in software, even making above-average salary for your area, you're very lucky. Also, and I sa

I say again: if all of that is true of the people you know, even in software, even making above-average salary for your area, you're very lucky. Also, and I say this as someone currently going through the process: given the way hiring for senior to C-level roles goes in 2017, do not expect "several months" of savings alone will be enough to cover you. Most of the large companies you might like to work for (Google, Microsoft) have hiring processes which can't move much faster than six weeks, and they can stretch out to six months or more.