I was a JW for 35 years, so I have many years of experience to draw upon. Often at their weekly meetings and invariably at their large assembly gatherings they stress people giving up their secular jobs, selling their possessions, and living a simpler life by becoming a full time minister going door-to-door for Jehovah. This is constantly stressed, but especially prior to 1975, which the Watchtower Society predicted would bring about the end of the world as we know it.
They would have slogans such as "Buying Out The Opportune Time", "Making Room For It", "Serving Where the Need is Greater", "Storing Up Treasures in Heaven," being "Joyful Workers", "Working Whole-Souled To Jehovah", and "Send More Workers Into the Harvest." This means basically that you quit your job to preach about Jehovah as often as you can, even up to 60, 75, 100, or even 150 hours per month. The time you get to do this is what you buy by giving up your 40 hour a week job. By doing this, you gain Jehovah's favor, and your salvation in the coming destruction of the world at Armageddon.
Their are tiers that a person can aspire to. There are Missionaries who are assigned to foreign countries in order to peddle the JW religion in growing third world countries. Their are Bethelites, who are assigned to the JW World HQ where they work 40 hours a week in a printing plant preparing religious publications for their room and board and a small monthly stipend for toiletries. There are pioneers and they come in several varieties, "special, regular, and auxiliary" who go to door to door in their own locale, but occasionally sell their home to move to a rural area where "the need is greater." This means that they don't have as many JWs to cover the territory. Then their are publishers who preach less than pioneers, but can be just as committed financially and emotionally to the ministry work.
I myself was a computer programmer who became a janitor for a while, but then realized that what I was doing was ludicrous, and so went back to working full time as a computer programmer again. I got a lot of flack for that from my peers, because not only do you get that pressure from the pulpit, but also from fellow members and all of the JW literature. My uncle sold insurance, but kept selling the less profitable lines because they allowed him more time to devote to the ministry and be a congregation elder. The better paying lines, such as group health, paid much better, but involved a lot of time away from home, so he never took that course in his career. They never had a fancy home. Actually they lived in a trailer on a very small lot.
Others I know sacrificed good paying jobs to pioneer. It was praised by all in the congregation, even though these people had much less money to get by on. It is actually a status symbol in most congregations.
I hope that answers your questions. This is all based on my experience, but feel free to ask as many more exJWs and JWs about their experiences as you need to.
Tammy