I think they have little chance to succeed in life. Limited education and being indoctrinated to not think critically are major handicaps for them. The few witnesses that I know that I would consider financially stable are either college educated or they got into decent jobs right out of high school and worked their way up without a college education. The problem is that those who worked their way up are older. Those kinds of opportunities may have been prevalent 20 years ago but they are few and far between now. An Associate's degree or military experience is required for bottom of the barrel entry level jobs at my employer, and if you want to move up you have to get your Bachelor's. All other jobs require a Bachelor's degree or higher. The company is pushing every one with an Associate's to get a Bachelor's, every one with a Bachelor's to get a Master's, and recommending anyone with a Master's start working on their Ph.D. There is so much emphasis on education that they are paying the tuition and book costs for anyone that wants to go back to school. Heck, they paid for my Bachelor of Science in Business Management degree six years ago and are paying for the Bachelor of Science in Materials Engineering that I am currently pursuing. The education requirements in all industries is getting tougher and a Bachelor's is becoming the equivalent of a high school diploma 20 years ago.
Lack of critical thinking skills is also a major roadblock for JW children. They are told to not question anything the GB says or publishes. Any independent thought is seen as dangerous. You can't go through life just doing everything someone says without question and be a healthy individual.
When I was still in I saw some of the younger JWs graduate high school and move out. Without fail every one either got DF'd or publicly reproved. They all lost their privileges because they went from this sheltered life into the real world. Instead of experimenting slowly they were suddenly free and did more rebellious things in a year than most kids do in all of their teen years. This happened three years in a row. None of the kids are successful at all. The ones that stayed out of the organization live in poverty on minimum wage and have more debt than they can handle. Most of the ones that were repentant moved back home and are financially dependent on their parents again. None of them have even tried to better themselves by going to community college or night school so they can get the first two years of college out of the way at little cost. They are all content to work at dead end jobs that pay nothing and provide no benefits because they view the world as evil. They don't realize that they just overindulged and made stupid decisions, and they will likely never see the errors of their ways because they are back being brainwashed.
I also hate when they say you can just learn a trade and start your own business. There is nothing wrong with doing manual labor and small business ownership is an admirable goal. But the GB doesn't tell these people how hard you have to work to be a successful small business owner. They say it frees up more time for field service. I say it does the opposite. When just starting out you have no capital and no clients. You have to work your tail off to build the business. Go out and find clients during the day, take care of the paperwork and books at night, and not take weekends off because you need as much work as possible to make ends meet. If you follow the law and get all of the required licenses, permits, bonds, insurance, etc. the costs to start a business are not insignificant. Most of the witnesses I know that owned small business (landscaping, window washing, office/house cleaning) were not licensed contractors, not bonded, not insured, and didn't carry business insurance on their vehicles. I guess Caeser's laws don't apply to them.