This is actually quite common, as the witlesses have spent your whole life drilling in you the fear of materialism. This is so they can retain control of you, and they hope it will eventually drive you back into the tower. They do not want you to go to college or get a decent job for the same reason.
In fact, they do this in every area of one's life. For some, it is the demons. Others have ongoing issues with the holidays. Still others will have a hard time accepting music. Others have trouble making friends on the outside (that didn't or wouldn't have had they remained in the world). For you, it is the idea of going out there, starting a career, and acquiring material things.
It is not easy to get into the workplace in a decent job. The government regulations were created specifically to protect their own power and the wealth of a few companies that do not want you in on it. So they will do all they can to prevent newbies from getting those good jobs (how often do you see "2-3 years experience required" in every single damn job aside window washers or dishwashers?). Which leaves you with a hassle to find the starting point that they so carefully hide, even now with the Internet. College and training classes cost you money that you won't have until and unless you complete it and find the job that they are trying so hard to keep out of range.
Then, starting one's own business is difficult and can take almost as much time as being a Jehovah Witless. You need to integrate every detail, make sure there is a market for your product or service, and then make sure you are better than your competition in some way. Worse, there always seems to be so much government hassle and regulations to cope with. The truth is that the government does not want newbies starting businesses that could put them in financial independence, nor do they want people to start a business that will put the established crap companies out of business. So, they do their best to hassle you, not being upfront, finding violations after they OK'd something and then come in and claiming that you are wrong, fabricating tax liabilities that were not there, and doing all they can to stop you from making it (so much for free enterprise). That might not have been true when this country was founded, but each new regulatory agency they created has eroded this country to the point where it is next to impossible to start new companies.
Even if you find an industry that still lacks regulations (so far, telecommunications and the computer industry are the only two that are still fairly free), you have to steer clear of scams. About 99.9% of all MLMs that you find in search engines have something in them to stop you from making any money. Most work at home/start your own "business" programs are actually either scams or require a lot of hard work on your part for uncertain results. If you do not have a product (which can legally be sold without the government regulators snooping in), most of the products they have to offer will not work.
All of which would be bad enough. But, the witlesses add additional problems to this. They have their own rules and bureaucracies to go through, and it is usually impossible for them to clear anything. Unless you go wash windows or get involved in those no-win MLMs that they push, you are basically out of luck. And they constantly drill into you that money is valueless, that the effort needed to make it could be better put in field circus, and that so many industries (including the computer industry) are from Satan. Conditioning from two sources to keep you poor.