This is a great thread. As a born-in who took 30 years to wake up, my story is of the "straw that broke the camel's back" type. Various little things about the WT teachings nagged at me, mainly the allowance of blood fractions as a conscience matter and the seemingly figurative nature of 144,000 in the Bible. Assorted dissonances such as seeing people look forward to the death of billions at Armageddon began to add up, silently. There are too many tiny things to count... yet I still was a true believer. After all, surely Witnesses were closest to the truth, at the very least! I have always been a very black-and-white thinker, and a cautious, studious sort of person; appeals to the heart meant little to me, but I enjoyed all the little details of the Witness beliefs -- the comfort and certainty that they gave me -- so I stayed "all in" mentally.
It wasn't until I was an adult that I began to really notice the intellectual glass ceiling. Other Witnesses, who I knew were intelligent, were quite open about how they avoided any information, apostate or not, that could weaken their faith. This seemed very strange to me; why should those who possess truth be afraid of anything? Surely no information could be a threat to them? Although I did not read apostate writings for years to come, I resolved that I was not going to avoid learning any science or reading any atheist writings just because it might conflict with my existing beliefs. I wanted to be confident that I had the truth. As I approached my thirties, I spent many hours defending the truth against imagined objections (essentially playing the dual roles of a cynical householder and a sincere Witness in my head). After years of hearing these bickering "voices", I started to wonder, "Could it be that the cynical voice in my head is not an imagined householder that I feel a need to be able to refute, but in fact my own subconscious trying to tell me something?"
In addition, the older I got, the more I could see the psychological aspects of what made Witnesses act the way they did (superstition being a big part of the explanation). I began to feel distanced from their mindset. But all of this was so gradual that I still believed that I believed it was the truth. I had a worldview that seemed more stable and secure than a worldly one, and I was afraid to question it and cause it to collapse like the house built upon sand. You see, I myself was also superstitious in one specific way. A family member had supposedly experienced a demonic attack, and that was enough to scare me. Even though I was no longer "all in", I felt that if I stayed in physically, and did a minimal amount of field service and other activity, then I could have a least a little of the holy spirit to protect me from demons. Disassociating myself would leave me open to the demons. But over time, not hearing any more credible stories of demonic activity, I began to grow skeptical that this really happened at all.
Finally, I read a word one day that I didn't understand, and looking up the definition to that word caused me to experience an almost electric shock: Jesusist. It had never occurred to me that it was possible to believe in Jesus' teachings and not belong to organized religion. For the first time I could imagine leaving the organization. I had always been afraid that leaving would somehow force me to throw all my beliefs away and live a life of debauchery (so the Watchtower warned), but this was a new concept: I could still be a good person, at least as far as my own willpower allowed me, even without being a Witness! I used to think that I couldn't be a Christian without God's help. As a teenager, I had tearfully pleaded in prayer for God to help me with his holy spirit many times. Now that I was older, I had started to wonder why I never clearly felt his helping hand back then. I began to suspect that I had been on my own all along, and I would do just as well at being a Christian without an organization as with one.
As I left behind the fears and superstitions of my youth, I finally decided that there was no reason not to read apostate material. At this point, JWFacts.com was very helpful for me. It used the Bible and common sense to argue against some of the same teachings I'd already felt were dubious, which really put my mind at ease. I also learned about some flip-flops in teachings which were surprising -- especially the stance on organ transplants. I finally felt confident that the Witnesses could not be God's approved organization if they made these kind of mistakes. I am very thankful to Paul Grundy for taking the time to make the site which helped me get peace of mind. Now I really feel free for the first time -- free from fear and unnecessary guilt, free from obligations of man.
Sorry for the long boring story, but since things just came to a head in this last year, the details are still vivid in my mind. Might as well write it all down for the sake of aiding my memory, and for anyone reading this who can relate to my experiences!