My first doubt was as a six-year-old child. The subject was birthdays. I simply did not understand why the fact that two birthday celebrations in the Bible resulted in executions meant that I could not eat a cupcake with my class. My little mind could not make the logical leap. I never really understood why God would smite me if I ate a cupcake or signed a birthday card...and today I still don't. But I was a good little Witness and did what my parents told me to do.
During the teenage years, I didn't have any real doubts about the JW religion being "The Truth." If anything, the struggle that all teenagers experience in toeing the moral line reinforced the idea that it must be The Truth. Otherwise, why would it be so difficult to be good...right?
As I got older and saw more of the congregation politics, I developed a "fleshly view of the organization." But I always rationalized that the Old Testament patriarchs, Israelite kings, and even First Century Christians had lots of issues. Despite those issues, the rank and file were still expected to stay with the organization. An elder once gave the example of King Menassah who worshipped false gods and even sacrificed his children to them. That sort of reasoning kept me going--even if the elders/C.O./etc. had flaws and did bad things, they weren't as bad as Menassah, right?
As I continued to get older, I became increasingly skeptical of some of the direction coming from the WTS. It seemed like they were "going beyond what is written." Comparatively minor issues such as vasectomies (condemned in 1999 WT article), discouraging college, and the like started to pile up. The answer to my questions was always to "wait on Jehovah" or to trust the FDS, and of course the old canard "where else are you going to go...nobody else is right."
All of these unanswered questions finally became too much to sweep under the rug. I realized that my "answers" to these questions always hinged on an assumption that (1) the FDS was a sort of clergy class that we had to obey; and (2) the WTS leadership was appointed by Jesus to be that FDS. One day I realized that I had always simple accepted these two foundational facts as true. So, I decided to investigate those facts. The rest is history.