Yes, sometimes I momentarily think I should have made that move sooner, to escape the Corporate rate race, but if I had, I doubt I would have been as successful since it is all those years of experience that add up to the expertise I'm able to share with clients now.  Plus it was last few W-2 years that really convinced me to get out, not to mention the 3 acquisitions I went through surrounded by people worried about losing their jobs again. Fortunately, I was never concerned for myself since I was always in a good position, but hated seeing so many co-workers plagued with so much uncertainty and concern about their futures and worst of all having to tell subordinates the bad news, but everyone survived and I was able to help some secure new positions as well. Truthfully never planned any of it, so there was no plan or period of time that I had to debate or decide to do, so I am not as brave as those who actually made the big leap intentionally.