Hi, Kook. I'm 2 years into retirement, and I know what you mean. It took me about 5 years to completely pull the trigger. I had a lot of the same struggles that you did -- a lifelong pattern of saving/accumulating, a reluctance to give up the paycheck, and worries about making a mistake. It all seemed so "final," to quit work completely. I also had some apprehension about whether I'd be able to make retirement work for me (e.g., establishing new friendships, moving to a new location, finding enough to fill my time).
...
At a certain point, I actually felt embarrassed about continuing to work. I felt as if it was a breach of personal integrity or courage, to continue to churn away at a job I no longer enjoyed, just for the sake of a paycheck I no longer needed. It felt shallow to me.
This is sort of where I'm at. I know I'm "close" but just haven't been able to summon the courage. My business is competitive and the chances of me finding the level of job I have again are slim to none.
But I totally get the "embarrassed" feeling. I have also been considering that by me staying just out of fear is preventing a younger person from having the opportunity I've had.
For the moment I'm trying to make the very best of my job, which means taking all my vacation and mentoring others while I'm in the seat. But I am really looking forward to the moment when "I'll know."