@4tify I've been struggling with this for a few months.
I "know" I have enough financially. I'm really looking forward to a break from work and the associated stress.
On the other hand, it has been amusing to watch the gyrations my mind goes thru about how to keep working.
...I could do this to keep it as a leave of absence instead of quitting;
there sounds really interesting...I could take a travel assignment there;
I've wanted to get back to that, this would be a good time;
I've always wanted to try x,y,z, maybe this is the time.
Like you, I've been working or training for a specific job since I was young. And I'm uncomfortable with the change, even while looking forward to it.
Plus there are aspects of all my jobs that I've enjoyed and miss/will miss.
So my current plan is to call it a sabbatical. 6-12 months and see how I feel as the time goes by. Several friends are on standby to remind me if I start talking about work plans in the first 6 months. I have a rather long list of things I'm interested in doing so plan to jump into some of them while not setting any alarm clocks.
And I'm open to the option of returning to paid work of some kind in the future. But under my constraints. I've been setting my own, part time schedule for the last couple years and that is a marvelous situation. I will not return to full-time or someone else's schedule. Financially-paid-work may vie with other-compensation-work for my time. Because I do get other compensation from volunteer work be it knowledge, skills, good feelings, company of coworkers, feelings of usefulness, satisfaction of a job done, etc..
Those are my thoughts at the moment.