Don't quit you job until you know all of the answers to your questions.

You mentioned you wanted to enjoy life. What is your definition of that? - From what I've seen, when I was working, If you are not enjoying life right now, quiting your job would only make you more miserable.

Do you have any life passions? - If not you might want to visit a Psychologist to help you define a passion/mission for you.

I am a similar age, with similar assets and financial situation and Er'd 2 years ago. I was enjoying life then, but did not enjoy the politics of the job. It was time for me to get out.

My wife still works for Medical Coverage and she is 8 years younger than myself. Health care coverage is something you need to work out. You need to work out a financial plan as well as life plan.

Also if you have not seen the movie 'About Schmidt' do so. It depicts about 60 million Americans today in retirement. It will get you thinking. It's not an 'action movie' - It's not supposed to be.

Good Luck!