When Jim and I left the first time, we did not have our financial ducks lined up adequately. We were out for a year, and instead of the hoped for thumbing of our noses and sailing off into the sunset, we sailed about 6800 mi. to windward, back to the Bay Area and the dreaded four letter word: w**k. Jim worked for 16 months in order to finish his project
, and I, for a year. We got married, and I sold the house I owned, to become the cruising kitty. The rest is (as they say) history
. We've chosen to stay out as long as we can, and we have no land base, no car (had one briefly in NZ in 1990, no bills, and no fixed address (which has its own problems).
For us, it has been a low stress lifestyle: so far, all the problems have had successful conclusions.
My first answer to your opening question reflects my personal money
anxiety. It is possible to use fear of loss of money
as an excuse for inaction. I've seen people do that. But for myself, once I had not all that much dollar wise, just what I perceived to be an adequate cushion, I quit worrying about it. I have been poor, and I have a hang up about it.
Maybe you've decided in advance what that adequate cushion was. You're the one to know that. For me, it just snuck up on me, and I knew when it was okay. There is no right nor wrong way.
weavis struck a chord for me with what he wrote about a known medical
condition, and if yours does produce anxiety, it seems like you're really between a rock and a hard place. If you can tolerate the idea, perhaps a support group for people with the same condition would give you a place to relax? or regular meditation?
So I'm wondering if there may not be a third alternative. If the boat is already ready to go now, how about working only 6 more months: time to rent out or sell the house, tie up loose ends and get gone. Having a date to begin your period of freedom could be a relief. If you want to work along the way, well, many things are possible once we've changed our lifestyle. If you want to be open to work opportunities, they'll come your way.
Maybe -- no offense, please-- it's time to question yourself if you're over-engineering your departure?
You're right, it is definitely not an easy decision. For us it was putting a period on one life and starting another "career"--sailing bum. It is a decision that has little support in our society. And then people will tell you you're lucky. They don't know about the years of living like a starving graduate student to save, save, save to make it all possible. One is lucky, too, but a whole lot of that luck is preparation.