This was a great thread earlier and as I prepare to leave on an extended trip, I suffer from constant worry. I am constantly doing an informal risk, assessment of our vessel.
The advantage of growing older is that you know more and have experienced more. The disadvantage of growing older is that you know more and have experienced more.
Which means that, having experienced more, you can imagine more things that can go wrong, require more effort than you thought, and so on. In other words, as you get older and have more life-experience under your belt, it becomes easier and easier to talk yourself out of doing things because the adventure can be overcome by the risk assessement.
I find that overcoming the tendency to talk myself out of doing things is far more difficult that actually doing them. We've flown a floatplane back and forth to SE Alaska and the BC interior so many times we can probably do it while sound asleep.
Operating the two boats we have in the PNW or a narrowboat in the UK has become second nature to us. We no longer have to think much about what lever to push or pull when, or what to do with the wheel/tiller.
But..... having learned a hell of a lot along the way, what we can now do is anticiapte all kinds of horror stories and situations that we never even conceived could happen back in our "newbie" days.
I took trips back in my twenties--- shipping my Land Rover from Honolulu to the mainland and driving for five weeks on the worst roads in the Yukon and then shipping it back to Hawaii, for example---- that I would probably not do today. I still have the Land Rover, the Yukon is still there, the roads we travelled are probably just as bad, but when I think of the effort I and my friend put into the journey, and all the things that could have gone wrong but didn't (probably because we didn't think of them), I'm not sure I'd want to put the effort into it again.
So make sure your boat's in as good a condition as you can practically make it, have the equipment you need on board, have contingency plans for the basic things that might go wrong, and then put your major effort into not worrying about stuff but about how cool the experience is going to be.
Most boaters don't die when something goes wrong. They deal with it. Thinking about it later is generally more scary than dealing with it at the time. So be prepared, but make an effort not to worry.
I'm half-French and have my father's natural pessimism about everything. So my biggest task before any undertaking is pushing the worry into the background. And I continue to find that getting out and doing things, despite the ease of talking oneself out of it, is ALWAYS worth the effort.
Have a great cruise.