I have already been trying to figure out how little I can live on. I am also looking into alternate careers/jobs I can do to earn money while cruising....consulting, writing, etc. Unfortunately my current career is the type where you have to be actively involved and current to get jobs again. If you take a year or two off it is very difficult to get hired anywhere again.
I wouldn't know about working while cruising, but I have a thought on it that I have expressed to others who have mentioned the idea. Here is what I think - imagine a moment that you are overseas on your boat and you roll into some foreign country and need money. You decide to get some work. Chances are they pay less there than here, it's going to be hard to find work on a whim, you are going to have trouble working since you will probably be an alien working illegally, etc. You are also going to be on a bicycle, probably, so you won't have an easy way to work, and if you're anchored out then you'll have to worry about your boat while you are away working, etc. It's a lot to contend with I think.
So eventually you think to yourself ... wow, I should probably just fly back to the United States and work a while, make some money, then come back and cruise more after I have saved up some more kitty. Well .... why not just do that now and skip all the hard parts ? You've probably already got a place to live, you can lower expenses (everyone can), you are already working, you already have transportation, you can already work legally, there is plenty of work to be had, etc ... now is the perfect time to work and save up kitty before you leave.
I have always had wanderlust, so I think staying motivated to cruise someday will not be a problem. So far I have journeyed all over the world in my career as a pilot, traveled all over the U.S. by motorcycle, so now I would like to see the world via a sailboat once my youngest is out of the house.
Same here, I have always enjoyed travel. Adventure is great fun!
Do you think it is possible to do that single-handed? If I an still single by then it may be necessary. I would like about a 40-footer (for now at least, that may get bigger or smaller by the time I do it) and it seems like a boat that large may be a handful by oneself.
I'm planning to cruise single handed, absolutely.
I would never dream of having a 40 foot boat, too big. Even if someone just gave me one I'd sell it and get a smaller one. I think 36 foot is as high as I would want to go and I'd really rather be between 29 and 34 foot. Bigger boats cost more in every way, and they are harder to sail. My biggest concern is that when something goes wrong it's harder to deal with. Even something simple like accidentally pulling a halyard up the mast is a lot bigger problem on a 40 foot boat than it is on a 30 foot boat. I imagine being in a storm out at sea and having a problem out on the bow and having to crawl out there with lifelines ... do I want to be dealing with 30 foot boat stuff out there, or 40 foot boat stuff ? Give me the 30.