I was thinking about this today:  I can actually very easily write a comprehensive to-do list for this effort, or for any effort, for that matter.  Here it is:
  1. Figure out what needs to be done.
  2. Figure out how to do it.
  3. Do it.
I'm going to start right now!

What needs to be done:
  1. Sail to an interesting place.  Stay awhile.  Repeat.
  2. Teach our girls what they need to know to thrive on their own.
Now we just need to figure out how to do these things.  I don't know how, but I do know how to start figuring out how, since I have a universal todo list.  So for each of these items, I will: Figure out what needs to be done, figure out how to do it, and do it.

So, first item -- "Sail to an interesting place.  Stay awhile.  Repeat."  What needs to be done?
  1. Get a sea-worthy, livable boat.
  2. Provision
  3. Cast off.
  4. Get to an interesting place.
  5. Drop anchor.
  6. Explore.
  7. Repair, reprovision, repeat.
OK, first item again -- "Get a sea-worthy, livable boat."  How the heck do we do that?  First thing -- figure out what needs to be done.
  1. Figure out what we need in a boat.
  2. Figure out what that's going to cost.
  3. Save or borrow and repay the money for the more affordable of these:
    • the most affordable boat that meets all our needs, or 
    • the most affordable combination of a boat that could meet our needs and the additional services and equipment to bring it into such condition that it does meet them.
    1. Buy the boat.
    2. Buy the equipment and services needed to bring the boat into the desired condition.
    First item again -- "Figure out what we need in a boat." What needs to be done to accomplish this?
    1. Become knowledgeable about the various aspects of cruising boats.
    2. Find out what other people with similar goals in similar circumstances have found important and unimportant and why.
    3. Make decisions about what is important and unimportant to us.
    First item again -- "Become knowledgeable about cruising boats." What needs to be done to accomplish this?  I'm going to start to do a couple levels at once, and we're starting to get to things we can actually get to step 3 on (do it) today.  
    1. Find out what the best sources for information are on cruising boats by:
      1. doing internet research to find out the comprehensive and accurate books and websites
      2. asking well-informed people what resources they find most comprehensive and accurate
    2. Get access to the information by:
      1. visiting and bookmarking websites
      2. getting the books
    3. Internalize the information.
      1. Read.
      2. Make notes.
      3. Think about the information.
    And now, our first second item -- "Find out what other people with similar goals in similar circumstances have found important and unimportant and why."  
    1. Find out what the best sources are for information on the opinions of experienced cruising families are by:
      1. doing internet research to find out the comprehensive and accurate books and websites
      2. asking well-informed people what resources they find most comprehensive and accurate
    2. Get access to the information by:
      1. visiting and bookmarking websites.
      2. getting the books.
    3. Internalize the information.
      1. Read.
      2. Make notes.
      3. Think about the information.
    OK, well, this could go on for awhile.  In fact I'm sure it will take the next several years at least.  This is the approach I'm going to try taking on the To-do list.  We'll see how it goes...