@ Jeff – Actually, I think we are saying the OPPOSITE It all depends on the planning timeframe … my view is that once we get to timeframes spanning many years, having the ultimate destination in mind (Number/Date) is sufficient … you will have plenty of opportunity to make a whole series of “today/tomorrow” plans of your ‘plan twice’ type depending on what you encounter as you go along ….

In a way, AJC, your plan is an insurance plan for those of us who -unlike Tim Ferriss – have fewer years left to recover if something were to happen to our ability to continue living that dream life. It gives us more headroom than simply “earning dollars while living on pesos” and wondering who will pay for medical needs if and when we need it, something most of us didn’t have to consider when we were Tim’s age. I love his book personally, and am trying to adapt what I can to my own needs. I’m glad to see you also seem to have taken points of his in while not simply ripping up your life and traveling to India to find your guro and “simplify your life” as one blogger seems to have done.

I took a first step last week. Unplanned. Yet it could have been planned as I’ve been working toward that unplanned conversation for about six months. We will see how things work out next.