Be cautious about the future
After working what seems a lifetime and finally getting financially comfortable, it's easy to start thinking about how life could be on the "outside" (i.e., retirement). A few bad days and one can start thinking about something like "Take this job and shove it!". Guess after reading the above posts which mentions a lot of the positive aspects of making the big leap, perhaps one could look at some of the reasons to be cautious.
1. Quicken: Great idea and this was mentioned a couple times and I'd give it a two-thumbs-up. Find out what your cash flows are, where it comes from and where it goes. It's absolutely necessary to develop a baseline to work from.
2. Medical expenses: This can be a real wild card but knowing what your health, and your partners health, is like you can make some judgements. Factor your genes in. This can all change with a simple slip on the ice, or wet deck -> pulled shoulder ligiment or broken hip bone can instantly alter the equation.
3. Dollar buying power: Since WWII it has been pretty good but this will probably change. The Government has been spending big-time in the past couple years. I'm no economist but if someone can show me how one can spend hundreds of billions of dollars and not have a significant impact the value I'd like to hear about it. The worst part is Congress has more spending plans in the works - read Sen. Tom Colburn's speech:
http://www.facebook.com/topic.php?uid=31862514825&topic=7179
4. More on Dollar: The US balance of payments has been out of balance for years and we're at the end of the rope. This is turning into an "economic war" and countries like India, and especially China, don't want to change their currency values. Americans are simply going to have to be able to produce something that other countries will buy. Read: "Lower income" and lower standard of living.
One way of producing better is via education of the existing and future workforce, however, our nations schools are struggling with the future part and have been for years. It's unlikely they're going to make any kind of significant breakthrough in the next year or two. Read this article on that topic:
http://edition.cnn.com/2010/BUSINESS/10/29/raghuram.rajan/index.html?iref=obinsite
5. Food and water shortage: This is already happening and will likely become exponentially worse as world population increases. We aren't talking centuries, we're talking years! Russia, a major wheat producer, stopped exporting wheat this year (or is it next?). Food prices are going to increase because of supply and demand.
So now what? Declining value of the dollar? Significantly lower standard of living? Higher medical expenses? More expensive food?
My guess is the future of America is going to look a heck of a lot like the world average.
Not to throw cold water on the idea, but factor these changes into the budget for the next 40 years and give a lot of serious thought before pulling the plug. This is a significant change in a persons life. (That's why you're asking the question for input)