We had a foreclosure on an investment property in 2008. One less lawn to mow. I went bankrupt in 2010. Ten less bills to worry about. We sold a business for 1/2 its value just to get out. The freedom was worth the loss. We sold another business for 1/2 it's value because we were exhausted. The market shifted, the new owner couldn't adapt, we would have lost it entirely if we waited to "see it through". My point: It's okay when there's a storm and it's okay to get wet. Your life will shift and that's okay, because it's always shifting, even when you're "prepared." Because it's LIFE.