I think it started to change when we discovered we were usually afraid to ask for something (like negotiate a price) out of fear of rejection; and we asked ourselves, "what is the worst thing that could happen?. . . They could say no." and as long as we were comfortable with that then we were willing to take the risk.
I am now much more connected with my impulse to avoid or run due to fear. We usually ask ourselves, "what's the worst thing that could happen?" and then we make a decision based on the consequences we can live with.
For example, this last weekend we started working on a sandbox for Tiger (See the post about Dirt). We have been talking about it for a couple of years and decided to do it on Saturday at 4:00 when it was 90 degrees. We bought 5 bags of sand and decided we needed more, a lot more. "Should we buy 25 more, 10 more, or what?" "If we buy them only 5 at a time the worst thing that could happen is that we end up with 4 more than we need." That seemed like the right number.
We make most of our decisions this way. It doesn't always mean that when the worst imaginable consequence is really bad we don't do it, it does mean though that we are prepared for disaster before it arrives. I wish we had this system in place the first time I got pregnant, but the outcome of that is part of what drove us to adopt this system.
We enjoy life with a positive perspective. We make ourselves aware of the minefields around us. When we muster the courage, we go forth prepared for (almost) anything. After all, what's the worst thing that could happen?