I agree that sometimes people don't reassess their goals or the reasons behind doing what they're doing frequently enough. I think people are afraid of the label of 'failure' and so dont want to give things up, even of it's bringing them no happiness or benefit. Like you pointed out, work is different, it has benefits even when it's not more spiritually fulfilling. But if you started doing something to bring you joy/wealth/friends and it's not doing that, then you should feel free to let it go.
I also recently changed my life philosophy! I always set myself a grand goal, and then try to bend everything in my life to accommodate that goal no matter how uncertain it was or how painful the process. Now I think more about what I can do in the present that can create opportunities for the future. I think there's an element of you Create, Elevate, Thrive philosophy in there, which is such a direct and beautiful way of putting it, I may have to co-opt it!
I agree that keeping the list small makes achieving things easier, and it looks like it's allowing you to be fulfilled in other areas of your life too. I'm excited to see some of your finished projects!