45 minutes into episode #175 of The Tim Ferriss show, Ferriss explains that he's never had reliable 5 or 10 year plans and has instead focused on 2 week experiments and 6 month projects. His view is:
If you make a 5 or 10 year plan that you can reliably hit, almost by definition you have to set a plan that is below your current capabilities. If you're an A student you have to set a C+ plan for it to be 100% achievable. That, I think is just a great way to paint yourself into a very unattractive corner.
It's a unique perspective on long-term plans and most certainly made me pause to consider my own plans and whether or not I'm shorting myself.