Five year plans

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 plans and whether or not I'm shorting myself.