You become a winner because you're good at losing
This is a great line to me. Many times I feel like people are afraid of trying things because they won't work, yet I feel like once you actually start trying them, whether they work or not, its a learning experience. I am facing this right now with my own ventures and its just now coming to me that it's not always going to work, yet just in taking steps towards my goals I am doing something positive. Remember, Thomas Edison failed countless times before he made the light bulb, its bound to happen (especially if your a serial entrepreneur) however, it only takes one to work for you to make it big.
Going out of your way to find uncomfortable situations isn't natural, but its essential
The worst thing you can do in life is become comfortable. Your comfort zone is a dangerous thing, it keeps you from becoming extraordinary in whatever facet of life or taking the chances that make life interesting and exciting. For me, what this means is that we have to become comfortable being uncomfortable, meaning that we have to get used to putting ourselves out there and taking those chances. It means learning to speak with investors / partners, learning to be comfortable talking about ideas and most importantly learning to get out there and make things happen (the most uncomfortable thing at all).
Finding good ideas is surprising easy once you deal with the problem of finding bad ideas
Creativity is not a simple thing. It doesn't come naturally to most yet its so critical to success. Think about it. Great companies thrive on originality (Apple) as do great musicians and artist. The point is emphasized in Linchpin because you cant win at being average. The low cost strategy doesn't cut it anymore because global behemoth like Wal-mart will always beat you on low cost. The same is true for some white collar jobs as well. Thus, the only thing left is truly original work that actually touches people. That's why musicians, sports star, actors etc have value - because their work cant be outsourced.
This goes back to the quote because ideas are the precursor for creativity and originality yet many people give up and say things like "I don't have any good ideas" when really they should be saying "what ideas can I come up with at all". Even if your ideas or horrible they still get you thinking and get you closer to whats right. Once we all figure out that brainstorming bad ideas is the key to getting a few good one's we'll be on the right track.
I'm going to write more about highlights but for now I'll leave you with one that is taken from a zen book that I think is quite good and makes daunting task easier in a practical way.
Attempt to create only one significant work a year. Break that into smaller projects and everyday find three task to accomplish that will help you complete a project