There's been a great deal of discussion of how to encourage startups, entrepreneurs, and Americans, in general, to take more risk. Venture capitalists, bloggers, and other venture role-models complain that entrepreneurs have lost their ambitious drive [1]. Additionally, educators see their American students are hopelessly losing out to their international counter-parts [2]. Some people of the current generation have written pieces about the inherent entitlement: "so in that sense, we’re a bit greedy, a bit selfish, a bit entitled, and a bit impatient" [3]. 

There's been an immense amount of effort in figuring out where the difficulty lies:

• Younger people have few examples of great entrepreneurship. [4]
• Statistically, you'll be more successful when you're 40...maybe? [5]
• Some people are just risk-adverse! [6]
• America is made of wimps! [7].

It turns out "all learning is based on trying something new, making a mistake, adjusting your actions, trying again, repeating until you get the results you desire" [8].  From my experience, I view risk as an external perception surrounding my activities. For me, most of what I do is a logical extension based on experience. Yet, for the uninitiated it seems like I'm stupid and/or fearless in my actions. Finally, I've learned "confidence comes not from always being right but from not fearing to be wrong.” [9]

If you feel that you would like to be able to stomach greater risk then start experimenting more. Start off with small projects that you know how to accomplish. Then start to iterate on the more projects by extending yourself into uncharted terrains e.g. if you're a developer see if you can learn market & sell your project. As you start to gain more insights from your projects start to iterate into areas that scare you. Eventually, you'll start to realize concepts that others have no idea about and that thinking will lead you to find opportunities others would never pursue. Risk is less about courage but more about careful exploitation by mitigating personal fears. 

Sources:

1. http://techcrunch.com/2009/09/17/memo-to-start-ups-you%E2%80%99re-supposed-to...
2. http://www.boston.com/bostonglobe/editorial_opinion/oped/articles/2009/12/21/...
3. http://sarahmerion.com/digitalanthropology/gen-y-talks-the-talk-but-they-dont...
4. http://bostonvcblog.typepad.com/vc/2010/01/a-lost-generation-of-entrepreneurs...
5. http://www.kauffman.org/uploadedFiles/FactSheet/entrep_and_economy_fast_facts...
6. http://techcrunch.com/2009/11/29/india-angel-investors/
7. http://steve-olson.com/when-did-america-become-a-nation-of-frightened-wimps/
8. http://steve-olson.com/10-things-i-learned-from-my-4-year-old/
9. http://steve-olson.com/7-things-my-7-year-old-learned-from-mma-mixed-martial-...

More reading:

1. http://techcrunch.com/2009/12/20/the-difference-between-1-billion-plus-in-exi...
2. http://techcrunch.com/2009/11/15/how-to-profit-off-the-poor%E2%80%A6-and-keep...