Risky?

Whenever the word risk is mentioned most people tremble.They think that the outcome of a risky undertaking is always negative.It's justifiable because from definitions such words as probability/threat/likelihood/possibility are used but none gives certainty that it must happen.So,does this mean that if a situation is risky they should be avoided?
Let's look at a 'risky' scenarios here:
-Not following what everyone else thinks is right.
The story of successful school drop out can be an example or those who due to circumstances,didn't get a chance to further their studies and they still turn out to be victorious.Also the fact there are people who have taken the path less taken and turned out to be heroes tells us a lot.


The best way I've found to analyze risk is looking at the worst case scenario of an undertaking.
An example would be between channeling our energy into getting employment and trying out business which is riskier?
Employment:

^What it takes to start get one
-Good formal education in advanced levels
-Faking that you Love the work and other hullabaloo during interview(I understand there are those whose    seek employment genuinely because they love what they do,but they are very few)
-Results oriented mentality and ability to meet crazy deadlines.
-.....
^Results
-Good pay
-Security(If it's a government job because in private sector it';s very dynamic)
-....
^Worst Case Scenario
-Losing your job
-Dissatisfaction
-Mind closure
-Financial rat race.
-.....
Business:

^What it takes to get started
-Passion
-Knowledge in your line of focus
-Capital
-Emotional stability
-.....
^Results
-Your own time master
-Financial Freedom
-Creativity and Innovation
-Job creation
-....
 ^Worst Case Scenario.
-One can lose their investments.

I'm tempted to ask which is riskier?

We risk death by being alive,why play safe anyway,let's take wise risks.We learn to walk by falling down simply because we took that risk,I doubt whether we could have ever learnt to walk.

And as Theodore Roosevelt in Strenuous Life put:
 “Far better it is to dare mighty things, to win glorious triumphs, even though checkered by failure, than to take rank with those poor spirits who neither enjoy much nor suffer much, because they live in the gray twilight that knows neither victory nor defeat.”