Failure’s hard but success is far more dangerous. If you’re successful at the wrong thing, the mix of praise and money and opportunity can lock you in forever. – Po Bronson
Success and failure are judgments of results. I don't think it is possible to encourage or discourage either. Process can be encouraged or discouraged. Different people have different interpretations of results though, and there are varying degrees of measurement costs associated with those interpretations.
I viewed this quote in the context of my recent thoughts about external versus internal feedback. So if someone pays me $1 million to do a job that's a piece of feedback that says I'm a success. Or if someone I care about is proud of me
because I have "a good job" that is clear feedback. But those are arbitrary measurements of success and I might be miserable inside.
Things like salary, job title, employed vs. unemployed, married vs. single, academic degrees, awards won, etc. are all very easy to measure. That does not mean they are valuable or accurate measurements, however.
An individual can get caught up in these easy measurements and ignore more important ones, and the problem comes when easy measures of success are followed and the more meaningful ones get ignored.
It is also difficult to place more weight on one's own judgement than other people's, even though one's own judgement is almost certainly more meaningful. This is because a person is fully aware of his own doubts but others appear certain when they give opinions. For example, if I ask you if I should take a CEO position at AIG or the store manager job at a local coffee shop, you'll give me some answer and sound sure of the answer, but in reality you probably put almost no thought into it and in any case its a judgement based on your values and your perception of what is best for me. I'll feel uncertain of the right decision but to you it was a no-brainer so I take the AIG job and before you know it I'm getting yelled at by idiot Congressmen.