Perhaps it is the contrast between personal goals, organizational goals, and the overall public perception of success. Success IMHO is firstly as a reward with parenting, occurs in the school environment with grades, and next, it is with the workplace with merit raises such as promotions contrast cost of living. Another specific within the work environment is sales, its rewards, and the means of obtainment. Success is quite possibly learned through conditioning and applied elsewhere.
With the first question, IMHO, with being "daunted by failure" that type of person possibly sees or feels punishment rather than reward regarding success and failure. There is an adage some follow which is "Surviving successfully and successfully surviving". I use that as a guide to ponder with success many times.
I pondered the second question. I can only speculate with moral transgression there may be an issue with what is 'bad' and what is correct. Or, the adage "Win at all costs" comes to mind. Consider morality is a personal issue whereas ethics is the group environment. Groups tend to have its own culture, even though it may be whispered rather than policy or procedure.
Moral issues quite possibly may be incorporated with 'all costs'. Maybe compromise occurs with acceptance possibly fueled by peer pressure as well as within a cultural environment seeking success. Perhaps that leads toward the next question asked with "missing the mark".
Off topic Interestingly within some Christian cultures that is used as a clue to read the book of Mark for guidance. However, God's and religion regarding morality is a different subject. Within the business environment the 'mark' is the goal such as total sales. A concept is the difference between the 'mark' and where upon arrived is measurable as chaos. New subject again. Another concept it is the difference of effectiveness seeking efficiency.
With sales regarding interpreting morality and the decision process an example is not telling a truth contrast telling a false truth with a successful sale. Some may decide the later is immoral while the first is culturally acceptable at times seeking success with a sale. Failure of making the sale may drive one to acceptance of culture contrast personal with morality.
Possibly that answers the second the question regarding transgression? Perhaps which mark - morality, contrast the goal is at issue and is in flux with the individual contrast culture with what is acceptable.