Ironically, that question was the first for a very prestigious business school’s applicants entering this fall.

Here is my pot shot at that question in all honesty. Considering all other factors for making your career decision to be more or less equal and  in the pursuit of purely monetary enhancements in your life, you had to choose. Who would you rather die as?

1. CEO of a fortune 50 /prestigious firms
2. Tremendously rich Private Equity/hedge fund manager
3. An entrepreneur, expanding and growing and on the verge of leaving behind an entity which could morph into a legacy in the next generation.

The funny thing about these choices are there are strong approving points for each of these choices.

1. CEO of a fortune 50/prestigious firms  : Least risk, public appreciation,establishment of achieved success , Social acknowledgement, options value, money ( definitely not as much as the founder though)
2. PE/HF  fund manager: Well $$$$, for one. But the problem with pursuing that  is there is always going to be someone around the corner with a larger fund, a bigger house, a costlier car, a prettier girlfriend, and much much more $$$$$. A justified reason for choosing this would be only if you thoroughly enjoy multiplying assets and see it as a game rather than a chore to be done to earn your living.
3. An entrepreneur: Not much respect and approval initially, especially in the Indian society ( in fact ,you will find more people disapproving this in the beginning than for the other options), the riskiest of the three, not much money and one maybe forced to live below one’s means for quite sometime. If at all lady luck turns around, you will find it hard to be a corporate lackey or even wear a suit, after exiting as a successful entrepreneur once.

The problem with choosing option A is risking discontentment. A man who has the ambitions to constantly move forward looking above him knows that there is no more to advance when he reaches the top of the pyramid and being a victim of his habits, he finds he doesn’t have a rank above him to conquer. At this juncture, some start to wonder if they should have chosen a fundamentally different path ( say, people who chose B ) , while others typically branch out to seek greater challenges.

People who chose B or C get tired of running around the tree trying to catch their own tail, decide they have seen it all and need to give it all back to the community.

Those who made millions  want to make billions but those who have made billions want to give it all  away. Go figure!