Specialist or Generalist?

Lately I have been thinking about my career trajectory which has made me wonder whether to be a generalist and acquire skills in multiple functions/industries or to become a specialist and carve a niche for myself.

To make the discussion more generic and not specific to myself, when does one choose to specialize? Also, how does one narrow down the field they wish to specialize in (especially if it does not come to them naturally and they are agnostic between a few fields). The greatest fear in specializing is being tied to a field which may cease to be of interest to you may pigeon hole you into something for the rest of your life.

Regardless, I would love to hear about people's experiences and thoughts regarding being a generalist or a specialist.

Looking to go to MBA school but cannot find good advisors in India?

One of the challenges I faced while applying to business school is the lack of expertise in the advisers provided by outfits in the Indian market. As a result, most of my research was extremely painstaking and came at a high personal time sink cost. I would have LOVED access to good, in-person, high quality advice. My hypotheses is that there are a lot of consultants available in India but if you're looking for advice from somebody who really knows what MBA admissions take, that's not an easy proposition. As a result, I want to take an informal poll to see if there are people in India who would be interested in consulting advice for MBA admissions abroad and are willing to pay for it. If interested, email me at whartonguru@gmail.com telling me a bit about yourself.

My motivations behind this exercise are three-fold:
1. Get to meet interesting people
2. Keep in touch with the B-school process
3. Get into entrepreneurial territory while keeping my day job