What does she have to do to ‘deserve’ success?
She might first accomplish something of value. At this point, everything she’s done has been without noted accomplishment, and thus she is rightly criticized as floating along on her parent’s coattails.
For example: She can never shake the accusation that McKinsey hired her because of her parents. HOWEVER, had she stayed with McKinsey since she was hired, made partner, and been the lead consultant on major accounts for them, then you would have an indication that she was an accomplished professional; McKinsey would never risk screwing up a major account by putting it in the hands of somebody who couldn’t handle it.
For example: Had she stayed at the hedge fund firm, and gained a reputation as a shrewd money manager amongst the wealthy, thus increasing the size of her fund’s portfolio, then she’d be demonstrating financial acumen and a high level of competence.
She is approaching her career midpoint. Education means something but not very much at this point in a professional’s career. Early in my career, at a growing software company, I had the opportunity to hire an MBA from Harvard. I quickly found out that even at Harvard Business School, somebody finishes at the bottom of the class. He was easily eclipsed by the state school MBAs, and ultimately left to become…..a consultant. :-)
If you gave me Chelsea’s resume with her name blocked out, I’d interview her because of her education; if she was state school, I wouldn’t even interview her. However, I wouldn’t hire her unless (a) she knocked my socks off in the interview, and was able to give cogent and good reasons for the fact that she’s (b) bounced around from job to job and industry to industry, and could somehow assure me that © she actually wanted a career in my business, and wasn’t going to jump ship in three years to try something else.
Hope that helps.