Ask the Expert: I-Banking for Ex-Entrepreneur

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A. Some advocates of work-life balance might decry the hardcore bootstrapping plan you've outlined here. But judging from its laser-like focus, you are quite committed. If you follow through, you will have gone a long way toward convincing a potential employer that you are a serious candidate. Now let's drill down into the particulars.

Your enthusiasm is infectious but more specifics would be helpful. For example, what was your entrepreneurial venture in? What did you do? It is the contacts you nurtured and the specific challenges you faced-not just the skills you acquired-that will be as important in your sales pitch for a new career as any academic credentials or professional experience.

Not that skills are unimportant. As you doubtless know from experience, the beauty of most entrepreneurial careers is that they are somewhat freeform. Contrast this to investment banking and private equity-areas where a certain amount of specialized skill is a prerequisite for the more creative aspects of the job. Therefore, you will need to have some solid background in financial analysis and accounting. 'This doesn't necessarily need to come from an Ivy League school,' says executive coach Maggie Craddock. 'But you will need to have your skills solidly grounded so that you make wise decisions in a fast-paced and tricky investment environment.'

While degrees from Harvard, Yale, or Wharton can certainly assist in opening up doors through a network of potential contacts, gilded degrees are by no means the only way. 'Much more importance should be attached to setting up a solid network of financial services professional contacts that can both mentor your development and open doors,' says outplacement counselor Rod Williams. Mentors can shepherd your development and give you the benefit of their experience. Door-openers can help you access decision-makers who can put you on a new career track.

Before you launch yourself head first toward that JD/MBA, do some networking within the private equities and investment banking industries to gain their perspective on whether the JD or international experience is necessary. You can also ask them about what schools they recommend. Alumni connections from this type of networking may help you going forward, too.

While age should not be a factor, whether you are in your thirties or sixties will affect your perspective on dealing with business challenges. A Depression-era mentality, for example, might not be compatible with a risk-taking environment.

Finally, don't be so focused on your ultimate goal that you forget to lift your eyes to the as-yet-unconsidered alternatives that will present themselves along your journey. Factor into your plan some room for contemplation and evaluation -and reassess periodically that where you're going is still where you want to wind up.

Next week's question: I am one of the 'comeback moms' who are in the news now, looking to return to a financial career after five years at home with my kids. I have a great resume, but I'm not naive--how do I handle the gap on my resume? I'm very motivated to get back to work, and can sell myself, but getting an interview is where the problem is.

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