As you climb of the organizational ladder, you have to redefine your role in the value chain from player to captain to coach to manager, and for some, to owner. These are different roles and you won't be able to succeed as a manager when you're acting like a player.

I got to carve through the streets of New York's financial district and discover the awesome feeling of being part of a system where, the harder you worked, the more of those scarce resources you earned! I never looked back.

I know a lot of great success stories of those who were excellent problem-solvers because they had found a need that they could fill well. As a result, they built organizations around them and those organizations had belief systems that could be described as a form of leadership.

As members of a minority, one that was often persecuted, that entrepreneurial perspective was burnished with a sense of "outsider" status - so not only were we committed to finding our own way of achieving success, we also grew up to believe that we'd have to fight to get whatever we wanted.

I've always wanted to get my share but, due to my tendency to overcompensate (work harder, push for the win more), I've ended up with more than my fair share. These are some of the life lessons I've drawn from watching my mother and grandfather struggle in the world compared to my own struggles.

The bottom line: All of your investing decisions should be grounded in your own investment policy statement. By taking a "top-down" look at your finances and writing out a road map, your policy statement will add an important element of discipline to your approach.

If the workers don't keep themselves current - with some assistance and guidance from their employers - then the workers who are in the legacy roles will have to be removed. That's what's so difficult.