Law school exams typically present seemingly simple fact patterns which, remarkably, implicate a multitude of issues. Many times, they are based on real world cases. In my third year, during the pendency of the actual court case involving the Celtics’ attempt to pry Danny Ainge from the Toronto Blue Jays, one professor, who was a maniacal Celtics fan, wrote his exam to consist of only one question on that case. But, that’s a story for another day. Anyhow, while it is important to be able to address the different issues, believe it or not, the biggest challenge is often just identifying them. …

When we were kids, certainly when we were teenagers, many of us had conversations at one time or another with our parents where we tried to convince them that we should be allowed to do something, or maybe not be penalized after the fact for having done something, simply because “everyone else is doing it.” In my family, that argument was always met with a variation of the same response: “If all your friends were jumping off a bridge, does that mean you should be doing it, too?” My dad was a brilliant lawyer and it was hard to beat him in any argument, but overcoming his “bridge jumping” …

Saving for college and retirement is hard enough. Maintaining the lifestyle we want during retirement, or while the kids are in college is harder, still. Of course, the market "correction" of 2008 has disrupted things even further, upsetting even the best laid plans. More important, though lost on most people, is that it exposed the deficiencies of what they were doing in an effort to build wealth and achieve their dreams. The bottom line is that when subjected to market forces and other real costs of living, the common approach to planning does not work well enough. What to do? Incur more …