It seems to me that most of us are pessimists, even the bulls. We all assume we will be in the 28% or lower brackets when we retire. It is quite clear to me that, to maintain that, I will have to make some lousy investment decisions before that, or greatly increase my charitable giving. If not, it looks extremely likely that Fools should consider that their ordinary income tax bracket may be quite a bit higher than it is now, and should consider their investment planning (Roth vs. regular IRA vs. taxed account) accordingly. Since I have had this realization only lately, I have not figured my own strategy (move IRA to Roth or not) yet.