My behavior is anticipation.
It is not something I simply remember to do. It is built into how my firm runs. Every client has a Five-Year Look Ahead. It is part of every review I do, twice a year, and it never looks less than sixty months ahead.
When to file for Social Security. Whether a Roth conversion makes sense this year, or makes things worse. The IRA threshold they are three thousand dollars away from crossing.
None of it is urgent when I bring it up. That is the whole point. I would rather raise something five years early than explain it after the window closed.
People hire me so they can settle into retirement and stop scanning the horizon. So the system scans it for them. They should never have to know which question to ask.
Every expensive retirement mistake I have been asked to help fix started the same way: a decision made late, alone, under pressure.