In this segment of the Motley Fool Answers podcast, Alison Southwick, Robert Brokamp, and special guest Ross Anderson from Motley Fool Wealth Management give some advice to a fan who is not quite ready to retire but is on the glide path in. But going from having most of your tax payment dealt with automatically via your W-2 to the situation when you’re living off Social Security, retirement account withdrawals, and your investments mean learning a different set of IRS-related strategies.