Money For the Rest of Us · Wednesday, August 12, 2026
David Stein discusses how many newly retired individuals feel unsettled and dissatisfied with their investment portfolios, often due to perceived complexity and unobtainable standards. He notes that while there's a desire to simplify, tax implications from selling appreciated assets create significant constraints.
“Many individuals haven't really looked at everything comprehensively. All of their Roth IRAs, their regular IRAs, their taxable accounts, their own, maybe their partners.”
“It it's almost as if they're just not satisfied with them. And as I've tried to dig in more, it it's almost as if they they have some standard that they're holding themselves to that isn't really obtainable.”
“And the biggest constraint is taxes. If if you have and all of us, most of us have some type of taxable portfolio, if we sell those those taxable holdings, we will often, we've held them for a long time, we'll have to realize a gain and pay capital gains tax on that.”