HumbleDollar

I used AI as an editorial assistant to help organize and refine my thoughts; the underlying ideas and personal experiences remain my own.

During the stock market boom of the late 1990s, an acquaintance of mine jokingly started an experiment. He tracked the daily performance of the S&P 500 alongside his own mood. I don’t know whether he ever calculated the ...

Is there a spreadsheet or app that illustrates cash flows under different Roth conversions. Or is there a spreadsheet ninja on this forum who has created one and would be willing to share?

The post Roth conversion cash flow appeared first on

If you want to better understand one of the major issues facing the US healthcare system, watch your TV and mail each Fall.  In a word choice.  No wonder people are confused when they are on Medicare.

Why should we need companies whose purpose is to help seniors make choices and why should new choices be encouraged each year? Why is insurance for healthcare bills that...

EVERY JANUARY, if you own an IRA and money must come out of it that year, your custodian writes to you. The letter gives you the amount or offers to work it out. We barely read it, but it is doing more than we notice. Most people never miss a required distribution, and the reason is not diligence. It is that somebody tells them. Inherited IRAs are different. T...

NATURE ABHORS a vacuum. That’s well known, but when it comes to investing, this poses a particular problem. Why? In the absence of anyone having the ability to predict the future, commentators and prognosticators are happy to step in with stories of their own. The reality, though, is that no matter how rigorous anyone’s analysis might be, no one can know for su...