Retirement

My math showed retirement was safe, but it took 18 months of actual spending to finally believe it.
Looking back on the two years before I retired, I’m slightly embarrassed by how fixated I became on financial planning. I built endless spreadsheets, explored every permutation of how spending and decumulation might interact, modeled worst-case scenarios, and tweaked our burn rate whenever a new bill or idea occurred to me. I checked the numbers compulsively, several times a day.

This past month the IRS issued guidance which disallows a much marketed technique many advisors are pitching to investors.  The technique involves transferring appreciated securities to a newly formed ETF without recognizing capital gains.  The idea is that forming a “new corporation” (the ETF) and transferring assets to it should be a nontaxable event under IRS Code Section 351.  For the past couple of years many advisors have been pitching this.  I even heard a Vanguard advisor recommending it.  

The lack of knowledge about one of our most important social programs is unfortunate because it minimizes the understanding of its value and distorts acceptance of necessary changes. Misinformation can also distort retirement planning.
Several surveys show that Americans do not understand Social Security, including how it’s funded. It has been funded the same way since 1939 by the way. 
A major point of confusion is when full benefits kick in. According to Allianz Life research,

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?

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. The IRS notice that creates the requirement says reporting is not required for the IRAs of deceased owners,

Early in my career, I spent six years with a company that offered a defined benefit retirement plan. I worked there just long enough to vest in the plan.  When I turn 65, I can choose monthly payments or a lump-sum cash-out.  The monthly payments are formulaic, related to years of service and my compensation at the time.  Once a year, I log in to make sure they haven’t forgotten me, moved websites, otherwise forgotten me,

FOR MORE THAN 20 years, I worked as a personal trainer. Now I’m a financial advisor. On the surface, the two professions look nothing alike. Human behavior makes them far more similar than most people realize.
Years ago, one of my fitness clients joined Weight Watchers. At her intake meeting, she asked whether she should cut back on carrots because she’d heard they’re high in sugar. The specialist didn’t miss a beat. She smiled and said “No one ever comes to us because they eat too many carrots.”

YEARS AGO, while practicing law, I was a frequent contributor to Humble Dollar. I loved Jonathan Clements’s vision for the site – a corner of the financial universe built on clarity, frugality, and the quiet dignity of living within one’s means.
Then my life took a sharp pivot. I left legal practice to teach gifted-and-talented students and coach varsity athletics at a public magnet high school. Almost immediately, my submissions here dried up.

YOU MAY BE familiar with a concept known as Pascal’s wager. Named for Blaise Pascal, a devout seventeenth-century French mathematician, it was a thought experiment in which he tried to weigh, in logical terms, the costs and benefits of believing in God. His conclusion: The cost of not believing—a potential eternity of damnation—was so extreme that it far outweighed any other consideration.
I mention Pascal’s wager because a common question is whether similar logic might apply to financial decision-making.

RECENTLY, A READER—let’s call him Tom—posed this question: If stocks historically have delivered far better returns than bonds, then why should an investor own any bonds at all? Even with the stock market’s unpredictable ups and downs, wouldn’t you end up way ahead by betting only on stocks over the long term?
It’s a fair question. Over the past 100 years, stocks have delivered returns of roughly 10% per year, while bonds have returned just 5%.

On 9/29/2026 the US Senate passed the Claiming Age Clarity Act that the US House passed in December 2025 and the the legislation is now on the way to the President for his signature to become law.
In a nutshell the law changes the terminology about how the claiming ages are referred to by the Social Security Agency.
H. R. 5284 Section 2 of the pending bill as adopted by the Senate without amendment reads as follows –

This recent article in the WSJ got me thinking.
https://www.wsj.com/personal-finance/inflation-proofed-retirement-cd2a387a?st=cvZSf3&reflink=desktopwebshare_permalink
I read it and tried to relate to it. I wanted advice on how to invest with this inflation that is causing my nest egg to be worth less. I found the article telling me to stop spending.  I got that under control but what about investing?
so HD readers what are you doing to inflation proof your retirement?

I listened to an interview with a former Social Security deputy commissioner, and one point stuck with me: Social Security isn’t going to vanish, but Congress still needs to deal with its funding problem.
I’m getting close to retirement, so I’d like to know what to plan for. I can run the numbers with a smaller benefit. What I can’t do is guess which changes Congress might make—or whether they’ll wait until the trust fund is nearly depleted before making them.

WHAT’S THE MOST important idea in personal finance? It’s hard to single out just one, but over the years, I’ve found the following dozen ideas to be among the most useful.

Whether it’s on TV or online, there’s never any shortage of market prognosticators. Especially during a bull market, everyone seems to have an opinion on where things are headed. The reality, though, is that people can only guess about how the economy, the market or any individual investment will perform.

A RECENT post by achnk53 about the impact of a spouse’s death on the survivor’s taxes piqued my interest.  The post referenced an interesting Kiplinger article about the “Widow’s Penalty”, or the negative tax implications on a surviving spouse after the death of a spouse. A surviving spouse can file Married Filing Jointly (MFJ) in the year of their spouse’s death. In the full year following the spouse’s death you must file Single.