Long-time Lurker who read Johnathan’s WSJ columns for decades and had several delightful conversation with him.
 
I thought I would share “Yet-Another Social Security Spreadsheet Analysis on what Age to Start taking Benefits” as I would appreciate (candid) commentary on how I can improve this from the financial wizards at Humble Dollar.
 
Thanks in advance for any suggestions.

WHEN MY HUSBAND and I moved into a continuing care retirement community, we were both in our late 70s, healthy, active, and living independently. We had been considering such a move for several years. Still, friends sometimes wondered why we would move before we needed care.
That was precisely the point.
We wanted to decide while the choice was ours—while we had the energy to explore alternatives, review the finances, and talk honestly about what each of us wanted.

Advice, please: My employer moved our 401(k) program from Vanguard to Empower. The offerings are skimpy: no target date retirement funds, no life strategy funds, no balanced or all-in-one funds.  Instead we can choose from 15 funds, many of them with fees higher than index funds.  When I ask Empower why it tolerates this weak menu, I get variations of, “Tolerate? I didn’t know we even allowed plans this narrow.” And when I invite the employer’s managers to broaden the selection,

AT FIRST GLANCE, Social Security appears straightforward. During our working years, we pay into it, and in retirement, it sends us a monthly check, guaranteed for life. Unfortunately, it isn’t always so simple. Below are five aspects of the system that are frequently misunderstood.
Benefits estimates. Look at a Social Security statement, and an easy-to-read chart provides estimates of the benefits available at various ages. The heading above the chart reads, “Personalized Monthly Retirement Benefit Estimates Depending on the Age You Start.” That seems clear.

BOB MADE A very expensive tax mistake. Doctors told Bob that he only has a year to live… What did Bob do?
He decided to gift a house to his only son before passing away. The house is worth $2,000,000 that he bought back in 1970 for $50,000 in an expensive suburb of California.
The son decided to sell the house and paid about $430,000 in federal taxes.
$430,000 that could have been $0 instead…
How?

Adam Grossman wrote this in an e-mail today. I didn’t know this did you?
“The spousal benefit is terrific, but a commonly misunderstood limitation is that—unlike a worker’s own benefit—it doesn’t continue to increase each year until age 70. It hits a maximum at the spouse’s FRA. For that reason, it’s important for a spouse to not delay beyond that point.”
On the other hand if the worker delayed beyond FRA those extra benefits pass on to survivors benefits.

I am 59 and have worked as an IT contractor for over 20 years. Recently, my contract ended, and I’m transitioning away from my primary career. While I’m financially able to retire, I’m open to taking on less demanding paid work if the right opportunity comes along.
For those who retired from your primary career but later did other paid work, how did that happen? Did you plan it, or did the opportunity find you? Was it through networking,

Within a ten-minute walk of my vacation home there’s a lovely nine-hole golf course, its main lateral hazard being the river made famous as the source of water for Bushmills Irish whiskey. I haven’t lost a ball to the River Bush since I retired. That isn’t because I’ve gotten any better at golf. It’s because I’ve recently realized I haven’t played the course since losing my regular wage after retirement.
Instead, I’ve subconsciously started playing a nine-hole links course twenty minutes’

When my twin brother Nick and I sold our landscape business at the end of 2012, at the age of 52, we agreed to stay on for another three years. Looking back, that may have been one of the best retirement decisions I never consciously made.
Those three years gave me time to ease into retirement instead of falling into it. They also gave me time to think about something I believe is far more important than deciding when to retire.

I saw this on the back page of today’s Wall St Journal.
“On this day in 1971, Wells Fargo launched the world’s first stock-index fund. One mutual-fund manager’s reaction: “If people start believing this random-walk garbage and switch to index funds, a lot of $80,000-ayear portfolio managers and analysts will be replaced by $16,000-a-year computer clerks. It just can’t happen.”

We all remember the 2022 bond collapse, triggered by rising interest rates. Most of us were caught out, a supposedly safe asset class posting double-digit losses. Some of those bond funds are still slightly underwater four years later. Which brings me to a question worth thinking about.
Right now, Treasury Inflation-Protected Securities (TIPS) are offering guaranteed real returns of roughly 2-3% above inflation. That’s a compelling, ultra-safe option for liability matching in retirement, and I think most people would do well to look into it.

TIPS are US Government securities that currently pay two to three percent real return depending on the maturity selected. You can buy them from your broker, Treasury Direct account, Exchange Traded Funds (ETFs) and mutual funds. So, if inflation for a time period is three percent, your bonds earn five to six percent depending on the time period. These real returns are guaranteed by the US Treasury. I will not give all the details here and am not giving advice.

Social media is full of seniors complaining about inflation, the inadequacy of Social Security and its COLAs to keep up.
I was curious. Is that true and what has happened to my purchasing power since retiring in January 2010?
To match the purchasing power of $100 in 2010, you would need approximately $153.15 in 2026.
Meanwhile, $100 in Social Security benefits in 2010 has grown through compounded Cost-of-Living Adjustments (COLAs) to $147.36 in 2026. Not equal,

THE WIDOW TAX is sold to the wrong households. It gets pitched to affluent couples as the reason to convert to a Roth or buy life insurance. The pitch says that when one spouse dies, the survivor files single, lands in a higher bracket, and gets clobbered. I ran the numbers for three couples at three incomes, and at the comfortable end the widow tax often costs nothing, or even less than nothing.
The real cost lands lower down,

WHEN IT COMES to financial decisions, many investors subscribe to an approach known as evidence-based investing. The idea, as the name suggests, is to base decisions, whenever possible, on data rather than on intuition or other informal methods.
This sounds logical. It isn’t perfect, though. Economic and financial indicators have weaknesses which are important to be aware of. 
Consider, for example, the Cyclically-Adjusted Price-to-Earnings, or CAPE, ratio, developed by Robert Shiller, a Yale professor and Nobel laureate,