Retirement

A POPULAR JOKE about retirement is that it can be hard work. That’s because financial planning is like a jigsaw puzzle, and retirement often means rearranging the pieces.
In the past, I’ve discussed two key pieces of that puzzle: how to determine a sustainable portfolio withdrawal rate and how to decide on an effective asset allocation. But there’s one more piece of the puzzle to contend with: taxes. Especially if you’re planning to retire on the earlier side,

According to a May 2025 Gallup survey, only 61% of Americans age 65 and older own stocks in any way, including IRAs, 401ks, etc. I found that a bit shocking and a little sad. I’m pretty certain HD readers and writers are not among the 39%. 
If that is an accurate percentage, no wonder many retirees are in poor financial shape, no wonder social media is full of videos with seniors claiming they need and deserve higher social security benefits and higher COLA adjustments.

I don’t have the right stuff to be an engineer, as the math involved boggles my mind. But that didn’t stop my infatuation with spreadsheets in the nascent days of computer ownership. That was around 1990, roughly the same time-frame as the implementation of my employer’s 401k. 
Oh boy, enabled by my new love of Excel, my life was planned out via extrapolations of future earnings, savings rates, and stock market performance. My plan had me comfortably retired at age 55.

Most personal finance advice is beautifully simple: save more.
Early in life, that advice is almost always right. But like most good rules, it has limits.
There comes a point in a saver’s life when retirement growth is driven far more by compounding than by new contributions. Past that point, continuing to save aggressively still increases your balance—but it may no longer be the best use of every additional dollar.
Recognizing when that shift has occurred can create flexibility without recklessly undermining your future.

I WAS THINKING ABOUT Jonathan the other day on my morning walk, which happens more often than you might think. It’s hard not to think about him when you have HumbleDollar coasters in your living room and a HumbleDollar shopping bag in your car that you use for groceries. My wife confiscated the HumbleDollar cup I had been using for my morning tea, and it now has a new home in our bathroom holding her toothbrush and toothpaste.

My wife was laid off the other day. After thirty years at one company. For the first time in her working life, forty years, she was told her services were no longer needed.
Even though we’re financially fine, and now that she may join me in retirement, I’m unsettled. I think it’s because we have both crossed the retirement line. We’re no longer actively working to make money. We’re now 100% earning money passively. We’re relying on all the acorns that we’ve saved,

ACCORDING TO THE World Happiness Report, Finland ranks as the happiest nation in the world, a title it’s held for eight years in a row.
Each time this report is updated, it makes the news for a day or two but then fades. That’s for good reason, I think. As much as Finland might be a nice place, it isn’t necessarily practical to suggest that anyone pick up and move.
The good news, though,

An article in Commonweal Magazine is a bit unkind to 401k plans from the interesting perspective that asking people to save on their own takes away from other uses.
“But there’s increasing evidence that our current approach is not only economically inefficient but also a key contributor to the precarity and isolation unraveling the social fabric. “
“What was once a balanced system of collective and individual support has come to rely on a single,

MANY PEOPLE FOCUS on building wealth through asset allocation and investment choices. Far fewer think about asset protection. In my opinion, protecting wealth is just as important as building it, especially since decades of disciplined saving and investing can be undone in one unfortunate event.
In this article, I wanted to discuss some of the strategies and tips that I’ve learned, and implemented in my personal finance journey.
Quick disclaimer: I’m not a lawyer,

I recently read the HumbleDollar guidance suggesting retirees consolidate old 401(k) accounts for simplicity. My husband and I are both retired (age 62) and are wondering whether that advice still holds when the existing plans are high quality.
We each have a former-employer 401(k):
– Mine is with a large financial institution
– My husband’s is with his union
Both plans have low costs (~ 65 bps all-in), solid investment options, and no required distributions yet.

Six months ago Scott Dichter wrote a forum post (Coast FIRE! Who would have thought that FIRE could have so many flavors? – HumbleDollar) about Michael Kitces’s blog post about Coast FIRE.  For those unfamiliar with the term, please check out the articles.
In a nutshell, Coast FIRE is when one accumulates enough money whereby the money currently saved for retirement is sufficient to meet one’s future goal to retire early without the need to continue adding to retirement savings.

Nothing like Christmas and the rolling of one year into the next for a little reflection. A chance to think a little more broadly than the daily minutia. And to catch up with friends and family that we haven’t seen for a while.
For me, this included a lot of us in our early fifties. I sensed a common theme in the discussions – everyone seems pretty sick of striving for a promotion or more money.

I am on schedule to retire in 18 months, at the age of 65.  But I have decided to allocate our assets now.  The stock market indexes are near/at all-time highs, so why put it off?   Within all of our necessary accounts, we have put 5 years worth of projected expenses into cash/cash equivalents.  5 years of spending and taxes in my Traditional retirement accounts.  5 years of Medicare/medical expenses in our HSA accounts.  5 years of QCDs in my wife’s Traditional IRA for charitable giving. 

When did you retire (what age), and what was the deciding factor that made you retire at that time—finances, health, job satisfaction, family needs, benefits timing (pension/SS/healthcare), or simply “I was done”?
Looking back, was it the right age for you, and would you do it the same way again?
 
Jeff

If you could go back to 5 years before you retired, what’s the one decision you’d change that would have made the biggest difference in your first 1–3 years of retirement and what do you wish you’d done sooner? Examples:
When to claim Social Security?
How you structured withdrawals/taxes
Whether you carried a mortgage?
Where you lived?
How you planned for healthcare/long-term care?
thanks,
Jeff