We spend decades preparing financially for retirement—and yet we give scant thought to what we’ll do with all that free time.
Sanjib Saha retired early from software engineering to dedicate more time to family and friends, pursue personal development and assist others as a money wellness mentor. Self-taught in investments, he passed the Series 65 licensing exam as a non-industry candidate. Sanjib is the president and cofounder of Dollar Mentor, a 501(c)(3) nonprofit organization offering free investment and financial education. Follow his nonprofit on LinkedIn, and check out Sanjib’s earlier articles.WHEN MOST PEOPLE retire, they have a good idea where they’ll live. It might be where they currently reside, or where they vacation, or a place near their children or grandchildren. Whatever the case, there’s usually a limited number of possibilities.
But what if you move to a new city for the last two years of your working life, never vacation in the same place twice, don’t own a vacation home, are childless and—upon retirement—sell your home, sell most of your stuff, pack the rest in a POD and then travel the world for the next year?
In that scenario, which just happens to be one that my wife and I found ourselves in, the world is a blank canvas and identifying a new home becomes just a little more complicated.
One option could have been to review articles such as Kiplinger’s “The Best Places to Retire in the World,” and then plan accordingly. Or maybe a spreadsheet could be created that compares different locations. But instead, Susan and I decided to take a less analytical and more Kerouacian approach. We would hit the road, man, and personally interview cities until one made the scene. Can you dig it?
We, of course, were looking for that perfect candidate—you know, the one with low taxes, modest housing costs, reasonable cost of living, great culture, James Beard award-winning restaurants, outstanding health care and an airport with direct flights to Paris, Tokyo and Hawaii.
I was immediately attracted to cities in Alaska, Florida, Nevada, South Dakota, Texas, Washington and Wyoming for the obvious reason: taxes. All but Washington were summarily dismissed due to the increased possibility of heat stroke, frost bite or cabin fever. Even Washington was eventually overlooked, because we never made it that far west.
After touring cities like Ann Arbor and Boulder, I realized that the successful candidate needed a certain amount of grit. Not too much, as there is a fine line between “urban lifestyle” and some half-naked guy screaming obscenities in the middle of the street. I wanted a dynamic interaction of races and cultures, access to decent pizza and some city noise. Not necessarily the sound of gun shots, but maybe a siren every now and again.
In our search for grit, Detroit was interviewed. The city had fallen on hard times and therefore I thought it might make for a strong candidate. It had a decent tax structure, though with much more sprawl than I imagined. The downtown had bottomed out a few years earlier, and was now filled with activity and a significant number of cranes.
In fact, the area was becoming quite fashionable. As it turns out, maybe too fashionable, as real estate prices were soaring. I also happened to interview Pulitzer-prize-winning, man-on-the-street journalist Charlie LeDuff, who informed me that much of the “new” Detroit was a facade, built on debt and endemic corruption.
Denver looked quite promising, with a good tax structure, some grit and no humidity. Unfortunately, the word was out, and property values reflected it, plus it was too late in life to learn to ski or develop a daily skin-care regimen.
[caption id="attachment_1540498" align="alignright" width="400"]
Pittsburgh, another city the Flacks didn't choose[/caption]Pittsburgh also looked promising, with affordable real estate, cultural offerings and a fair amount of grit. It’s actually quite picturesque and ranked as the second most “livable city in the U.S.” by The Economist. We visited in the fall and the weather was decent, though locals informed us the winter can be a little “chilly,” with more than a little “precipitation.” And, oh yeah, air quality could be an issue. Still, it was shortlisted.
It was starting to get a little cold, so I figured a little southern sojourn was in order. Savannah was purely an informational interview. I knew going in that it wouldn’t make the cut. Yes, it’s easy to fall in love with the place: the food, the hospitality, the city squares and the laid back way of life. I even found myself looking at real estate. But then a few days of warm, humid weather set me straight, reminding me of my two years in Houston: the four months of fall never made up for the eight months of summer.
After a stopover in Texas to vote, we decided to hunker down in Kansas City to ride out the pandemic. While the tax structure in the Paris of the Plains wasn’t optimal, housing costs were quite reasonable, it had good health care and everybody was really, really nice.
[caption id="attachment_1540497" align="alignright" width="400"]
Kansas City, where the wandering Flacks finally settled[/caption]We ended up falling in love with the neighborhood where we were staying. It had a small town feel, but was located a five-minute walk from a downtown area, and it offered the perfect amount of grit. Unfortunately, none of the houses we looked at was worthy.
But then, just as the interview was drawing to a close, we came across a modern townhouse condo filled with light, a dramatic three-story staircase and an owner who was in a hurry to sell. In the end, the specific house and neighborhood were the deciding factors. Also, it may have been that the road was getting just a little old and we were hankering to put down some roots.
Looking for the perfect retirement location is much like investing in the stock market. All the information is very public, with a never-ending discussion in The Wall Street Journal, Kiplinger and a sizable portion of the internet. Result? Finding that income-tax-free beach community, offering low property taxes, low home values and low cost of living, plus a symphony hall and the Mayo Clinic nearby, is much like finding that wide moat, high-yield, increasing dividend, tax-advantaged security that’s selling at a 13% discount.
You may wonder about the one criterion I didn’t mention during the interview process: politics. When I once mentioned the desire to live in San Francisco, a friend dismissed it as “too liberal.” I agree. But I’d live there in a New York minute if it weren't for the ridiculous cost of living. Before some of you say “exactly,” one thing I learned during the interview process: Almost every city of any size leans just a little to that side of the political spectrum. If you want urban, it comes with the territory.
Michael Flack blogs at AfterActionReport.info. He’s a former naval officer and 20-year veteran of the oil and gas industry. Now retired, Mike enjoys traveling, blogging and spreadsheets. Check out his earlier articles. [xyz-ihs snippet="Donate"]NO. 23: IF WE DON’T have much money, we should compensate with time—by starting to save when we’re young, holding stocks for decades and encouraging our children to do the same.
RENT OUT YOUR HOME for 14 days or less each year. If you stay under this limit, you don’t have to pay taxes on the income you receive, though you also can’t deduct any expenses you incur. Such short-term rentals can be lucrative if, say, you live near a major annual sporting event or near a college where hotel rooms are in short supply during graduation.
NO. 15: JUST BECAUSE folks appear rich doesn't mean they are. The big house may be heavily mortgaged, the luxury sedans could be leased, the landscaper might be awaiting payment—and the couple who appear to have it all may be agonizing over how to pay the bills. Make no mistake: Those who put on a display of wealth are less wealthy as a result.
NO. 119: OUR CHANCES of dying are 100%—so the insurance component of permanent life insurance, which is intended to be held until death, is costlier than that of term insurance, which provides coverage for maybe 20 or 30 years. Permanent insurance also involves high commissions, plus you’re required to pay into an investment account.
NO. 23: IF WE DON’T have much money, we should compensate with time—by starting to save when we’re young, holding stocks for decades and encouraging our children to do the same.
JONATHAN CLEMENTS’S final book was released this week. Titled Money and Me, it traces the arc of Jonathan’s nearly four-decade career as a personal finance columnist.
Money and Me starts with the story of a man named George Cope, who was a nineteenth century tobacco baron. At the time of his death in 1888, Cope was one of Britain’s richest men. But within just two generations, his fortune was gone.
IN THE SUMMER of 1966, author John McPhee spent two weeks lying on a picnic table in his backyard. Why?
McPhee was suffering from writer’s block. As he described it, “I had assembled enough material to fill a silo, and now I had no idea what to do with it.”
Investors find themselves in a similar situation today. There’s no shortage of financial information around us. But that doesn’t make it easier to know what to do with it.
MOST PEOPLE THINK their retirement accounts are completely locked until age 59½ due to the 10% early withdrawal penalty, but that’s not really true. There are many ways to access your money earlier without the penalty, and knowing them can give you flexibility. Of course, you shouldn’t be touching your retirement accounts unless you’re ready to retire.
Here are some distributions that are not subject to the 10% penalty, per the IRS list:
Birth or adoption (up to $5,000 per child)
Series of substantially equal payments (72t)
First-time homebuyer (up to $10,000,
I WAS SCROLLING through social media recently and saw somebody dismiss retirement accounts as “paper wealth.” The argument was familiar: Your money is locked away and you’re waiting for permission to access it.
There’s a grain of truth here. Retirement accounts do come with rules. But much of the discussion online ignores how flexible these accounts actually are. More important, it ignores the enormous tax advantages.
Most people today will likely live well beyond age 59½.
WHEN I STARTED writing for HumbleDollar, Jonathan gave me some simple but important advice: “Don’t brag about your financial situation. You want readers to like you.” Perhaps that’s one of the reasons he named his financial site HumbleDollar.
I try to follow this advice not only regarding money, but in other aspects of my life. I know how fleeting things can be—especially when it comes to health. Life can change on a dime. It can humble you.
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.
Blood Money
Michael Flack | Mar 28, 2026
Feeling TIPSy?
ArticleSanjib Saha | Aug 22, 2026
Americans and their credit cards
R Quinn | Aug 24, 2026
A Place At The Table
Andrew Clements | Aug 26, 2026
You Heel!
Michael Flack | Aug 24, 2026
The Intentional Spendthrift
Mark Crothers | Aug 21, 2026
On the Road to Home
ArticleMichael Flack | Oct 18, 2023
WHEN MOST PEOPLE retire, they have a good idea where they’ll live. It might be where they currently reside, or where they vacation, or a place near their children or grandchildren. Whatever the case, there’s usually a limited number of possibilities.
But what if you move to a new city for the last two years of your working life, never vacation in the same place twice, don’t own a vacation home, are childless and—upon retirement—sell your home, sell most of your stuff, pack the rest in a POD and then travel the world for the next year?
In that scenario, which just happens to be one that my wife and I found ourselves in, the world is a blank canvas and identifying a new home becomes just a little more complicated.
One option could have been to review articles such as Kiplinger’s “The Best Places to Retire in the World,” and then plan accordingly. Or maybe a spreadsheet could be created that compares different locations. But instead, Susan and I decided to take a less analytical and more Kerouacian approach. We would hit the road, man, and personally interview cities until one made the scene. Can you dig it?
We, of course, were looking for that perfect candidate—you know, the one with low taxes, modest housing costs, reasonable cost of living, great culture, James Beard award-winning restaurants, outstanding health care and an airport with direct flights to Paris, Tokyo and Hawaii.
I was immediately attracted to cities in Alaska, Florida, Nevada, South Dakota, Texas, Washington and Wyoming for the obvious reason: taxes. All but Washington were summarily dismissed due to the increased possibility of heat stroke, frost bite or cabin fever. Even Washington was eventually overlooked, because we never made it that far west.
After touring cities like Ann Arbor and Boulder, I realized that the successful candidate needed a certain amount of grit. Not too much, as there is a fine line between “urban lifestyle” and some half-naked guy screaming obscenities in the middle of the street. I wanted a dynamic interaction of races and cultures, access to decent pizza and some city noise. Not necessarily the sound of gun shots, but maybe a siren every now and again.
In our search for grit, Detroit was interviewed. The city had fallen on hard times and therefore I thought it might make for a strong candidate. It had a decent tax structure, though with much more sprawl than I imagined. The downtown had bottomed out a few years earlier, and was now filled with activity and a significant number of cranes.
In fact, the area was becoming quite fashionable. As it turns out, maybe too fashionable, as real estate prices were soaring. I also happened to interview Pulitzer-prize-winning, man-on-the-street journalist Charlie LeDuff, who informed me that much of the “new” Detroit was a facade, built on debt and endemic corruption.
Denver looked quite promising, with a good tax structure, some grit and no humidity. Unfortunately, the word was out, and property values reflected it, plus it was too late in life to learn to ski or develop a daily skin-care regimen.
[caption id="attachment_1540498" align="alignright" width="400"]Pittsburgh also looked promising, with affordable real estate, cultural offerings and a fair amount of grit. It’s actually quite picturesque and ranked as the second most “livable city in the U.S.” by The Economist. We visited in the fall and the weather was decent, though locals informed us the winter can be a little “chilly,” with more than a little “precipitation.” And, oh yeah, air quality could be an issue. Still, it was shortlisted.
It was starting to get a little cold, so I figured a little southern sojourn was in order. Savannah was purely an informational interview. I knew going in that it wouldn’t make the cut. Yes, it’s easy to fall in love with the place: the food, the hospitality, the city squares and the laid back way of life. I even found myself looking at real estate. But then a few days of warm, humid weather set me straight, reminding me of my two years in Houston: the four months of fall never made up for the eight months of summer.
After a stopover in Texas to vote, we decided to hunker down in Kansas City to ride out the pandemic. While the tax structure in the Paris of the Plains wasn’t optimal, housing costs were quite reasonable, it had good health care and everybody was really, really nice.
[caption id="attachment_1540497" align="alignright" width="400"]We ended up falling in love with the neighborhood where we were staying. It had a small town feel, but was located a five-minute walk from a downtown area, and it offered the perfect amount of grit. Unfortunately, none of the houses we looked at was worthy.
But then, just as the interview was drawing to a close, we came across a modern townhouse condo filled with light, a dramatic three-story staircase and an owner who was in a hurry to sell. In the end, the specific house and neighborhood were the deciding factors. Also, it may have been that the road was getting just a little old and we were hankering to put down some roots.
Looking for the perfect retirement location is much like investing in the stock market. All the information is very public, with a never-ending discussion in The Wall Street Journal, Kiplinger and a sizable portion of the internet. Result? Finding that income-tax-free beach community, offering low property taxes, low home values and low cost of living, plus a symphony hall and the Mayo Clinic nearby, is much like finding that wide moat, high-yield, increasing dividend, tax-advantaged security that’s selling at a 13% discount.
You may wonder about the one criterion I didn’t mention during the interview process: politics. When I once mentioned the desire to live in San Francisco, a friend dismissed it as “too liberal.” I agree. But I’d live there in a New York minute if it weren't for the ridiculous cost of living. Before some of you say “exactly,” one thing I learned during the interview process: Almost every city of any size leans just a little to that side of the political spectrum. If you want urban, it comes with the territory.
Reaching Two-thirds of a Century!
Rick Connor | Sep 3, 2024
How Did You Find Paid Work After Retiring from Your Primary Career?
Jeffrey Chan | Jul 31, 2026
Beyond Bank Accounts
ArticleSanjib Saha | Jun 13, 2026
I OPENED MY FIRST bank account in the US at a local credit union (CU) close to my workplace. The CU had several convenient offers for employees of our company. With minimal effort, I opened checking and savings accounts, got free checkbooks and a credit card despite having no credit history in the US.
I was so pleased with the convenience that I handled all my banking needs through this CU for many years. That included direct deposit of my salary, payments and withdrawals, a car loan, and certificates of deposit (CDs) as my savings grew. I still maintain my checking account here and occasionally enjoy special favors as a longtime loyal customer.
Eventually, I realized that I earned very little interest from the bank deposits. I shopped around, found other banks with better rates, opened several accounts here and there, and moved my money around.
I felt good about being proactive and getting a better return on my cash reserve. But that feeling was short-lived as I started learning more about personal finance and investments. Tired of chasing yields in bank accounts, I eventually embraced US Treasurys (debt issued and backed by the US Government) as my alternative to savings accounts and CDs.
For those unfamiliar with US Treasurys, think of them as CDs with maturities ranging from four weeks to 30 years. They're widely used as a "safe investment" by individual, institutional and even sovereign investors around the world.
There are some key differences, though. Bank deposits are insured only up to $250,000. US Treasurys, on the other hand, are backed by the full faith and credit of the US Government. Therefore, there is virtually no default risk regardless of the investment amount.
Treasury interest rates, both short-term and long-term, are heavily influenced by monetary policy actions of the US Federal Reserve (Fed). Treasury interest rates directly affect many interest rates we encounter in everyday life: bank accounts, CDs, mortgage, car loans, personal and business loans, and so on.
Treasury interest rates are often higher than comparable bank products. Why? Because the intermediary financial institutions take their cut for operational costs and profits. Result? Suboptimal, or sometimes almost non-existent, interest on bank deposits.
But wait. What if I need my money back?
With bank deposits, I can walk in and withdraw cash from my account. If my money is locked in a CD, I may have to pay a penalty for early withdrawal, but I can still access it fairly quickly. What happens if I'm holding Treasurys? Do I need to wait until maturity?
That leads us to another important aspect of US Treasurys: their extremely high liquidity.
I can certainly buy newly issued Treasurys and wait until maturity, but I don't have to wait for these events. Investors around the world buy and sell Treasurys in the open market every day, making them one of the most liquid investments in existence.
Their liquidity, safety and meaningful return make Treasurys a compelling alternative for both short- and long-term cash reserves.
Sounds interesting? That's exactly how I felt after doing my own research. All I needed to figure out was the best way to invest in them.
Instead of buying Treasurys directly from the US Treasury, I use my brokerage accounts and buy and sell individual Treasurys or Treasury exchange-traded funds (ETFs) in the open market, just like stocks or funds. (I used to participate in Treasury auctions through the brokerage account to buy new issues and set my holdings to auto-roll upon maturity, but I eventually stopped doing that to keep things simple.)
For annual expenses and short-term cash needs, I like short-term, highly liquid, Treasury ETFs with a practically negligible expense ratio.
For money expected in three to four years, I favor short- and intermediate-term Treasury Inflation Protected Securities (TIPS) ETFs. TIPS have a lower interest rate compared to equivalent regular Treasurys, but their principal is adjusted with inflation, helping mitigate the risk of unexpected inflation.
For cash reserves further into the future, five years or more, my preference is a ladder of individual TIPS bonds, each maturing in a specific future year. Bond trading is slightly more involved than ETFs or stocks, so target-maturity TIPS ETFs can also be a reasonable alternative despite their slightly higher management fees.
Is there a catch compared to keeping money in conventional bank accounts?
I can't think of any, but there are two noticeable differences worth understanding.
First, unlike money sitting in bank accounts, Treasury investments fluctuate in value because they constantly change hands in open markets. For short-term Treasurys, the fluctuations are usually tiny. For intermediate- and long-term Treasurys, the swing can be more noticeable, especially when there's a major change in the interest rate expectation. Thankfully, these fluctuations are usually modest, and over time Treasurys often come out ahead compared to bank deposits.
The second difference deserves a bit more attention.
With a bank account, you can get hold of your money almost immediately. Treasury investments, however, may take a couple of business days to turn into spendable cash. You need to sell the ETF or bond during market hours. Once the transaction settles, usually the next business day, the proceeds can then be transferred out to the checking account for spending. In some cases, you may be able to carry on your spending activities directly from the brokerage account.
Over time, I shifted most of my liquid savings to Treasurys because of the improved result. Yet I still see many people leaving large cash balances in bank products or chasing yields from one bank to another.
I suspect the main reason is simple: lack of familiarity with US Treasurys.
TreasuryDirect changing login procedure to mandate ID.me later in 2026
William Perry | Aug 15, 2026
Tax Complications – How SS Benefits interact with Other Income
Rick Connor | Aug 18, 2026