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Reaching Two-thirds of a Century!

Rick Connor | Sep 3, 2024

"The below UGH lyrics was sung often by the camp staff at Camp Buck Toms when a birthday occurred during summer camp. So Happy Birthday to a Scout leader and thank you for all you have done. Best, Bill Happy Birthday, Ugh. Happy Birthday, Ugh. Ha-a-a-a-appy Birthday, Ugh.

Pain and sorrow in the air,
Death around us everywhere.
But...
One year closer to the grave,
Think of all the food we'll save
But...
Easter Bunny broke his leg,
Bled all over the Easter Eggs,
But...
Santa Claus wrecked his sleigh,
No more presents Christmas day.
But...

- William Perry

The Intentional Spendthrift

Mark Crothers | Aug 21, 2026

"That’s from Nick Maggiuli I believe."

- Michael1

New in 2025 – Code Y on 1099-R box 7 for QCD’s

William Perry | Apr 26, 2025

"Here is a link to the 2026 draft 1099-R instructions dated Jun 17, 2026 wherein the IRS writes, on a preliminary basis, the following - ...unexpected issues occasionally arise, or legislation is passed—in this case, we will post a new draft of the form to alert users that changes were made to the previously posted draft... Code Y for box 7a on Form 1099-R. We added code “Y” to the list of codes for box 7a to identify a qualified charitable distribution (QCD). See Qualified charitable distributions (QCDs), later. For tax year 2026, the use of code Y to report a QCD is optional. If you are completing and filing a 2026 Form 1099-R, you may choose, but are not required, to enter code Y in box 7a. It is difficult to provide timely, clear and objective guidance when the agency who interprets the laws passed by congress and writes the detailed regulations have not finalized their rules for the tax year we are more than halfway through. My intent in this updated post was to encourage using a direct from IRA custodian to charity method for those who are making qualified distributions to avoid potential tax compliance headache for you and your tax preparer. I do not have any idea if your broker will choose to use code "Y" regardless of the method of how the QCD is distributed."

- William Perry

$40 Trillion of Debt

ArticleAdam M. Grossman | Aug 22, 2026

SOME MILESTONES are auspicious. Others are not. This week, the Treasury announced that the federal government’s debt had topped $40 trillion for the first time. Government debt is nothing new, but the problem is now of more concern, for two reasons. First, the scale has grown. An apples-to-apples way to look at the government’s debt load is to compare it to GDP—the economy’s total annual output. On this basis, outstanding debt now exceeds 100% of GDP, a level we haven’t seen since the period immediately after World War II. That brings us to the second concern: If the government isn’t able to balance its books while the economy is strong, as it is today, lawmakers will have less flexibility to act when the next recession occurs. For a brief period about five years ago, a theory known as modern monetary policy entered the conversation. The idea, popularized by a book titled The Deficit Myth, was that we shouldn’t be so concerned with deficits—that the U.S. government should be able to borrow more or less as much as it wants. What we’ve seen, though, is that eventually deficits do matter. In simple terms, the government now takes in about $6 trillion per year in revenue, but it's spending almost $8 trillion, resulting in deficits of roughly $2 trillion. And just like a consumer who's run up a big credit card bill, interest payments now consume an ever-larger portion of annual spending. In round numbers, the government this year will spend about one in every six tax dollars it collects on interest and will spend more on interest than on defense. Why have the numbers gotten so much worse? The first factor was Covid. The government had to take extraordinary measures to pull the economy out of recession. But while that spending was mostly justified, the problem is that Congress grew accustomed to larger budget shortfalls and has been unwilling to rein things back in. Congress, in fact, went in the opposite direction when it passed a set of tax cuts a few years back. Those cuts might not have been such a problem, except that one of the lasting effects of the pandemic was inflation. It hit a high near 10% in 2022, and while it’s come down from that peak, it's still higher than it was prior to 2020. What’s the connection between inflation and the deficit? It’s more indirect, but it may be the government's biggest problem at this point. The Federal Reserve's primary strategy in fighting inflation is to raise interest rates, and that's exactly what it did beginning in 2022. That helped with inflation but became a problem for the deficit because the government is such a large borrower, and higher interest rates translated to higher borrowing costs. Unfortunately, the issue has now started to compound on itself. Despite the Fed’s lowering rates, which it has done a handful of times over the past few years, market interest rates have remained stubbornly high, especially long-term rates. That’s because the government is being forced to pay more to borrow, just like any prospective borrower whose finances look shaky. This has become something of a chicken-or-the-egg problem. If rates were lower, the deficit might shrink considerably. But rates may not drop until investors see that lawmakers have gotten serious about the issue. Why hasn’t Congress addressed the problem? In short, it’s because the two most obvious solutions—raising taxes or cutting spending—are the last thing any politician wants to do. Ironically, this may be the one area where both parties are fully aligned. Hopefully Washington begins to get serious about the problem. For better or worse, though, this is the situation we’re in. Against this backdrop, what steps might you consider for your portfolio? Because the deficit is so closely tied to interest rates, the first area I’d focus on would be your bond holdings. With long-term interest rates at multi-decade highs, there might appear to be an opportunity to profit from long-term bonds if rates were to drop. I would be cautious, though. Just this week, we’ve seen volatility in long-term rates, and things could easily go the other way. For that reason, I recommend a conservative posture toward bonds, with the majority in short-term holdings, only a small amount in intermediate-term and none at all in long-term bonds. To be sure, this might mean forgoing some profits if rates come down, but in my view, the bond side of a portfolio should be the part that helps investors sleep at night rather than another area to worry about. What other steps could you take? I’d give thought to your long-term tax exposure. It’s possible that politicians will eventually get serious and raise taxes, and if they do, you’d want to be in a position to manage your own tax bill. Fortunately, there is one clear route to inoculating part of your portfolio against tax increases, and that’s to look for ways to build up dollars in a Roth account: If you’re in your working years, you could contribute to a Roth IRA or a Roth 401(k). Your employer might even allow for so-called mega back-door Roth contributions. If you’re retired or happen to have a low-income year, consider a Roth conversion. A final recommendation: If you have a net worth over $10 million or so, you might give thought to estate tax strategies. Today the federal estate tax applies only to individuals with more than $15 million in assets, but this threshold has been a political football and could easily end up much lower. As recently as 2008, it was at just $2 million. Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.

Feeling TIPSy?

ArticleSanjib Saha | Aug 22, 2026

NOT TOO LONG ago, Treasury Inflation Protected Security (TIPS) was a relatively obscure investment for safe long-term fixed-income investments. For the first twenty years of the new century, consumer prices were mostly stable or rising at a too-slow-to-notice rate. Why bother with anything related to inflation? Sadly, persistently low inflation made us complacent on the biggest long-term risk of bond investments -- the insidious unexpected inflation that robs us of the purchasing power of our “safe” investments. Yes, let’s not forget that the biggest risk of bond or bond-like investments is unexpected inflation. Any bond or CD with a maturity beyond a few years must either offer a sufficiently high interest rate to compensate for sudden bouts of inflation, or have its principal adjusted for the inflation actually realized. The former is nearly impossible to find without sacrificing safety. The latter is what TIPS is for. To be clear, the market and investors always expect some level of inflation. Therefore, a bond’s effective interest rate - measured by its YTM (Yield to Maturity) - must be high enough to not only compensate for “expected” inflation and the uncertainties around it but also provide a meaningful increase in the purchasing power of the original principal. A concrete example might help. Consider a 10-year US Treasury nominal bond with a face value of $1,000, selling at $1,000 and paying 5% annual interest. The interest rate reflects the expectations about inflation and other factors over the next 10 years. The rate would be lower if market expected lower inflation, and higher if market expected the opposite. The omnipresence of inflation means we’re likely to lose some purchasing power when we get our $1,000 in 10 years. It won’t buy what $1,000 buys today. By how much? That’s the thousand dollars question (pun intended). There isn’t a readily available number that explains why that 10-year Treasury Bond yields 5% instead of 3% or 7%. Investors essentially take a leap of faith that annual inflation stays low enough over the 10-year period for the interim interests to compensate for the purchasing power loss, plus some changes. Most of us are perfectly comfortable assuming that inflation won’t be as high as 5% for 10 years. But are we fooling ourselves? I suggest using an inflation calculator to see for ourselves. Spoiler alert: Late 1960s through early 1980s can be an eye-opening period. How’d we feel if the next 10 years turn out to be something similar? Think about how you might feel when you safekeep your money in a so-called secure investment, give up higher returns available from risky investments, and then encounter an inflationary regime. Your minimum expectation was that your purchasing power would remain intact and perhaps improve a little by the time your bond matures. Instead, unforeseen inflation erodes your purchasing power and compromises the financial goal the fund was supposed to cover. Your “safe” investment fails you completely. You realize that it wasn’t safe at all. If unexpected inflation is so devastating, why are we so lax about it? I can think of two reasons. First, our minds haven’t adapted to the reality that, unlike to a “real” asset like a bag of rice or a gallon of gasoline, money in its current form is inherently self-eroding. It slowly loses its worth over time. A hundred dollars sitting around will still be a hundred dollars next year, but it won’t buy the same amount. We don’t intuitively perceive the continuous loss of purchasing power. Even when we do internalize it with some effort, we get used to the “pace” of the loss. In other words, we view inflation as steady and unexpected inflation as highly unlikely. Alas, all it takes is a single prolonged inflationary period to change that perception. By then, however, the damage to existing fixed income investments may already be done. Frankly, I’d be very wary of keeping my long-term “safe” money -- fund that I need to preserve beyond a three-year horizon - in any form that isn’t protected against unexpected inflation. For bond investments, the most meaningful option would be TIPS. Why? Because, in addition to being secured by the full faith and credit of the US Government just like any other Treasury securities, TIPS provides three important assurances upfront. First, it provides protection against unexpected inflation, which is a realized inflation that differs from what we expected when purchasing it. If the actual inflation averages 12% instead of the expected 2%, the principal is automatically adjusted to reflect the actual inflation. No guesswork or unexpected risk involved. Second, it provides a “real interest rate” upfront that tells us how much the purchasing power of the investment will increase over time, regardless of what the actual inflation turns out to be. Buying a 10-year TIPS with real 2% annual interest means the investment’s purchasing power will grow 2% per year over the holding period, before considering taxes and other factors. The third aspect is more nuanced. It involves the possibility of inflation being lower than expected, or even negative inflation (aka deflation). Let me elaborate. If a regular nominal 10-year Treasury Bond offers 5% annual yield and an equivalent TIPS offers a real annual interest rate of 2.75%, the market-implied inflation, the breakeven inflation rate, is roughly 2.25% (5% minus 2.75%). Actual inflation, of course, will be known only after 10 years when the bond matures. Suppose the actual inflation turns out to be only 1.25%. The nominal Bond investor would end up with more purchasing power than the TIPS investor because the TIPS principle would be adjusted by only the actual 1.25% inflation rate. The primary objective of the TIPS investor would still have been met: preserving and improving purchasing power by about 2.75% annually. But there would be a “missed opportunity”. The nominal Treasury investor would end up with even greater purchasing power. Does it mean that a TIPS investor can face an unlimited opportunity cost if inflation turns out to be negative? What happens if the actual inflation is, hypothetically speaking, negative 5%, in a severely deflationary period? Does the TIPS investor get back proportionately reduced principal at maturity? Thanks to the third assurance of TIPS, the answer is NO. TIPS guarantees that the principal returned at maturity will never fall below the original face value. During periods of deflation, the inflation-adjusted principal can fall below its face value and the interim interest payments will decline accordingly. But at maturity, the principal is floored at the original principal amount. Therefore, the breakeven inflation rate, the difference between the yield of a nominal Treasury bond and the real yield of an equivalent TIPS, represents the maximum annual yield advantage that the nominal bond can have over TIPS in an unexpectedly low inflation regime. To summarize, a TIPS investor gets unlimited protection against unexpectedly high inflation, while accepting a limited opportunity cost should the actual inflation be low or even negative. The magnitude of that trade-off is reflected in the breakeven inflation rate at the time of the TIPS purchase. An aside: given the destructive impact of deflation on economy and society, policy makers are generally more concerned about preventing prolonged deflation than about preventing modest inflation. Therefore, prolonged deflation is usually considered less likely. Still, we cannot ignore deflation risk altogether and should be prepared for the possibility that TIPS can underperform a nominal bond if inflation runs low. Therefore, the decision to favor TIPS over an equivalent nominal Bond hinges in part on the current breakeven inflation rate. If it’s low enough, favoring TIPS can be an easy decision. Getting unlimited protection against unexpectedly high inflation is worth accepting the relatively small opportunity cost if inflation comes below the breakeven rate. There is, however, a cautionary note about buying TIPS bonds in the secondary market, especially older issues. Consider a 30-year TIPS bond issued 20 years ago and a 10-year TIPS issued within last 6 months. Both might appear to be valid choices if they mature within a few months of each other and offer similar yields. But beneath the surface, one may be more favorable than the other. The older TIPS will likely have a much higher inflation-adjusted principal because it accumulated 20 years of inflation adjustments. But the protection against unexpected deflation applies only to the bond’s original face value, which is typically $1,000. In a prolonged deflationary period, the older bond has much more room for its inflation-adjusted principal to decline before reaching the $1,000 floor. The newer issue, whose adjusted principal is much closer to the $1,000 face value, has less exposure to this risk. Therefore, all else being equal, I’d favor a TIPS with a low inflation-adjusted factor when buying in the secondary market. All things considered, my vote goes to TIPS for long-term “safe” investments, provided the break-even inflation is reasonably low. For secondary market purchases, however, a high inflation-adjustment factor would give me pause. 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.

The Federal Debt and Social Security Payments

DavidHLancaster | Aug 19, 2026

"Some really good thoughts here. I was pondering this topic after reading a WSJ article on the deficit. My conclusion:the typical representation of huge deficits generated from Social Security and Medicare ignores revenue from employers, employees and taxation of SS."

- Harold Tynes

If Retirement is Getting Close

Dan Smith | Aug 18, 2026

"This way that extra distribution above the RMD will be tax-free to her heirs instead of taxed as ordinary income."

- Randy Dobkin

Federal debt

R Quinn | Aug 19, 2026

"I think we have caught up with Greece!"

- Nick Politakis

Tax Complications – How SS Benefits interact with Other Income

Rick Connor | Aug 18, 2026

"Great article will help many. My overall opinion is our tax laws are way too complicated, but I persevere, as I have been doing them since age 16. I still prefer the post card tax or flat tax 17% of income. Done."

- William Dorner

Simplicity Is a Virtue

ArticleDavid Gartland | Feb 4, 2025

FORD MOTOR COMPANY introduced the world to the convertible hard top in 1957 with a car called the Skyliner. It was a marvel of engineering.

To retract, the Skyliner hard top first tilted up and away from the front windshield. Then the top folded in half overhead. The trunk lid opened wide. The folded hard top swung into the trunk, which then closed. All by flipping a single dashboard switch. You can see it in operation in this commercial featuring Lucille Ball and Desi Arnaz.

To make this contraption work, Ford engineers installed seven electric motors, four jack lifts, 10 limit switches, 10 solenoids, four locking mechanisms for the roof, two locking mechanisms for the trunk and 610 feet of wire. It's hugely complicated—and difficult to repair.

I’ve never been a fan of complicated. This applies to investing as well as cars. My introduction to investing came from opening a savings account at my local bank when I was a kid. With time, I could see how my money grew in value if I just left it alone. Simple.

For years, I invested in either savings accounts or certificates of deposit. It wasn’t until I worked for a company with a 401(k) plan administered by Vanguard Group that I dove into the stock market. I chose a one-stop shopping 60% stock-40% bond balanced fund. I contributed an amount that I felt comfortable losing, should things go badly wrong. I knew I had cash in the bank to cover whatever surprises might arise.

I’m sure many others enjoy deciding when, where and how they’re going to invest next. Yet everything that I’ve read tells me the key isn’t timing the market, but time in the market. Just invest and wait patiently.

I keep in mind the old saying, “A watched pot never boils.” Just forget about it until you need the money. Then look up your balance.

Could I have done better with a more complicated investment approach? Maybe. But who cares? As long as I have money in the bank, I’m good.

The Lottery of Birth

Andrew Clements | Aug 19, 2026

"Why do you think some people who could raise themselve up fail to do so? I suspect you think it is solely their fault. However, that explanation fails to make any effort to understand why someone would choose to remain poor and unsuccessful. It also ignores such things as research on identical twins reared apart that found that the personality trait of conscientious, which includes plan unless, goal setting, has a heritability of 45%-50%. (Conscientiousness subtracts include achievement striving, planfunless, dutifulness, competence, and self-discipline.) You also ignore enviornmental factors such as having spendthrift parents. While you brought yourself up from a very modest childhood, your clearly won the intelligence lottery and I suspect to also won the genetic portion of the conscientiousness lottery."

- parkslope

Income taxes on retirees with Social Security

R Quinn | Aug 14, 2026

"The government is us, all 340 million of us. There aren’t too many laws and regulations that have not been changed as the times require."

- R Quinn

Reaching Two-thirds of a Century!

Rick Connor | Sep 3, 2024

Pain and sorrow in the air,
Death around us everywhere.
But...
One year closer to the grave,
Think of all the food we'll save
But...
Easter Bunny broke his leg,
Bled all over the Easter Eggs,
But...
Santa Claus wrecked his sleigh,
No more presents Christmas day.
But...

- William Perry

The Intentional Spendthrift

Mark Crothers | Aug 21, 2026

"That’s from Nick Maggiuli I believe."

- Michael1

New in 2025 – Code Y on 1099-R box 7 for QCD’s

William Perry | Apr 26, 2025

- William Perry

$40 Trillion of Debt

ArticleAdam M. Grossman | Aug 22, 2026

Feeling TIPSy?

ArticleSanjib Saha | Aug 22, 2026

The Federal Debt and Social Security Payments

DavidHLancaster | Aug 19, 2026

- Harold Tynes

If Retirement is Getting Close

Dan Smith | Aug 18, 2026

"This way that extra distribution above the RMD will be tax-free to her heirs instead of taxed as ordinary income."

- Randy Dobkin

Federal debt

R Quinn | Aug 19, 2026

"I think we have caught up with Greece!"

- Nick Politakis

Tax Complications – How SS Benefits interact with Other Income

Rick Connor | Aug 18, 2026

- William Dorner

Manifesto

Aug 23, 2026

NO. 69: WE CAN’T control whether stocks rise or fall, but we can ensure we pocket whatever the market delivers—by diversifying broadly, holding down investment costs and minimizing taxes.

Truths

Aug 23, 2026

NO. 129: FOREIGN shares tend to rise and fall in sync with U.S. stocks, but that close correlation doesn’t mean you’ll get the same return. In many years, there’s a big performance difference between U.S. and foreign shares—and the gap is even larger in any given decade, with the two asset classes often taking turns posting strong results.

act

Aug 22, 2026

SHORTEN YOUR commute. Thinking of moving home or taking a new job? Research suggests that if you can keep your daily commute to under 20 minutes—and preferably walk to work—you will be happier. By contrast, a long commute, especially by car, is associated with greater unhappiness, worse physical health and a higher divorce rate.

Truths

Aug 21, 2026

NO. 45: THIS YEAR’S winners often continue to shine next year. This momentum may reflect an initial underreaction to good news, followed by a catch-up period. Trading costs make it hard to profit from the momentum effect. Still, if you own an investment that’s lately started outperforming, maybe you shouldn’t rush to sell.

Money Guide

Manifesto

Aug 23, 2026

NO. 69: WE CAN’T control whether stocks rise or fall, but we can ensure we pocket whatever the market delivers—by diversifying broadly, holding down investment costs and minimizing taxes.

Spotlight: Family

Happy Birthday America

Marjorie Kondrack | Jul 4, 2024

My grandmother immigrated to America from Kilkee, county Clare, Ireland. I always wanted to learn more about her life there, but she spoke very little of it. It seems she decided to just let go of hungry Ireland and cast her lot in her new country.
Because of family struggles she had to return to Ireland, but was able to return to the land she now loved and fully embraced. My grandmother loved patriotic poems. I offer an excerpt from her favorite;

Helping family

R Quinn | Nov 19, 2024

I have mentioned previously my joy helping our grandchildren like funding 529 plans.
Now our oldest grandchild is in college. A few days ago I texted him to let me know if he needed anything.
Today I received this text. “I was wondering if you can get me a cheese burger with just lettuce, cheese and pickles, fries and a lemonade from the pizza house near my dorm and you can order online. I’ll pick it up.”
So I placed the order.

Holiday Habits

Edmund Marsh | Nov 24, 2024

What creates a family tradition? Why is a certain vacation spot more special than another with the same basic attributes? Why must the family Christmas celebration repeat the annual ritual to seem authentic? Chances are, these events evoke memories of happy times, perhaps shared with loved ones who are long-gone. Traditions often become fixed in our minds as children, when we’re still learning how things ought to be done.
We’re entering the season of traditions. In the physical therapy clinic during this time,

Family Dynamics, Part 2: Supporting Adult Children

DrLefty | Jul 22, 2025

As I mentioned in my last post, I’ve been thinking about various ways that complex family dynamics can affect one’s own finances, especially when we’re in or headed toward the retirement years. Today’s topic is about having adult children on the “family payroll,” long after one might have assumed they’d be completely independent.
A 2024 study published by the Pew Research Center reported that about one-third of young adults (ages 18-34) still live with their parents and that about 55% of American parents provide varying degrees of financial assistance or support to their young adult children.

Playing Ball

Juan Fourneau | Jan 8, 2025

MY SON IS A FRESHMAN in high school, and I’m beginning to be more purposeful about his baseball aspirations. But after dropping $85 on a one-hour pitching lesson, I was wondering, was my money well spent?
My search for an answer began with the Netflix series Receiver. I tuned in to see football player George Kittle, a former University of Iowa Hawkeye and bigtime professional wrestling fan. Kittle was kind enough to send autographed memorabilia for a softball fundraiser we had a few years ago.

Navigating the Unknowns of Financial Decisions

Adam M. Grossman | Sep 13, 2025

WHEN IT COMES to financial decisions, there are, as I’ve argued before, two answers to every question: what the calculator says, and how you feel about it. There’s a fly in the ointment, though: Calculator answers might appear to be based in logic, but they’re still imperfect.
Why?
Ian Wilson, a former executive at General Electric, explained it this way: “No amount of sophistication is going to allay the fact that all knowledge is about the past,

I’d like to take all the credit, but ……

greg_j_tomamichel | Feb 22, 2026

We would all like to be happy, right? And there is no shortage of advice on the internet about how to get there, often by buying someone's book or online course. The trouble is, does any of that advice actually work? Is there anything behind the claims? After selling our business last year, I had a "void" that I imagine many experience in their early phase of retirement. I was keen to work again, and sent out lots of applications. None of them were succeeding. I worked in a role for about a month ....... and despised it! Whilst I had more time on my hands and was feeling a little lost, I thought it would be a good time look for evidence-based ways to feel better. Long story short, I completed a really interesting and completely free course by Dr. Laurie Santos. Dr. Santos is a Professor of Psychology at Yale University, which is a pretty good start for my "evidence based" criteria. She created a course called “Psychology and the Good Life" which became Yale's most popular course and had nearly 1 in 4 Yale students enrolled. I completed the on-line version of that course, and found it really interesting. It leads you through all the things that we think we will make us happy but don't - better grades, more money, a better job. Then, more importantly, it provides a long list of techniques that are shown empirically to work. It guides you through these techniques, and at the conclusion steers you towards making your favoured practice a daily habit. My choice was simple - writing a daily entry in a gratitude journal. Each day I take time to right a paragraph or so about three things that I am grateful for. These can be large, globally…

Selling our business – a done deal

greg_j_tomamichel | Aug 15, 2025

So, Friday August 8th, the sale of our business settled. We had struck a 2 week delay, which was quite an annoyance, but ultimately didn't prevent the sale and handover from going remarkably well. It's wonderful to feel that we have given the new owners the very best chance of success. In the last few weeks customers and staff were spending more time talking with the new owners and less with us, exactly as we hoped! We had said for several months that we wanted the new owners to succeed and to grow the business beyond what we had achieved. It feels like we have given them every opportunity to do so. The benefits of being younger and coming into the business with enthusiasm and a fresh perspective all bode well for prosperous times ahead. HD has talked a lot about luck lately. At this moment I feel like we have been very lucky. We stumbled upon a run down business in a small country town with a very robust, stable economy. It wasn't purchased after lots of thorough analysis and consideration. More accurately, it was purchased on gut feel and a healthy dose of hope. The town came to embrace the business and our particular approach. Our staff came from a broad and varied background. Our turnover was low, so typically we saw people stay with us, learn, develop and grow. I don't think we were experts in recruiting, but we stumbled upon some very good people. When it came time to sell, a buyer came along that was well suited and could secure the funds for the sale. The handover was excellent and I look forward returning as a customer. We could take undue credit for this, but it feels like good fortune also played a very…

Selling our business – the journey so far

greg_j_tomamichel | Jun 16, 2025

I’m sure that there are several on Humble Dollar who have navigated this path – selling a family business and moving on to whatever is next. We are part way along that journey, and it feels like a good time begin sharing our story. For some background, we own and operate an automotive workshop in a small country town called Heyfield in Victoria, Australia. My Dad is now a 60 year veteran of the automotive industry, having commenced his apprenticeship at 16, and looking to finally exit at the age of 76. Dad tried to exit working life at 68 but found out he was not very good at retirement. He still really needed to be in business, so decided it would be a great idea to buy a workshop in Heyfield that had been on the market for some time. I was 20 years in engineering and project management. I was reasonably successful, so each project got larger than the last. Once the budget got over a certain mark, everything went from interesting and satisfying to very stressful. So owning and operating an automotive workshop sounded pretty good. Over the last 9 years we have exceeded our expectations. We started with no operating software, no customer list, no staff. Just a workshop and a steady trickle of local customers. We have been able to increase to 8 staff, build a really strong customer base and create a steady, profitable business. But with my Dad now well into his seventies, and starting to see 80 on the horizon, we decided that it would be a good time to sell the business. This would give my Dad a chance to try out retirement again – I hope this attempt is better than his last! And at 51 it gives me the…

Wisdom, from the wisest women I know

greg_j_tomamichel | Apr 9, 2026

In his book "Die with Zero", Bill Perkins lays out a framework for how to spend money to maximise your life. Ramit Sethi has his "money dials" to explain how to both enjoy money whilst still building a strong financial base. But I reckon that the two wisest women in my life, specifically my wife and Mum, have it all worked out. And they didn't have to write a book or start a podcast. Mum was raised in a comfortable family home. But as was typical for the time, there was always a focus on saving pennies - turn that light off, shut the door so we don't lose the heat, don't use too much toilet paper. As the years went by and I saw my parents start to have some freedom to enjoy the fruits of their hard work, my Mum never wanted new cars or overseas travel. Instead, she left a light on whenever she wanted, heated the whole house to whatever temperature she pleased, and had more toilet paper on hand than might reasonably be required. For Mum, financial freedom was about breaking the shackles of frugality that she grew up with. Simple, relatively low cost, but meaningful. For my dear wife, Cindy, growing up with a single mother suffering quite complex chronic illness meant that money was always very tight. I'm still amazed at how they managed to get by. So many of the small pleasures that other kids enjoyed were simply out of reach. Cindy seemed to take all of this in her stride. But now that we have some financial flexibility, online shopping provides a pleasant little treat. Nothing that ever moves the needle on our financial health, nor does it fill our house with clutter. But it gives Cindy the thrill of buying…

When to walk away

greg_j_tomamichel | Nov 15, 2025

I'm sure we could swap stories about working particularly hard at some point in our life. Feeling exhausted, worn out, temperamental and not performing at our best. In an ideal world we would avoid such stresses and strains, but in reality going "above and beyond" seems to be part of securing some financial stability, raising a family, buying a house, funding retirement, or whatever your financial goals might be. But a recent local news article got me thinking about where each of us draws the line and says "enough". ABC News (Australia) reports that Miwah Van, a senior executive, is suing Woolworths for discrimination and adverse action. Woolworths is one of our two large supermarket chains. Ms Van has reported suffering from a suspected stroke, temporary blindness and being hospitalised 5 times. A diagnosis of breast cancer and subsequent treatment from her employer also raised claims of bullying. After reading the article, I remain unsure of where any fault might lay. Senior executive roles obviously require a very strong personal commitment, including long hours, high stress levels and a need to shoulder a lot of responsibility. But maybe Woolworths' demands were excessive, putting way too much on Ms Van's plate. Honestly, I don't know. What I do know is that if I was in Ms Van's position, once my health was noticeably suffering, I would have been out of there. I'm sure that Ms Van was compensated handsomely in a senior role with one of our largest companies. But what value is a large salary if the situation sends you to hospital with a stroke? After persisting at Woolworths whilst her health deteriorated, she is now bringing legal action that will no doubt take many months, if not years. That legal action will be stressful. The whole ordeal will be…

Perfection, enemy of good

greg_j_tomamichel | Apr 5, 2026

Like most people, I'll get to feeling overwhelmed. Too many choices, too much complexity, just too much. Once the overwhelm kicks in, there are two ways forward; take a big deep breath and calmly work through the issue, or simply put the whole thing aside. I would like to think that I do more of the former, but as a human being, sometimes it's the latter. And it worries me that when financial advice is broadcast to a wide audience, the vast majority will feel their heads spinning. Like most people here as part of the Humble Dollar community, I would like to think that I've got a good grasp of the basics. But when the discussion turns to tax efficiency, sequence of return risk, inflation hedges and myriad other topics, I can be left feeling a little dazed. So I can just imagine how Joe or Janet Average might feel trying to get their head around these issues. Once Janet or Joe is feeling thoroughly confused, I suspect that it all gets too hard and they take no action to improve their financial situation. In fact, they may even do the opposite and gravitate to a seemingly simple scheme that is "too good to be true", and destroys their financial health. Specifically for retirement preparation, I tend to think that society as a whole would be well served with a very simple approach. Something like: - Put 12% of your wage, or as close as you can possibly get, into a target date fund. - Keep doing this until retirement age. - Once in retirement, always have 3-7 years worth of spending into a high yield savings account. Avoid topping this up on years when your index funds are down. - Keep the remainder in a suitable mix of…

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