Jonathan Clements's Blog, page 4
November 19, 2025
A Retirement Paradox: Why My Retired Friends Judge My Downtime, But Not Their TV
I seem to fit the profile of a typical guy who had the good fortune of retiring in his late fifties. I spend a considerable amount of time doing physical activities: racket sports, cycling, running, hiking. I'm also a keen reader of history, science and financial content. I volunteer my time coaching sports development courses and volunteering at a local church youth group, lots of very fruitful and productive activities to be getting on with.
When you add in working in my large garden, hanging out with my wife and social engagements with friends and family, plus handling the school run and childcare for my grandkids, I really don't get a lot of downtime. I'm also one of those strange individuals who doesn't watch TV with any regularity. But I have, from what I can ascertain, one frowned-upon time-wasting little pleasure I enjoy indulging in.
Video games are that little guilty pleasure. I don't get much time to indulge, but I love a few hours of online killing mayhem playing Call of Duty or a few snatched hours playing Tiger Woods Golf. Nobody I know who's my age ever seems to admit to spending a few hours with a bit of gaming... I seem to be a sample size of one in my social circle.
To be honest, I really don't feel guilty. Why should I? I seem to spend a lot of time listening to my friends discussing the plotlines of the latest Netflix series they devote many happy hours to watching, but if I ever mention my gaming interest, they turn up their nose and suggest I could find better things to do with my limited spare time. What? Watch a miniseries maybe? No thanks.
What strikes me as particularly odd is how arbitrary these judgments seem. Spend six hours binge-watching a Danish crime thriller and you're cultured. Spend two hours playing a strategic video game and you're wasting your life. Both involve sitting in front of a screen, both are forms of escapism. Yet somehow we've collectively decided that passive consumption is respectable while interactive entertainment is frivolous.
Is it a generational thing? Probably. Is it a class thing? Possibly. But mostly I think it's just prejudice dressed up as concern. My friends will happily dissect characters and plot twists from their latest streaming obsession for an entire dinner party, but mention that I've just completed a particularly challenging mission and the conversation dies. The implicit message is clear: your hobby is less valid than mine. But nobody can quite articulate why.
I suspect there are more of us out there than anyone realizes, closet gamers of a certain retirement age, quietly enjoying our hobby while everyone else assumes we're watching Masterpiece Theatre or tending roses. If you're one of them, consider this your invitation to come out of the shadows. We're not harming anyone, we're having fun, and honestly, our hand-eye coordination is probably better than most of our Netflix/Britbox watching peers. Game on.
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Cash Delivered to Your Door: What Could Possibly Go Wrong?
The Wall Street Journal reported last week that the brokerage Robinhood is partnering with Gopuff to deliver cash directly to customers’ homes. For $6.99 (or $2.99 if you’ve got over $100K in your account), skip the teller, skip the ATM, and get your money in a sealed paper bag at your doorstep.
I’m already picturing it: an alert pops up—“Your money has been delivered!”—complete with a photo of a cash bag on my front stoop next to the Amazon delivery. Brokerage firms have been competing with traditional banks since the introduction of the money market account, which gave brokerage clients daily liquidity and check-writing privileges. Now, like Amazon, challenging Walmart with delivery, Robinhood challenges your corner bank with delivery.
What could go wrong? asks the guy who runs an app helping seniors avoid financial fraud.
Start with everything that already happens at banks: miscounts (happened to me), wrong denominations, and the fact that criminals target people leaving banks with cash. At least banks have security cameras recording everything that can be used to identify the crooks after the fact.
Now picture this: A delivery driver on a moped pulls up with a box marked “Robinhood.” (Mel Brooks would have them in tights, no doubt.) Your nosey neighbors notice: “The Neighbor got a cash delivery today.” Mmaybe it becomes a status symbol. A Mercedes parked in the driveway that we do not have to drive, as we get everything delivered. Maybe that is no different than being spotted at the bank or ATM.
Except it is different-you have lost security and opened another door to your wealth. Someone across town hacks your account—or has “befriended” you. The hacker changes your address today and tomorrow, rerouting the cash delivery. Or they wait at your door, pretending to be you. Or they hold you at gunpoint inside while signing for the cash—no security cameras. No witnesses.
Maybe withdrawal limits will be small enough that criminals won’t bother. Maybe. But what amount makes it worthwhile for the bad guys? What limit is so small that you would not use the service?
Speed is a double-edged sword. In today’s mostly cashless world, with Zelle and Venmo readily available, I see far more ways cash delivery exposes people—especially seniors—to unnecessary risk than legitimate use cases. Ask yourself, how often do you really need cash?
Here’s the truth about convenience: ease for the consumer means ease for the swindler.
Yes, two-factor authentication is a hassle. Seat belts are uncomfortable. They also save lives. By one estimate, financial frauds cost people $400 million a day. Many do not get reported because people are too embarrassed to admit that their Romeo swindled them, or that their best friend broker invested in his son’s pizza business.
Maybe you’re working now and can absorb a loss to a scammer. But once you retire? Financial setbacks are hard to recover from when you have no income. The good news: you’re not punching a clock anymore. You have time. How long does it take to drive to the bank or to pay via Zelle? That’s nothing compared to the loss.
Use time to your advantage. Slow down the money movement.
Matt Halperin, CFA, is the founder of Act2 Financial, an app that helps seniors avoid financial fraud. For 30 years, he worked as a portfolio manager and risk manager at large U.S. money managers. Matt currently serves on the investment committee of two endowments. He has a BA and MBA from the University of Chicago, and resides outside of Boston.
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What I Learned Trying to Leave an Employer-Sponsored Medicare Advantage Plan
A Cautionary Tale: What I Learned Trying to Leave an Employer-Sponsored Medicare Advantage PlanThis is the story of a friend I helped when she tried to move from her employer’s Group Medicare Advantage plan to Original Medicare and a Supplement. Her experience is a cautionary tale.
I want to share this story because I don’t want others to go through the stress, confusion, and sleepless nights that we did.
When I retired, the company I worked for offered my husband and I a Medicare Advantage plan ,along with a $50,000 Future Health Account credit. This credit could only be used for this specific Group Medicare Advantage plan. It sounded like a great deal. For almost three years, that account covered all our premiums and most out-of-pocket expenses. The plan had a $750 maximum for each of us and worked fine—at first.
But then, almost by accident, I learned that the premiums for 2026 were going to nearly double. No letter. No notification. Nothing. I only found out because I called to ask.
That was the moment I realized how vulnerable we really were.
Trying to Switch: Where the Stress BeganWe decided to look into moving to Original Medicare + a Supplemental Plan (Medigap). We wanted to be able to go to the top hospitals and see the best specialists if we needed care.
We started working with an agent who walked us through the Medicare landscape. It was helpful—I knew I would need to pass the medical underwriting requirement, and initially I thought I would be able to do so.
To switch to a Medigap plan outside your initial window, you must “pass” medical underwriting in most states:
The questionnaire was one page. It seemed pretty simple at first. Since I had chronic asthma, my Medicare insurance agent thought only one plan - United American would take me.They look at your medical records.Even one note or referral buried in your chart can change everything.I decided to double check my medical records myself and it is a good thing I did.
My doctor had pre-authorized knee surgery if injections didn’t work. Even though I’m doing great with injections and feeling fine, that note alone could have meant future claims could be denied under a medically underwritten plan. The insurance companies will go back through your records to try to deny your large claims.
That realization stopped me in my tracks.
The Confusion and the FearThe agent believed that if I dropped my corporate Group Medicare Advantage plan, my husband would be automatically dropped as well and would receive Guaranteed Issue for a Medigap plan (meaning no underwriting required). He said this confidently.
But I needed it in writing. The corporation I had worked for outsourced all of the retiree benefits to a third party. I could not call my previous employee for any information. I had to talk to the third party and my Medicare Advantage provider.
I made:
Five phone callsSpoke to five different representativesReceived five conflicting answersNo one would put anything in writing.
Every call left me more anxious. I didn’t want to gamble with our healthcare. I didn’t want one wrong move to leave us at risk or uninsured.
That is when the panic started to set in.
I was luckier than most.This is where learning my state’s Medigap protections changed everything. By poor dumb luck, I found out that Illinois had a small loophole with one insurance company.Because of a special Illinois rule, people 65 and older can get Medigap coverage each year without medical underwriting, but only through the specific higher-cost Blue Cross Blue Shield of Illinois plan.
We didn’t have to pass the medical underwriting.We could get Blue Cross Blue Shield of Illinois directly.We could stop depending on my previous employer, the third party and my Medicare provider for answers they wouldn’t give us.
This meant:And something else we didn’t know:
I can reapply anytime during the year. If my knee improves, or even if I go through surgery, after surgery and PT, I can pass the medical questions and qualify for a lower premium. That flexibility does not exist with Medicare Advantage.
The Emotional RealityThis process wasn’t just confusing—it was scary.
We felt:
powerless against large insurance companiesunsure who to trustafraid of making one wrong move that could cost us access to care laterI had to make all of my decisions and get through this process by December 7th- the end of Medicare Open Enrollment. If I made the wrong decision, we could lose our healthcare.
It should not be this hard.
Where We LandedWe are approved for the BCBS of Illinois Medigap plan beginning January 1, 2026.
Yes, we are paying a slightly higher premium today.
And it is still about $700/year less than staying in the Employers Medicare Advantage plan once the new premiums hit.
More importantly:
We can go to any hospital and see any specialist without prior approval. This is better than the insurance I had while employed.We are no longer at the mercy of yearly plan changes. Nearly 1 in 5 health systems—about 20%—stopped accepting one or more Medicare Advantage plans just in the past year.We can relax, knowing we won’t face a surprise denial when we need care most.
What I Want Others to Know Employer subsidized Medicare Advantage plans feel generous—but they can become golden handcuffs.
Once health changes, switching may be impossible. Check your medical records before answering underwriting questions.
What’s written there can change everything. Insurance companies may go through your records to deny claims and increase profits. Only you can decide whether the extra cost is worth having the freedom to go to the top hospitals and the best specialists without needing prior approval.The LessonWe were lucky—truly lucky—to get out when we did.
Many people don’t realize that Medicare Advantage is easy to get into but can be very hard to get out of once real health issues begin.
If I could give just one message to anyone approaching Medicare:
Do not choose based on today’s health.
Choose based on what you will need when you are sick.Because that is when the differences matter most
If you’d like to make the best Medicare decision for you or your parents watch Medicare:What the insurance companies won’t tell you.
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November 18, 2025
Which Brokerage Works Best for U.S. Expats?
1. Charles Schwab — Best for U.S. Expats
Schwab is easily the most expat-friendly of the major brokerages. It allows U.S. citizens abroad to open and maintain accounts, including its dedicated Schwab International Account. Trading stocks and ETFs is usually unrestricted, customer service understands expat needs and the linked Schwab Bank makes moving money internationally simple.
Bottom line: The smoothest choice for most expats.
2. Fidelity — Works Only If You Already Have It
Fidelity generally won’t open new accounts for Americans living overseas. Existing customers can usually keep their accounts, but certain trades—especially mutual funds—may be limited.
Bottom line: Fine if you already use Fidelity, but not ideal for new expats.
3. Vanguard — The Most Restrictive
Vanguard typically requires a U.S. residence for full service. Expats often face blocked account openings and limits on buying Vanguard mutual funds from abroad.
Bottom line: Usually not practical for Americans overseas.
Recommendation
For U.S. citizens living abroad, Charles Schwab stands out for flexibility, access and expat-friendly policies.
_________________________________________________________
I personally use Vanguard, I am considering making a change. But I am not sure the juice is worth the squeeze.
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November 17, 2025
Four People, One Stupid Observation
I've a sore back and I'm a bit irritated at the moment, but not because of the lower back pain, but another more irritating pain, namely people. I spent today locked in combat with the leaves in our garden, a battle I was destined to lose, as four separate pedestrians felt compelled to inform me. There I was, hunched over, rake in hand, working the grass verge out front. This is where things got interesting, by which I really mean deeply irritating.
The first passerby offered his observation with the casual confidence of someone delivering profound wisdom: "What's the point? Sure, more leaves are going to fall." I smiled. I nodded. I may have even chuckled in that way you do when you're pretending someone has said something delightful rather than something that makes you want to fling your rake at them.
Then came pedestrian number two. "What's the point? More leaves are going to fall." By the third iteration, I'd begun to wonder if I was trapped in some very dull episode of The Twilight Zone. The fourth person sealed it. Same comment. Same self-satisfied tone. On each occasion I agreed with them. "You're absolutely right." And then I carried right on working, because, and this seemed to have escaped my stream of sidewalk philosophers, there's always a point.
To me, it's a spectacularly poor attitude to think there's no point in trying. I couldn't help wondering how many of these people applied this logic elsewhere. Take housing. Saving for your first deposit requires financial discipline and the patience of someone waiting for the repair company. But adopt the "what's the point?" philosophy, and you've signed yourself up for a lifetime subscription to the Rent-Forever plan, missing out entirely on property value gains.
Or retirement savings. "What's the point? I'll never save enough anyway." Well, yes, if you don't save anything, that prediction will be remarkably accurate. It's the same logic as saying, "What's the point of eating? I'm just going to get hungry again." Technically true, but missing something rather fundamental about survival.
The leaves will fall again. Absolutely. Probably tomorrow. But here's what my advisory committee of sidewalk philosophers failed to grasp: the point isn't achieving some permanent, leaf-free utopia. The point is that right now, my garden looks better. The grass can breathe. I've done something rather than nothing.
Small, consistent efforts compound into something resembling progress, or at least prevent complete disaster. Acknowledge that more leaves will fall, that's just life. But if your response to every difficult task is to shrug and say, "What's the point?" you're in for a messy garden, an empty savings account, and a very long lifetime of wondering why nothing ever works out.
Me? I'm going to keep raking. Tomorrow, when the leaves have fallen again, I'll probably rake those too. Because the alternative is surrendering to shortsightedness, and shortsightedness doesn't need my help…anyway, What's the point?
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I think billionaires are under appreciated
Of course that is exactly what we do. Everyone is subject to the IRC and the same type of income is taxed the same way for all. I think billionaires get a bad rap.
A 2021 study by economists from the Council of Economic Advisers and the Office of Management and Budget, using data from Forbes and public records said the top 400 wealthiest taxpayers paid an average income tax rate of 8.2%. Many people jumped on that as proof these folks were grossly undertaxed. However, to arrive at that percentage, the growth in net worth from unrealized capital gains was used. Hardly apples to apples.That’s like including the growth in your home value and 401k to determine your effective tax rate.
Nevertheless, I have decided to become a billionaire myself. I have the same chance as anyone, but time may not be on my side.
I invest in the stock market, in a single company stock and in real estate. That’s what billionaires do. I don’t have a garage or dorm room to start a business, but there are other ways. Unfortunately, I don’t have the entrepreneurial skills or desirable personality either.
On the other hand upon realizing that one billion is one thousand million, and looking at my current net worth, I have the same chance as Don Quixote.
Are billionaires self-made? Most are, but even those who inherited big bucks, inherited it from someone who did earn it. The Waltons are a good example. Some of the wealthy inherit a nice nest egg and then grow it on their own.
I look at a list of some well known billionaires and think to myself about how they changed the world, made life better, more pleasurable for the rest of us. About the millions of jobs they created around the world and about the many other small businesses that thrive by leveraging what the entrepreneurs created.
Steve Jobs / Steve Wozniak Jeff Bezos, Mark Zuckerberg, Larry Page & Sergey Brin, Elon Musk, Michael Dell, Larry Ellison, Reed Hastings, Brian Chesky, Joe Gebbia, Daniel Ek, Evan Spiegel, Jack Ma, Sam Walton, James Sinegal, Philip Knight, Oprah Winfrey, George Lucas, Ralph Lauren
Many of the people on this list did the same thing, they took risk, created something, eventually issued an IPO while holding millions of shares and let the stock market take over. And then they diversified.
While many Americans envy such actions, the Philadelphia Fed found only 42.8% of U.S. adults personally own stocks. Pew Research Center, says only 21% of American families own individual shares directly. Roughly 60–65% of Americans have some exposure to the stock market through retirement accounts like 401k, but relatively few invest directly-many fear the risk. The thing is you don’t need big bucks to get started. Getting ahead requires constant change, growth, a bit of risk. You won’t improve your economic standing working in a minimum wage job relying on increases in the minimum wage.
To be honest, if they never paid a penny in income taxes, I think society at all income levels more than receives its moneys worth from these billionaires.
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My new goal is to be a billionaire, but me thinks I should have started my quest sooner. At least I benefit from those who made it.
If you win a million dollars in a lottery, you will pay approximately $370,000 in federal taxes. An X post complained about the tax on such a windfall and said that we should tax billionaires the same way.
Of course that is exactly what we do. Everyone is subject to the IRC and the same type of income is taxed the same way for all. I think billionaires get a bad rap.
A 2021 study by economists from the Council of Economic Advisers and the Office of Management and Budget, using data from Forbes and public records said the top 400 wealthiest taxpayers paid an average income tax rate of 8.2%. Many people jumped on that as proof these folks were grossly undertaxed. However, to arrive at that percentage, the growth in net worth from unrealized capital gains was used. Hardly apples to apples.That’s like including the growth in your home value and 401k to determine your effective tax rate.
Nevertheless, I have decided to become a billionaire myself. I have the same chance as anyone, but time may not be on my side.
I invest in the stock market, in a single company stock and in real estate. That’s what billionaires do. I don’t have a garage or dorm room to start a business, but there are other ways. Unfortunately, I don’t have the entrepreneurial skills or desirable personality either.
On the other hand upon realizing that one billion is one thousand million, and looking at my current net worth, I have the same chance as Don Quixote.
Are billionaires self-made? Most are, but even those who inherited big bucks, inherited it from someone who did earn it. The Waltons are a good example. Some of the wealthy inherit a nice nest egg and then grow it on their own.
I look at a list of some well known billionaires and think to myself about how they changed the world, made life better, more pleasurable for the rest of us. About the millions of jobs they created around the world and about the many other small businesses that thrive by leveraging what the entrepreneurs created.
Steve Jobs / Steve Wozniak Jeff Bezos, Mark Zuckerberg, Larry Page & Sergey Brin, Elon Musk, Michael Dell, Larry Ellison, Reed Hastings, Brian Chesky, Joe Gebbia, Daniel Ek, Evan Spiegel, Jack Ma, Sam Walton, James Sinegal, Philip Knight, Oprah Winfrey, George Lucas, Ralph Lauren
Many of the people on this list did the same thing, they took risk, created something, eventually issued an IPO while holding millions of shares and let the stock market take over. And then they diversified.
While many Americans envy such actions, the Philadelphia Fed found only 42.8% of U.S. adults personally own stocks. Pew Research Center, says only 21% of American families own individual shares directly. Roughly 60–65% of Americans have some exposure to the stock market through retirement accounts like 401k, but relatively few invest directly-many fear the risk. The thing is you don’t need big bucks to get started. Getting ahead requires constant change, growth, a bit of risk. You won’t improve your economic standing working in a minimum wage job relying on increases in the minimum wage.
To be honest, if they never paid a penny in income taxes, I think society at all income levels more than receives its moneys worth from these billionaires.
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November 16, 2025
Another week, another data breech notification letter…
This past week I received notice that my radiologist’s office experienced a “data security event”. Name, social security number, date of birth, driver’s license, incriminating pictures of my herniated lumbar disc, etc., could have been obtained. I’ve lost count of how many similar letters I, my spouse, and my children have received over the past years. For early ones, I took them up on their offer of one free year of credit monitoring. Several years ago, I placed a credit freeze on all three of the credit monitoring bureaus for everyone in my family.
Now I am wondering if I even need to react to this latest data breech, or future ones. The free one-year service offers “basic dark web monitoring” for name, DOB, SSN, email, and also offers “change of address monitoring”. But other than those features, my credit freezes exceed what they offer. If I sign up with “epiq Privacy Data Solutions ID” to use the one-year free monitoring, I have to enter my SSN, DOB, email address, name, & address, exactly the information I do not want to be spreading out to additional companies who could be broken into in the future. I do realize this whole thing could be a scam to obtain my SSN, DOB, email address, name, & address; the letter came from a “Secure Processing Center” in another state and had a header logo and correct lead physician name of the local radiology office. I could call the local office to verify if the letter is legitimate. But if it is legitimate, I come back to asking myself if I even need to react to data breeches anymore, given my credit freezes in place.
I am thinking I will start ignoring these data breeches. Thoughts?
Thanks in advance.
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Why would index investing be different?
From Benjamin Graham in 1972: “Any approach to moneymaking in the stock market which can be easily described and followed by a lot of people is by its terms too simple and too easy to last.”
Why wouldn’t this apply to indexing?
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The Messy Human side of Social Security Claiming
American social security advice is admirably clear, I'll give you that. Delay Social Security until seventy to maximize your monthly benefit and create the ultimate hedge against outliving your savings. The maths is clear and unarguable, an eight percent per year, guaranteed return for every year you wait past your Full Retirement Age. It's presented with such confidence, if only one's life was such a tidy actuarial table.
But for millions of Americans, watching this from my perch in the UK, the decision of when to claim benefits is decidedly not a math problem. It's a human story, a deeply personal calculation of current utility, health, and peace of mind that often trumps the pursuit of the largest possible future check. There's something almost cheeky about a spreadsheet trying to tell people how to live, regardless of which side of the Atlantic one resides on.
The most common reason for claiming early, between 62 and 67, is refreshingly simple: need. A job loss in one's early sixties, an unexpected medical crisis, or the crushing weight of high-interest debt can quickly turn a retirement plan into a rather urgent struggle for solvency. In these scenarios, the immediate infusion of cash from a Social Security check, even a reduced one, becomes a lifeline, not some theoretical optimization problem.
It provides financial stability today, right now, ensuring bills are paid and high-interest debt is eliminated before it transforms into something truly ghastly. For many Americans, the peace of mind derived from having a consistent income floor now, when they need it most, is far more valuable than the promise of a bigger check a decade down the road. The models seem to forget people are actually living these years, not just calculating through them.
The mathematical model rests rather optimistically on the assumption that you'll live long enough to reach the break-even age, typically around eighty, and collect enough of the higher payment to justify the delay. Lovely theory.
But what if health conditions or family history suggest a shorter lifespan? What if you've watched your father, two uncles, and your older brother all depart this mortal coil before seventy-five? For those facing such cheerful realities, delaying benefits becomes a gamble they cannot afford to win, or rather, cannot afford to lose. The goal shifts from maximizing the dollar amount to maximizing the enjoyment of the money they contributed over decades of work. Taking the benefit early ensures they receive their due while they're alive and well enough to actually use it for travel, hobbies, or simply reducing the financial stress that can accompany poor health. The spreadsheet people rarely account for the utility of joy.
For married couples, the claiming decision often revolves around longevity insurance for the lower-earning spouse. The highest earner delaying until seventy creates the largest possible survivor benefit, a decision that protects their partner from potential poverty later in life. Very sensible, really, assuming everyone cooperates by living to the appropriate age.
The opposite can also be a utility play, and a rather sensible one at that. If the higher earner is in poor health, claiming early, even a reduced benefit, ensures the household has access to that cash flow when they need it most, rather than leaving the couple cash-strapped in their early retirement years while waiting for an uncertain future benefit. It's all well and good to maximize survivor benefits if you're around to see your spouse actually receive them, but living on rice and regret for eight years hardly seems like optimal retirement planning.
Social Security is a foundational retirement pillar that must be built on one's real-life circumstances, not just a spreadsheet that's never had to choose between medication and heating. The greatest utility may not be the largest final number, but the benefit that provides the most security, comfort, and opportunity during the time you need it. 62 is definitely not ideal, 67 is much better and 70 is perfect…it's just a shame life is messy and human need has to come before logic for many ordinary people. Sometimes you have to come out of the high castle and meet the common folk.
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