Intelligent Investing

Insightful. Independent. Innovative.

Hans Blake, CFA, CPA

Twenty Years as a Customer Wasn’t Enough for Free Checks

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Reading Time: 4 minutes

Stark big box hardware store compared to warm local friendly hardware store

A Phone Call That Should Have Been Simple

I’ve banked with the same local bank for more than twenty years. Long enough that I don’t remember which president was in office when I opened the account. Long enough that I’ve carried a decent balance through most of it, without much drama on either side.

Recently I called them with a small request. I needed a new set of blank checks. Nothing complicated. I was hoping, given two decades of history and a balance that’s never given them a reason to worry, that they might just send me a checkbook and a register at no charge.

Instead, I was told I could get a free checkbook — but only if I upgraded to a different account tier. They assured me my current balance would easily qualify. Which is true. It also wasn’t the point.

The Part That Bothered Me

I told the representative I don’t like babysitting these things. Tiered accounts come with conditions. Balances dip below a threshold — because of a big purchase, a slow month, a transfer that hasn’t cleared yet — and suddenly there are fees where there weren’t any before. I’d be signing up for a new set of rules to watch, in exchange for something that should have just been a courtesy.

They told me there was really no way around that.

I don’t buy it. A bank that size can absolutely mail a longtime customer a set of checks without making him re-paper his entire account relationship first. What they can’t seem to do is make that decision without a system telling them to.

That’s not a story about one bank being unusually stingy. It’s a pattern. Big financial institutions have gotten very good at finding small, defensible-sounding reasons to charge for things that used to just be part of the relationship. Thirty dollars for shipping a booklet of paper. A tier you have to opt into to get treated the way loyalty probably should have already earned you.

Two Types of Hardware Stores

There’s a hardware store near where I live that gives you a small bag of popcorn when you walk in, and if you’re standing in an aisle looking confused, someone walks you straight to the drawer with the exact screw you need.

Compare that to when you go to the big box hardware stores (think dark blue or orange) doing the same errand of needing a screw. You walk in, you’re on your own, and you’re quietly praying someone in an orange vest happens to be within shouting distance of the hardware aisle, and not on break.

Both stores sell screws. Both will get the job done. But one of them is built around helping you find what you need correctly, and quickly. The other is built around volume, and the help you get is more or less a matter of luck and staffing that day.

Banking, investing, and financial advice work on a similar spectrum. Some of it is structured for scale — a lot of customers, moving through a lot of confusing tiers and complex products, with internal rules on how to nickel-and-dime the public. Customers are just another number.

At our boutique wealth firm, we operate independently (think independent book store, or coffee shop). We work 100% for our clients, with no “back-office deals” like revenue sharing, where a third party pays us if we put our clients into certain funds. We do not sell products, nor get paid commissions. 

Both approaches are not the same thing, and it’s worth knowing which one you’re working with.

Whose Side of the Table Are They On?

At Intelligent Investing, we’re a fee-only, fiduciary firm. We are paid directly by our clients for the amount of wealth we are managing for that client — not a commission, not an insurance product, not a third party paying us to make a recommendation. Also, not charging separately, or charging more for a financial plan. (This has recently crept up in years by other financial firms as a way to make more revenue)

I’d be lying if I said this makes every financial decision effortless. It doesn’t. Markets are still uncertain. Tax rules still change every year, sometimes in ways that genuinely surprise even people who follow them closely. Humans have a broad range of emotions and financial backgrounds that we uniquely guide, in order to remove the emotions from the portfolio, and be their accountability partner. Nobody, including us, can promise a particular outcome, and anyone who tells you otherwise is selling something. However, we work together to discover your goals and time line. We then create an Intelligrations® plan together, and from that plan, comes a portfolio that aligns with your risk tolerances. 

There’s a real difference between an institution that’s built to serve a lot of people through products, and one that’s small enough, and nimble enough, to just handle the request our clients need without all that red tape.

Worth Asking About Your Own Setup

I didn’t write this to complain about a checkbook. Thirty dollars isn’t going to change my financial life. But it’s a small, honest window into something bigger: the incentives built into the institutions holding your money, and whether those incentives are quietly working for you or around you.

It’s worth asking your own bank, brokerage, or financial advisor a plain question: when you make a simple request, does the answer depend on their protocols — or on what actually makes sense for you? 

If you’re not sure how to answer that about your own financial accounts, we’d love to have a chat and give you a second opinion.

Our passion is to minimize your financial stress, so you can focus on maximizing your life.

Is Your Financial Firm working for you?

If you’re not sure if your financial firm is working only for you, then let’s talk. We’d love to have a deep, honest conversation about your goals, your legacy, your tax situation, and risks, and what a plan built on truth and transparency actually looks like.

Schedule a Conversation

 

Disclosure: This blog may reflect the perspectives and research of Intelligent Investing and, where applicable, incorporates insights from guest interviews or expert opinions. Any external views or opinions shared do not necessarily reflect the stance of Intelligent Investing. We may also utilize tools such as ChatGPT to enhance readability, grammar, and flow, while all core ideas remain proprietary to our firm.
Please note that Intelligent Investing does not provide specific tax or legal advice. All investments carry risks, including the potential loss of principal, and past performance is not indicative of future results. Any specific securities, sectors, or investment strategies mentioned are for informational purposes only and should not be considered a recommendation. We encourage readers to consult with Intelligent Investing for advice tailored to their unique financial situation. Unauthorized reproduction or distribution of this content is prohibited without proper credit to Intelligent Investing.

The Tension Between Saving Money and Living Life

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Reading Time: 5 minutes

 

The Spreadsheet That Never Sleeps

Over the years, I’ve noticed a pattern among a certain kind of client. Often — though not always — an engineer by training. Methodical. The kind of person who built a savings spreadsheet sometime in their thirties, updated it faithfully every year since, and can tell you their net worth to the dollar without opening the file.

That discipline is exactly why they’re sitting across from us with $1 million or more saved. It worked. In fact, it worked for twenty-five or thirty years.

And then retirement arrives, and the same discipline that built their nest egg becomes a sort of trap standing between them and their money. The income faucet gets turned off, and their spreadsheet can’t accommodate all the risks, assumptions, and factors they may face over the next 30-40 years of retirement. They also have a hard time distributing from their fortified nest egg.

The Real Question Isn’t Math

Here’s the part that surprised me the first few times I saw it, but doesn’t surprise me anymore: the hardest conversation in retirement planning usually isn’t about returns, fees, risk, or asset allocation. It’s about permission.

Somewhere along the way, “save more” became identity, not just strategy. Disciplined people form habits. But in a twist of irony, breaking that habit of saving is difficult to break. Flipping that switch — going from accumulate to spend — isn’t a math problem. The math can say yes. The spreadsheet can be airtight. And the person who built it can still feel like they’re doing something wrong every time they book a flight to visit their grandchildren.

I want to be fair, because the instinct isn’t irrational. It’s the same discipline that got them to where they are. Nobody accidentally saves a million dollars. The caution that feels like an obstacle in retirement is the same caution that made retirement possible in the first place. They were faithful in spending less than they earned for years.

But a plan that doesn’t account for spending in retirement isn’t a plan. The downside is that it trades real experiences with family while you can, for a bigger legacy that your kids may not be prepared for mentally.

Three Phases, Not One Long Retirement

J.P. Morgan has a useful way of thinking about this that I like: retirement isn’t one flat period. It tends to move through three phases.

  1. The go-go years — roughly the first decade after retirement, when health and energy are highest and travel and activity tend to be at their peak.
  2. The slow-go years — the following decade or so, when the pace naturally eases.
  3. And the no-go years — the final phase, when travel becomes limited and priorities shift toward health, care, and often a very different kind of budget.

The reason this framework matters isn’t the labels. It’s the reminder that the money saved for “retirement” isn’t meant to be spent evenly across thirty flat years. The go-go years are often the only years where a certain kind of spending — travel, in particular — is even physically possible. I spoke to a gentleman recently who had been on over 50 cruises, and he said, “I do it because one day, I may not be physically able to do it.” A dollar not spent in the go-go years doesn’t necessarily get spent later. Sometimes it just goes unused. During the no-go years, spending shifts dramatically toward healthcare and away from travel.

What “Probability of Success” Is Actually For

This is where stress testing earns its keep, and it’s also where I think a lot of retirees get more comfort than they expect.

One of the things we’re able to show clients through the planning software we use is a probability of success number — a way of asking, given everything we know today, how sound this plan looks if spending increases, if travel goes up, or if the market has a rough few years right after retirement — a risk retirees carry that’s sometimes called sequence of return risk: the danger of a downturn landing early in retirement, when withdrawals are happening at the same time the portfolio has less time to recover.

Even though we can’t predict the future, what we can do is run your financial plan through different scenarios. We stress test the plan. We revisit your Intelligrations® plan every year, because markets change, health changes, and your spending will change. A plan built on this year’s assumptions is worth updating with next year’s facts.

In fact, our software gives clients access to their financial plan and lets them, in a “sandbox playground” sort of way, modify their assumptions and goals without touching the official plan. This gives them the psychological freedom to see whether buying that dream car they always wanted will harm their plan. That freedom is valuable. We often see clients’ faces light up when they realize, mathematically, that they have permission to follow their dreams.

The goal isn’t a guarantee. It’s a written plan a client can actually look at and ask, “given everything we know, is this still solid?” — and get an honest answer, updated annually, instead of guessing once and hoping for the best.

When One Spouse Wants to Go and the Other Wants to Wait

There’s a second version of this same tension, and it shows up almost as often: one spouse ready to spend and enjoy the years they worked for, the other nervous every time a big trip gets booked.

Neither position is wrong. One partner is usually thinking about experiences while there’s still health and energy to enjoy them. The other is usually thinking about what happens if the money runs short later, or if something unexpected — health, family, a market downturn — changes the picture. Both concerns are legitimate. They’re just aimed at different points on the same timeline.

What I’ve found helps most isn’t persuading one spouse to think like the other. It’s putting real numbers in front of both of them — the same plan, the same stress test, the same probability of success — so the conversation moves from a disagreement about feelings to a shared look at facts. Often, that’s enough to get two people who’ve been talking past each other for years back on the same page.

Before the Ink Dries

No plan survives contact with reality unchanged. Markets move. Health changes. Priorities shift once the grandchildren show up or the knees stop cooperating. That’s not a flaw in planning — it’s the reason a plan gets revisited every year instead of filed away once and forgotten.

If any of this sounds familiar — a spreadsheet that’s hard to stop feeding, or a spouse who’s ready to go while the other one hesitates — it might be worth putting real numbers behind the conversation instead of having it in the abstract.

We’d love to demo our proprietary Intelligrations® and show you what a sample Intelligrations® report looks like.

We love to minimize your financial stress, so you can focus on maximizing your life.

Is Your Current Plan Flexible enough to survive retirement changes?

We want to have a complimentary call or coffee with you, if any of the above is what you are struggling with. We love helping couples figure this stuff out in a casual, pressure-free meeting where we can listen to your needs. Reach out and let us know how we can help. Don’t try and do it alone, as you only get one chance to get it right.

Schedule a Conversation

 

Disclosure: This blog may reflect the perspectives and research of Intelligent Investing and, where applicable, incorporates insights from guest interviews or expert opinions. Any external views or opinions shared do not necessarily reflect the stance of Intelligent Investing. We may also utilize AI tools to enhance readability, grammar, and flow, while all core ideas remain proprietary to our firm.
Please note that Intelligent Investing does not provide specific tax or legal advice. All investments carry risks, including the potential loss of principal, and past performance is not indicative of future results. Any specific securities, sectors, or investment strategies mentioned are for informational purposes only and should not be considered a recommendation. We encourage readers to consult with Intelligent Investing for advice tailored to their unique financial situation. Unauthorized reproduction or distribution of this content is prohibited without proper credit to Intelligent Investing.

If the Fed Didn’t Do Anything, Why Did the Market Move?

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Reading Time: 4 minutes

 

The Question I Keep Getting This Week

“If the Fed didn’t do anything, why did my portfolio move?”

I’ve had some version of this conversation more times than I can count over the past few days. A client sees a headline that says the Fed held rates steady, then opens their statement and sees stocks or bonds moved anyway. It feels like a contradiction. It isn’t.

Markets are forward-looking. They don’t just react to what happened in a meeting room in Washington. They react to what that meeting tells us about what’s likely to happen next. A “hold” is not nothing. It’s information. And sometimes information changes minds even when it doesn’t change rates.

Markets Trade the Future, Not the Present

Here’s the simplest way I can put it: by the time the Fed announces a decision, markets have usually already priced in what they expect. The move you see afterward is the gap between what was expected and what was actually said or signaled.

If the Fed holds rates steady but its language, its forecasts, or its tone shift even slightly, that’s new information. Maybe the market had priced in a strong chance of a future cut, and the Fed’s comments made that look less certain. Maybe the opposite happened. Either way, the rate itself didn’t move — but the expectation of where rates are heading did. And expectations are what asset prices are built on.

This is worth sitting with, because it explains a lot of confusing market days. The news can say “no change” and the market can still swing. Both things are true at once.

The Fed’s Two Jobs

It helps to remember what the Fed is actually trying to do. Its mandate, set by Congress, has two parts. Keep prices stable. Keep employment as high as sustainably possible.

Those two goals don’t always pull in the same direction. Fighting inflation often means slowing the economy down, which can cost jobs. Supporting employment often means keeping money cheap, which can let inflation run hotter. Every meeting, every statement, every “hold” or “cut” or “hike” is the Fed trying to signal how it’s weighing those two competing goals in that moment.

When you view Fed decisions through that lens, a hold makes sense as its own kind of statement. It can mean “we think we’re close to the right balance for now.” It can mean “we need more data before we move again.” The market’s job is to guess which one it is — and adjust.

A Fed That Wants to Talk Less

There’s a development this week that’s relevant here, even though it’s a little inside baseball.

According to reporting on people familiar with the matter, Fed Chairman Kevin Warsh has floated with colleagues the idea of the Federal Open Market Committee meeting less often — perhaps six times a year instead of the current eight. It was described as a subject for discussion, not a formal proposal, and this came during only his second meeting presiding over the 12-person committee. The idea was reported earlier by the New York Times.

Whether or not this idea goes anywhere, it tells you something. It suggests a Fed under Warsh that wants to speak less frequently and command less of the market’s constant attention.

I find that interesting, because so much of what moves markets in between meetings isn’t policy — it’s commentary. Speeches, minutes, press conferences, stray comments from officials. A Fed that meets less often, by design, would be handing markets fewer opportunities to overreact to language and more reason to focus on actual data and outcomes.

I don’t know if that shift happens, or how the committee would actually vote on it. Nobody outside that room does yet. But it’s a reminder that the process of Fed communication is itself something that shapes market behavior — separate entirely from whether rates go up, down, or nowhere at all.

What Intelligent Investors Should Do

The wiser posture, in my view, is not to try to out-guess the Fed or the market’s reaction to the Fed. It’s to build a portfolio and a financial plan that doesn’t depend on guessing correctly meeting after meeting.

That doesn’t mean ignoring what’s happening. It means understanding why markets moved — without feeling compelled to trade on it. A Fed holding rates that resets expectations for future cuts is exactly the kind of moment that tempts people into action. It’s also exactly the kind of moment where patience tends to be rewarded more than reflexes.

Where This Leaves Us

Nobody — not me, not the Fed, not the sharpest analyst on television — knows with certainty where rates go from here, or how many more meetings it will take to get there, or whether the FOMC will actually start meeting six times a year instead of eight.

What we can do is understand the mechanics well enough not to be spooked by headlines that seem contradictory on their surface. A quiet meeting can still move markets. That’s not a flaw in the system. That’s the system working the way it’s supposed to.

If you’ve been staring at a headline this week trying to figure out what it means for your own plan, that’s a good conversation to have — not a decision to make alone based on a news alert. Our goal is always to help you minimize your financial stress so you can focus on maximizing your life.

Schedule a Conversation

 

Disclosure: This blog may reflect the perspectives and research of Intelligent Investing and, where applicable, incorporates insights from guest interviews or expert opinions. Any external views or opinions shared do not necessarily reflect the stance of Intelligent Investing. We may also utilize tools such as ChatGPT to enhance readability, grammar, and flow, while all core ideas remain proprietary to our firm.
Please note that Intelligent Investing does not provide specific tax or legal advice. All investments carry risks, including the potential loss of principal, and past performance is not indicative of future results. Any specific securities, sectors, or investment strategies mentioned are for informational purposes only and should not be considered a recommendation. We encourage readers to consult with Intelligent Investing for advice tailored to their unique financial situation. Unauthorized reproduction or distribution of this content is prohibited without proper credit to Intelligent Investing.

Lindsey Graham Died Worth Only $1.4 Million — Here’s What That Actually Tells Us About Wealth

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Reading Time: 5 minutes

A Senator’s Modest Estate

When news broke that Senator Lindsey Graham died with a net worth of roughly $1.4 million, a lot of people were surprised.

Graham had served in Congress for decades. A senator’s salary isn’t Wall Street money, but it’s a comfortable, stable income — well over $150,000 a year for most of his career, plus a military pension from his time in the Air Force Reserve. By the standards of most Americans, that’s a high earner.

And yet the number attached to his estate is one that plenty of dual-income households in their 50s could match, or beat.

I want to be upfront: I haven’t independently verified every detail of his estate, and net worth reported at death can be incomplete — it doesn’t always capture things like real estate held in trusts, life insurance payouts to beneficiaries, or other structures that don’t show up cleanly in a public filing. So take the exact figure with some caution.

But even with that caveat, the broader point holds up, because it echoes something else I read recently: most physicians are not millionaires by their 60s, despite decades of high income.

That one stopped me too. Doctors, as a group, are among the highest earners in the country for most of their working lives. And yet a large share of them reach their 60s without the kind of wealth their income would suggest.

Earning and Building Are Not the Same Skill

Here’s what I think both of these stories are really pointing at.

Earning money and building wealth are two separate disciplines. One is about your career — your training, your reputation, your ability to command a high salary or win elections or run a practice. The other is about what you do with the money once it shows up in your account.

A lot of high earners assume the second discipline will just take care of itself. If you make enough money, surely some of it accumulates on its own, right?

Not really. Income without a plan tends to get absorbed — by lifestyle, by taxes, by the sheer busyness of a demanding career. Doctors, lawyers, senators, business owners — people whose jobs already consume enormous time and attention — often don’t have the bandwidth left over to also become disciplined investors. That’s not a character flaw. It’s a bandwidth problem.

Compounding doesn’t ask how talented you are or how hard you work. It asks how long your money has been invested, and how consistently. A modest amount saved and invested early, left alone to grow, can outpace a much larger amount that starts late or moves in and out of the market. That’s not a promise about returns — nobody can guarantee those, and I won’t pretend otherwise. It’s simply the nature of time and consistency.

Let Me Steelman the Other Side

Now, I want to be fair to a different way of looking at this.

Maybe Graham simply didn’t prioritize accumulating wealth. Plenty of people in public service could have made far more money in the private sector and chose not to. Maybe he was more interested in the work itself than in what he’d leave behind. There’s nothing wrong with that. Not everyone’s goal is to die with a large estate, and it would be unfair to treat a modest net worth as a failure if it reflects someone’s actual values and choices.

The same could be true of some physicians. Some may have made deliberate decisions to spend on their families, give generously, or simply enjoy their income rather than defer everything for a future that isn’t guaranteed to arrive.

That’s a legitimate way to live. I’m not here to say everyone must maximize their net worth at all costs.

But I’d guess that’s not the whole story for most people in this position. More often, in my experience, high earners intend to get around to a real plan — and life simply keeps them too busy earning to do it.

The Other Half of the Story: What Happens After

There’s a second layer to this that doesn’t get talked about enough.

Even people who do build wealth often don’t have a clear plan for what happens to it when they’re gone. And none of us knows exactly when that will be. That’s an uncomfortable thing to sit with, but it’s true, and I’d rather say it plainly than avoid it.

This matters most for the person left behind.

My wife and I work with a number of widows, and one thing we’ve seen repeatedly is how much harder an already difficult time becomes when there wasn’t a clear plan in place — when a surviving spouse doesn’t know where accounts are, how they’re titled, what the tax implications look like, or who to call first. Grief is hard enough without also trying to become a financial expert overnight.

A plan doesn’t have to be complicated to be useful. It just has to exist, and the people who need to know about it need to actually know about it.

Two Questions Worth Considering

If you take one thing from Lindsey Graham’s story, or from that stat about doctors, let it be these two questions:

Is the money I’m earning actually being put to work, or is it just accumulating without direction?

And if something happened to me tomorrow, would the people I love know what to do — or would they be starting from zero, at the worst possible moment?

Neither question has a single right answer. But both are worth answering on purpose, rather than by accident.

A Conversation, Not a Verdict

None of this is a judgment on how anyone has lived their life or spent their money. Careers like medicine, law, and public service ask a lot of the people in them, and it makes complete sense that building a financial plan often falls to the bottom of the list.

But the two disciplines — earning well and building a legacy — really are separate skills, and most people only ever get good at one of them by accident.

If any of this sounds familiar, it might be worth a conversation. Our goal is simple: to help you minimize your financial stress so you can focus on maximizing your life.

Schedule a Conversation
Disclosure: This blog may reflect the perspectives and research of Intelligent Investing and, where applicable, incorporates insights from guest interviews or expert opinions. Any external views or opinions shared do not necessarily reflect the stance of Intelligent Investing. We may also utilize tools such as ChatGPT to enhance readability, grammar, and flow, while all core ideas remain proprietary to our firm.
Please note that Intelligent Investing does not provide specific tax or legal advice. All investments carry risks, including the potential loss of principal, and past performance is not indicative of future results. Any specific securities, sectors, or investment strategies mentioned are for informational purposes only and should not be considered a recommendation. We encourage readers to consult with Intelligent Investing for advice tailored to their unique financial situation. Unauthorized reproduction or distribution of this content is prohibited without proper credit to Intelligent Investing.

The Gap Years: The Most Valuable Years of Your Financial Life

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A Question That Arrives Too Late

Over the last decade or so, I’ve noticed a pattern in the questions I get from prospective clients. Someone will ask me about converting part of their traditional IRA to a Roth IRA. It’s a smart question. It’s often the right question.

But by the time I hear it, the person asking has usually already started Social Security. And once that happens, the window for doing much with Roth conversions is already closing, or closed.

Nobody told them the window existed in the first place. That’s not their fault. Nobody had a reason to.

The Switch Nobody Warns You About

Most of the people I work with spent twenty-five or thirty years doing one thing with their 401(k): contributing. Paycheck after paycheck, on autopilot, building a balance through nothing more exotic than discipline and time. They didn’t need an advisor for that. Contributing to a 401(k) isn’t complicated.

Then, somewhere around retirement, the job changes. It stops being about putting money in. It starts being about taking money out — and deciding, all at once, how to coordinate Social Security, Medicare, required withdrawals, and a tax return that suddenly looks nothing like it used to.

I call this the switch. Flipping from accumulation to distribution. And for most people, these are the scary years, because they’ve genuinely never done this before. There’s no twenty-five-year track record to lean on. You get one run at it.

The Years Between Retiring and Claiming

Right in the middle of the switch sits a stretch of time that’s easy to overlook: the years after you retire but before you start Social Security.

Call them the gap years. For some people it’s a year or two. For others, it can stretch out longer, especially if the plan is to delay Social Security to increase the benefit.

During these years, something interesting happens to a retiree’s taxable income: it often drops. No more W-2 wages. Social Security hasn’t started. Maybe there’s a pension, maybe not. For a window of time, many people find themselves sitting in a lower tax bracket than they’ve occupied in years, and possibly lower than they’ll ever occupy again once Social Security and RMDs are both running.

That’s the opportunity. It’s also the part nobody explains at the retirement party.

What a Roth Conversion Actually Does Here

A Roth conversion, in plain terms, means moving money from a traditional, tax-deferred account into a Roth account and paying the tax on it now, at today’s rate, instead of later, at whatever rate applies then.

Normally that’s a trade-off worth thinking hard about. But in the gap years, with income already lower, that trade-off can look different. The idea is to fill up the current, lower tax bracket — converting enough to use the space in that bracket without spilling over into the next one — rather than leaving that space unused and paying more tax on the same dollars down the road.

This isn’t something to eyeball. It takes coordinating year by year with the client’s CPA: what did they actually earn this year, what deductions apply, where does the next bracket start, how much room is really there. As a client’s advisor, I can sit down with their CPA directly and work through exactly how much conversion makes sense for that specific year — not as a one-time decision, but as something revisited annually while the gap window is open.

Why It’s a One-Shot Decision, Twice Over

Two things happen only once in this story.

The first is Social Security itself. You get one decision about when to start, and once you’ve started, that decision is largely locked in. Claim early and you accept a smaller check for the rest of your life. Wait, and each year of delay increases it. There’s no redo button.

The second is the gap years themselves. Once Social Security starts, that lower-income window generally closes. Add required minimum distributions a few years later — often the point where people are genuinely baffled, since their prior advisor never let them know what an RMD is — and the room to do meaningful Roth conversions shrinks even further.

I understand the instinct to just start Social Security as soon as you’re eligible. There’s something reassuring about locking in income you’ve earned, especially in the first year or two of not having a paycheck. That instinct isn’t wrong. For some people, claiming early is genuinely the right call, depending on health, other income, and what the money is needed for.

But it’s worth knowing what you might be giving up before you decide, rather than after. The value of the gap years doesn’t come from any exotic strategy. It comes from paying attention to a window that’s open for a limited, and often brief, amount of time — and closes whether or not you noticed it.

The Value of These Years

None of this is a guarantee of a better outcome. Tax law changes. Every household’s numbers are different. What makes sense for one couple’s bracket, pension, and Social Security timing won’t automatically make sense for the couple next door. This is general education, not a recommendation for your specific situation — that conversation happens with your own CPA and advisor, looking at your own numbers.

But the pattern is consistent enough that it’s worth pointing out: the years between retirement and Social Security are some of the most valuable, and most overlooked, years in the whole retirement picture. They deserve more attention than a passing thought while you’re also trying to figure out Medicare enrollment and whether the pension has a survivor option.

We love working with couples who are standing right at this point or approaching it — the ones who built something real over three decades perhaps without ever needing help, and now have real questions for the first time. If you’re approaching the switch, or already in the middle of it, it’s worth a conversation before the gap years quietly close.

We are passionate about minimizing financial stress, so you can focus on maximizing your life.

The Real Parent Trap: How Hayley Mills Lost 90% of Her Fortune

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Reading Time: 5 minutes

Growing up, one of my sisters’ favorite movies was The Parent Trap. I can still hear “Let’s Get Together” playing over and over in my mind every time I think of it. Hayley Mills was pure magic on screen.

Which is why her real-life story hit me so hard when I learned the full truth behind it.

Imagine spending seven years as one of the most beloved child stars in Hollywood — Pollyanna, The Parent Trap, That Darn Cat! — accumulating what would be worth roughly $17 million today. Now imagine turning 21 and having almost all of it taken away in a single envelope slid across a green baize tablecloth by the man your family trusted most.

That is exactly what happened to Hayley Mills. And it wasn’t bad luck. It wasn’t a stock market crash. It was a failure of professional oversight — a cautionary tale that is as relevant to today’s high-net-worth families as it was in 1960s Britain

A Fortune Built, and a Trap Quietly Set

From the age of nine, Hayley Mills was a Disney darling, signing a lucrative multi-picture contract that generated millions during her childhood years. Because Britain’s post-war “super tax” rate sat at an astonishing 90–91%, her family’s solicitor, Stanley Passmore, placed her earnings into a trust fund — a seemingly sound strategy to shield her wealth until she came of age.

The Mills family was, by any measure, surrounded by success. Her father, Sir John Mills, was one of Britain’s most decorated actors — an Academy Award winner and a national institution. Her mother, Mary Hayley Bell, was an actress and playwright. These were not naive people. They were accomplished, respected, and well-connected.

But being accomplished in your field is not the same as understanding the complexities of tax law. And that distinction cost Hayley Mills everything.

“And so, when I reached 21, instead of being given the key to the door, I was handed an envelope across a green baize tablecloth by Stanley — which was the Inland Revenue basically saying, ‘Thank you. You owe us 90% of your earnings.” – Hayley Mills, The Rosebud Podcast

One Advisor. One Flawed Structure. A Legal Precedent That Changed Everything.

Here is where the story gets technically instructive. Passmore had also set up a nearly identical trust structure for fellow actor Jack Hawkins. When the British Inland Revenue successfully attacked Hawkins’ trust, it didn’t just affect Hawkins — it created a binding legal precedent that reached directly into Hayley’s trust as well. The structure that was supposed to protect her became the instrument of her financial ruin.

When Mills discovered what had happened, she turned to Passmore for guidance. His advice? “Nothing you can do, really. You could contest it — but if I were you, I’d leave the country.” She later described him plainly: “He was a crook.”

She didn’t leave the country. She fought.

Seven Years. Three Courts. And a House of Lords Defeat.

What followed was a decade-long legal odyssey through the British court system that reads like a financial thriller — and ends in heartbreak.

Mills appealed the Inland Revenue’s ruling. She lost. She appealed again. She lost again. Then, in 1972, a rare moment of hope: Lord Denning — the legendary Master of the Rolls — ruled in her favor. His reasoning was sound: she had already paid tax on her earnings and should not face an additional surtax on top of that. A stunning, hard-won victory.

But the Crown appealed Lord Denning’s ruling to the House of Lords. In 1974, the final judgment came down — unanimously — in favor of the Crown. With costs.

Seven years of legal battles. Mounting solicitor fees on top of the original loss. And a conclusion that left Mills emotionally and financially exhausted.

“The state had plundered my trust like a horde of pirates. The Disney money was all gone. I never saw it.” — Hayley Mills, Forever Young (memoir)

The financial devastation was so complete that it forced Hayley Mills to relocate to America simply to find work — not because she had failed as an actress, but because she had no financial cushion left.

Love and Trust Are Not a Financial Strategy

Here is the part of the Hayley Mills story that I think gets overlooked in most retellings: the people who made these decisions were not villains. Sir John Mills was described as having “an innocence and a sort of optimism” about financial matters. He trusted his business manager. He trusted his solicitor. He trusted the people in his inner circle to handle the complexity he didn’t understand.

That trust was reasonable. But it was not sufficient.

Well-meaning is not the same as well-qualified. And when you are dealing with the intersection of tax law, trust structures, and multi-decade wealth preservation, the gap between those two things can cost your family everything.

Don’t let your “financial junk drawer” — the collection of accounts, advisors, policies, and decisions accumulated over a lifetime — become a legacy of “what ifs.”

  1. No independent fiduciary oversight. One solicitor made all the decisions, with no checks, no second opinion, and no accountability structure.
  2. A flawed trust structure that created legal exposure. The same advisor using the same template for multiple clients created a single point of failure that, when challenged, took everyone down with it.
  3. No proactive tax strategy review. When the legal landscape shifted with the Hawkins precedent, no one caught it in time to act. The window to “repudiate the trust before age 21” closed without anyone at the table who understood it was open.

“Outperformance” Is Often a Distraction. What You Keep Is What Matters.

At Intelligent Investing, we are a fee-only, fiduciary firm led by a CFA® Charterholder and CPA. Those credentials represent thousands of hours of elite technical training — not to impress you with letters after a name, but because the complexity that destroyed Hayley Mills’ fortune is real, it is ongoing, and it requires genuine expertise to navigate.

We don’t blow smoke about market performance. We act as behavioral coaches and accountability partners, focused on protecting what you’ve built — not just growing it on paper.

Our proprietary Intelligrations® platform was built specifically to help high-net-worth families organize their entire financial life — across accounts, advisors, tax situations, and estate structures — and avoid doing the wrong things at the wrong times for the wrong reasons.

The biggest fee most investors never see coming isn’t a management expense ratio or a trading commission. It’s taxes. And it’s not what you pay — it’s what you could have kept with a proactive plan in place before the envelope arrives.

What Fiduciary, Fee-Only Advice Actually Means:

  1. Proactive tax planning — we minimize the biggest “fee” most investors overlook, across every year of your financial life, not just at tax time.
  2. Independent, objective advice — no commissions, no conflicts of interest, no “family dynamics” influencing recommendations.
  3. Intelligrations® platform — your entire financial picture, organized and monitored, so nothing falls through the cracks.
  4. CFA® + CPA credentials — elite technical training specifically designed to navigate the complexity that good intentions alone cannot handle.
  5. Behavioral coaching — helping you avoid the emotional decisions that turn good plans into costly mistakes.

You deserve an advisor whose moral compass is backed by elite technical training — not just good intentions.

The green baize tablecloth moment comes for every family eventually. The question is whether someone is in your corner before the envelope arrives — or after.

Is Your Current Plan Truly Tax-Efficient?

Not just this year — but structured correctly for the long game? Let’s have a deep, honest conversation about your goals, your tax exposure, and what a plan built on truth and transparency actually looks like.

Schedule a Conversation

Disclosure: This blog may reflect the perspectives and research of Intelligent Investing and, where applicable, incorporates insights from guest interviews or expert opinions. Any external views or opinions shared do not necessarily reflect the stance of Intelligent Investing. We may also utilize tools such as ChatGPT to enhance readability, grammar, and flow, while all core ideas remain proprietary to our firm.
Please note that Intelligent Investing does not provide specific tax or legal advice. All investments carry risks, including the potential loss of principal, and past performance is not indicative of future results. Any specific securities, sectors, or investment strategies mentioned are for informational purposes only and should not be considered a recommendation. We encourage readers to consult with Intelligent Investing for advice tailored to their unique financial situation. Unauthorized reproduction or distribution of this content is prohibited without proper credit to Intelligent Investing.

The Fail-Safe Plan

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Reading Time: 2 minutes

Imagine booking the flights, the hotels, and the tours for your dream trip to Iceland, only to be turned away at the airport because of a passport rule you didn’t know existed.

​A client of mine recently faced this exact heartbreak. Despite having everything “ready,” a small detail—a passport expiring within six months of return—stayed behind while the rest of the family flew out.

​Retirement planning is no different. You can have the savings, but if you miss a technical detail like a Required Minimum Distribution (RMD) date or pick the wrong date to start income, your “dream retirement” can hit a major roadblock.

​At Intelligent Investing, we leave nothing to chance:

  • We Stress-Test for the Unexpected: When we build your financial plan, we run 1,000 simulations through Monte Carlo analysis to see how your strategy holds up against the “what-ifs” of the market.
  • ​We Handle the Deadlines: From ensuring RMDs are satisfied by year-end to optimizing tax distributions, we manage the technicalities so you don’t have to.
  • ​We Are Your Fiduciary Safety Net: As we age, managing complex details gets harder. As fiduciaries, we act as a permanent second set of eyes, looking out for your best interests and protecting your plan even when you’d rather be focusing on family and life. 

Cleared For Takeoff

Our client from the Iceland story stayed productive by tackling house projects, but our goal is to make sure you never have to miss the “trip” in the first place. We use our Intelligrations® process to organize your “financial junk drawer” and catch the expiration dates before you get to the gate.

​Is your financial plan truly “cleared for takeoff”? Let’s run the simulations and organize the details. Message us to start your journey with a plan that’s built to last.

Get Started!

 

Disclosure: This blog may reflect the perspectives and research of Intelligent Investing and, where applicable, incorporates insights from guest interviews or expert opinions. Any external views or opinions shared do not necessarily reflect the stance of Intelligent Investing. We may also utilize tools such as ChatGPT to enhance readability, grammar, and flow, while all core ideas remain proprietary to our firm.
Please note that Intelligent Investing does not provide specific tax or legal advice. All investments carry risks, including the potential loss of principal, and past performance is not indicative of future results. Any specific securities, sectors, or investment strategies mentioned are for informational purposes only and should not be considered a recommendation. We encourage readers to consult with Intelligent Investing for advice tailored to their unique financial situation. Unauthorized reproduction or distribution of this content is prohibited without proper credit to Intelligent Investing.

The Best Valentine’s Day Gift Isn’t in a Box

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Reading Time: 3 minutes

No one wants to admit they are struggling. We all have pride and want to put on an appearance that our marriages are perfect. Social media has exacerbated this facade.

I had a conversation with a spouse that reminded me of a much deeper expression of love: the gift of unity.

This person reached out to me deeply concerned about the state of their marriage and finances. As we talked, it became clear that the primary source of their anxiety wasn’t just the balance in the bank account—it was the fact that they and their spouse were no longer walking in the same direction. 

They are not alone. Almost half of couples avoid money talks because they’re afraid of conflict. We get it. Marriage is hard work.

Communicating with our spouse can be tough, especially when it comes to money. It can bring out some strong emotions. But those conversations if done in the right way, are where deeper connection (and stronger marriages) actually happen.

 

Beyond the “Roommate”

In Genesis 2:24, we find the foundational blueprint for marriage:

Therefore a man shall leave his father and his mother and hold fast to his wife, and they shall become one flesh.

This “leaving and cleaving” is often applied to our family connections and our living arrangements, but it must extend to our finances as well. When we maintain “his and hers” money or keep financial secrets, we are essentially resisting the call to become “one flesh.” We inadvertently become financial roommates instead of spiritual partners.

Walking in Agreement

The Bible asks in Amos 3:3:

Do two walk together unless they have agreed to do so?

When a couple isn’t in agreement on their finances, they are walking toward two different futures. This division is where stress thrives. However, when you choose total financial transparency and shared goals:

  • The Burden is Shared: You no longer face debt or inflation alone.
  • Trust is Fortified: Transparency in the checkbook builds trust in the heart.
  • Peace is Multiplied: As Mark 3:25 suggests, a house united is a house that stands firm.

This Valentine’s Day, while the chocolate and flowers are wonderful, I want to encourage you to give the gift of alignment. True financial unity turns a solitary struggle into a shared mission.

Let’s Get on the Same Page

If money has become a source of friction rather than a tool for your future, my wife and I would love to help. Our passion is to minimize financial stress and maximize lives. We love getting couples on the same page financially and working towards joint goals.

As a husband-and-wife advisory team at Intelligent Investing, we have a unique passion for helping couples bridge the gap. We believe that when you align your finances with your faith and your spouse, you experience a level of peace that no candlelit dinner can provide. Over the past 10 years or so, we have been helping couples transition into retirement, not only financially, but emotionally as well. 

We believe that when you get your finances right, it strengthens the very fabric of your marriage. It takes work, but it is worth the effort.

Ready to get on the same page? We would love to help you build a unified plan for your future.

Get Started!

 

Disclosure: This blog may reflect the perspectives and research of Intelligent Investing and, where applicable, incorporates insights from guest interviews or expert opinions. Any external views or opinions shared do not necessarily reflect the stance of Intelligent Investing. We may also utilize tools such as ChatGPT to enhance readability, grammar, and flow, while all core ideas remain proprietary to our firm.
Please note that Intelligent Investing does not provide specific tax or legal advice. All investments carry risks, including the potential loss of principal, and past performance is not indicative of future results. Any specific securities, sectors, or investment strategies mentioned are for informational purposes only and should not be considered a recommendation. We encourage readers to consult with Intelligent Investing for advice tailored to their unique financial situation. Unauthorized reproduction or distribution of this content is prohibited without proper credit to Intelligent Investing.
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