Jonathan Clements's Blog, page 12

October 5, 2025

The Real Wealth of Retirement (Hint: It’s Not Financial)

Times have changed. Six months ago, ten minutes of sitting still felt impossible, I got restless very easily. Since retiring, I can happily sit in the sunroom for an hour simply watching the clouds float by. I actually find it very therapeutic. It reminds me of my ten-year-old self, drifting off watching clouds from the classroom window instead of doing my work.

I keep coming back to this topic. Having time that's truly mine has changed something fundamental in me. Somewhere between those daydreaming school days and starting work, I seemed to have misplaced the ability to just...be, I suppose is the correct word.

The work-a-day world, with its pressures and deadlines, had quietly shut down that part of me, the part that could just sit and watch clouds without needing a reason. Retirement, by removing the external pressure, has simply allowed that innate, childlike capacity for wonder and ease to resurface.

I wonder if everyone rediscovers this easily, or if some people fight it, maybe that old work-world guilt makes doing nothing feel wrong, even when you've earned the right to do it. I suppose the world of work taught me that being busy was good, stillness not so much.

I personally find it wonderful. I used to meditate a few days a week to clear my mind. I don't feel the need anymore. My rediscovered ability to simply spend time doing essentially nothing has filled that need, I guess it's a form of meditation without the focus or mantra.

This ability to do nothing and feel no guilt in doing nothing is, paradoxically, a springboard toward productivity and mental insight. Writing articles only seems to happen after periods of sunroom mindfulness. At other times I find it impossible to think of anything to say. And any problems I might have seem to find solutions during these quiet periods.

My time in the sunroom has drawn back a curtain and revealed a paradox: it seems the most effective way I can be productive is during periods of deep, guilt-free unproductivity. It's the antithesis of what I formerly believed. True breakthroughs require the quiet processing time that simply watching a cloud provides. If you want to solve a tough problem or find a fresh thought, don't press harder, step away and do nothing.

Without conscious effort, I've reclaimed the part of my mind the working world had quietly shut down. The true gift of my retirement isn't freedom from work, but the freedom to remember who I was before the world told me who I had to be, that ten-year-old gazing out the window, whose peaceful, non-productive contemplation was, in fact, laying the mental groundwork for an entire lifetime of insight. By honoring that stillness, I've not just retired, I've found my way back to clarity.

I find the irony of the situation delightfully amusing. If you're reading this flow of words and thoughts, it's strange to think that it's a product of doing absolutely nothing. Try figuring that truth out with corporate efficiency and logic..

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Published on October 05, 2025 12:14

Remembering Jonathan Clements

Jonathan Clements liked to joke that he was born at 6:00am and on January 2nd, “thus establishing a lifetime habit of starting early.” But he truly did get a fast start and seemed to waste no time.


Jonathan—who passed away this week—discovered his love of writing early on. He described his English boarding school as a “brutal” environment: “cold dormitories, disgusting food, endless bullying.” But that was also where he began to write, earning a spot on the staff of the school magazine.


With fondness, he recalled one of his first articles, titled “Organ Transplant.” It described how the school had spent an inordinate sum on a new organ while neglecting other facilities. “Somehow, I managed to get it published,” Jonathan said, “which earned me the enmity of a host of people. But in many ways, that was my entrée to becoming a journalist.”


Later, Jonathan became editor of the student newspaper at Cambridge University and, after graduation, spent time at Forbes before joining the Journal, where he became the paper’s first personal-finance columnist and wrote more than 1,000 columns between 1994 and 2008. After a stint at a wealth management firm, Jonathan returned to journalism, developing HumbleDollar to provide investors with his signature plainspoken guidance.


Jonathan was one of a kind and will be greatly missed. Jason Zweig, Jonathan’s successor at the Journal, put it best: “I have just lost a friend, and so have you.”


Perhaps more than anything, Jonathan was known for his generosity. He happily gave of his time and his wisdom. I experienced that personally. In 2016, I was unhappy in my job, and—for reasons I can’t fully explain—decided I should reach out to Jonathan for advice. I was amazed when he replied to my email the next morning, then spent a further hour on the phone. It changed everything for me. I wonder how many others Jonathan helped along the way.


This generous spirit formed the foundation of HumbleDollar, which Jonathan founded at year-end 2016. With his well-known reputation, Jonathan could’ve recruited professional journalists. Instead, he invited amateur writers to contribute to the site and happily took on the task of editing piles of submissions.


In his own writing, a favorite topic was the intersection of money and happiness. The reality is that Jonathan was a fundamentally happy person. He signed off every email the same way: “cheers.” Even after he received his diagnosis, he was never bitter and never complained, even when others expected him to.


Last fall, he wrote: “I’ve been endeavoring to approach these final months as a cheerful warrior, making the most of each day and avoiding anger over my grim prognosis...I’m not grieving my own demise.”


After he died, Jonathan’s wife, Elaine, posted a final message: “I consider myself beyond fortunate,” he wrote. “I had spent almost my entire adult life doing what I love and surrounded by those that I love. Who could ask for more?”


In many ways, it was the simple things that brought joy for Jonathan. Though he and Elaine traveled more in his final year, he emphasized the value of simple pleasures: “that first cup of coffee, exercise, friends and family…” He got special joy from living an eight-minute walk from his daughter and grandchildren in Philadelphia and, despite his illness, was able to see his son get married in London last December. That was how Jonathan measured wealth.


Part of Jonathan’s formula for happiness may have been his even-keeled outlook on the world. I doubt readers ever detected an inkling of his political leanings. I certainly never did. In recent years, Jonathan co-hosted a podcast with Peter Mallouk, the president of Creative Planning. Peter noted that it was Jonathan who named the show: “Down the Middle.” Jonathan’s even-tempered outlook helped investors stay focused on what really mattered.


I never heard Jonathan say a critical word about anyone, but he certainly had strong feelings about the investment industry. In that way especially, he was ahead of his time. Jonathan began preaching the virtues of index funds back in the mid-1990s, when they represented just a fraction of investor dollars. But Jonathan knew he had the facts on his side, having reported on the mutual fund industry long enough to have seen their pattern of underperformance up close. Jason Zweig lauded Jonathan’s persistence: “Brokerage and fund executives hated what Jonathan wrote. He persisted through a nonstop blizzard of complaint and criticism.”


Index funds were one pillar of Jonathan’s philosophy. Frugality was another. “I credit the frugality to what I call our big family story,” he said. “When my great-great grandfather died in 1888, the newspapers said that he was one of the richest men in England. All that money was inherited by my great-grandmother Lillian, and she lived the Downton Abbey lifestyle.” From there, “the fortune was blown in short order.”


“That was the story I grew up with, and the message was clear: You’ve got to be careful about money. My two brothers, my sister and I are all very different people, but all of us are frugal, and I credit this great family story.”


A point of pride for Jonathan was that he successfully conveyed those values to his children, though he worried sometimes that he’d conveyed them “too well.”


Another key pillar of Jonathan’s philosophy: humility. That was a personal characteristic—he often talked about “squeaking” into Cambridge University—but it extended to his view of investment markets as well. Hence the name HumbleDollar.


In his early years at the Journal, Jonathan observed the lackluster results of “sophisticated” financial strategies. So in the advice he gave, and with his own investments, Jonathan’s approach was simple: He took the long view. He never tried to outsmart the market, recognizing that as a fool’s errand, and never let the news of the day worry him. “I’ve always had a strong faith in capitalism and in the stock market,” he said last fall. I’ve never had any doubt during a market decline that share prices would recover. I’ve almost always had at least 80% in stocks. Right now, I’m at 92%.”


At the end of the day, though, investing wasn’t just about dollars and cents. “What is the reason for all this saving and investing?” Jonathan asked in his final column at the Journal. It was, he said, to enable us to enjoy our time here.


For his wit and his wisdom, his generosity and good cheer, Jonathan Clements will be greatly missed.

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Published on October 05, 2025 07:12

October 4, 2025

Nope, you didn’t pay for YOUR Social Security benefits

I’ve heard it many times, it’s all over social media. I earned my Social Security benefits, I paid for them.

We certainly paid taxes (actually under a separate law) to fund Social Security and all its benefits beyond retirement income, but we did not pay for OUR benefits. 

According to SSA actuaries and Congressional Budget Office studies:

A typical medium-wage worker retiring at full retirement age (66–67) usually recoups their own payroll contributions within about 3–5 years of collecting benefits.If we include the employer’s 6.2% contribution as well, the break-even point is more like 6–9 years of collecting benefits.

A medium wage worker with a non-working spouse also collecting on the workers earnings will shorten the recovery period. 

Connie and I are collecting on my earnings record and after looking up my SS earnings record our combined benefits exceeded both my and my employer’s taxes paid about ten years ago. 

If workers received SS benefits based only on FICA taxes they and their employers paid, their benefits would generally stop after 6-9 years. 🤔

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Published on October 04, 2025 09:28

November 7 HumbleDollar Reader/Writer Meet Up

This is  just in case you missed it. 

Dave Lancaster was kind enough to post all the information for Jonathan’s memorial on Saturday, November 8: 

https://humbledollar.com/forum/information-on-jonathans-memorial-service/

He also asked if there was interest in HDers meeting for pizza at Pizzeria Vetri on Chancellor St on Friday 11/07. I would sure like to put faces with the names of my HumbleDollar friends. I hope you can add your name to the list.

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Published on October 04, 2025 06:47

October 3, 2025

Managing Concentration Risk

LARRY ELLISON, THE 81-YEAR-OLD cofounder of Oracle Corporation, recently became the world’s wealthiest person.

Oracle, a software company, isn’t nearly as large as its peers. So how did Ellison’s net worth manage to surpass that of Bill Gates, Jeff Bezos and the founders of other much larger companies?

The answer is simple: In the nearly 50 years since Oracle’s founding, Ellison has almost never sold a share of his company’s stock. According to an analysis by Smart Insider, which tracks executives’ share sales, Ellison has sold only a tiny fraction—less than 2%—of his shares over the years. The result is that today he still owns more than 40% of the company, worth nearly $400 billion. 

In contrast, Ellison’s Silicon Valley peers have sold, or given away, shares much more aggressively. Mark Zuckerberg now owns less than 15% of Meta. Jensen Huang’s stake in Nvidia is under 4%. And Bill Gates’s stake in Microsoft is down to just 1%, following years of systematic sales and gifts to his foundation. 

Ellison’s unwavering bet on Oracle has worked out well, but the company’s fortunes easily could have gone the other way. That’s why, for anyone else with a concentrated position in a single stock like this, diversification is what I’d recommend in virtually every case.

Diversification is probably the most important principle in personal finance. The obstacle for many people, though, is the prospective tax bill. At the federal level, the top capital gains tax bracket is 20%. At that level, an additional 3.8% surtax would apply, plus state—and even city—taxes in many places.

How can you strike a balance between managing risk and limiting taxes? Fortunately, the range of available options has expanded in recent years. If there’s a concentrated stock position in your portfolio, here are steps to consider.

You might start by assessing the risk. While there’s no single litmus test, I suggest asking these questions:

How large a portion of your assets does the stock represent? As a rule of thumb, holdings that top 5% are worth closer examination.
How does the weight of the stock in your portfolio compare to its weight in a market index like the S&P 500? Suppose, for example, you own Apple shares that account for 7% of your portfolio. That seems like a lot. But because Apple is so large, its weight in the S&P 500 is actually in the neighborhood of 7%. For that reason, a holding of that size in Apple might not be such a concern. On the other hand, a 7% position in a smaller company would merit further review.
How diversified is the rest of your portfolio? Because stocks in the same industry tend to move together, you’d want to assess the level of industry diversification across your holdings. Counterintuitively, a portfolio of 30 stocks could be riskier than a group of just 10. What matters more than the number of holdings is the degree to which they’re diversified across the economy.
Is the stock in question your employer’s stock? If so, that would be a point in favor of diversifying more quickly.
How much would a loss impact you? As with most questions in personal finance, there are two answers to this question: how it might affect you in dollar terms, and the degree to which it would simply be upsetting. Both considerations are important.

If you determine that the stock does represent a risk, the next step is to assess the tax situation. There are a number of questions to ask here: How highly appreciated is the stock? What would the tax be if you exited the entire position? Would it push your income into the next capital gains tax bracket? Do you own multiple tax lots, which could provide more flexibility?

If the answer is that the tax bill would be significant, then you’d want to evaluate strategies for reducing the holding. For starters, you’d want to decide on a target percentage for the stock. I recommend bringing individual stocks down to somewhere between 5% and 10% to manage risk. Why? The great investor Bernard Baruch put it this way: “Sell to the sleeping point.” That answer will be different for each of us, but that’s the gauge I’d use.

How can you begin reducing your holdings?

Many of the strategies are well known. You could sell a fixed number of shares each month and maybe accelerate those sales when the share price is strong. Or you could plan your sales so that you’d stay inside a particular tax bracket. And when you reinvest, you could employ a direct indexing service to diversify without inadvertently buying back the stock you’d just sold.

If you have charitable intentions, you could donate shares to a donor-advised fund, thus sidestepping the capital gains and capturing a deduction on the donation.

If you have adult children who are in lower tax brackets, you could gift them shares.

A somewhat more involved strategy would be to move your shares into what’s known as an exchange fund. How do these work? Imagine three friends. One has a concentrated position in Apple, another has a big holding in Amazon and the third has a big stake in Microsoft. Individually, they are each bearing a lot of risk. But if they contribute their shares into a common pool, the result would be instant diversification. They’d each own a third of a three-stock portfolio instead of just a single stock.

In reality, an exchange fund would have many more participants and many more stocks, providing an even greater benefit than in this simplified example.

Exchange funds have been around for years, but as noted recently in The Wall Street Journal, new competition has helped drive down the cost of these services. They can still be a bit pricey, at 0.4% to 0.9% per year, but investors are only obligated to remain in the fund for seven years. After that, they’re free to exit the fund, taking with them a pro rata share of the diversified portfolio.

If that seven-year lockup is a deterrent, there’s a new option to consider. A firm called Alpha Architect has devised a new ETF structure to help with concentrated stock holdings. This past summer, it launched an ETF (ticker: AAUS) that functions similarly to an exchange fund but with a few wrinkles.

On the one hand, the requirements for entry are more stringent, but in exchange for that, they offer two key advantages: First, they don’t require a seven-year commitment. Investors are free to sell the ETF at any time. And second, the fees are much lower, at just 0.15%. Alpha Architect is launching its second such fund later this year (ticker: AAEQ).

While this construct is new, it’s certainly worth watching.

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.

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Published on October 03, 2025 22:00

Cash Balance Plan Explained

IMAGINE YOU ARE already doing all things possible to minimize your taxes:

You are maxing out your pre-tax 401k
You do tax loss harvesting
You did tax efficient placement
You are maximizing Roth IRA through Backdoor Roth

But what other strategies can you use to minimize taxes? You also might not want to start a business or buy real estate.

Another option that many people aren’t aware of is the cash balance plan (CBP). It’s available to business owners (including solo owners) and some employers offer it to high earning professionals (doctors, lawyers, consultants, etc), so check with your employer if one is available to you.

It’s basically a hybrid between a 401(k) and pension. The contributions you put into CBP are tax deductible and grow tax deferred until withdrawal. It’s best suited for people in peak earning years, since you have to commit to contribute for a few years.

The main benefits of CBP are massive tax savings. Your contributions can be very large (like $100,000+). You can also have the flexibility to rollover CBP into 401k/IRAs.

Another unique benefit is that CBPs can be designed alongside your 401(k), allowing you to contribute to both plans in the same year. This "stacking" can supercharge your tax deductions compared to relying on a 401(k) alone.

 

Risks


If you are a business owner creating a plan for yourself, it’s not something you can DIY. The calculations are complex and require actuaries and CPAs to do it correctly. There are also some specific rules related to overfunding and underfunding, along with structuring and maintaining. But if you are working for a big employer, you shouldn’t worry about it.

These plans typically come with a high fee (>0.5% AUM), but it can still be worth it depending on the tax savings and your circumstances.

Another consideration is that CBPs typically require minimum funding each year (which is why they’re better suited for consistent high earners). If your income is volatile, this could create stress.

 

Example

Say you are a high earner physician. You might have an option of cash balance plan available to you.

The limit you can contribute to such plan depends on age/income, but let’s say ~$100,000 is your max.
You generally must commit this $100,000 for at least 3 years, and there is flexibility to adjust afterwards. This also means that if you are strapped for cash (e.g. life circumstances have changed) you could adjust your 401(k) amounts you are contributing to adjust for such events.

Investments are typically managed by a third party, with a conservative allocation. The plan might be invested in ~50% bonds, which means the average historical returns are 4-5%. This means that if you do go through with this plan, you can rebalance your other pre-tax accounts (like 401k) to be invested more aggressively and rebalance bonds into the CBP. The funds invested in CBP generally will be allowed to rollover in a 401k or IRA.

Continuing with our example, say you are a 57 year old high earner. Your plan is to retire in 3 years.

Your current marginal tax rate is 37% federal plus 9.3% for state tax rate. So, for every $100,000 you contribute, you defer $46,300 in taxes.

Since you will be retiring in 3 years, you can comfortably predict your tax rate by taking into consideration your pension, 401k withdrawals, taxable dividends, interest, etc. Say you will be in a 22% marginal tax rate once you are retired, with 6% state. This means that your CBP contributions will be able to save you tens of thousands of dollars of tax throughout the 3 year period.

In addition, if you plan carefully, you may be able to pair CBP contributions with Roth conversion strategies after retirement, letting you shift pre-tax balances into tax-free Roth accounts at a much lower tax rate.

 

Flexibility

As you can imagine, the CBP is relatively inflexible in a sense of withdrawals. The details depend on your plan, but generally the most common scenarios for withdrawing your funds are when you retire or separate from service with the employer.

This means that if you need cash you will need to get it from other places (e.g brokerage account). This is why planning ahead is crucial with CBP. If you do anticipate a large cash outflow, understand exactly where that money would come from if you do enroll in CBP.

This is exactly why cash balance plans are typically recommended for individuals soon to retire. In other words, chances for large cash outflows might be lower.

At the end of the day, a cash balance plan isn’t for everyone. But for high earners in their peak years, it can be one of the most powerful ways to reduce taxes and boost retirement savings.

 

Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.

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Published on October 03, 2025 21:57

Spreadsheets: A Luddite’s Necessary Inconvenience?

Ah, retirement. That grand, glorious moment when I traded the frantic pace of business ownership for... well, for whatever mischief I could inflict on my wife Suzie. I don't like spreadsheets, the temptation to take a stab in the dark when your spreadsheet adverse is strong.

It’s easy to do, isn't it? You look at your savings, you subtract a few zeros, and you just decide—right there, in a sudden burst of confidence—that you can safely withdraw, say, $10,000 a month. It sounds perfectly reasonable, doesn't it? It feels right. But that gut feeling is the equivalent of me telling Suzie her dress looks weird ten minutes before leaving for dinner…things aren't going to end well.

This is the reason why I stopped guessing and started building a spreadsheet model for retirement. I don't like them but, unfortunately , they're much better than a stab in the dark. It's tedious, but they work. It lets you take that big question—Do I have enough?—and break it down into manageable, less alarming pieces.

I couldn't just put my total nest egg in one cell and start subtracting. A proper model isolates the different streams of income (state pension here, private investments there), the core expenses ( groceries, utilities etc), and, crucially, the "fun" money. By breaking down the expenditures, you suddenly realise that the $10,000 you plucked out of thin air needs to cover $4,500 in fixed costs and leaves $5,500 for travel, hobbies, and random spontaneous generosity. It replaces the single, dangerous, gut feeling with a logical, year-by-year financial blueprint.

The power of this model comes from using best guess assumptions. In retirement planning, you’re dealing with long stretches of time. I simply can’t know what inflation will be in 15 years, or what return my investments will generate next decade. A random stab at a 10% return is just a wish.

A best guess assumption is not a short in the dark, it's an informed variable. You look at historical inflation rates, you use a slightly cautious long-term average for your investments, and you factor in a realistic life expectancy. Although if I keep criticising dresses, it won't be very long. You isolate these figures, maybe assuming a 3% annual inflation rate or a 4% real return, (this simply means taking inflation of the historical nominal return) in their own cells.

This allows you to play the most important game of all: scenario testing. What if inflation spikes to 5% for the next five years? What if Suzie decides, for some strange reason, to draw an extra $10,000 for new dresses? With a model, you change that one key assumption, and instantly, you see the impact on your money in year 25. It's a dress rehearsal, pun intended, for financial survival. You move from the anxiety of not knowing to the confidence of knowing the risks.

As a spreadsheet luddite, even I have to concede, running a few scenarios with educated assumptions is a far better way to spend your time than trying to guess a single magic number. It turns your hopes into a real plan that can weather the inevitable unknowns of life, leaving you free to enjoy the reality of retirement, without the fear of ending up broke twenty years too soon and having to spend your last $500 on a four season tent.

 

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Published on October 03, 2025 12:36

You can’t prove the assumptions you may rely on. How did you test yours?

Within the archives of HD is this comment:

“I built a spreadsheet and proved that the math worked for me and my wife with our facts and assumptions.”

Making assumptions means accepting something as true or certain without proof, often based on your own beliefs, past experiences rather than on concrete evidence. You can’t prove an assumption, but you can test it. 

The exact subject associated with the above comment, is not important. Suffice to say though that it related to lifetime retirement income security - important stuff. The validity of those assumptions will not be tested for many years. 

People sometimes make assumptions (sometimes unconsciously) that steer them toward the answers they want. This tendency is linked to cognitive biases. For example, our emotions or goals can shape how we interpret information—so we may make assumptions that favor our preferred outcome.

Planning for years in the future with many possible variables requires assumptions, nothing can be known with certainty. 

How did you go about setting your assumptions? How did you become comfortable with your final choice? Have you had the opportunity yet to test those you relied on to make financial/retirement decisions?

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Published on October 03, 2025 06:30

October 2, 2025

Taxpayers Say the Darndest Things

Significant changes to tax law took effect in 2018. I heard some interesting comments from clients. Some didn’t believe taxes went down because their refunds didn’t increase. To be fair, taxes did go down for most people, but so did tax withholding from paychecks, keeping many refunds level with prior years. I guess people didn’t notice the extra take home pay. 

The other thing I sometimes heard was that they thought their tax return would fit on a single piece of paper. That one made me chuckle because all of the lines eliminated from Form 1040 found their way onto a handful of new schedules, making for more pages than ever.

What might preparers hear and see this year?

 

Clients will show up with clipped articles about the changes, just to be certain we don’t miss anything.
Younger clients will complain about not being able to take the new $6k/$12k deduction for seniors. Some may try to furnish false birth dates. That doesn’t work because the IRS knows when you were born.
Taxpayers with no tip or overtime income to deduct from their taxable income will curse those who do. 
Someone will buy a new car, not understanding the difference between a tax credit and a tax deduction. “I’m supposed to get $10K back for the interest on my new truck?”
Some will cheer lower taxes and moan about the deficit in the same breath. 
A few might even notice how long and confusing their tax return has become. 
Finally, some will be upset that the price of preparation increased. Well, new laws mean additional work for preparers, which translates into higher fees for taxpayers. 

 

Of course there are the recurring questions we hear every year.

1. “I’m filing as head of household,” a client told me.

You can’t be head of household,” I explained. “You don’t have any dependents".

“Yeah, but I’m still the head of my household.”

2. Why does my friend get a bigger refund than me? We have no idea why, and if we did, we are not allowed to tell you. 

3. That income doesn't have to be on my return, they already taxed me on that! We often hear this one when a worker takes an early withdrawal from a 401K and has tax withheld, or when a casino withholds taxes on a jackpot. 

Feel free to add to the list.

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Published on October 02, 2025 18:23

Your Portfolio, Your Business

When I first started investing, my father-in-law, a longtime investor, gave me advice that echoes in my mind almost every day: “It is a business.”

At first, it sounded simple, maybe even boring. But the truth is, that advice has kept me from making a lot of mistakes. It runs contrary to the old adage, “Set it and forget it.” A business owner doesn’t forget their business. They know their numbers, track results, and adjust when circumstances change. Your portfolio deserves the same attention. After all, no one is more concerned with your financial future than you.

That doesn’t mean you have to do it all yourself. You can hire help—advisors, managers, planners—but remember what Jesus said about the hired hand: “The hired hand is not the shepherd and does not own the sheep. So when he sees the wolf coming, he abandons the sheep and runs away” (John 10:12-13). You can hire help, but you must oversee them.

Thinking of my portfolio as a business has shaped how I handle it:

• Strategy. Set goals, allocations, and a growth plan.

• Numbers. Track returns, dividends, and costs. Profit is what you keep after expenses.

• Risk management. Diversify like a business spreads risk across products.

• Growth. Reinvest dividends, stay educated, and focus on the long term.

Bad management can sink both businesses and portfolios, and I’ve been guilty of all of these mistakes: overtrading, overthinking, chasing fads, ignoring costs, obsessing over short-term swings, and neglecting periodic review. Activity without discipline is just noise.

The lesson is simple: manage your portfolio like the business you own. Show up, know your numbers, review your strategy, and oversee anyone you hire. You are the CEO of your financial future—and the success of your “company” depends on you.

I’m curious—how do you run your portfolio? Have you made any of the mistakes I’ve mentioned, or found strategies that work particularly well? Share your experiences—I’d love to hear what you as CEO of your company are doing with your financial “companies.”

AI-assisted editing

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Published on October 02, 2025 15:43