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How did you avoid being in the 39%?

"I know I have banged on about this before, but our superannuation system here in Australia means that every employee saves 12% of their wage for their entire working life. And all superannuation funds have a fiduciary requirement, to act in the best interest of their fund members. This should see most people well set up financially for retirement, and a significant reduction of the burden on our aged pension scheme. (An aged pension is available as a "safety net" for those without sufficient funds to service their own retirement.)"
- greg_j_tomamichel
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The Case for Kids

I RECENTLY HIT THE “pay now” button on what I believe will be the last of 20 years of college tuition bills. That’s right, we have five kids. All went to college. None took out student loans. Was it worth it—not just paying the tuition bills, but the decision to have children in the first place? It’s a pressing question. A birth dearth is hitting the U.S. and other countries around the world, as many adults opt to go childless. Today, roughly half of all countries have fertility rates that are so low that the population is either stagnant or shrinking. That brings me to today’s topic: the case for children. It’s a complex subject. I don’t want to suggest I know how others ought to decide. Everybody’s situation is unique and shouldn’t be judged by anyone else—and certainly not by me. Still, I think those of us with good stories about raising kids should share our experiences. We can balance out today’s narrative that children are more trouble than they’re worth. I remember the subtle pressure in the 1980s and ‘90s from others, as our family kept growing. Folks expressed concerns about having so many children. I suppose that, if you treasure a quiet and peaceful life above all else, having kids may not be a good idea. Children are messy and bring chaos. I remember answering the door, only to come face to face with our upset neighbor. He was a prominent doctor in the community and complained about my kids shooting at the deer in the backyard from our second story bedroom windows. “Thank you, Dr. Smith, for letting me know. I’ll take care of it.”  Ugh. But probably the greatest reason the U.S. no longer has a fertility rate necessary to maintain a stable population is related to financial concerns. The U.S. Department of Agriculture estimates the cost of raising a child through age 17 is more than $230,000. That number sounds ridiculously high to me. Still, whatever the right number is, the cost is daunting when you’re just getting started. [xyz-ihs snippet="Mobile-Subscribe"] I went back and looked at our financial records and found that, when our first child was born, we had a paltry net worth of $12,000. On top of that, my salary was modest. Why did my wife and I believe we could support a family? I’m a conservative banker and my tribe doesn’t believe “faith” is a business plan. So why did we do it? There were five reasons—some of which were clear to us at the time and some of which only became clear later. First, rather than just complain about our culture, we thought our best opportunity to change the world was by having children. Today, by God’s grace, we have two entrepreneurs, one banker, one IT guy and a social worker. In addition, thanks to marriage, we now have two health care workers and an oil man in the family. The world is better as a result of their service to others. We now know we changed the world for the better. I’m a finance guy, so I can’t help but estimate the financial return on investment. All five kids have good jobs. What if I assume they average $100,000 a year in earnings over a 40-year career? What kind of impact could that have? Assuming they give away 10% of their income, as we taught them, they’ll have contributed $2 million to charities over their careers. Social Security and Medicare contributions at current rates would be $3 million. State, local and federal taxes come in at an estimated $4 million. I’d call that a decent return on investment. Second, having children matures us. If I’d never advanced in my career, we would have struggled to raise five children. But the financial challenge of having kids meant I approached my career with a new fervor. As we awaited the birth of our first son, I studied hard for the CPA exam. Next was an MBA program, which I completed while working. That led to some nice raises and promotions. Third, by necessity, having children squeezed a lot of ugly selfishness out of me. I’m a selfish person by nature. But selfless service to family prepared me for selfless service at work and to charitable organizations. Fourth, researchers say children don’t necessarily make people happier at first. But ultimately, the satisfaction of a purposeful life devoted to family trumps any temporary happiness we give up. Finally, as we age, it can become harder to find true purpose, joy and passion. But having three grandchildren sure helps. Joe Kesler is the author of Smart Money with Purpose and the founder of a website with the same name, which is where a version of this article first appeared. He spent 40 years in community banking, assisting small businesses and consumers. Joe served as chief executive of banks in Illinois and Montana. He currently lives with his wife in Missoula, Montana, spending his time writing on personal finance, serving on two bank boards and hiking in the Rocky Mountains. Check out Joe's previous articles. [xyz-ihs snippet="Donate"]
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What is the best way to donate to charity in 2026?

"+1 on using a DAF. I use mine to growth my donated money. I limit gifts to 3% less admin and fund fees. The will and trust are set to move final assets to my DAF administrator, and they have instructions to continue my plan as an endowment (perpetual "DAF"). Donations to the DAF are also helping with tax efficiency - paying less taxes now (still doing roth conversions) and reducing RMDs (future taxes). My brokers advisors have been a big help establishing a plan and showing it's many benefits."
- Gordy Vytlacil
Read more »

Loose Change

"In 1993 my girlfriend and I made the bold choice to not bring travelers checks with us to Europe. We had to hunt for the correct ATM machines, but we were able to get local currencies with the debit card I had. It was a new financial world."
- Cammer Michael
Read more »

New to building a CD or Bond Ladder?

"We have three bond funds (all Vanguard ETFs) in our traditional IRA, all about 1/3 of our bonds: 1) BSV short term- for minimal volatility 2) VTIP short term tips- for above plus inflation protection 3) BND intermediate term for slightly higher returns"
- David Lancaster
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Allan Roth’s 2/13/26 article references Jonathan Clements

"I'm in agreement with Richard here, it's not possessions OR experiences. Some folks garner tangible value from possessions (I'm thinking Porsches, which doesn't necessarily apply to me). I'm in the process of moving, so have been organizing (read: throwing out) a lot of possessions collected over a 30 year span. And while I don't view myself (nor do others) as particularly materialistic, I'll happily admit to coming across long forgotten possessions that when found have brought me a lot of happiness as the memories they stir. This TBH is in distinction to my SO, who is almost opposite in her attachment to old things (she simply views them as old). But what I try to apply, both in possessions and experiences, is a version of Marie Kondo, "does this possession/experience bring you joy?" That's been a terrific barometer for me in making the qualitative aspects of a decision."
- Leonard Go
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Home Tax Tips

IF YOU OWN a home or are planning to buy one, there are a few things you need to know from the tax standpoint that could save you money: 1. Mortgage Interest If you have a mortgage, you can typically deduct the interest you pay on the loan up to $750,000 ($1,000,000 if taken before December 16, 2017) but only if you itemize your deductions (schedule A) You can also deduct points you paid if you itemize. Many people miss deducting points on their tax returns when they purchase a house, but you have to meet some criteria like:
  1. The points relate to a mortgage to buy, build or improve your principal residence
  2. Points were reasonable amount charged in that area
  3. You provide funds (at or before closing) at least equal to the points charged
  4. The points clearly show on the settlement statement
In general, points to get a new mortgage or to refinance an existing mortgage are deducted ratably over the term of the loan.  Note that the deductible points not included on Form 1098 (the mortgage interest form) should be entered on Schedule A (Form 1040), Itemized Deductions, line 8c “Points not reported to you on Form 1098.” 2. Property taxes Property taxes can be deducted on your tax return if you itemize deductions. The total amount of taxes (including state and local income taxes) is capped at $40,400 for 2026. This cap is temporary and will increase by 1% annually through 2029 before reverting to $10,000 in 2030. If you make between $500k to $600k of modified adjusted gross income, the $40.4k deduction is reduced by 30% for each dollar you make. At $600k MAGI, the deduction drops to $10k, potentially raising marginal tax rates to 45.5% (!) for singles due to “SALT torpedo” if you are in the $500-600k range. If you are at that range, it’s recommended to mitigate this by lowering AGI/MAGI by maximizing pre-tax 401(k)/403(b), HSA, FSA contributions, timing RSU sales, tax loss harvesting, or deferring income/accelerating expenses for business owners. 3. Improvements Improvements are significant enhancements made to your home that increase its value. Many people overpay on taxes when they ultimately sell their house because they don’t keep track of these improvements. Here are some examples provided by the IRS: > Putting an addition on your home > Replacing an entire roof > Paving your driveway > Installing central air conditioning > Rewiring your home > Building a new deck > Kitchen upgrades > Lawn sprinkler system > New siding > Built in appliances > Fireplace Now, these costs aren’t deducted, but they are added to your home’s cost basis. This could lead to lower capital gains taxes when you sell your property (more on this later). Repairs, on the other hand, don’t impact your basis and don’t affect your taxes (e.g. repairing a broken fixture, patching cracks, etc) You will need to document every improvement, as this can help you save money on taxes. Keep your receipts and invoices (upload them to Google Drive) and record the dates and descriptions of the work done. Taxes when selling your house When you sell your house, here’s the formula: Selling price  > Selling expenses (like realtor fees) > Adjusted cost basis (how much you purchased it for + all these capital improvements I talked about above + any closing costs you paid when you acquired the home (legal fees, recording, survey, stamp taxed, title insurance) = Gain/Loss You will need to pay capital gains tax if there is a gain, but, luckily there is a gain exclusion (Section 121 exclusion) that can also help you save on taxes: 4. Gain exclusion If you sell your primary residence, you may be able to exclude up to $250,000 ($500,000 for married) of the gain from taxes if you meet some conditions. > Ownership (must have owned the home for at least 24 months within the 5 years prior to sale. For married couples only one spouse needs to meet this requirement) > Residence (you must have used the home as your main residence for at least 24 non-consecutive months during the 5 years before the sale. For married couples both spouses must meet requirements. > Look-back (you must not have claimed the exclusion on another home within the 2 years before this sale) Now, many people don’t know this but there is actually a partial exemption.  1. Work related move (i.e. you started a new job at least 50 miles farther from home) 2. Health related move (you moved to obtain, provide, or facilitate care for yourself or a family member) 3. Unforeseeable events (casualty, divorce, death, financial difficulty) 4. Special circumstances So, instead of claiming the full exclusion, you can exclude a prorated portion of the $250,000/$500,000 limit based on how long you owned and lived in the home. By the way, you can rent out a home for 2 years and still qualify for the exemption, as long as you lived there for the required period before selling (many people do this). 5. Tax example selling a home You bought a home for $200,000 (including all other costs) in 2018. You built a new deck, new roof and siding totaling $50,000. You now sold your home for $500,000. You are single. Selling costs are $20,000 (agent fees, etc) Sale price: $500,000 -$20,000 of selling costs (200,000 + 50,000) = -$250,000 (adjusted basis) Total Gain = 230,000 Exclusion = $250,000. Total taxes paid = $0. But what if you didn’t keep track of all your renovation costs like new siding or a deck? You would’ve had to pay taxes on $20,000 of capital gains!  Overall, knowing how these things work can literally save you thousands in taxes. Do you have any tips with homeownership? Share some in the comments!   Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.
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Always an investor?

"That gave no reason for their suggestion, no proposed strategy?"
- R Quinn
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Vanguard’s Transfer on Death Plan Kit

"It is unclear to me why Vanguard had taken the position they did in regards to previously not allowing beneficiaries to be appropriately named on their jointly owned taxable accounts. I feel the same way towards my state laws that still does not allow us an option for a transfer on death in our deed as many states do. I know that we could have a revocable living trust to accomplish the same objective upon our deaths, I just do not understand why the large organizations do not allow the simple options."
- William Perry
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Sector Fund by Stealth

I'VE RECENTLY MADE the most significant change to my own portfolio in thirty five years. For the first time I've moved away from pure market-cap investing, tilting meaningfully toward Europe and Southeast Asia and bringing my US technology concentration down to around fifteen percent. I'm retired. I don't need to chase the outperformance that concentration might deliver, and I don't need the potential volatility that comes with it. This is a personal position rather than any kind of recommendation; it's nothing more than a risk management decision made at a point in life where I simply don't need the risk. What prompted it was a growing discomfort with something I suspect many everyday investors haven't fully reckoned with: the S&P 500 is no longer quite the animal it once was. A broad market index fund casts a wide net across the economy, and the S&P 500, which tracks the 500 largest US businesses by market value, has long been held up as the sensible default: low cost, well diversified, a bet on the whole rather than any one part of it. A sector fund works differently; it makes a deliberate, concentrated bet on a specific industry. If you believe technology is going to outperform the market as a whole, it gives you the ability to concentrate your capital into exactly the sector your research or gut instinct suspects is going to be the place to be and let it run. The theory behind each is straightforward enough. A broad market fund captures a larger slice of the investment universe and is generally considered the lower-risk path. A sector fund comes with a well-understood trade-off: higher potential returns in good times, sharper drawdowns when sentiment turns. Investors who consciously choose a technology sector fund know what they're signing up for. The risk profile is understood, accepted, and priced into the decision. The problem is that the line between these two things has become a bit fuzzy, and most everyday investors haven't noticed. A handful of technology and technology-related companies (Apple, Microsoft, Nvidia, Amazon, Meta, Alphabet) have grown so dominant in their market valuations that they now represent a disproportionate share of the entire index. During the last year, the top ten holdings have accounted for roughly a third of the total weight of all 500 companies. The mechanism behind this is simply how the index works. The S&P 500 is market-cap weighted, meaning the bigger the company, the bigger its slice of the pie. As technology companies scaled their dominance through the 2010s and into the 2020s, their weight within the index ballooned accordingly. The index didn't change its rules; the market just rewarded one particular group of companies so heavily that they came to dominate the scoreboard. This means the investor who bought the S&P 500 believing they were spreading risk broadly across the American economy (energy, healthcare, financials, industrials, consumer staples) owns something that looks quite different to the story they were sold. You buy five hundred companies and a third of your money lands in ten stocks, most of them operating in the same broad technological ecosystem. That is a concentration risk, whether it is labelled as one or not. It's a sector fund “light”, acquired by stealth through the natural mechanics of market-cap weighting. The issue is that millions of everyday investors are carrying a version of that same risk without necessarily knowing it. Although I've used the S&P 500 as an example here, it isn't alone. Most broad-based indexes including developed world trackers will exhibit the same characteristics to varying degrees, because the same companies sit near the top of those indexes too. The MSCI World, often marketed as the global diversifier, allocates somewhere in the region of seventy percent to US equities, and within that, the familiar names reappear. You can cross borders on paper without ever really leaving the room. None of this is an argument against the S&P 500. The concentration reflects real, earned dominance; these companies grew to the top of the index because they genuinely deserved to. And whether my reallocation turns out to be the right call is genuinely unknowable. The concentrated index could continue to outperform for another decade and I'll have left returns on the table, a real possibility I've made my peace with. The point isn't that I've found the correct answer. The point is that I had the information to make a considered choice, weighed it against my own circumstances, and acted accordingly. That's all any investor can do. The uncomfortable truth is that a great many people haven't been given the chance to do the same. They're holding a product that has quietly changed its character, and nobody has thought to mention it. Better information doesn't guarantee better decisions, but it at least puts the decision where it belongs: with the person whose money it is. ___ Mark Crothers is a retired small business owner from the UK with a keen interest in personal finance and simple living. Married to his high school sweetheart, with daughters and grandchildren, he knows the importance of building a secure financial future. With an aversion to social media, he prefers to spend his time on his main passions: reading, scratch cooking, racket sports, and hiking.
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Tax Smart Retirement

A POPULAR JOKE about retirement is that it can be hard work. That’s because financial planning is like a jigsaw puzzle, and retirement often means rearranging the pieces. In the past, I’ve discussed two key pieces of that puzzle: how to determine a sustainable portfolio withdrawal rate and how to decide on an effective asset allocation. But there’s one more piece of the puzzle to contend with: taxes. Especially if you’re planning to retire on the earlier side, it’s important to have a tax plan. When it comes to tax planning for retirement, there’s one key principle I see as most important, and that’s the idea that in retirement, the goal is to minimize your total lifetime tax bill. That’s important because a fundamental shift occurs the day that retirement arrives: In contrast to our working years, when taxes are, to a large degree, out of our control, in retirement, taxes are much more within our control. By choosing which investments to sell and which accounts to withdraw from, retirees have the ability to dial their income—and thus their tax rate—up or down in any given year. The challenge, though, is that tax planning can be like the game Whac-A-Mole. Choose a low-tax strategy in one year, and that might cause taxes to run higher in a future year. That’s why—dull as the topic might seem—careful tax planning is important. To get started, I recommend this three-part formula: Step 1 The first step is to arrange your assets for tax-efficiency. This is often referred to as “asset location.” Here’s an example: Suppose you’ve decided on an asset allocation of 60% stocks and 40% bonds. That might be a sensible mix, but that doesn't mean every one of your accounts needs to be invested according to that same 60/40 mix. Instead, to help manage the growth of your pre-tax accounts, and thus the size of future required minimum distributions, pre-tax accounts should be invested as conservatively as possible. On the other hand, if you have Roth assets, you’d want those invested as aggressively as possible. Your taxable assets might carry an allocation that’s somewhere in between. If you can make this change without incurring a tax bill, it’s something I’d do even before you enter retirement. Step 2 How can you avoid the Whac-A-Mole problem referenced above? If you’re approaching retirement, a key goal is to target a specific tax bracket. Then structure things so your taxable income falls into that same bracket more or less every year. By smoothing out your income in this way from year to year, the goal is to avoid ever falling into a very high tax bracket. To determine what tax rate to target, I suggest this process: Look ahead to a year in your late-70s, when your income will include both Social Security and required minimum distributions from your pre-tax retirement accounts. Estimate what your income might be in that future year and see what marginal tax bracket that income would translate to. In doing this exercise, don’t forget other potential income sources. That might include part-time work, a pension, an annuity or a rental property. And if you have significant taxable investment accounts, be sure to include interest from bonds. Then, for simplicity, subtract the standard deduction to estimate your future taxable income. Suppose that totaled up to $175,000. Using this year’s tax brackets, that would put your income in either the 24% marginal bracket (for single taxpayers) or 22% (married filing jointly). You would then use this as your target tax bracket. Step 3 With your target tax bracket in hand, the next step would be to make an income plan for each year. The idea here is to identify which accounts you’ll withdraw from to meet your household spending needs while also adhering to your target tax bracket. This isn’t something you’d map out more than one year in advance. Instead, it’s an exercise you’d repeat at the beginning of each year, using that year’s numbers. What might this look like in practice? Suppose you’re age 65, retired and not yet collecting Social Security. In this case, your income—and thus your tax bracket—might be quite low. To get started, you’d want to withdraw enough from your tax-deferred accounts to meet your spending needs but without exceeding your target tax bracket. This would then bring you to a decision. If you’ve taken enough out of your tax-deferred accounts to meet your spending needs and still haven’t hit your target tax rate, then the next step would be to distribute an additional amount from your pre-tax accounts. But with this additional amount, you’d complete a Roth conversion, moving those dollars into a Roth IRA to grow tax-free from that point forward. How much should you convert? The answer here involves a little bit of judgment but is mostly straightforward: You’d convert just enough to bring your marginal tax bracket up into the target range. Some people prefer to go all the way to the top of their target bracket, while others prefer to back off a bit. The most important thing is just to get into the right neighborhood. What if, on the other hand, you’ve taken enough from your pre-tax accounts to reach your target tax rate, but that still isn’t enough to meet your spending needs? In that case, you wouldn’t take any more from your pre-tax accounts, and you wouldn’t complete any Roth conversions. Instead, you’d turn to your taxable accounts, where the applicable tax brackets will almost certainly be lower. Capital gains brackets currently top out at just 20%. Thus, for the remainder of your spending needs, the most tax-efficient source of funds will be your taxable account. What if you aren’t yet age 59½? Would that upend a plan like this? A common misconception is that withdrawals from pre-tax accounts entail a punitive 10% penalty. While that’s true, it isn’t always true, and there’s more than one way around it. One exception allows withdrawals from a workplace retirement plan like a 401(k) as long as you leave that employer at age 55 or later. In that case, as long as you don’t roll over the account to an IRA, you’d be free to take withdrawals without penalty. If you’re retiring before age 55, you’ll want to learn about Rule 72(t). This allows for withdrawals from pre-tax accounts at any age, as long as you agree to what the IRS refers to as substantially equal periodic payments (SEPP) from your pre-tax assets. The SEPP approach definitely carries restrictions, but if you’re pursuing early retirement, and the bulk of your assets are in pre-tax accounts, this might be just the right solution.   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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How did you avoid being in the 39%?

"I know I have banged on about this before, but our superannuation system here in Australia means that every employee saves 12% of their wage for their entire working life. And all superannuation funds have a fiduciary requirement, to act in the best interest of their fund members. This should see most people well set up financially for retirement, and a significant reduction of the burden on our aged pension scheme. (An aged pension is available as a "safety net" for those without sufficient funds to service their own retirement.)"
- greg_j_tomamichel
Read more »

The Case for Kids

I RECENTLY HIT THE “pay now” button on what I believe will be the last of 20 years of college tuition bills. That’s right, we have five kids. All went to college. None took out student loans. Was it worth it—not just paying the tuition bills, but the decision to have children in the first place? It’s a pressing question. A birth dearth is hitting the U.S. and other countries around the world, as many adults opt to go childless. Today, roughly half of all countries have fertility rates that are so low that the population is either stagnant or shrinking. That brings me to today’s topic: the case for children. It’s a complex subject. I don’t want to suggest I know how others ought to decide. Everybody’s situation is unique and shouldn’t be judged by anyone else—and certainly not by me. Still, I think those of us with good stories about raising kids should share our experiences. We can balance out today’s narrative that children are more trouble than they’re worth. I remember the subtle pressure in the 1980s and ‘90s from others, as our family kept growing. Folks expressed concerns about having so many children. I suppose that, if you treasure a quiet and peaceful life above all else, having kids may not be a good idea. Children are messy and bring chaos. I remember answering the door, only to come face to face with our upset neighbor. He was a prominent doctor in the community and complained about my kids shooting at the deer in the backyard from our second story bedroom windows. “Thank you, Dr. Smith, for letting me know. I’ll take care of it.”  Ugh. But probably the greatest reason the U.S. no longer has a fertility rate necessary to maintain a stable population is related to financial concerns. The U.S. Department of Agriculture estimates the cost of raising a child through age 17 is more than $230,000. That number sounds ridiculously high to me. Still, whatever the right number is, the cost is daunting when you’re just getting started. [xyz-ihs snippet="Mobile-Subscribe"] I went back and looked at our financial records and found that, when our first child was born, we had a paltry net worth of $12,000. On top of that, my salary was modest. Why did my wife and I believe we could support a family? I’m a conservative banker and my tribe doesn’t believe “faith” is a business plan. So why did we do it? There were five reasons—some of which were clear to us at the time and some of which only became clear later. First, rather than just complain about our culture, we thought our best opportunity to change the world was by having children. Today, by God’s grace, we have two entrepreneurs, one banker, one IT guy and a social worker. In addition, thanks to marriage, we now have two health care workers and an oil man in the family. The world is better as a result of their service to others. We now know we changed the world for the better. I’m a finance guy, so I can’t help but estimate the financial return on investment. All five kids have good jobs. What if I assume they average $100,000 a year in earnings over a 40-year career? What kind of impact could that have? Assuming they give away 10% of their income, as we taught them, they’ll have contributed $2 million to charities over their careers. Social Security and Medicare contributions at current rates would be $3 million. State, local and federal taxes come in at an estimated $4 million. I’d call that a decent return on investment. Second, having children matures us. If I’d never advanced in my career, we would have struggled to raise five children. But the financial challenge of having kids meant I approached my career with a new fervor. As we awaited the birth of our first son, I studied hard for the CPA exam. Next was an MBA program, which I completed while working. That led to some nice raises and promotions. Third, by necessity, having children squeezed a lot of ugly selfishness out of me. I’m a selfish person by nature. But selfless service to family prepared me for selfless service at work and to charitable organizations. Fourth, researchers say children don’t necessarily make people happier at first. But ultimately, the satisfaction of a purposeful life devoted to family trumps any temporary happiness we give up. Finally, as we age, it can become harder to find true purpose, joy and passion. But having three grandchildren sure helps. Joe Kesler is the author of Smart Money with Purpose and the founder of a website with the same name, which is where a version of this article first appeared. He spent 40 years in community banking, assisting small businesses and consumers. Joe served as chief executive of banks in Illinois and Montana. He currently lives with his wife in Missoula, Montana, spending his time writing on personal finance, serving on two bank boards and hiking in the Rocky Mountains. Check out Joe's previous articles. [xyz-ihs snippet="Donate"]
Read more »

What is the best way to donate to charity in 2026?

"+1 on using a DAF. I use mine to growth my donated money. I limit gifts to 3% less admin and fund fees. The will and trust are set to move final assets to my DAF administrator, and they have instructions to continue my plan as an endowment (perpetual "DAF"). Donations to the DAF are also helping with tax efficiency - paying less taxes now (still doing roth conversions) and reducing RMDs (future taxes). My brokers advisors have been a big help establishing a plan and showing it's many benefits."
- Gordy Vytlacil
Read more »

Loose Change

"In 1993 my girlfriend and I made the bold choice to not bring travelers checks with us to Europe. We had to hunt for the correct ATM machines, but we were able to get local currencies with the debit card I had. It was a new financial world."
- Cammer Michael
Read more »

New to building a CD or Bond Ladder?

"We have three bond funds (all Vanguard ETFs) in our traditional IRA, all about 1/3 of our bonds: 1) BSV short term- for minimal volatility 2) VTIP short term tips- for above plus inflation protection 3) BND intermediate term for slightly higher returns"
- David Lancaster
Read more »

Allan Roth’s 2/13/26 article references Jonathan Clements

"I'm in agreement with Richard here, it's not possessions OR experiences. Some folks garner tangible value from possessions (I'm thinking Porsches, which doesn't necessarily apply to me). I'm in the process of moving, so have been organizing (read: throwing out) a lot of possessions collected over a 30 year span. And while I don't view myself (nor do others) as particularly materialistic, I'll happily admit to coming across long forgotten possessions that when found have brought me a lot of happiness as the memories they stir. This TBH is in distinction to my SO, who is almost opposite in her attachment to old things (she simply views them as old). But what I try to apply, both in possessions and experiences, is a version of Marie Kondo, "does this possession/experience bring you joy?" That's been a terrific barometer for me in making the qualitative aspects of a decision."
- Leonard Go
Read more »

Home Tax Tips

IF YOU OWN a home or are planning to buy one, there are a few things you need to know from the tax standpoint that could save you money: 1. Mortgage Interest If you have a mortgage, you can typically deduct the interest you pay on the loan up to $750,000 ($1,000,000 if taken before December 16, 2017) but only if you itemize your deductions (schedule A) You can also deduct points you paid if you itemize. Many people miss deducting points on their tax returns when they purchase a house, but you have to meet some criteria like:
  1. The points relate to a mortgage to buy, build or improve your principal residence
  2. Points were reasonable amount charged in that area
  3. You provide funds (at or before closing) at least equal to the points charged
  4. The points clearly show on the settlement statement
In general, points to get a new mortgage or to refinance an existing mortgage are deducted ratably over the term of the loan.  Note that the deductible points not included on Form 1098 (the mortgage interest form) should be entered on Schedule A (Form 1040), Itemized Deductions, line 8c “Points not reported to you on Form 1098.” 2. Property taxes Property taxes can be deducted on your tax return if you itemize deductions. The total amount of taxes (including state and local income taxes) is capped at $40,400 for 2026. This cap is temporary and will increase by 1% annually through 2029 before reverting to $10,000 in 2030. If you make between $500k to $600k of modified adjusted gross income, the $40.4k deduction is reduced by 30% for each dollar you make. At $600k MAGI, the deduction drops to $10k, potentially raising marginal tax rates to 45.5% (!) for singles due to “SALT torpedo” if you are in the $500-600k range. If you are at that range, it’s recommended to mitigate this by lowering AGI/MAGI by maximizing pre-tax 401(k)/403(b), HSA, FSA contributions, timing RSU sales, tax loss harvesting, or deferring income/accelerating expenses for business owners. 3. Improvements Improvements are significant enhancements made to your home that increase its value. Many people overpay on taxes when they ultimately sell their house because they don’t keep track of these improvements. Here are some examples provided by the IRS: > Putting an addition on your home > Replacing an entire roof > Paving your driveway > Installing central air conditioning > Rewiring your home > Building a new deck > Kitchen upgrades > Lawn sprinkler system > New siding > Built in appliances > Fireplace Now, these costs aren’t deducted, but they are added to your home’s cost basis. This could lead to lower capital gains taxes when you sell your property (more on this later). Repairs, on the other hand, don’t impact your basis and don’t affect your taxes (e.g. repairing a broken fixture, patching cracks, etc) You will need to document every improvement, as this can help you save money on taxes. Keep your receipts and invoices (upload them to Google Drive) and record the dates and descriptions of the work done. Taxes when selling your house When you sell your house, here’s the formula: Selling price  > Selling expenses (like realtor fees) > Adjusted cost basis (how much you purchased it for + all these capital improvements I talked about above + any closing costs you paid when you acquired the home (legal fees, recording, survey, stamp taxed, title insurance) = Gain/Loss You will need to pay capital gains tax if there is a gain, but, luckily there is a gain exclusion (Section 121 exclusion) that can also help you save on taxes: 4. Gain exclusion If you sell your primary residence, you may be able to exclude up to $250,000 ($500,000 for married) of the gain from taxes if you meet some conditions. > Ownership (must have owned the home for at least 24 months within the 5 years prior to sale. For married couples only one spouse needs to meet this requirement) > Residence (you must have used the home as your main residence for at least 24 non-consecutive months during the 5 years before the sale. For married couples both spouses must meet requirements. > Look-back (you must not have claimed the exclusion on another home within the 2 years before this sale) Now, many people don’t know this but there is actually a partial exemption.  1. Work related move (i.e. you started a new job at least 50 miles farther from home) 2. Health related move (you moved to obtain, provide, or facilitate care for yourself or a family member) 3. Unforeseeable events (casualty, divorce, death, financial difficulty) 4. Special circumstances So, instead of claiming the full exclusion, you can exclude a prorated portion of the $250,000/$500,000 limit based on how long you owned and lived in the home. By the way, you can rent out a home for 2 years and still qualify for the exemption, as long as you lived there for the required period before selling (many people do this). 5. Tax example selling a home You bought a home for $200,000 (including all other costs) in 2018. You built a new deck, new roof and siding totaling $50,000. You now sold your home for $500,000. You are single. Selling costs are $20,000 (agent fees, etc) Sale price: $500,000 -$20,000 of selling costs (200,000 + 50,000) = -$250,000 (adjusted basis) Total Gain = 230,000 Exclusion = $250,000. Total taxes paid = $0. But what if you didn’t keep track of all your renovation costs like new siding or a deck? You would’ve had to pay taxes on $20,000 of capital gains!  Overall, knowing how these things work can literally save you thousands in taxes. Do you have any tips with homeownership? Share some in the comments!   Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.
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Always an investor?

"That gave no reason for their suggestion, no proposed strategy?"
- R Quinn
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Vanguard’s Transfer on Death Plan Kit

"It is unclear to me why Vanguard had taken the position they did in regards to previously not allowing beneficiaries to be appropriately named on their jointly owned taxable accounts. I feel the same way towards my state laws that still does not allow us an option for a transfer on death in our deed as many states do. I know that we could have a revocable living trust to accomplish the same objective upon our deaths, I just do not understand why the large organizations do not allow the simple options."
- William Perry
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Tax Smart Retirement

A POPULAR JOKE about retirement is that it can be hard work. That’s because financial planning is like a jigsaw puzzle, and retirement often means rearranging the pieces. In the past, I’ve discussed two key pieces of that puzzle: how to determine a sustainable portfolio withdrawal rate and how to decide on an effective asset allocation. But there’s one more piece of the puzzle to contend with: taxes. Especially if you’re planning to retire on the earlier side, it’s important to have a tax plan. When it comes to tax planning for retirement, there’s one key principle I see as most important, and that’s the idea that in retirement, the goal is to minimize your total lifetime tax bill. That’s important because a fundamental shift occurs the day that retirement arrives: In contrast to our working years, when taxes are, to a large degree, out of our control, in retirement, taxes are much more within our control. By choosing which investments to sell and which accounts to withdraw from, retirees have the ability to dial their income—and thus their tax rate—up or down in any given year. The challenge, though, is that tax planning can be like the game Whac-A-Mole. Choose a low-tax strategy in one year, and that might cause taxes to run higher in a future year. That’s why—dull as the topic might seem—careful tax planning is important. To get started, I recommend this three-part formula: Step 1 The first step is to arrange your assets for tax-efficiency. This is often referred to as “asset location.” Here’s an example: Suppose you’ve decided on an asset allocation of 60% stocks and 40% bonds. That might be a sensible mix, but that doesn't mean every one of your accounts needs to be invested according to that same 60/40 mix. Instead, to help manage the growth of your pre-tax accounts, and thus the size of future required minimum distributions, pre-tax accounts should be invested as conservatively as possible. On the other hand, if you have Roth assets, you’d want those invested as aggressively as possible. Your taxable assets might carry an allocation that’s somewhere in between. If you can make this change without incurring a tax bill, it’s something I’d do even before you enter retirement. Step 2 How can you avoid the Whac-A-Mole problem referenced above? If you’re approaching retirement, a key goal is to target a specific tax bracket. Then structure things so your taxable income falls into that same bracket more or less every year. By smoothing out your income in this way from year to year, the goal is to avoid ever falling into a very high tax bracket. To determine what tax rate to target, I suggest this process: Look ahead to a year in your late-70s, when your income will include both Social Security and required minimum distributions from your pre-tax retirement accounts. Estimate what your income might be in that future year and see what marginal tax bracket that income would translate to. In doing this exercise, don’t forget other potential income sources. That might include part-time work, a pension, an annuity or a rental property. And if you have significant taxable investment accounts, be sure to include interest from bonds. Then, for simplicity, subtract the standard deduction to estimate your future taxable income. Suppose that totaled up to $175,000. Using this year’s tax brackets, that would put your income in either the 24% marginal bracket (for single taxpayers) or 22% (married filing jointly). You would then use this as your target tax bracket. Step 3 With your target tax bracket in hand, the next step would be to make an income plan for each year. The idea here is to identify which accounts you’ll withdraw from to meet your household spending needs while also adhering to your target tax bracket. This isn’t something you’d map out more than one year in advance. Instead, it’s an exercise you’d repeat at the beginning of each year, using that year’s numbers. What might this look like in practice? Suppose you’re age 65, retired and not yet collecting Social Security. In this case, your income—and thus your tax bracket—might be quite low. To get started, you’d want to withdraw enough from your tax-deferred accounts to meet your spending needs but without exceeding your target tax bracket. This would then bring you to a decision. If you’ve taken enough out of your tax-deferred accounts to meet your spending needs and still haven’t hit your target tax rate, then the next step would be to distribute an additional amount from your pre-tax accounts. But with this additional amount, you’d complete a Roth conversion, moving those dollars into a Roth IRA to grow tax-free from that point forward. How much should you convert? The answer here involves a little bit of judgment but is mostly straightforward: You’d convert just enough to bring your marginal tax bracket up into the target range. Some people prefer to go all the way to the top of their target bracket, while others prefer to back off a bit. The most important thing is just to get into the right neighborhood. What if, on the other hand, you’ve taken enough from your pre-tax accounts to reach your target tax rate, but that still isn’t enough to meet your spending needs? In that case, you wouldn’t take any more from your pre-tax accounts, and you wouldn’t complete any Roth conversions. Instead, you’d turn to your taxable accounts, where the applicable tax brackets will almost certainly be lower. Capital gains brackets currently top out at just 20%. Thus, for the remainder of your spending needs, the most tax-efficient source of funds will be your taxable account. What if you aren’t yet age 59½? Would that upend a plan like this? A common misconception is that withdrawals from pre-tax accounts entail a punitive 10% penalty. While that’s true, it isn’t always true, and there’s more than one way around it. One exception allows withdrawals from a workplace retirement plan like a 401(k) as long as you leave that employer at age 55 or later. In that case, as long as you don’t roll over the account to an IRA, you’d be free to take withdrawals without penalty. If you’re retiring before age 55, you’ll want to learn about Rule 72(t). This allows for withdrawals from pre-tax accounts at any age, as long as you agree to what the IRS refers to as substantially equal periodic payments (SEPP) from your pre-tax assets. The SEPP approach definitely carries restrictions, but if you’re pursuing early retirement, and the bulk of your assets are in pre-tax accounts, this might be just the right solution.   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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Manifesto

NO. 53: STRIVING toward our goals is usually more satisfying than achieving them. Yes, we should think hard about our goals—but we should also ask whether we’ll enjoy the journey.

think

FOCUSING ILLUSION. Those with high incomes or significant wealth are more likely to say they’re happy. But this could be a focusing illusion. When asked about their happiness, the well-to-do ponder their good fortune—and that prompts them to say they’re happy. But are they? Research also suggests high-income earners suffer more stress and anger during the day.

Truths

NO. 18: WATCH OUT for crowds. Popularity is typically a good sign when picking a movie, cellphone or restaurant. But it’s bad when selecting investments. If an investment is highly popular, the eager buying likely means it's overpriced. Why do we favor popular investments? They’re comfortable to own because we get validation from those around us.

humans

NO. 70: FOCUS on the negative and we’ll feel miserable, while focusing on the positive can boost our mood. Suffering through a long workout? Imagine how good breakfast will taste afterwards. Upset because stocks are struggling? Focus on how well the rest of your portfolio is holding up, or on how your nest egg is worth so much more than it was five years ago.

Basics

Manifesto

NO. 53: STRIVING toward our goals is usually more satisfying than achieving them. Yes, we should think hard about our goals—but we should also ask whether we’ll enjoy the journey.

Spotlight: Estate Plan

All in the Execution

A FRIEND WAS RECENTLY asked by his father to be executor of his estate—and, without hesitation, my friend agreed. But then the conversation quickly moved on to other topics, leaving my friend confused about his role.
My suggestion to my friend: Have another conversation with your dad—and ask these four questions:
What are your expectations? Someone who creates a will is known as a testator. The primary role of an executor is to settle the testator’s estate.

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That Final Payment

IT’S IMPORTANT TO BE familiar with what happens with Social Security benefits when someone dies. Otherwise, you may find yourself in a long, painstaking battle to get the payment to which your loved one was entitled. I found this out the hard way.
My father-in-law Bernard died in September 2015. My wife was his executor and the agent under his power of attorney (POA). But I’d earlier served as POA and executor for my mother,

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What’s Your Plan?

MICK JAGGER IS AMONG the most successful entertainers of our time. But despite his wealth, Jagger tells his eight children that they’ll need to make their own way. Similarly, Shaquille O’Neal tells his children that they can earn some of his millions, but it won’t necessarily be given to them. Actor Jeff Goldblum puts it more bluntly: “Row your own boat,” he’s said. Other public figures have echoed a similar theme.
Why do these wealthy folks take such a seemingly uncharitable view?

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CDs and Cemeteries

“A YEAR TO LIVE.” That’s the name of a class I’ve been teaching on and off for the past 20 years. My hope: Participants will gain more understanding, acceptance and peace about one of life’s few guarantees—death. This year’s class members have a little over five months left to live.

Every group is a little different. Some people resist the practicalities of preparing for death: putting things in writing, making medical and funeral arrangements,

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How young is too young to receive an inheritance?

My wife and I just had our wills and POAs redone. We changed our domicile form PA to NJ a few years ago, and it was recommended we have them updated. I was surprised how different some of the documents were from state to state. For example, NJ has an 11 day period before a will can be probated, starting form the date of death. PA does not have that. The Medical POA and Advanced Directive was very narrative driven;

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The Status of Inherited IRAs in 2025

Here is the link to Christine Benz of Morningstar interviewing Ed Slott, who many consider THE expert in the country on the IRS’s interpretation of IRA laws/rules for 2025.
Ed is a gold mine of information as to how to decide on whether to convert traditional IRAs to Roths, and it’s effect on your beneficiaries.
https://app.mscomm.morningstar.com/e/er?utm_source=eloqua&utm_medium=email&utm_campaign=MorningDigest&utm_content=None_62004&utm_id=32087&s=1258972516&lid=91893&elqTrackId=894e84e4e6dd4e4ea71a9bc97420afd2&elq=c1c50cb96d48485491b4d81fbe5a229d&elqaid=62004&elqat=1&elqak=8AF55770D8A5B2AC19A42DE86CB56351215EDD04764F052A1F72EA4FA79B9C459194

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Spotlight: Housley

Resolutions? What will you do?

Time for resolutions: •Logging off social media: No Facebook, no YouTube, no X—basically, no scrolling my life away. •Call the doctor and finally trade in these knees for the deluxe model. That’s it. Let’s not get crazy—baby steps!
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What Kind of Loss Is This?

On Tuesday, I underwent a partial knee replacement on my right knee. It was a necessary step after more than a year—perhaps longer—of persistent pain that disrupted my sleep and made daily walks nearly impossible. But here’s the twist: while the surgery was meant to relieve my suffering, the post-operative pain is even more intense. Even with strong medication, it’s a new level of discomfort. And physical therapy? That promises its own form of agony for the next three months. After that, I’ll go through it all again with my left knee. So, in essence, I traded a long-term, chronic pain for a sharper, more intense—but temporary—one. A lifetime of suffering exchanged for a concentrated period of hardship with the promise of relief. What kind of loss is this? How do we define it? And more importantly—doesn’t this feel familiar? Markets experience pain too. Long-term economic drags, unsustainable trends, and financial misalignments eventually reach a breaking point. Sometimes, the market chooses to rip the Band-Aid off—an intense, painful correction in exchange for future stability. Is that what’s happening now? Are we enduring a necessary, short-term pain that ultimately leads to a stronger foundation? I certainly hope so. Because in both surgery and investing, the goal isn’t just to avoid pain—it’s to ensure a healthier future. WDH
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Average vs. Humble Average

No one describes themselves as average at anything. We’re above-average drivers. Above-average parents. Above-average judges of character. Statistically, that can’t be true—but it’s how we think. Investing is no different. The average investor almost always believes they are above average. They read. They pay attention. They try to make smart decisions. And yet, year after year, investors as a group earn returns that fall short of the market itself. That raises a simple but uncomfortable question: What’s the difference between earning the market’s average return and earning the return of the average investor? Two Very Different “Averages” When we talk about average in investing, we usually mean one of two things: The market average The average investor They sound similar. They are not. The Market Average The market average—think of the S&P 500—is “average” only in the sense that it owns everything: Every sector Every style Every winner and every loser When you look at long-term sector performance charts, the S&P 500 is never at the top and never at the bottom. Because it owns every sector, it must fall between the extremes. What looks like mediocrity is actually design. The index doesn’t chase leadership or flee weakness. It simply holds everything and lets time do the work. The market average: Never chases performance Never panics Never second-guesses itself Rebalances automatically Its advantage doesn’t come from prediction or insight, but from limiting mistakes. The Average Investor The average investor, by contrast, is very human. They: Chase recent winners Sell laggards just before recoveries Trade too often React to headlines Confuse activity with progress Ironically, the average investor rarely earns the market’s average return. Not because they lack intelligence—but because they make predictable behavioral mistakes. The tragedy isn’t that investors get average returns. It’s that most don’t. Sector Chasing in Action Each year, a handful of sectors dominate performance. Technology one year. Energy the next. Financials after that. The problem is simple: You only know the winners after the fact By the time leadership is obvious, prices already reflect it Leadership rotates faster than investor conviction Chasing sectors becomes a dog chasing its tail—busy, exhausting, and ultimately unproductive. The market average doesn’t chase. It waits. Average Isn’t the Problem—Behavior Is We’re taught that average means mediocre. In investing, the opposite is often true. The market’s average return reflects: Broad ownership Discipline Patience Humility The average investor’s return reflects: Overconfidence Timing errors Emotional reactions Market average limits mistakes. The average investor multiplies them. The Real Advantage of Indexing Index funds don’t succeed because they’re clever. They succeed because they’re behaviorally superior. They remove the need to predict, eliminate most bad decisions, and protect investors from themselves. Indexing isn’t about settling for average. It’s about refusing to pretend you’re above average. A Final Thought Everyone wants to be an above-average investor. Ironically, the most reliable way to get there has been to accept the market’s average—and stop trying to outsmart it. So the real question isn’t whether you’re above average—it’s whether you’re willing to accept the humble dollar average. I know how hard that is, because I’m an average investor too—and I still catch myself believing I’m above average more often than I should.
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You DRIP?

I used to think DRIP was something only plumbers worried about. Then I started investing. Dividend ReInvestment Plans — DRIPs — are a favorite tool among long-term investors. “Always reinvest your dividends,” the logic goes. “Compounding is king.” For a long time, I agreed completely — and I still do for people who are in the wealth-building stage of life. But at some point, I stopped using DRIP entirely. Today, every dividend my portfolio generates goes into cash instead of back into the market. That wasn’t a reaction to fear or market timing. It was a deliberate decision shaped by age, income planning, and risk management. DRIP Works — Until Your Goals Change In the accumulation years — when you’re working, saving, and building — DRIP is hard to beat. Reinvesting dividends means: Your money stays fully invested Compounding happens automatically You avoid “cash drag” Emotion stays out of the process The formula is powerful: Earlier reinvestment = more shares = more growth. For younger investors, DRIP is usually the cleanest, simplest, and most effective strategy available. But the Question Eventually Changes Eventually, the investing question stops being: “How fast can I grow my portfolio?” and becomes: “How smoothly can I live off this portfolio?” That shift changes everything. Growth remains important — but stability, cash flow, and control rise to the top. That’s when I turned DRIP off. Why I Route Dividends to Cash Today, my dividends all flow into a cash account. I don’t treat that cash as idle money — I treat it as a working tool. Dividends now serve multiple purposes: 1. Rebalancing Discipline Rather than automatically reinvesting into whatever stock or ETF paid the dividend, I pool all the cash and periodically invest into whichever part of the portfolio is underweight. This avoids: Buying high simply because a holding paid a dividend Allowing asset classes to drift overweight Emotional portfolio adjustments Dividend cash becomes forced “buy low” capital. 2. Volatility Management In drawdown years, forced selling hurts. A cash dividend stream: Reduces the shares I must sell during bear markets Smooths income flows Lessens sequence-of-returns risk Having steady dividend cash increases psychological comfort as much as financial stability. 3. RMD Readiness Once Required Minimum Distributions (RMDs) enter the picture, the portfolio changes roles. Part of your nest egg becomes an income generator rather than a growth engine. Dividend cash: Helps meet RMD obligations naturally Reduces the need to pull principal from investments at poor times Keeps withdrawal management calm and flexible 4. Withdrawal Simplicity When income is needed — gifts, expenses, taxes, generosity — I use dividend cash first. That avoids untimely sells and makes budgeting simpler: Income comes from income; assets stay invested. But Doesn’t DRIP Earn More? Yes — in pure long-run math, DRIP usually wins. Studies suggest reinvesting dividends may outperform by about 0.1%–0.4% per year. But for someone in the spending phase, absolute return isn’t the only metric that matters. Risk management matters. - Cash-flow stability matters. - Behavior matters. Dividend-to-cash produces nearly identical long-term outcomes — while offering much greater control during retirement and withdrawal years. Age Matters Dividend strategy should follow life stage. Under 45 DRIP is king. Your priority is growth — not cash flow. 45–60 This becomes a gray zone. Some investors still lean fully into DRIP. Others begin collecting income for emerging needs. Both approaches can work. 60+ Now withdrawals become real. Stability matters more than squeezing out the last few basis points of growth. Cash dividends become not a drag — but a feature. Does Account Type Matter? Inside Retirement Accounts There is no tax cost either way. Choosing cash over DRIP is purely a decision about: Income management Volatility control Emotional comfort In Taxable Accounts Dividends are taxed whether reinvested or not — so DRIP doesn’t shield you from the IRS. Collecting dividends as cash can actually be more efficient, allowing you to: Avoid unnecessary selling Limit capital gains realization Fund income without portfolio disruption My System Today Right now: All dividends flow into cash. Cash funds withdrawals, giving, and tactical rebalancing. Shares remain invested unless there’s a deliberate reason to sell. This setup: Keeps volatility under control Simplifies income planning Prevents emotional portfolio tinkering Most importantly: It fits where I am in life. The Real Lesson DRIP isn’t a lifetime commandment. It’s a tool — and tools change with the job at hand. When you’re building wealth: Reinvest everything. When you’re living off wealth: Use dividends as income and control capital. So… You DRIP? Good — if you’re still building the tower. But when the time comes to live in it: Turning off DRIP might be the smartest upgrade you’ll ever make.
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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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Sleeves or Buckets?

Like most investors, I learned early about the elegance of the 60/40 portfolio. Sixty percent stocks for growth. Forty percent bonds for stability. I studied why it worked. Stocks historically delivered long-term returns, bonds reduced volatility, and periodic rebalancing enforced discipline.  60/40 has proved itself as a durable framework. It wasn’t exciting, but it was resilient. I understood its importance. It shaped how I thought about diversification, risk, and balance—and it still does. For many investors, 60/40 remains a perfectly reasonable default, particularly for those saving steadily, reinvesting dividends, and not yet drawing on their portfolios. When 60/40 feels incomplete The issue wasn’t whether 60/40 worked. It clearly had. The issue was what happens when a portfolio shifts from accumulating wealth to supporting spending. When markets fall, the textbook advice is straightforward: rebalance. Sell bonds. Buy stocks. That’s sound in theory. It’s harder in practice when: Stocks and bonds fall together Interest rates are rising Withdrawals are funding real expenses At that point, the central question isn’t about expected returns. It’s more basic: Where does my spending money come from when markets misbehave? That question led me to buckets. Buckets: a spending framework The bucket approach organizes money by time. Short-term bucket: cash for near-term expenses Intermediate bucket: bonds for the next several years Long-term bucket: stocks for long-term growth Buckets made immediate sense. By separating spending from growth, they reduce the risk of selling stocks at the wrong time and provide emotional comfort during market declines. Buckets work—and they work well—especially for managing sequence-of-returns risk early in retirement. But over time, I noticed a limitation. Buckets answered when money would be spent. They didn’t fully explain why I owned each investment. That realization pushed me toward sleeves. Sleeves: a portfolio framework At first, sleeves sounded like semantics. Aren’t sleeves just buckets with a different name? In practice, they aren’t. Buckets are time-based. Sleeves are function-based. Instead of organizing assets by years of spending, I began organizing them by roles: Growth sleeve: assets whose job is long-term compounding Income sleeve: assets whose job is reliable cash flow Cash sleeve: assets whose job is flexibility and stability Each sleeve has a purpose. Each earns its place. Most importantly, each sleeve is judged differently. Why sleeves work better for me With sleeves, I stopped asking whether an investment was “good” or “bad.” Instead, I ask: “Is this investment doing the job I hired it to do?” Growth assets don’t need to produce income. Income assets don’t need to be exciting. Cash doesn’t need to outperform anything. This shift changed how I respond to markets. Volatility in one sleeve doesn’t feel like failure—it’s simply that sleeve doing its job. A framework, not a verdict This isn’t an argument against 60/40 or buckets. 60/40 still matters as a foundational lesson in diversification and discipline. Buckets remain a powerful tool for clarifying spending. Sleeves simply work better for me because they move beyond spending and toward understanding—understanding what each part of the portfolio does, why it’s necessary, and how the pieces work together. My evolution wasn’t from right to wrong, but from theory to application: 60/40 taught balance Buckets taught security Sleeves taught purpose Today, I think less in percentages and more in jobs—and that has made me more disciplined, and more comfortable with uncertainty.
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