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On average, you’ll earn a higher return by investing a lump sum right away. Problem is, you won’t get an average result.

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How to build your nest egg

PETER WINKLER  |  Nov 29, 2025

"Peter - great post about lessons learned, regardless of the source."
- Jeff Bond
Read more »

The 4 Year Rule for Retirement Spending

mytimetotravel  |  Nov 29, 2025

"I find all these discussions about various rules for spending to be very interesting. As I consider their advice, I find myself having to put them into the context of the amount of retirement assets which a person has to help judge their validity. What I think I am saying in a round-about way, is if you don't have a meaningful amount of retirement assets, all the rules won't help you. And, if you are really flush with $$, the rules don't really apply. Or, said another way, if you have enough retirement assets to cover 25 years of spending (excess of SS/pension), then putting 4 years of spending into MMFs or CDs and following this plan will no doubt work. However, if funding your 4 years of expenses takes most of your bucks, you might struggle over your retirement. Interestingly, the 4% spending rule also works if you have 25 years of spending covered......:-)"
- stelea99
Read more »

HSA Proposal

Bogdan Sheremeta  |  Nov 27, 2025

"David, you're right on the money that Medicare Supplement premiums can't be paid or reimbursed by an HSA. But I believe Part D (and even Medicare Advantage) premiums can be. How Your HSA Can Reimburse You for Medicare Premiums and Expenses | Kiplinger"
- Andrew Forsythe
Read more »

Property taxes, our schools, our towns and seniors. Shared responsibility.

R Quinn  |  Nov 28, 2025

"Absolutely, and I don’t understand why people don’t get that. Plus the majority of those taxes are for teachers. At the same time ask people if teachers are underpaid and survey after survey says people agree teachers deserve higher paid. Where do they think the added expense will come from?"
- R Quinn
Read more »

My Investing Journey, Just Do It

Dan Smith  |  Nov 28, 2025

"Thanks for your supportive comment. You are right that it may time for the lessons learned to manifest themselves. I will check out the Winker book."
- Oscar Barbarin
Read more »

Happy Hour, or The Panic Button? Why Early Retirement Anxiety Is Real.

Mark Crothers  |  Nov 30, 2025

"I have been retired 16 years from a high profile, high level job I enjoyed for many years. When I retired I experienced none of what you refer to — loss of professional identity, assured income, and daily structure. Yes, I am unique because of my pension providing assured income and with SS added there was no drop in the income that we lived on before retirement although 16 years later there has not been a COLA to my pension and never will be. However, by investing all income (mostly equity) above base salary our investments today can easily provide dividend and interest income to make up for inflation. But at our ages we are truly in the slow, near no go years so our discretionary spending has declined. We used to spend $25-30,000 a year on travel. Since we can’t go to Florida this year, that’s a savings of $25,000 or so. But the loss of professional identity (I was once named Employee Benefit Professional of the Year by a national magazine) and daily structure never bothered me and honestly I don’t know why. Perhaps we spent so much time traveling the first several years after I retired I didn’t notice. It may also be that I took phased retirement for 18 months before full retirement and got used to the idea. . You’re right, often I don’t know what day of the week it is or actually care much of the time. These days I know the days mostly by healthcare appointments. 😟 People don’t change because they retired. The events of life don’t change, both good and bad. Perhaps expectations for retirement are unrealistic sometimes. The biggest stress factor is finances for most people, eventually followed by health. Both are things that take decades of preparation but are the majority of people willing to do it? PS For some I think early retirement (mid to early 50s) can be difficult and not able to live up to expectations and with an enhanced longevity risk. "
- R Quinn
Read more »

Asset Location Decisions

Bogdan Sheremeta  |  Nov 29, 2025

WHERE YOU PUT your investments can make a huge difference for your after-tax wealth.  As you know, we have 3 main investment accounts:
  1. Taxable account. A traditional brokerage account where you are taxed every time you dividends or sell investments at a gain.
  2. Tax deferred account. Traditional 401(k), 403(b), and traditional IRAs allow taxes to be deferred to the future. You pay taxes when your investments are withdrawn, and generally come with an immediate tax deduction.
  3. Tax exempt account. Roth IRA, Roth 401(k), and Roth 403(b) allow you to avoid future taxes while providing no immediate tax deduction. The growth of these accounts is tax free.
Asset location Say, as part of your investment strategy, you want to start putting money in bonds. You have a 401(k), Roth IRA, and a brokerage account. Where do we put them? Brokerage account When you hold bonds, like BND (Total Bond Fund ETF), you pay taxes on non-qualified dividends (e.g. interest from the bond) up to a max rate of 37%, plus net investment income tax, if applies. This means that if you receive $1,000 from the bond, you will pay approximately $370 in taxes if you are in the highest tax bracket. Of course, not all of us are in such bracket, and perhaps a more reasonable number would be ~$220-240 for most people. But is taxable brokerage the right choice for you? Not really. You would be paying $200+ every year, plus state/local taxes. Personally, I'm 100% invested in equities, because I want to be aggressive with my portfolio in my 20s, but if I did have bonds, I wouldn't hold them in a brokerage account.   Roth IRA/Roth 401k When you purchase bonds in a Roth IRA, you will not pay taxes on the interest since it’s a tax-free account! That’s much better than the $200+ in taxes you would pay in a brokerage account. But is it the best choice? Well, bonds are considered “fixed income” funds, and they don’t grow much. Since Roth IRA is a tax-free account (meaning we pay no taxes when we sell these investments), we want as much growth as possible in it. Bonds would hinder that performance. So, holding bonds is better than brokerage, but likely not the most ideal place.   Traditional 401(k)/403(b) By holding bonds in an account like a traditional 401(k)/403(b), the interest income avoids immediate taxation, compounding tax free until withdrawal.  So, we avoid the ~$200+ of taxes and aren’t sacrificing the tax-free compounding like we are with a Roth IRA. This makes the pre-tax 401(k) the perfect location for bonds. Of course the 401(k)/403(b) choices are limited and are provided by your employer. So, if they don’t offer a bond fund, you might not have a choice. Some other examples:
  • REIT stocks/ETFs also pay non-qualified dividends and would follow similar logic like bond funds.
  • Actively managed funds (I’m strongly against these, as I believe passive funds are the best & lowest fees) have a lot of turnover, so they ideally shouldn’t be in a brokerage account due to capital gain distributions.
  • Stocks that pay 0% dividends (like Netflix) are the most efficient to hold within the brokerage account, but may need a more robust overall investing plan.
I really like this visual from Fidelity to reference:
But how much does this matter? Vanguard's research finds that a thoughtful asset location strategy can add significantly more value than an equal location strategy. The value added typically ranges from 5 to 30 basis points of after-tax return, depending on circumstances (e.g. income, portfolio size) Overall, I hope you think about all of your investments & how they get taxed.    Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.
Read more »

What’s Really on My Mind These Days

Dennis Friedman  |  Nov 26, 2025

"Martin, I was listening to a talk show on Saturday, and one of the guests said that about 40 million jobs considered repetitive could be replaced by AI today. If that’s true, maybe we’re underestimating the impact these companies are going to have on the economy, and their ability to make money."
- Dennis Friedman
Read more »

Bearing Witness: Retirement From the Wrong Side of the Divide

Mark Crothers  |  Nov 25, 2025

"Juan, I hope my agency in life would have overcome different roadblocks along the way, but it would certainly not be a foregone conclusion; luck certainly plays a role."
- Mark Crothers
Read more »

The Magic of the Season: From Turkey to Rollercoaster Spending in 72 Hours.

Mark Crothers  |  Nov 28, 2025

"Thanks for the explanation, Chris. A simple but excellent idea: it basically stops you from drawing heavily from your portfolio for annual expenses, a good tool to manage cash flow."
- Mark Crothers
Read more »

Decision Frameworks

Adam M. Grossman  |  Nov 29, 2025

IN THE SUMMER of 1966, author John McPhee spent two weeks lying on a picnic table in his backyard. Why? McPhee was suffering from writer’s block. As he described it, “I had assembled enough material to fill a silo, and now I had no idea what to do with it.” Investors find themselves in a similar situation today. There’s no shortage of financial information around us. But that doesn’t make it easier to know what to do with it.  When it comes to financial decision-making, there is, of course, one fundamental problem: None of us can see around corners. But that doesn’t leave us completely empty-handed. Whenever possible, I suggest employing decision frameworks. They can help us to do the best we can in the absence of complete information. Here are four such frameworks you might consider as you look ahead to the new year. Trading decisions Suppose you’re lukewarm on an investment and thinking of selling it. How should you think through this decision? To start, you might evaluate the investment’s merits. If it’s an individual stock, you could examine its valuation and study the company’s financials. If it’s a fund, you could look at its track record and management fees. And if it’s held in a taxable account, you could also check its tax efficiency.  Against those factors, you would then assess the tax impact of selling your shares. But how should you weight each factor in your decision? A fund might be tax-inefficient, for example, but have a good track record. When making decisions like this, the framework I suggest is to evaluate three factors: risk, growth potential and tax impact. And I would consider them in that order. Estate taxes The federal estate tax can be punitive for those with assets over the lifetime exclusion. Under current law, that’s $15 million per person, but it’s a political football and could easily change down the road. Many states also impose their own estate taxes, with much lower exclusions. For those with assets even in the neighborhood of the applicable exclusion, it might seem like an obvious decision to pursue estate tax strategies. Indeed, many families conclude that it’s worth virtually any amount of time, effort and cost to limit their exposure to these steep taxes. That’s a logical conclusion, but it’s not the only way. Other families take a different view. They reason that if their estates will be subject to tax, then, by definition, their children will be receiving substantial sums. Since that’s the case, they don’t see the need for acrobatics to leave their children even more, especially since those strategies usually introduce cost and complexity.  The most typical estate tax strategy, for example, is an irrevocable trust. In addition to the legal work required to set one up, these trusts require third-party trustees, and trustees typically ask to be compensated. This kind of trust also requires a separate tax return each year. Also, assets in trusts like this don’t benefit from a cost basis step-up at death, making the tax benefit a little more uncertain. Estate tax strategies, in other words, might make sense, but they aren’t the obvious “right” answer in all cases. That’s why, as you think through this question for your own family, you might employ this simple framework: Start by asking yourself which objective is more important: to keep taxes to an absolute minimum or, on the other hand, to keep complexity to a minimum. Let that be your guide. Portfolio construction How much effort should you put into your portfolio? Author Mike Piper draws an apt analogy. Building a portfolio, he said, is like making a fruit salad. Here’s how he explained it: “If you choose to have just 3-4 ingredients in your fruit salad instead of 7, that’s fine…There’s no one single recipe that beats the others…And you don’t have to be super precise about it—a little more or less of something than you had intended is not a disaster.” It’s an important point. Because there are so many available investment options, and because there is so much information and commentary around us, it can sometimes feel like we need to do more to optimize our investments. The reality, though, is that this is a choice. Just as with estate tax strategies, you might yield a benefit by fine tuning your portfolio, but you shouldn’t feel compelled to. The most important thing is that it be reasonable. As long as you aren’t taking inordinate risk, it’s a choice whether you choose to have five, 10 or 500 holdings in your portfolio. As Piper points out, you won’t necessarily go wrong with whichever path you choose, so choose the path that suits you. A 360-degree view Earlier in my career, I worked as an investment analyst at a firm where we were responsible for picking stocks. In discussing an idea with a colleague one day, it occurred to us that if you knew enough about any given stock, you could easily make an argument either for or against that stock. It was in the eye of the beholder. Consider a stock like Nvidia. On the one hand, it’s the dominant player in a fast-growing market and has enviable profit margins. But those margins are inviting competition, and there are concerns that the market is becoming saturated. Which set of arguments is correct? As with all financial decisions, we can’t know without the benefit of hindsight. That’s why I suggest what I call the “five minds” approach. Instead of taking a single position on a given question, try to look at it from all sides, balancing the viewpoints of an optimist a pessimist, an analyst, a psychologist and an economist. How would this work in practice? If there’s an idea that looks like it makes sense, pause and ask what the opposing argument might be. If you’re looking at a question through a quantitative lens, pause and ask what the qualitative factors might be. And always consider the broader context. Suppose, for example, you’re considering a Roth conversion. A key element in that equation is whether future tax rates will be higher or lower than they are today. To help answer this question, we could consult history as a guide, looking at historical tax rates and government debt levels. No one has a crystal ball. But since that’s the case, frameworks like this can help us manage through decisions with incomplete information.   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.
Read more »

Discussing money matters with friends- a slippery slope

R Quinn  |  Nov 7, 2025

"Not sure what might be uworse, your friends learning you have more or you have less. I don’t think there is a win either way so best to keep it private IMO"
- R Quinn
Read more »

How to build your nest egg

PETER WINKLER  |  Nov 29, 2025

"Peter - great post about lessons learned, regardless of the source."
- Jeff Bond
Read more »

The 4 Year Rule for Retirement Spending

mytimetotravel  |  Nov 29, 2025

"I find all these discussions about various rules for spending to be very interesting. As I consider their advice, I find myself having to put them into the context of the amount of retirement assets which a person has to help judge their validity. What I think I am saying in a round-about way, is if you don't have a meaningful amount of retirement assets, all the rules won't help you. And, if you are really flush with $$, the rules don't really apply. Or, said another way, if you have enough retirement assets to cover 25 years of spending (excess of SS/pension), then putting 4 years of spending into MMFs or CDs and following this plan will no doubt work. However, if funding your 4 years of expenses takes most of your bucks, you might struggle over your retirement. Interestingly, the 4% spending rule also works if you have 25 years of spending covered......:-)"
- stelea99
Read more »

HSA Proposal

Bogdan Sheremeta  |  Nov 27, 2025

"David, you're right on the money that Medicare Supplement premiums can't be paid or reimbursed by an HSA. But I believe Part D (and even Medicare Advantage) premiums can be. How Your HSA Can Reimburse You for Medicare Premiums and Expenses | Kiplinger"
- Andrew Forsythe
Read more »

Property taxes, our schools, our towns and seniors. Shared responsibility.

R Quinn  |  Nov 28, 2025

"Absolutely, and I don’t understand why people don’t get that. Plus the majority of those taxes are for teachers. At the same time ask people if teachers are underpaid and survey after survey says people agree teachers deserve higher paid. Where do they think the added expense will come from?"
- R Quinn
Read more »

My Investing Journey, Just Do It

Dan Smith  |  Nov 28, 2025

"Thanks for your supportive comment. You are right that it may time for the lessons learned to manifest themselves. I will check out the Winker book."
- Oscar Barbarin
Read more »

Happy Hour, or The Panic Button? Why Early Retirement Anxiety Is Real.

Mark Crothers  |  Nov 30, 2025

"I have been retired 16 years from a high profile, high level job I enjoyed for many years. When I retired I experienced none of what you refer to — loss of professional identity, assured income, and daily structure. Yes, I am unique because of my pension providing assured income and with SS added there was no drop in the income that we lived on before retirement although 16 years later there has not been a COLA to my pension and never will be. However, by investing all income (mostly equity) above base salary our investments today can easily provide dividend and interest income to make up for inflation. But at our ages we are truly in the slow, near no go years so our discretionary spending has declined. We used to spend $25-30,000 a year on travel. Since we can’t go to Florida this year, that’s a savings of $25,000 or so. But the loss of professional identity (I was once named Employee Benefit Professional of the Year by a national magazine) and daily structure never bothered me and honestly I don’t know why. Perhaps we spent so much time traveling the first several years after I retired I didn’t notice. It may also be that I took phased retirement for 18 months before full retirement and got used to the idea. . You’re right, often I don’t know what day of the week it is or actually care much of the time. These days I know the days mostly by healthcare appointments. 😟 People don’t change because they retired. The events of life don’t change, both good and bad. Perhaps expectations for retirement are unrealistic sometimes. The biggest stress factor is finances for most people, eventually followed by health. Both are things that take decades of preparation but are the majority of people willing to do it? PS For some I think early retirement (mid to early 50s) can be difficult and not able to live up to expectations and with an enhanced longevity risk. "
- R Quinn
Read more »

Asset Location Decisions

Bogdan Sheremeta  |  Nov 29, 2025

WHERE YOU PUT your investments can make a huge difference for your after-tax wealth.  As you know, we have 3 main investment accounts:
  1. Taxable account. A traditional brokerage account where you are taxed every time you dividends or sell investments at a gain.
  2. Tax deferred account. Traditional 401(k), 403(b), and traditional IRAs allow taxes to be deferred to the future. You pay taxes when your investments are withdrawn, and generally come with an immediate tax deduction.
  3. Tax exempt account. Roth IRA, Roth 401(k), and Roth 403(b) allow you to avoid future taxes while providing no immediate tax deduction. The growth of these accounts is tax free.
Asset location Say, as part of your investment strategy, you want to start putting money in bonds. You have a 401(k), Roth IRA, and a brokerage account. Where do we put them? Brokerage account When you hold bonds, like BND (Total Bond Fund ETF), you pay taxes on non-qualified dividends (e.g. interest from the bond) up to a max rate of 37%, plus net investment income tax, if applies. This means that if you receive $1,000 from the bond, you will pay approximately $370 in taxes if you are in the highest tax bracket. Of course, not all of us are in such bracket, and perhaps a more reasonable number would be ~$220-240 for most people. But is taxable brokerage the right choice for you? Not really. You would be paying $200+ every year, plus state/local taxes. Personally, I'm 100% invested in equities, because I want to be aggressive with my portfolio in my 20s, but if I did have bonds, I wouldn't hold them in a brokerage account.   Roth IRA/Roth 401k When you purchase bonds in a Roth IRA, you will not pay taxes on the interest since it’s a tax-free account! That’s much better than the $200+ in taxes you would pay in a brokerage account. But is it the best choice? Well, bonds are considered “fixed income” funds, and they don’t grow much. Since Roth IRA is a tax-free account (meaning we pay no taxes when we sell these investments), we want as much growth as possible in it. Bonds would hinder that performance. So, holding bonds is better than brokerage, but likely not the most ideal place.   Traditional 401(k)/403(b) By holding bonds in an account like a traditional 401(k)/403(b), the interest income avoids immediate taxation, compounding tax free until withdrawal.  So, we avoid the ~$200+ of taxes and aren’t sacrificing the tax-free compounding like we are with a Roth IRA. This makes the pre-tax 401(k) the perfect location for bonds. Of course the 401(k)/403(b) choices are limited and are provided by your employer. So, if they don’t offer a bond fund, you might not have a choice. Some other examples:
  • REIT stocks/ETFs also pay non-qualified dividends and would follow similar logic like bond funds.
  • Actively managed funds (I’m strongly against these, as I believe passive funds are the best & lowest fees) have a lot of turnover, so they ideally shouldn’t be in a brokerage account due to capital gain distributions.
  • Stocks that pay 0% dividends (like Netflix) are the most efficient to hold within the brokerage account, but may need a more robust overall investing plan.
I really like this visual from Fidelity to reference:
But how much does this matter? Vanguard's research finds that a thoughtful asset location strategy can add significantly more value than an equal location strategy. The value added typically ranges from 5 to 30 basis points of after-tax return, depending on circumstances (e.g. income, portfolio size) Overall, I hope you think about all of your investments & how they get taxed.    Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.
Read more »

What’s Really on My Mind These Days

Dennis Friedman  |  Nov 26, 2025

"Martin, I was listening to a talk show on Saturday, and one of the guests said that about 40 million jobs considered repetitive could be replaced by AI today. If that’s true, maybe we’re underestimating the impact these companies are going to have on the economy, and their ability to make money."
- Dennis Friedman
Read more »

Bearing Witness: Retirement From the Wrong Side of the Divide

Mark Crothers  |  Nov 25, 2025

"Juan, I hope my agency in life would have overcome different roadblocks along the way, but it would certainly not be a foregone conclusion; luck certainly plays a role."
- Mark Crothers
Read more »

Decision Frameworks

Adam M. Grossman  |  Nov 29, 2025

IN THE SUMMER of 1966, author John McPhee spent two weeks lying on a picnic table in his backyard. Why? McPhee was suffering from writer’s block. As he described it, “I had assembled enough material to fill a silo, and now I had no idea what to do with it.” Investors find themselves in a similar situation today. There’s no shortage of financial information around us. But that doesn’t make it easier to know what to do with it.  When it comes to financial decision-making, there is, of course, one fundamental problem: None of us can see around corners. But that doesn’t leave us completely empty-handed. Whenever possible, I suggest employing decision frameworks. They can help us to do the best we can in the absence of complete information. Here are four such frameworks you might consider as you look ahead to the new year. Trading decisions Suppose you’re lukewarm on an investment and thinking of selling it. How should you think through this decision? To start, you might evaluate the investment’s merits. If it’s an individual stock, you could examine its valuation and study the company’s financials. If it’s a fund, you could look at its track record and management fees. And if it’s held in a taxable account, you could also check its tax efficiency.  Against those factors, you would then assess the tax impact of selling your shares. But how should you weight each factor in your decision? A fund might be tax-inefficient, for example, but have a good track record. When making decisions like this, the framework I suggest is to evaluate three factors: risk, growth potential and tax impact. And I would consider them in that order. Estate taxes The federal estate tax can be punitive for those with assets over the lifetime exclusion. Under current law, that’s $15 million per person, but it’s a political football and could easily change down the road. Many states also impose their own estate taxes, with much lower exclusions. For those with assets even in the neighborhood of the applicable exclusion, it might seem like an obvious decision to pursue estate tax strategies. Indeed, many families conclude that it’s worth virtually any amount of time, effort and cost to limit their exposure to these steep taxes. That’s a logical conclusion, but it’s not the only way. Other families take a different view. They reason that if their estates will be subject to tax, then, by definition, their children will be receiving substantial sums. Since that’s the case, they don’t see the need for acrobatics to leave their children even more, especially since those strategies usually introduce cost and complexity.  The most typical estate tax strategy, for example, is an irrevocable trust. In addition to the legal work required to set one up, these trusts require third-party trustees, and trustees typically ask to be compensated. This kind of trust also requires a separate tax return each year. Also, assets in trusts like this don’t benefit from a cost basis step-up at death, making the tax benefit a little more uncertain. Estate tax strategies, in other words, might make sense, but they aren’t the obvious “right” answer in all cases. That’s why, as you think through this question for your own family, you might employ this simple framework: Start by asking yourself which objective is more important: to keep taxes to an absolute minimum or, on the other hand, to keep complexity to a minimum. Let that be your guide. Portfolio construction How much effort should you put into your portfolio? Author Mike Piper draws an apt analogy. Building a portfolio, he said, is like making a fruit salad. Here’s how he explained it: “If you choose to have just 3-4 ingredients in your fruit salad instead of 7, that’s fine…There’s no one single recipe that beats the others…And you don’t have to be super precise about it—a little more or less of something than you had intended is not a disaster.” It’s an important point. Because there are so many available investment options, and because there is so much information and commentary around us, it can sometimes feel like we need to do more to optimize our investments. The reality, though, is that this is a choice. Just as with estate tax strategies, you might yield a benefit by fine tuning your portfolio, but you shouldn’t feel compelled to. The most important thing is that it be reasonable. As long as you aren’t taking inordinate risk, it’s a choice whether you choose to have five, 10 or 500 holdings in your portfolio. As Piper points out, you won’t necessarily go wrong with whichever path you choose, so choose the path that suits you. A 360-degree view Earlier in my career, I worked as an investment analyst at a firm where we were responsible for picking stocks. In discussing an idea with a colleague one day, it occurred to us that if you knew enough about any given stock, you could easily make an argument either for or against that stock. It was in the eye of the beholder. Consider a stock like Nvidia. On the one hand, it’s the dominant player in a fast-growing market and has enviable profit margins. But those margins are inviting competition, and there are concerns that the market is becoming saturated. Which set of arguments is correct? As with all financial decisions, we can’t know without the benefit of hindsight. That’s why I suggest what I call the “five minds” approach. Instead of taking a single position on a given question, try to look at it from all sides, balancing the viewpoints of an optimist a pessimist, an analyst, a psychologist and an economist. How would this work in practice? If there’s an idea that looks like it makes sense, pause and ask what the opposing argument might be. If you’re looking at a question through a quantitative lens, pause and ask what the qualitative factors might be. And always consider the broader context. Suppose, for example, you’re considering a Roth conversion. A key element in that equation is whether future tax rates will be higher or lower than they are today. To help answer this question, we could consult history as a guide, looking at historical tax rates and government debt levels. No one has a crystal ball. But since that’s the case, frameworks like this can help us manage through decisions with incomplete information.   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.
Read more »

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Get Educated

Manifesto

Nov 29, 2025

NO. 44: WE SHOULD view our debts as negative bonds. Instead of earning interest, we’re paying it. Tempted to buy bonds? First, we should see if we can earn more by paying down debt.

act

Nov 30, 2025

TAKE REQUIRED minimum distributions. If you’re age 73 or older, the government insists you pull a minimum sum each year from your retirement accounts, except Roths. The deadline is Dec. 31, unless it’s your first year taking RMDs. Failure to comply can result in a tax penalty equal to 25% of the sum that should have been withdrawn but wasn't.

think

Nov 30, 2025

LAPSE PRICING. Some buyers of long-term-care (LTC) and cash-value life insurance drop their coverage, which means they paid premiums but got little or nothing in return. Aware of this, insurers often charge lower premiums to all policyholders. But this backfired with LTC insurance: The lapse rate proved lower than expected—hurting insurers’ profitability.

Truths

Nov 29, 2025

NO. 85: DELAYING Social Security to get a larger benefit could be your best retirement investment. Benefits are government guaranteed, inflation-linked, at least partially tax-free, you get them for life and your benefit may outlive you—as a survivor benefit for your spouse. Indeed, delaying is especially smart if you were the family’s main breadwinner.

Money Guide

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Manifesto

Nov 29, 2025

NO. 44: WE SHOULD view our debts as negative bonds. Instead of earning interest, we’re paying it. Tempted to buy bonds? First, we should see if we can earn more by paying down debt.

Spotlight: Taxes

Fox in the Henhouse

Marjorie Kondrack   |  Mar 27, 2024

ALBERT EINSTEIN reportedly once said, “The hardest thing in the world to understand is income taxes.” Which makes me wonder: How did I end up wandering into this mind-boggling field? 

I like knowing how my money gets taxed because it helps me better control our finances. By managing taxes, we can significantly boost how much money we have for retirement.

Why is the tax system so complicated? The system is trying to do more than just collect taxes.

Read more »

Time to Settle Up

Matt C. White   |  Apr 12, 2022

TAX DAY IS ALMOST here, and I have a feeling that some of you may be less than excited. The cash that changes hands every year around this time gets a lot of attention, but it tells an incomplete story. The size of the check you write—or the refund you’re receiving—doesn’t, by itself, say much of anything about your tax situation.

Back in the days before technology made transferring money so convenient, did you ever let a tab run both ways with a friend?

Read more »

Are taxes too high? I don’t think so

R Quinn   |  May 28, 2025

My perception is Americans have become obsessed with taxes. They complain loudly about high taxes. Some vocal seniors don’t think they should pay property taxes or income taxes on Social Security or extra premiums for Medicare (not actually taxes).  
There seems a general lack of understanding of what taxes provide.  The tax collector has been vilified throughout history. Our Country was founded as the result of taxation. 
Paul in Romans 13:1-7, explicitly mentions paying taxes: “This is also why you pay taxes,

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Roth Hidden Benefits

Bogdan Sheremeta   |  Oct 25, 2025

WHEN MOST PEOPLE think of Roth IRAs or Roth 401(k)s, they just think “tax-free withdrawals.” But that’s only part of the story.
Roth accounts can protect you from financial traps that catch many retirees off guard. Here are five key advantages to keep in mind:
 
1. Tax Rate Protection
One thing we can’t control is future tax rates.
Did you know that in the 1980s, the highest federal tax rate was 50%?

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Ten Points of Pain

Richard Connor   |  May 18, 2022

I JUST COMPLETED my fourth year preparing tax returns as part of the federal government’s Volunteer Income Tax Assistance (VITA) program. I’ve seen first-hand how confusing our tax code can be for many taxpayers. Here are the 10 areas of confusion I’ve encountered most often:
1. Income. Anyone looking through a tax return will see multiple definitions of income. There’s total income, adjusted gross income (AGI), modified adjusted gross income, provisional income and taxable income.

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TCJA – What to Keep, What to Toss

William Perry   |  Apr 22, 2025

Every few decades or more often our federal tax system has a major upheaval. After I got my accounting degree in 1977 my first two jobs were working in state government auditing focused on matters internal to the function of the government. I still feel I learned a lot during those jobs but it was not a good fit for me.
In the early 1980’s I entered the world of public accounting which to a large extent is broken into two segments.

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Spotlight: Perry

The 2024 Bogleheads Conference videos are now available online

William Perry   |  Dec 4, 2024

I have been checking the Bogle Center looking for the release of the 2024 conference videos. I have enjoyed and learned from the prior year conference videos. The 2024 conference videos are now available. https://boglecenter.net/2024conference/
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Kitces – Analyzing Congressional Republicans’ Budget Proposal For The 2025 TCJA Extension

William Perry   |  May 1, 2025

On April 30, Kitces posted an comprehensive article regarding the Tax Cuts and Jobs Act (TCJA) describing in detail where the congress is currently at and what steps are necessary to extend and/or change the the TCJA before the current tax law sunsets at the end of 2025. https://www.kitces.com/blog/tax-cuts-and-jobs-act-tcja-sunset-budget-resolution-reconciliation-salt-cap-qbi-deduction-congress-republication-house-senate-bill/ I agree with the conclusion of the article to currently "wait and see" before taking action until I have a concrete expectation of what the individual income tax rules will look like in 2026. For me that means I plan to delay any traditional to Roth conversions and, as I have earned income for 2025, I will wait until 2026 to decide to fund any 2025 traditional or Roth IRA. The one action I am doing is to have sufficient 2025 federal income tax and estimated tax payment paid in to protect us from the possibility of underpayment penalty based on the safe harbor rule determined using our 2024 adjusted gross income and 2024 tax liability. Any other tax actions you are planning to take during 2025?
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EO 14249 Mandated Electronic Payments

William Perry   |  May 8, 2025

On March 25, 2025, the President of the United States signed Executive Order #14249 titled Protecting America’s Bank Account Against Fraud, Waste, and Abuse, which was published in the Federal Register on March 28. The fact sheet states that, effective September 30, 2025, the Federal government will cease issuing paper checks for all disbursements, including intragovernmental payments, benefits, vendor payments, and tax refunds. The fact sheet also states payments made to the Federal government, such as fees, fines, loans, and taxes, must also be processed electronically where permissible under existing law. You can read the full Executive Order as it appears in the Federal Register here and the White House Fact Sheet which summarizes the Executive Order here. If you are still writing paper checks to pay your estimated tax payments or the balance due then you may want to switch over to electronic payments sooner rather than later to avoid the learning curve. I was stationed in Germany in 1973 and the first half of '74 in a maintenance company for the Army's Third Armored Division. When my company XO was promoted to CO, I was his personal clerk and driver for a while. The standard process to pay enlisted troops on our base was that once a month the XO, his driver and a appropriate armed detail would go to a nearby Kaserne where we received and counted the cash to pay everyone who did not have direct deposit which I would guess to be 90%+ of the enlisted men in our company of about 200 men (we had no women assigned to our company). When we returned to our base we then divided the cash into the amount each man would receive. At that point usually mid-morning the company would fall into formation. After announcements those with direct deposit would be dismissed to go to their assigned duty post and then the XO and his clerk would pay those without direct deposit, man by man. I would count the money out and then the payee would also count the money and then sign their paper check to acknowledge payment in full as the XO supervised. The XO and I hated payday. When the XO was promoted he did something about this procedure. On the first payday after his promotion to CO we had our normal formation but then things changed. No one was dismissed and the entire company walked (marching would not describe this) to the Kaserne at Erlensee from the  Fliegerhorst Kaserne at Hanua a distance of about 7Km a little over 4 miles. We paid the men without direct deposit at Erlensee, and then the entire company walked back to Fliegerhorst. When we arrived back near the end of the day, we had another formation and my CO announced that he hoped everyone had enjoyed the day and noted that we would be following the same process every month until at least 90% of the company had elected direct deposit. We did not have to make the walk again as most everyone had elected to have direct deposit by the next payday.  My CO had found the right incentive. Yes, the CO and I also walked. So, what motivates you best, the carrot or the stick?  
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Do you know about community property trusts?

William Perry   |  Sep 24, 2024

Five non community property states - Alaska, Florida, Kentucky, South Dakota and Tennessee, currently allow married couples to create community property trusts (CPT). The benefit of a CPT is the potential income tax savings to a surviving spouse via the full 'step-up' in basis of a home or other trust assets that occurs when the first spouse dies when assets held in the CPT are later sold. There are likely a lot of negatives to establishing a CPT including complexity, cost and limited asset protection. My financial situation leads me to conclude that I do not require a CPT  for my wife to avoid capital gains on our JWROS appreciated home should I predecease her due to the home gain exclusion available under IRC 121. I was at a continuing education course regarding probate earlier this month and the attorney speakers briefly spoke about the availability of community property trusts. If you want to know more about CPTs just google "What is a community property trust". After reading the comments on a few law firm websites you will then know as much (or as little) as I do about community property trusts. Best, Bill    
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Trust – The reason I read HumbleDollar

William Perry   |  Jul 28, 2024

I have just read a guest post dated 7/25/2024 to Collabfund.com titled Fill The Bathtub by Ted Lamade the managing Director at the Carnegie Institution for Science. I recommend reading this thoughtful article about trust. A link to the article is - https://collabfund.com/blog/fill-the-bathtub/ I have been thinking a lot about why I read HumbleDollar most every day. I think the key for me is the trust I have that what is posted is the truth as experienced by the writers whether the source is the editor, the writers or the commenters. The linked article reminded me of this special gift we have received. Thanks to Jonathan for creating this blog.
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New Inherited IRA RMD final rules

William Perry   |  Jul 19, 2024

The IRS on Thursday issued final regulations regarding Required Minimum Distribution (RMD) requirements for those who inherit retirement accounts which were published in the Federal Register today 7/19/2024. The final regulations requires Non-Eligible Designated Beneficiaries to take RMDs starting in 2025 if the decedent had already reached their required beginning date. The full final regulations can be read here - https://www.federalregister.gov/documents/2024/07/19/2024-14542/required-minimum-distributions The summary of the rule as published in the Federal Register is effective 9/17/2024 follows- This document sets forth final regulations relating to required minimum distributions from qualified plans; section 403(b) annuity contracts, custodial accounts, and retirement income accounts; individual retirement accounts and annuities; and certain eligible deferred compensation plans. These regulations affect administrators of, and participants in, those plans; owners of individual retirement accounts and annuities; employees for whom amounts are contributed to section 403(b) annuity contracts, custodial accounts, or retirement income accounts; and beneficiaries of those plans, contracts, accounts, and annuities. Bottom line for the final rule - for most beneficiaries (excluding the decedent's spouse and a few other groups) who have recently inherited a traditional tax deferred account where the decedent was already obligated to take a RMD then beginning in 2025 you need to take a annual RMD as well as fully empty the inherited account, typically a traditional IRA, by 10 years after decedent died or you will get hit with a 25% tax penalty (per year) of the RMD amount that should have been distributed but wasn't  as well as the the actually IRA distribution being taxable in the year when the  distribution withdraw is made. You will be well served by talking to the plan / IRA custodian(s) to assure you are taking timely RMDs.
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