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My Sister – A Reflection One Year Later

Andrew Clements | Aug 12, 2026

"Thank you, Jack. Over the past year, I’ve realized that I can’t change the sadness of losing Tory, but I can choose how I remember her. Focusing on the laughter, love, and wonderful memories she left behind has helped make the grief a little easier to carry. I appreciate your kind words."

- Andrew Clements

Medicare Advantage Part C — Not too soon to start planning for 2027

R Quinn | Aug 11, 2026

"Actually the number of choices retirees have for MA plans has been declining so replacing one MA for another MA is more difficult. A lot depends on where you live."

- R Quinn

Roth Conversions and Taxes

ArticleJohn Urban | Aug 8, 2026

EVERY ARTICLE ABOUT Roth conversions says the same thing: pay the tax from taxable money, not from the IRA. That is good advice if you have taxable money. Plenty of retirees do not. Their savings sit almost entirely in a traditional IRA, built from years of 401(k) contributions and a rollover at retirement, with little brokerage money and no cash reserve worth naming. For them, “pay from outside money” is not advice. It is a condition they do not meet. Their real choice is a self-funded conversion or no conversion at all. The familiar warning is that self-funding requires a gross-up. You withdraw money to pay the conversion tax, that withdrawal is itself taxable, so you have to withdraw a little more. Less discussed is what else that withdrawal sets off. It makes more of your Social Security taxable, it raises your Medicare premiums two years later, and in a high-tax state it enlarges the amount that has to leave the IRA. Here is what those three cost, on one household. A cautious conversion Meet Dianne, a composite rather than a real person. She is 66, single, retired to Florida, with $1 million in a traditional IRA and nothing outside it. Social Security pays her $28,000 a year. She is past 59 and a half and already on Medicare. Florida keeps state income tax out of the arithmetic for now. She converts $40,000. Careful, modest, the size people choose when they are trying not to do anything dramatic. The tax on that conversion, paid from a checking account she does not have, would be $4,234. Funding it from the IRA instead, the withdrawal that covers it is $5,125, and her tax rises to match. That extra $891 is 17.4% of the $5,125 she withdrew. Her ordinary-income bracket is 12%. Twelve of those points are the tax on the withdrawal itself, which is the gross-up everybody expects. The other 5.4 points come from $2,300 of her Social Security being pulled into taxable income by that same withdrawal. Paying from cash, $21,500 of her benefit would be taxable. Self-funding, $23,800 is. The difference is caused by how she paid, not by what she converted, and nothing on her return will label it. Not a smaller version of a large one The effect is not linear. Run the same woman at $150,000 and 85% of her benefit, the statutory maximum, is already taxable before she funds the tax. The funding withdrawal drags in nothing further, and this particular cost is zero. That is not an argument for converting more. It is an argument against assuming a small conversion is simply a smaller version of a large one. The one that looks cautious can carry the higher marginal rate. What self-funding actually costs Give Dianne the $150,000 conversion, still with no outside cash, and add the state question. Still in Florida, $195,469 has to leave the traditional IRA to put $150,000 into the Roth. Move her to California, changing nothing else, and it is $219,751. That is $1.30 of IRA spent for every dollar reaching the Roth, against $1.47, and the gap is California income tax compounded through the gross-up. If a move across state lines is anywhere in your plan, the order of operations may matter more than the size of the conversion. But $1.47 invites a conclusion it does not support, and I would rather correct that myself than let it travel. A conversion is taxable whichever pocket pays. Of the $69,751 Dianne withdraws in California, roughly $44,639 replaces cash she would have spent anyway. The incremental cost of self-funding, in wealth given up, is $25,111. About 17% of the conversion, not 47. The bill that arrives in 2028 At that $150,000 conversion, self-funding also costs Dianne $1,735 in higher Medicare premiums, a surcharge of $6,355 rather than $4,620, charged on top of the standard premium, for one year, and hers alone as a single filer. The bill arrives two years late. Medicare sets her 2028 premiums from her 2026 income, so the cost is invisible at the moment she is deciding how to pay the 2026 tax. When it can still make sense Doing nothing is not free either. Money left in a traditional IRA comes out eventually, under required distributions, at whatever rates apply then, possibly to a survivor filing single, possibly to heirs facing a 10-year deadline. Where self-funding still holds up, a few things tend to be true. The rate gap is durable rather than a one-year accident. Whether it repays a cost this size depends on time, future tax rates and investment returns. A temporary dip in income is a thin foundation. A structural window, after retirement and before Social Security or required distributions begin, is more compelling. There is runway, because shrinking the portfolio to change its tax character needs years of tax-free growth to earn back. Age 59 and a half is cleanly behind you. The converted amount is not subject to the 10% additional tax on early distributions. A separate distribution taken to pay the tax generally is, unless an exception applies. And enough is left afterward. Check the balance after the funding withdrawal, not after the conversion. Dianne’s California IRA drops to $780,249, and whether that funds the next 30 years matters more than whether the conversion was tax-efficient. A practical warning about withholding Withholding from the conversion is not a cheaper way to pay the tax. It reduces what reaches the Roth. Elect 24% on Dianne’s $40,000 conversion, as this illustration does rather than as any custodian requires, and $9,600 goes to the IRS while $30,400 lands in the Roth, against $4,234 actually owed. The cash comes back next spring as a refund. The Roth room does not come back at all. Restating the rule Pay the conversion tax from outside cash if you have it. That remains the best answer. It is not an answer for the retiree whose savings are almost entirely in a traditional IRA. For that person, “never pay from the IRA” skips the actual decision, which is whether a self-funded conversion, with its full marginal cost, beats leaving the money where it is. Before deciding, count the gross-up, the Social Security effect, state tax and the Medicare bill two years later. Sometimes that arithmetic still says no. It beats applying a rule written for somebody with a different balance sheet. ________________________________________________________________________________ John Urban is the founder of RetireSmartIRA, a retirement tax-planning app. Earlier, he founded GT Nexus, a supply-chain software company acquired by Infor in 2015. He lives in Northern California with his wife, Kathy, and enjoys time with family, travel, reading, Bay Area sports, and the occasional deep dive into the fine print of the tax code.

What is the right percentage?

R Quinn | Aug 9, 2026

"I log on to my investments everyday, just out of habit. My bank sends automatic updates on account balances. I make sure I stick with my theory, but there is no budget. I see no difference between my method at any income level. It’s a forced way to live within one’s means, you can’t spend more than you have. Of course, your example is an exception. There are always exceptions. In the example, it probably means a lower lifestyle, lower budget, lower everything regardless."

- R Quinn

Don’t Let a Roth Conversion Trigger a Penalty

John Urban | Jul 8, 2026

"Hi Grant, and thanks for the article (John Urban) and this comment. Sorry to be a few months late commenting but I think your approach is very intriguing and I have questions for you if you have time to help me understand your process. Firstly, my situation is retired, no W2 income and RMDs to be satisfied from conventional IRA before the end of the year. Also, not yet concerned over IRMAA impact at this time. Q1. The 1, 2, 3 process says one can do a rollover contribution to the Roth account with money from a regular brokerage or other non-IRA account within 60 days. Is this correct? I thought that a rollover should be IRA to IRA (Roth and/or conventional). Q2. About the 1, 2, 3, process. Why not make the conversion and pay the taxes directly from the converting IRA at the same time. Brokerage will withhold the amount specified to make it a single operation on my part. THEN I take money from the non IRA account and rollover the amount withheld in taxes into the target Roth account. I realize this violates the guidance that taxes shouldn't be withheld from a conversion, however, since the taxable amount is being deposited almost immediately back into the Roth account then it would seem to be a wash. What are your thoughts? Am I missing something? Thanks, Derek"

- Derek Shuttleworth

For most retirees, the greatest fear is not death—it is running out of money before they die.

Matt Halperin | Aug 6, 2026

"I understand, thanks, Dunn"

- DAN SMITH

Can a Value fund also be a Growth fund?

Harold Tynes | Aug 11, 2026

Be the first to comment.

Risk and Taxes

ArticleAdam M. Grossman | Aug 8, 2026

AFTER YEARS OF heady gains in the stock market, many investors are facing the same question: To manage risk, they’d like to cut back on one or more of their holdings. But because of the potentially costly tax bill that might result, they aren’t sure exactly how to do that. How can you square this circle? One easy option would be to donate appreciated assets to charity. But that would make sense only if it aligns with your charitable goals and, of course, if you don’t need those funds for other uses. How else could you strike a balance between managing risk and limiting taxes? Here’s how I would answer this question. Step 1. I’d start by estimating the potential risk level among your holdings. While there’s no single litmus test, you could ask the following questions. First, how large a portion of your assets does any single holding represent? As a rule of thumb, I’d focus first on individual stocks that top 5%. Why 5%? My operating assumption is that any individual stock could experience a 50% decline during a crisis. So if a holding is limited to 5%, then a 50% drop would result in an overall portfolio impact of just 2.5%. I see that as very manageable. To be sure, stocks can certainly decline by more than 50%, but I view this as a reasonable figure for risk management. While I worry most about the risk posed by single stocks, it’s also important to examine the overall composition of your portfolio. That’s because, counterintuitively, a portfolio of 30 stocks could end up being riskier than a group of just 10. Harry Markowitz, the father of Modern Portfolio Theory, explained why. In his initial work back in the 1950s, Markowitz used railroad company stocks to explain the concept of diversification. There’s nothing inherently wrong with railroad stocks, Markowitz explained. But if a portfolio consists of only railroad stocks, then that would be a problem—because companies in the same industry are often impacted by the same economic factors. In other words, a portfolio consisting of a large number of holdings might only appear diversified, so it’s important to look under the hood. Another risk factor to consider: Do you work for a public company and own the company’s stock? If so, that would be a reason to consider diversifying more quickly (within the permitted time windows). What if you own only mutual funds or ETFs? Diversified funds tend to be less risky than individual stocks, but that’s not always the case. The fund industry launches as many as 1,000 new funds each year, including many with very aggressive strategies. So it’s important to check each fund’s holdings. You can find that information on the fund company’s website or on a site like Morningstar (Here, for example, are the top holdings in Vanguard’s S&P 500 index fund). Step 2. Next, you’d want to estimate how much a loss might impact you. As with most questions in personal finance, there are two answers to consider: how it might affect you in dollar terms, and the degree to which a loss would simply be upsetting. Both are important. Step 3. If you determine the holding in question does represent a material risk, then you’d want to estimate the potential tax impact. Here are questions you might ask: What would the tax be if you exited the entire position? Would it push your income into the next capital gains bracket? Are there tax lots with less appreciation you could take advantage of? Do you have losses you could use to offset some of the gains? Do you expect to be in a higher or lower tax bracket next year? Step 4. If you conclude that the tax bill might be significant, what steps could you take to reduce a holding tax-efficiently? Here are strategies to consider: For starters, I suggest deciding on a target percentage for the holding. While ideally I prefer bringing any individual stock down to a 5% weighting, that figure isn’t a rule. All things being equal, the larger a portfolio, the more risk you can afford. After deciding on a target percentage, the simplest approach would be to set up a long-term sale plan—like dollar cost averaging but in reverse. Suppose you’d like to sell 1,200 shares of a given stock. You could sell 100 shares each month for twelve months. You’d do that regardless of whether the stock happens to be up or down that month. That 12-month schedule isn’t a rule. If your holding is very significant, you might opt for a longer timeframe. On the other hand, if you feel the stock has a particularly highflying valuation, you might choose a quicker pace. The key, in my view, is just to get started. As the writer Carveth Read wrote, “it’s better to be roughly right than precisely wrong.” Selling a stock down over time is the simplest way to reduce risk, but it’s hardly the most tax efficient. Another approach that’s been gaining in popularity is known as a 351 exchange fund. With a 351, the idea is that a group of investors, each with their own portfolios of appreciated securities, come together and collaborate to diversify their respective holdings. To provide a simplified illustration, imagine two investors, each with a concentrated holding, one in Microsoft and the other in Apple. Each would benefit by diversifying, and that’s what a 351 exchange fund allows. Each would contribute their respective shares into a common pool that would then hold some Apple and some Microsoft. This new investment would be structured as an ETF, and each investor would be issued shares proportional to the size of their contribution. Importantly, the initial creation of a 351 fund doesn’t entail any tax. Taxes are due only when an investor later sells shares of that ETF. This is a simplified example. In reality, a 351 exchange fund would hold many more than just two holdings. They’re actually required to meet various diversification requirements. As a result, investors in 351 funds may end up feeling sufficiently diversified and thus comfortable holding their fund shares for the long term. That would make this strategy potentially the most tax-efficient way to manage portfolio concentration risk. This is just an overview, though. If you’re interested in 351 strategies, I suggest further research. In July, The Wall Street Journal discussed these funds in some detail. In addition, a firm called Alpha Architect, the largest player in this area, has a number of helpful explanatory videos on its site. 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.

“Gerontocracy” in America

Chris Rush | Aug 6, 2026

"I’ll not render an opinion of a book that I have not read, but several age impaired presidents and numerous lawmakers are a fine argument for age limits. Otherwise, like Mark and David write below, it’s no surprise that based on wealth and numbers, we boomers remain a powerful voting bloc."

- DAN SMITH

Looking Back On My Hard Luck Days

DAN SMITH | Aug 7, 2026

"Dick, your 3rd point is so powerful that it overshadows the first two. Connie is going through so much at this time, and she is lucky to have you in her corner. While you strive to take good care of Connie, don’t forget to take care of yourself as well. "

- DAN SMITH

FIFA Financials

R Quinn | Jul 19, 2026

"Me, too. Prices not outlandish."

- Jeff Bond

Before Someone Else Decides

Kathleen Rehl | Aug 2, 2026

"What a difficult and unsettling situation for all of you. You’ve described one of the hardest parts of planning ahead: family members can clearly see that living alone is becoming unsafe, yet the older adult is still entitled to make his own choices—even choices that others find baffling, like adopting a puppy while recovering from surgery. Your words, “we’re living some of it in real time” really struck me. This is precisely the narrow window when candid conversations and acceptable choices may still be possible, before a medical crisis forces the decision. I hope his upcoming surgery goes well and that your family can help him accept some form of support, whether in his home or closer to one of you, while he can still have a meaningful voice in what happens next. Thank you for sharing such a vivid, honest example of why these conversations matter."

- Kathleen Rehl

My Sister – A Reflection One Year Later

Andrew Clements | Aug 12, 2026

- Andrew Clements

Medicare Advantage Part C — Not too soon to start planning for 2027

R Quinn | Aug 11, 2026

"Actually the number of choices retirees have for MA plans has been declining so replacing one MA for another MA is more difficult. A lot depends on where you live."

- R Quinn

Roth Conversions and Taxes

ArticleJohn Urban | Aug 8, 2026

What is the right percentage?

R Quinn | Aug 9, 2026

- R Quinn

Don’t Let a Roth Conversion Trigger a Penalty

John Urban | Jul 8, 2026

- Derek Shuttleworth

For most retirees, the greatest fear is not death—it is running out of money before they die.

Matt Halperin | Aug 6, 2026

"I understand, thanks, Dunn"

- DAN SMITH

Can a Value fund also be a Growth fund?

Harold Tynes | Aug 11, 2026

Be the first to comment.

Risk and Taxes

ArticleAdam M. Grossman | Aug 8, 2026

“Gerontocracy” in America

Chris Rush | Aug 6, 2026

- DAN SMITH

Manifesto

Aug 12, 2026

NO. 8: RETIREMENT may be our final financial goal, but we should always put it first. Why? It’s easily our most expensive goal, so it takes decades of savings and investment gains to amass enough.

think

Aug 13, 2026

DIVERSIFICATION. While diversifying is important with bonds, it’s crucial with stocks—and involves investing in hundreds and perhaps thousands of companies from a host of market sectors and countries. If we don’t diversify, and instead buy a handful of stocks or a single sector, there’s a danger we’ll take the risk of stock investing—without getting the reward.

act

Aug 12, 2026

GET YOUR CHILDREN age 18 and older to draw up a health care power of attorney, specifying that you can make decisions on their behalf if they become incapacitated. If they have an accident—and you have no power of attorney—you may be unable to make medical decisions for them or even learn basic information about the state of their health.

Truths

Aug 11, 2026

NO. 33: MOST INVESTORS trail the market averages. That’s true whether a market is considered efficient or inefficient. Before investment costs, we collectively earn the results of the market averages. After costs, we must inevitably earn less. In fact, investors—as a group—will trail the market by a sum equal to the investment costs they incur.

Money Guide

Manifesto

Aug 12, 2026

Spotlight: College

Budgeting 102

Catherine Horiuchi | Sep 30, 2021

IT’S BEEN A MONTH since I dropped off my twins at college, one east, one west. Each has a debit card for an account with the credit union here in our hometown. One has downloaded the credit union’s mobile app. Both are already developing their own ideas and strategies for managing college life on a shoestring budget.
I got them their debit cards some time ago. I also opened a teen account for their brother,

Degrees of Doubt: When Higher Education Misses the Mark

Mark Crothers | Jul 16, 2025

I perhaps have a contrarian view of the utility of some higher education courses. This opinion has developed over the last 20 years or so, talking and interacting with younger staff I employed within my past business. Degree courses seem to have somewhat transformed into a business model, more influenced by volume over suitability of the course and proper weight being given to the future earning and retirement outcome expectations the course will achieve.
To use a fishing analogy,

On the House

Howard Rohleder | Aug 31, 2021

WANT A CONSERVATIVE strategy that can help you prepare for college costs? Consider prepaying your mortgage.
In 1992, when my oldest was 10 years old, we moved to a new home. We opted for a 15-year mortgage at 7.625% with 33% down. With our son’s graduation set for 2000, we began to prepay the mortgage so the last payment would coincide with the month before he began his freshman year. Thereafter, the payments previously sent to the mortgage company were instead directed to the college.

Saved by Borrowing

Morgen Henderson | May 12, 2020

IN HIGH SCHOOL, I worked at a local roller-skating rink to save money for college. I calculated that, if I kept working at the same rate once I was in college, I could make it through my four-year degree without taking on any student loans.
I was determined to make it work.
In my freshman year, my plan started with a budget—and that budget included this simple edict: Spend the least amount possible on everything.

A+ for Effort

Charles Schafer | Jun 3, 2022

WE HAVE A PROBLEM: We may have saved too much for our daughter’s college education.
My wife and I started contributing aggressively to our daughter’s 529 college savings account as soon as she was born. For the first two years, we invested the full amount of the annual gift-tax exclusion, which was then $14,000. Now, the exclusion is at $16,000, but lately we haven’t been saving as much as we used to. The reason: Our early aggressive saving,

Getting a Break

Logan Murray | Nov 2, 2023

STUDENT LOANS ARE a hot topic—one that’s fraught with confusion and complexity. Still, many borrowers should consider taking action this year. Want to get a better handle on what’s happening? Let’s start with three changes that have lately been in the spotlight:

Federal student loan payments, along with the interest charged, were paused from March 2020 to September 2023. That gave borrowers more than three years to make principal-only payments or, alternatively, to potentially accrue credit toward loan forgiveness without the need to make payments.

Affordable Care?

Howard Rohleder | Apr 6, 2022

WHEN PLANNING OUR early retirement, I realized that getting and paying for health insurance for my wife and me would be our biggest financial challenge. Before 2010’s Affordable Care Act (ACA) took effect in 2014, we talked to an insurance agent who gathered our medical histories and submitted them to insurers for consideration. Despite two major surgeries, I was deemed insurable. My wife, due to a congenital condition that had never caused a problem but might, was not. When I actually retired, it was six months before key provisions of the ACA kicked in. We continued my employer’s coverage through COBRA to cover the gap and then switched to coverage under the ACA. That means I’ve been insured through the health care exchange created by the ACA for the entire time of its existence. My wife was also on an ACA plan until she enrolled in Medicare two years ago. Under the ACA, we’ve watched premiums escalate far faster than inflation. Our doctor of 25 years dropped us. And our choices for in-network hospital care got tighter and tighter. Being relatively healthy, each year we chose a bronze-level plan with a high deductible and a health savings account (HSA) option. We fully funded the HSA but stopped using it for current expenses after the first year. We realized it was better to allow the account to grow tax-free to pay for medical expenses later in retirement. We’ve accumulated a tidy sum that way. From January 2014 until my wife entered Medicare in December 2020, we paid $113,000 in ACA premiums. The compound annual increase in our premiums averaged more than 9%. More disconcerting: Our rising premiums bought less coverage. Our deductible rose from $4,000 apiece in 2014 to $7,000 each in 2020. We also went from having a wide network…

Lifecare Compared

Howard Rohleder | Mar 21, 2022

MY IN-LAWS AND MY mother all moved into continuing care retirement communities after giving up their homes. My in-laws were not yet 70 when they moved in and my mother was age 75. They lived in two different communities about a 45-minute drive from one another. Both communities provided excellent care, but had differing levels of service and had different ways of being paid. I’ve garnered further insights as a volunteer board member for a third continuing care retirement community (CCRC), a private, not-for-profit facility near where I live. Much retirement planning is driven by fear of running out of money. Retirement communities that include a “lifecare” or “lifeplan” contract are a hedge against this risk. They provide a continuum of services to meet changing needs as you age, while also reserving you a spot in the appropriate care facility. The lifecare contract guarantees that, no matter what happens to your assets, there will be a place where you can receive the appropriate level of care. Besides paying a monthly fee, lifecare residents may be responsible for an entry fee. Many people use proceeds from the sale of their home to pay it. There may be an option to pay the entry fee gradually over time, or a refund provision if you leave the community within a given period. Lifecare services typically include three stages: independent living, assisted living and long-term care. The independent living options often include individual homes—sometimes called cottages or villas—as well as apartments. The long-term care component includes skilled nursing services. Memory care is also increasingly available as a separate unit. Usually, this array of services is located on one campus, but it can also be offered at multiple sites in a metropolitan area. Lifecare contracts are categorized as types A, B and C. There is…

Many Unhappy Returns

Howard Rohleder | Jun 19, 2024

I WAS INSPIRED BY Rick Connor and other HumbleDollar contributors to sign up for the AARP’s volunteer-run Tax-Aide program. After completing 48 hours of training at a local college and passing the required tests, I volunteered two days a week at two different senior centers. I completed my first tax season in April. Two clients, with whom I spent extra time, stood out. The first was a widow in her late 60s whose husband had always handled their finances. She had an account with a large brokerage firm. There were lots of transactions that generated lots of losses, which were on top of the large capital-loss carryforwards she already had. I tried to coach her on questions to ask her advisor, but she was afraid to call the advisor because she could never understand what he said. I asked if she had adult children who could participate in a call, but she had none. Being new, I was giving the advisor the benefit of the doubt. The more experienced volunteer who reviewed my work was more blunt: The advisor was taking advantage of her. In fact, her capital losses were so large, she could have offset them against ordinary income and hit the $3,000 annual maximum for the next 30 years. For me, it was eye-opening—a lesson about the dangers of leaving an advisor-managed portfolio to a spouse with little financial understanding. I wondered if the advisor, who had been selected by the deceased husband, had been churning the account before the husband died, or if he only started after. The second client was a woman in her mid-60s, never married and who was planning to retire in 2024. She had a good job and a sizable 403(b) balance. She asked how to prepare for next year's taxes, given that…

Taxes Season 3

Howard Rohleder | Apr 11, 2026

This was my third season as an AARP volunteer tax aide…and my third post about my experiences. I volunteer two days a week from February 1 to tax day at two different senior centers which draw from different socioeconomic strata: one is definitely middle class; the other has many clients living on very little. I began the season wondering how the Big Beautiful Bill would impact our clients. Since most are over 65, I expected the new $6000 senior deduction to have a big, across-the-board impact. Many came in asking about it: They had either heard about the “$6000 deduction” or “no tax on Social Security.” The impact was not as much as I expected. I quickly realized that the income of many clients is so low that they are already paying little or no taxes… another deduction doesn’t matter. I did see the advantage of a flat deduction versus eliminating tax on Social Security. We have government or railroad pensioners who receive other government retirement, but no Social Security. They were able to benefit. With the phase-out for higher incomes, the BBB hit its target: my middle-income seniors were the beneficiaries. Since we see few working people, I only saw few examples of “no tax on tips” or “no tax on overtime.” I had one young married couple where she was a waitress, he was a firefighter, and they had a new baby in 2025. They hit the trifecta: her tips were excluded, as was his overtime. And, the baby was eligible for a $1000 deposit into a Trump account. The new emphasis by the IRS to eliminate paper checks caused some consternation. We have clients who do not trust the IRS to have their banking information. We try to explain that if they receive Social Security, the government…

A Difficult Choice

Howard Rohleder | Nov 27, 2021

FEAR OF MISSING OUT, or FOMO, seems to be everywhere. We suffer it when we read about our friends’ fabulous experiences on social media. We can also suffer it when investing, as we fret that our friends are making more on their investments than we are. My own concern in recent months, however, hasn’t been FOMO, but FOLB. No, it doesn’t roll off the tongue like FOMO. It’s my own invention—and it stands for fear of losing big, a particular worry of mine. The U.S. stock market is near record highs. With my regular rebalancing, my stock allocation sits at 60%. When I look at the dollar value of that 60%, and think about the possibility of losing 30% to 40% of it in a bear market, I hear alarm bells. When I focused on the percentage I had in stocks, I thought I could weather a bear market. But I’d lost sight of the total dollars at risk. Losing 30% to 40% of that money doesn’t feel nearly as manageable. That’s why I’ve let my stock allocation trend down from 64% a year ago. I’ve lived through several bear markets. I’d learned to look at them as buying opportunities. I also have sufficient cash reserves to go several years without having to sell a stock or stock fund. Theory says that as long as I don’t sell after a big drop, the possible paper loss is irrelevant. I can add to my positions while the market is down, and the next bull market will make me whole again and then some. These thoughts should be comforting. But the sheer magnitude of the potential dollar loss is disquieting. The other concern I have: There are few good alternatives to owning stocks. Cash earns next to nothing. Bonds have the potential…

Quick Work

Howard Rohleder | May 3, 2022

I'VE USED QUICKEN since the DOS version, with my first entry made in August 1992. I’m trying to decide if I qualify as a power user. The fact is, there are so many Quicken features that I simply don’t use. The product was first released in 1984 as a basic digital checkbook. It later moved to Windows and it’s now a subscription service. I love the ability to manage my checkbook, but over the years Quicken has added features aimed at managing my entire financial life. I did experiment with tracking some basic investment accounts, only to revert to my own homemade spreadsheets. In the beginning, all entries had to be typed by hand. This required diligence but, for me, the payoff was the ability to manipulate the data once it was entered. For a while, I used the one-click update feature, where Quicken would initiate an automatic download of transactions from all my bank accounts at once. Various glitches led me to give up on that. Now, I enter my checkbook entries manually and download my credit card transactions from the card websites, rather than initiating the transfer within Quicken. When the subscription service was added in an effort to increase Quicken’s revenues, I thought I might use the web feature to access my checkbook, rather than relying solely on the installed software on my desktop. It worked for a while. But when I had problems with the web version, I didn’t see enough value to call the help desk to try to fix it. They have a mobile app, but I haven’t tried it. I’ve never tried the budgeting feature, either. I don’t budget, so it had no value to me. Likewise with bill pay. During the years I’ve used Quicken, I’ve migrated from snail-mailing checks to bill…

My Sister – A Reflection One Year Later

Medicare Advantage Part C — Not too soon to start planning for 2027

Roth Conversions and Taxes

What is the right percentage?

Don’t Let a Roth Conversion Trigger a Penalty

For most retirees, the greatest fear is not death—it is running out of money before they die.

Can a Value fund also be a Growth fund?

Risk and Taxes

“Gerontocracy” in America

Looking Back On My Hard Luck Days

FIFA Financials

Before Someone Else Decides

My Sister – A Reflection One Year Later

Medicare Advantage Part C — Not too soon to start planning for 2027

Roth Conversions and Taxes

What is the right percentage?

Don’t Let a Roth Conversion Trigger a Penalty

For most retirees, the greatest fear is not death—it is running out of money before they die.

Can a Value fund also be a Growth fund?

Risk and Taxes

“Gerontocracy” in America

Free Newsletter

Get Educated

Manifesto

think

act

Truths

Money Guide

Manifesto

Spotlight: College

Budgeting 102

Degrees of Doubt: When Higher Education Misses the Mark

On the House

Saved by Borrowing

A+ for Effort

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