FREE NEWSLETTER

You’re far less important to your employer than you think—but far more important to your family than you could ever possibly imagine.

Latest PostsAll Discussions »

Social Security – Why I Chose FRA

"I think "wifey" is a term of endearment. It sounds like Langston both likes his spouse and appreciates her. Delightful!"
- John Verlautz
Read more »

Humble Christmas and Holiday Message

"Gratitude is the key to happiness. Merry Christmas! And Chag Chanukah Sameach for my fellow Jewish HDers."
- Ben Rodriguez
Read more »

The Benefits of 401(k)

I WAS HAPPY to read in The Wall Street Journal that 401(k) plans are “minting a generation of moderate millionaires.” I spent the last two decades of my professional life promoting 401(k) plans to workers, so the news felt like validation. Moderate millionaires were loosely defined as coupon-clippers with seven figures. Sound familiar? It should to many HD readers. At Fidelity, a record 654,000 investors had a million or more in the 401(k) in the third quarter of 2025. I can’t get too carried away, however. The typical 401(k) balance is way, way lower—a median of $38,176 in 2024 among 4.7 million savers at Vanguard. That dismal figure is due in part to young employees and recent job changers who haven’t had much time to save. Those with 10 or more years in a 401(k) plan had a median balance of $165,000.  Still not enough to keep us warm, fed, and housed in retirement. Yet the evidence suggests that the 401(k) has growing value to workers. In plans run by Vanguard, 85% of workers contribute, or nearly seven out of eight employees. Why? Here are five benefits that make the 401(k) hard to kick:
  1. Tax saving is habit-forming. Section 401(k) was originally introduced to help Eastman Kodak employees save their big, year-end bonuses before paying federal income taxes. Even today, most workers save their pay into the 401(k) before taxes are paid. Yes, they will owe taxes on withdrawals, and, yes, after-tax Roth contributions make sense for all kinds of reasons. 
Once you’ve filed a tax return sheltering a big hunk of income within a 401(k), however, it’s hard to imagine backtracking. I came to depend on the 401(k) as a big tax shelter every April 15, along with millions of other workers. Eventually, I maxed out my plan savings and, later on, so did my wife.
  1. The employer match is a big gain. Under a typical formula, workers save 6% of their pay to collect their employer’s 3% match. Now, 3% doesn’t sound like a lot. If you hang around long enough to vest, however, it’s a 50% gain on your contributions. Where else can I earn that much risk-free return? Not down at the bank.
  2. The early withdrawal penalty encourages the long view. If I withdrew money from my 401(k) before age 59½ (or 55 under certain circumstances), Vanguard would have withheld 20% in federal income taxes plus a 10% penalty. On a $10,000 withdrawal, that would have felt like throwing $3,000 out the window.
The phone representatives at Vanguard go over these numbers in excruciating detail on a recorded line before asking, “Do you still wish to continue?” For anyone not in dire need of money, that cold shower tends to keep 401(k) balances intact. Because returns compound, being a long-term investor has great value.
  1. Low fees, high services. When a truck driver invests in the 401(k), he’s treated like a big shot. That’s because most large employers—where most 401(k) savers work—have billion-dollar balances in their 401(k) plans. They use that size to bargain for lower-cost institutional funds and the latest services. 
Employers put out requests for proposals all the time. Investment companies scrap for the business, cutting investment fees and adding benefits like automatic enrollment, target-date index funds, and free investment checkups. Workers are better invested, at lower cost, than ever before. 
  1. The magic of the market. Stock prices in the United States have a 200-year history of rising. Not every year, but two out of three, on average. Seeing the magic of stock returns over the long run has made millions of working Americans committed long-term investors.
Little wonder. The idea of making money without setting an alarm, or joining another Zoom meeting from home, has greater appeal the longer you work.   Greg Spears was HumbleDollar's deputy editor. Earlier in his career, he worked as a reporter for the Knight Ridder Washington Bureau and Kiplinger’s Personal Finance magazine. After leaving journalism, Greg spent 23 years as a senior editor at Vanguard Group on the 401(k) side, where he implored people to save more. He currently teaches behavioral economics at St. Joseph’s University in Philadelphia as an adjunct professor. The subject helps shed light on why so many Americans save less than they might. Greg is also a Certified Financial Planner certificate holder. Check out his earlier articles.
Read more »

Can we be completely safe?

"A recent White Coat Investor podcast talked about ACATS fraud and how it's hoped Vanguard will be adding a feature like Fidelity's lockdown."
- Randy Dobkin
Read more »

The Festive Sweater and the Dilemma

"Possibly the reality of adult life has struck them between the eyes?"
- Mark Crothers
Read more »

Boring……

"Similar story for us. Invested in traditional IRA's until Roths came around. I'm still 100% Index ETF's in retirement"
- L H
Read more »

Six Ways to Grow Income

"Greg, Thank you for the two articles this week. Both spurred enjoyable HD discussion."
- Andy Morrison
Read more »

Personal Finance Reading List

LOOKING FORWARD TO some downtime over the holidays? Below are some favorite new personal finance books and articles to consider for your reading list. A Richer Retirement by William BengenBack in the 1990s, financial planner William Bengen developed what’s come to be known as the 4% rule. It’s a framework to help retirees determine a sustainable portfolio withdrawal rate. This year, Bengen updated and expanded his research. The most compelling addition: Bengen addresses the question of asset allocation. In one volume, we now have a guide to both building and withdrawing from a portfolio. How to Retire by Christine Benz – This book is an eminently useful field guide to every aspect of retirement. Where should you live? How should you think about healthcare? How should you structure your time? These questions, and many more, are answered by the group of experts that Morningstar’s Christine Benz assembled for How to Retire. If you're approaching—or even thinking about—retirement, this book will be an excellent companion. The Trick to Enjoying a Vacation (and Investing Successfully) by Mike Piper - Historian Charles Kindleberger observed that, “there is nothing as disturbing to one’s well-being and judgment as to see a friend get rich.” The reality is that there will always be someone who bought Nvidia or some other high-flying investment and can’t wait to tell you about it. To combat this dynamic, author Mike Piper offers a helpful perspective: In building a portfolio, he says, “no matter what you pick, there’s going to be countless other options that would have been better.” But, Piper says, “as long as your original decision was reasonably well informed, it’s not helpful to spend a bunch of time looking at other allocations, other mutual funds, or other individual stocks that you could have selected instead.” Not only could that lead to regret, Piper says, but it could lead to performance chasing. Oddball Funds Gave Investors Fits by Jeff Ptak - One of the more amusing facts about Wall Street is that there are far more mutual funds and ETFs than there are stocks. The result: There’s no shortage of unusual strategies vying for our attention. Morningstar’s Jeff Ptak asks the obvious question: Are these witch’s brews worth investing in? You can probably guess the answer. In related research, Ptak looked at so-called thematic funds, where the results were similar.  Rebuffed: A Closer Look at Options-Based Strategies by Cliff Asness – Investment manager Cliff Asness and a colleague looked at a breed of funds that gained popularity this year: buffer funds, also known as defined-outcome funds. Their conclusion was blunt: These funds are “a failure for investors lured in by the overpromise of magical equity returns without equity risk and then overcharged for the pleasure.” The Complexities of Moving Toward Simplicity by Allan Roth - What if you already have an oddball fund in your portfolio? Should you simply sell it? “Simplicity is a virtue,” financial planner Allan Roth argues, “but not always easy.” In part, that’s because of tax constraints. And certain investments are so complex that it’s hard to know how to evaluate them. “Analyzing a permanent insurance product makes rocket science look simple.” Roth walks through his framework for evaluating whether to hold or to sell various types of investments. Mutual Fund Skill by Javier Vidal-García and Marta Vidal - We’ve all seen the research: Actively-managed funds, on average, lag their index-based peers. An interesting question, though, is why that’s the case. To be sure, cost is a factor. But how should we think about investment managers’ stock-picking skills? This study’s finding: Fund managers actually do a reasonably good job at picking stocks. When it comes to timing decisions, though, fund managers struggle. Stock-pickers, in other words, are good at picking stocks but not very good at deciding when to buy or sell them. How Not to Invest by Barry Ritholtz - How Not to Invest offers investors a cautionary tale—many of them, in fact. Bad actors like Charles Ponzi and Bernie Madoff are well known. The reality, though, is that they represent just one of the many types of financial risk investors encounter. To help us navigate the “bad ideas, bad numbers and bad behavior” that pervade the world of investing, How Not to Invest is a very useful, and also very entertaining, guide. Is it a Bubble? by Howard Marks - Investor and author Howard Marks compares today’s market to past market bubbles and delivers this characteristically even-keeled conclusion: “Since no one can say definitively whether this is a bubble, I’d advise that no one should go all-in without acknowledging that they face the risk of ruin if things go badly. But by the same token, no one should stay all-out and risk missing out on one of the great technological steps forward. A moderate position, applied with selectivity and prudence, seems like the best approach.” I find this sentiment very useful. At times like this, when valuations are high, a good approach is to be prudent but not to panic. Trillion Dollar Market Caps: Fairy Tale Pricing or Great Businesses? (video) by Aswath Damodaran - NYU professor Aswath Damodaran is the author of a thousand-page book titled Investment Valuation and offers his own perspective on the AI economy, digging deep into the numbers. I recommend this video not because I think everyday investors should be analyzing stocks but because I think work like Damodaran’s should get more attention. Instead of hand-waving and story-telling, Damodoran focuses on facts and logic. That can help investors remain balanced in their thinking. Should You Build a TIPS Ladder in Retirement? (video) by Rob Berger - In 2022, when inflation surged, investors were disappointed to see their inflation-linked bonds lose money. Vanguard’s popular Inflation-Protected Securities Fund (ticker: VAIPX) saw shares sink nearly 12% that year. It was not what people expected, and that led many to question the wisdom of holding TIPS. In this video, investment educator Rob Berger clearly explains how TIPS work, then looks at the difference between TIPS funds and individual TIPS bonds. Should You Just Buy Stocks Until You Die? by Jason Zweig - Over time, stocks have handily outperformed bonds. Everybody knows that. So if you’re in your working years, with no near-term withdrawal needs, does that mean you should hold only stocks in your portfolio? Zweig discusses new research which makes precisely that argument. But he goes on to offer investors this clear-eyed advice: “​You can’t just take an analysis of the past, no matter how careful it is, and assume you can extrapolate it into the future…Let’s say the odds that stocks will outperform bonds in the future—if, but only if, the future resembles the past—are something like five out of six. As investing author William Bernstein points out, ‘That is also how often you win at Russian roulette.’” Farewell Friends by Jonathan Clements - The world lost a kind and decent person this year when Jonathan Clements died at age 62. He was a friend and a mentor to his many followers and was endlessly generous with his time and his wisdom. In this article, published posthumously, Jonathan talks about his family, life and career. His parting words: “I faced the final months not with sorrow, but with great gratitude. I had spent almost my entire adult life doing what I love and surrounded by those that I love. Who could ask for more?” 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 »

Business and Side Hustle Tax Tips

BUSINESS OWNERS HAVE far more control over their tax bill than W-2 employees. But only if you know how the rules actually work.  The tax code is structured to reward self employment, business investment, and retirement saving, yet many business owners leave significant money on the table simply because they are unaware of all the strategies. If you are eligible, a Solo 401(k) plan can be an effective way to lower your taxes or shield your investments from future taxation. The amount you can contribute to a Solo 401(k) depends on your self-employment income, your age, whether you participate in another plan (like having a 401(k) at a W-2 job), the type of contribution, and your business entity. For example, say you are 40 years old and have an S corporation with which you pay yourself $100,000 of wages. You can contribute:
  • $23,500 to a pre-tax account as an employee
  • $25,000 as an employer (up to 25% of your W-2 compensation)
In total, you can contribute $48,500 to your Solo 401(k).However, if your Solo 401(k) plan allows, you may also take advantage of a strategy called the “Mega Backdoor Roth,” also known as the after-tax account. Going back to our example, the maximum 401(k) contribution (employee + employer + after-tax) allowed under the rules is $70,000.  Since we already contributed $48,500, we still have $21,500 of room left (the maximum limit you can contribute to such a plan is $70,000, or $77,500 if age 50+, up to your compensation). You can contribute to an after-tax account and roll it over into a Roth 401(k) or Roth IRA. This strategy is extremely useful for someone with a high-earning W-2 and a side hustle. For example, if someone has $500K per year in W-2 income, already maxed out the employee side ($23,500) at their main job with no match, and has a $100K (net self-employment earnings) consulting gig on Schedule C, they can effectively contribute:
  • $20,000 to an employer pre-tax account
  • $26,500 to an after-tax account, for a total of $70,000 in retirement contributions.
  Having the right entity If you are self-employed, you have to pay self-employment taxes (7.65% as the employee and 7.65% as the employer, for a total of 15.3%) if you are a sole proprietor. However, you could elect your business to be taxed as an S corporation, which could potentially help you save money on self-employment taxes. You would have to pay yourself a reasonable salary and can take the rest of your income as a distribution. As a rule of thumb, an S corporation could help you save once you make $100,000 net from your self-employment activity. But it comes with extra steps, such as:
  • Filing Form 1120-S
  • Filing a W-2 and paying yourself a salary
  • Paying FUTA/SUTA taxes
  • State tax compliance and potential additional fees
So, it’s important to analyze the cost of the additional compliance fees to determine whether it’s worth it for your specific scenario.   Shifting income/expenses Something that not a lot of people think about is how you can be strategic about the timing of your expenses and income. Most self-employed business owners are on a cash basis. This means that they pay taxes on the cash that is constructively received, not when it is earned and services are provided. This provides an opportunity to shift income depending on when you invoice and receive the money. For example, say you are going to retire next year and your income will drop. In that case, it could make sense to bill a customer (for services provided) next year (the year of retirement) rather than in the current year. Similarly, if you are experiencing incredible growth where you will make, say, $200K this year but are expecting $300K next year, it may make sense to postpone some of your expenses to the next year. For example, instead of upgrading your computer in 2025 and using bonus depreciation to write off 100% of the cost, you could buy it in 2026 instead and save money. So it all depends on your current income and your projected income next year. If income will be higher next year, try to postpone expenses to next year. If income will be higher next year, try to realize as much income as you can this year.   Hiring your child Hiring your child could be a legitimate tax and wealth-building strategy for business owners, but it must be done correctly. And it’s one of those strategies that is often abused or incorrectly set up. Here are some tips:
  • The work must be legitimate. Your business must have age appropriate, reasonable tasks your child can actually perform (e.g. admin work)
  • Pay reasonable wages. Pay what you would pay an unrelated worker for the same job. Document how you determined the wage.
  • Track everything. Hours worked, duties performed, and proof of work.
  • Have your child complete and sign time logs.
  • Run payroll and file forms. Issue a W-2, file required payroll reports (941, 940, state filings), and tax return
  • Actually pay your child
  • Follow child labor laws. Comply with federal, state, and local rules (e.g. work permit for minors).
The tax savings would depend on your circumstances (e.g. are you in a 37% tax bracket?) Just have to make sure you do it legitimately and document (!). Have you used any of these strategies? Let me know in the comments!   Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.
Read more »

Modest Leverage for Young Investors

"If you're young and want leverage, then have a mortgage and don't try to pay it off, invest the money instead. You don't have to have the debt in the same place as your investments, you have to look at your total personal balance sheet."
- Ormode
Read more »

Under the Tree-a Christmas story

"I never found out what possessed my mother to do that. Since she didn’t drive I assume my father drove her to where she sold it. The whole event is something I will never understand. My father died the following August in 1988. I’m just glad we found out about the sale."
- R Quinn
Read more »

Interest Rates Battle

EARLIER THIS WEEK, the Federal Reserve’s Open Market Committee met and decided to lower interest rates by a quarter-point. This immediately sparked a war of words. At a press conference, Fed chair Jerome Powell took a swipe at the White House, blaming the president’s new tariff policies for an uptick in inflation. President Trump wasted no time in responding. All year, he has been lobbying Fed officials to move rates lower. And while they have been taking steps in that direction, the pace has been incremental, frustrating the president. Powell is “a stiff,” Trump said on Wednesday. “Our rate should be much lower.” This is just the latest chapter in a long-running feud. Trump first appointed Powell to the Fed during his first term but grew frustrated with him after a short time. As far back as 2019, Trump was chiding Powell online, calling him a “bonehead” at one point.  In 2022, the Biden administration reappointed Powell for a second term, with the result that the Trump-Powell feud continues today. Why would the White House prefer to see rates lowered? In short, lower rates make life more affordable for everyone. They make mortgages cheaper, along with car loans and credit cards. Lower rates also make it less expensive for businesses to borrow. Thus, from a political perspective, lower rates are almost always popular.  The challenge for the president, though, is that he has only indirect control over the Federal Reserve. The Fed is technically an independent entity and not part of the executive branch, though the president does have the authority to appoint members to the Federal Open Market Committee (FOMC), which makes rate-setting decisions. The president also appoints the chair of that committee. But as with all appointees, there’s never a guarantee which way committee members will go once they’ve been appointed. And their terms are staggered, meaning the president can’t easily make changes. Earlier this year, in fact, the president explored the idea of firing Powell but found that his hands were tied. That helps explain the ongoing war of words. In addition to making purchases cheaper for consumers, lower interest rates are also positive for the stock market. Why? According to finance theory, the value of a company should equal the sum of all of its future profits. But future profits have to be adjusted for the time value of money—the idea that a dollar next year is worth less than a dollar today. When interest rates are lower, future profits are discounted less. All things being equal, that translates to higher stock prices. That’s another reason the White House would like to see the Fed take quicker action. If lower rates carry so many benefits, why isn’t the Fed moving more quickly? That brings us to what’s known as the “dual mandate.” In its role setting rates, the Fed is responsible, on the one hand, for maintaining full employment. Lower rates help in that regard. At the same time, the other side of the Fed’s dual mandate requires it to manage inflation. Economists talk about the risk of the economy “overheating,” and that’s Powell’s key concern. Especially after seeing prices spike nearly 10% in the wake of the pandemic, the Fed wants to avoid a repeat of that unpleasant experience. Higher rates help keep inflation in check. The Fed’s job, in other words, is to strike a delicate balance between rates that are too high and too low. This ends up being a tricky task, and for that reason, presidents have often tangled with their counterparts at the Fed. In the 1830s, prior to the creation of the Federal Reserve, there was an entity known as the Second Bank of the United States. It was the closest thing to a central bank at the time. But President Andrew Jackson had bitter conflict with the leaders of the Second Bank. He ultimately revoked its charter and had it shut down. That’s why the United States lacked a central bank for decades, until the Fed was created. But almost as soon as the Fed was created in 1913, conflict with successive White Houses resumed.  In the 1950s, the Fed, under chair William McChesney Martin, was moving more slowly than President Truman had wanted, leading him to brand Fed officials “a bunch of cowards.”  Martin stood his ground though. In a speech that same year, he explained that the Fed’s role was akin to that of a chaperone who is obligated to “take away the punch bowl” before things got out of hand. Martin, in fact, is credited with coining that term. From Truman’s point of view, though, lower rates would have served a larger national purpose. In the wake of World War II, the government was saddled with a historically high level of debt. Truman’s hope was that if the Fed lowered borrowing costs, it would help the government work down its debt load more quickly. It was for that reason that Truman also excoriated Martin as a “traitor.” This tension very much mirrors the situation today. Since Covid, the federal government has been running dramatically higher deficits. This year, the federal government will bring in about $5 trillion but spend $7 trillion. Each year that deficits like this persist cause the government’s total debt load to grow. That, in turn, causes interest expenses to consume more and more of the budget. This year, interest will top $1 trillion, equal to one-seventh of all spending. Just as in Truman’s day, this is another reason today’s White House would like to see rates lower. Lyndon Johnson also butted heads with Fed chair Martin, at one point summoning him to his Texas ranch to press his case. Martin had wanted to keep rates higher because he feared that spending for Johnson’s Great Society would be inflationary. A frustrated Johnson reportedly shoved Martin against a wall and bellowed at him. Johnson also asked his attorney general if he could fire Martin but was advised that he couldn’t legitimately remove him. The debate about the Fed goes beyond the question of higher rates vs. lower rates. More fundamentally, the debate today is about the Fed’s overall role. In recent decades, the Fed has taken on the role of serving as lender of last resort during crises. In 2008, it helped stabilize banks by giving them cash in exchange for wobbly assets on their balance sheets. During Covid, the Fed dramatically expanded on its 2008 playbook. You may recall, for example, the stimulus checks and other payments the government issued. Those programs cost trillions. They were financed by the Federal Reserve, which has the unique ability to create dollars essentially out of thin air. The Fed has also stepped in to help various other crises over the years.  In light of this history, most people today see the Fed’s expanded role as a good thing. But not everyone agrees. Treasury secretary Scott Bessent recently published an opinion piece in which he criticized the Fed for taking its lender-of-last-resort playbook too far, flooding the economy with too much easy money for too many years. In Bessent’s view, this has contributed to widening wealth inequality. “The Fed must change course,” he wrote in September, and he is working to do what he can from the outside. Where does all this leave individual investors? Recently, I outlined ways an individual investor could build a portfolio of bonds to manage market risk. As this debate over the Fed reminds us, another reason to diversify is to protect against potential public policy changes that could affect the bond market. As investor and author Howard Marks often says, “we can’t predict, but we can prepare.”   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 »

Social Security – Why I Chose FRA

"I think "wifey" is a term of endearment. It sounds like Langston both likes his spouse and appreciates her. Delightful!"
- John Verlautz
Read more »

Humble Christmas and Holiday Message

"Gratitude is the key to happiness. Merry Christmas! And Chag Chanukah Sameach for my fellow Jewish HDers."
- Ben Rodriguez
Read more »

The Benefits of 401(k)

I WAS HAPPY to read in The Wall Street Journal that 401(k) plans are “minting a generation of moderate millionaires.” I spent the last two decades of my professional life promoting 401(k) plans to workers, so the news felt like validation. Moderate millionaires were loosely defined as coupon-clippers with seven figures. Sound familiar? It should to many HD readers. At Fidelity, a record 654,000 investors had a million or more in the 401(k) in the third quarter of 2025. I can’t get too carried away, however. The typical 401(k) balance is way, way lower—a median of $38,176 in 2024 among 4.7 million savers at Vanguard. That dismal figure is due in part to young employees and recent job changers who haven’t had much time to save. Those with 10 or more years in a 401(k) plan had a median balance of $165,000.  Still not enough to keep us warm, fed, and housed in retirement. Yet the evidence suggests that the 401(k) has growing value to workers. In plans run by Vanguard, 85% of workers contribute, or nearly seven out of eight employees. Why? Here are five benefits that make the 401(k) hard to kick:
  1. Tax saving is habit-forming. Section 401(k) was originally introduced to help Eastman Kodak employees save their big, year-end bonuses before paying federal income taxes. Even today, most workers save their pay into the 401(k) before taxes are paid. Yes, they will owe taxes on withdrawals, and, yes, after-tax Roth contributions make sense for all kinds of reasons. 
Once you’ve filed a tax return sheltering a big hunk of income within a 401(k), however, it’s hard to imagine backtracking. I came to depend on the 401(k) as a big tax shelter every April 15, along with millions of other workers. Eventually, I maxed out my plan savings and, later on, so did my wife.
  1. The employer match is a big gain. Under a typical formula, workers save 6% of their pay to collect their employer’s 3% match. Now, 3% doesn’t sound like a lot. If you hang around long enough to vest, however, it’s a 50% gain on your contributions. Where else can I earn that much risk-free return? Not down at the bank.
  2. The early withdrawal penalty encourages the long view. If I withdrew money from my 401(k) before age 59½ (or 55 under certain circumstances), Vanguard would have withheld 20% in federal income taxes plus a 10% penalty. On a $10,000 withdrawal, that would have felt like throwing $3,000 out the window.
The phone representatives at Vanguard go over these numbers in excruciating detail on a recorded line before asking, “Do you still wish to continue?” For anyone not in dire need of money, that cold shower tends to keep 401(k) balances intact. Because returns compound, being a long-term investor has great value.
  1. Low fees, high services. When a truck driver invests in the 401(k), he’s treated like a big shot. That’s because most large employers—where most 401(k) savers work—have billion-dollar balances in their 401(k) plans. They use that size to bargain for lower-cost institutional funds and the latest services. 
Employers put out requests for proposals all the time. Investment companies scrap for the business, cutting investment fees and adding benefits like automatic enrollment, target-date index funds, and free investment checkups. Workers are better invested, at lower cost, than ever before. 
  1. The magic of the market. Stock prices in the United States have a 200-year history of rising. Not every year, but two out of three, on average. Seeing the magic of stock returns over the long run has made millions of working Americans committed long-term investors.
Little wonder. The idea of making money without setting an alarm, or joining another Zoom meeting from home, has greater appeal the longer you work.   Greg Spears was HumbleDollar's deputy editor. Earlier in his career, he worked as a reporter for the Knight Ridder Washington Bureau and Kiplinger’s Personal Finance magazine. After leaving journalism, Greg spent 23 years as a senior editor at Vanguard Group on the 401(k) side, where he implored people to save more. He currently teaches behavioral economics at St. Joseph’s University in Philadelphia as an adjunct professor. The subject helps shed light on why so many Americans save less than they might. Greg is also a Certified Financial Planner certificate holder. Check out his earlier articles.
Read more »

Can we be completely safe?

"A recent White Coat Investor podcast talked about ACATS fraud and how it's hoped Vanguard will be adding a feature like Fidelity's lockdown."
- Randy Dobkin
Read more »

The Festive Sweater and the Dilemma

"Possibly the reality of adult life has struck them between the eyes?"
- Mark Crothers
Read more »

Boring……

"Similar story for us. Invested in traditional IRA's until Roths came around. I'm still 100% Index ETF's in retirement"
- L H
Read more »

Six Ways to Grow Income

"Greg, Thank you for the two articles this week. Both spurred enjoyable HD discussion."
- Andy Morrison
Read more »

Personal Finance Reading List

LOOKING FORWARD TO some downtime over the holidays? Below are some favorite new personal finance books and articles to consider for your reading list. A Richer Retirement by William BengenBack in the 1990s, financial planner William Bengen developed what’s come to be known as the 4% rule. It’s a framework to help retirees determine a sustainable portfolio withdrawal rate. This year, Bengen updated and expanded his research. The most compelling addition: Bengen addresses the question of asset allocation. In one volume, we now have a guide to both building and withdrawing from a portfolio. How to Retire by Christine Benz – This book is an eminently useful field guide to every aspect of retirement. Where should you live? How should you think about healthcare? How should you structure your time? These questions, and many more, are answered by the group of experts that Morningstar’s Christine Benz assembled for How to Retire. If you're approaching—or even thinking about—retirement, this book will be an excellent companion. The Trick to Enjoying a Vacation (and Investing Successfully) by Mike Piper - Historian Charles Kindleberger observed that, “there is nothing as disturbing to one’s well-being and judgment as to see a friend get rich.” The reality is that there will always be someone who bought Nvidia or some other high-flying investment and can’t wait to tell you about it. To combat this dynamic, author Mike Piper offers a helpful perspective: In building a portfolio, he says, “no matter what you pick, there’s going to be countless other options that would have been better.” But, Piper says, “as long as your original decision was reasonably well informed, it’s not helpful to spend a bunch of time looking at other allocations, other mutual funds, or other individual stocks that you could have selected instead.” Not only could that lead to regret, Piper says, but it could lead to performance chasing. Oddball Funds Gave Investors Fits by Jeff Ptak - One of the more amusing facts about Wall Street is that there are far more mutual funds and ETFs than there are stocks. The result: There’s no shortage of unusual strategies vying for our attention. Morningstar’s Jeff Ptak asks the obvious question: Are these witch’s brews worth investing in? You can probably guess the answer. In related research, Ptak looked at so-called thematic funds, where the results were similar.  Rebuffed: A Closer Look at Options-Based Strategies by Cliff Asness – Investment manager Cliff Asness and a colleague looked at a breed of funds that gained popularity this year: buffer funds, also known as defined-outcome funds. Their conclusion was blunt: These funds are “a failure for investors lured in by the overpromise of magical equity returns without equity risk and then overcharged for the pleasure.” The Complexities of Moving Toward Simplicity by Allan Roth - What if you already have an oddball fund in your portfolio? Should you simply sell it? “Simplicity is a virtue,” financial planner Allan Roth argues, “but not always easy.” In part, that’s because of tax constraints. And certain investments are so complex that it’s hard to know how to evaluate them. “Analyzing a permanent insurance product makes rocket science look simple.” Roth walks through his framework for evaluating whether to hold or to sell various types of investments. Mutual Fund Skill by Javier Vidal-García and Marta Vidal - We’ve all seen the research: Actively-managed funds, on average, lag their index-based peers. An interesting question, though, is why that’s the case. To be sure, cost is a factor. But how should we think about investment managers’ stock-picking skills? This study’s finding: Fund managers actually do a reasonably good job at picking stocks. When it comes to timing decisions, though, fund managers struggle. Stock-pickers, in other words, are good at picking stocks but not very good at deciding when to buy or sell them. How Not to Invest by Barry Ritholtz - How Not to Invest offers investors a cautionary tale—many of them, in fact. Bad actors like Charles Ponzi and Bernie Madoff are well known. The reality, though, is that they represent just one of the many types of financial risk investors encounter. To help us navigate the “bad ideas, bad numbers and bad behavior” that pervade the world of investing, How Not to Invest is a very useful, and also very entertaining, guide. Is it a Bubble? by Howard Marks - Investor and author Howard Marks compares today’s market to past market bubbles and delivers this characteristically even-keeled conclusion: “Since no one can say definitively whether this is a bubble, I’d advise that no one should go all-in without acknowledging that they face the risk of ruin if things go badly. But by the same token, no one should stay all-out and risk missing out on one of the great technological steps forward. A moderate position, applied with selectivity and prudence, seems like the best approach.” I find this sentiment very useful. At times like this, when valuations are high, a good approach is to be prudent but not to panic. Trillion Dollar Market Caps: Fairy Tale Pricing or Great Businesses? (video) by Aswath Damodaran - NYU professor Aswath Damodaran is the author of a thousand-page book titled Investment Valuation and offers his own perspective on the AI economy, digging deep into the numbers. I recommend this video not because I think everyday investors should be analyzing stocks but because I think work like Damodaran’s should get more attention. Instead of hand-waving and story-telling, Damodoran focuses on facts and logic. That can help investors remain balanced in their thinking. Should You Build a TIPS Ladder in Retirement? (video) by Rob Berger - In 2022, when inflation surged, investors were disappointed to see their inflation-linked bonds lose money. Vanguard’s popular Inflation-Protected Securities Fund (ticker: VAIPX) saw shares sink nearly 12% that year. It was not what people expected, and that led many to question the wisdom of holding TIPS. In this video, investment educator Rob Berger clearly explains how TIPS work, then looks at the difference between TIPS funds and individual TIPS bonds. Should You Just Buy Stocks Until You Die? by Jason Zweig - Over time, stocks have handily outperformed bonds. Everybody knows that. So if you’re in your working years, with no near-term withdrawal needs, does that mean you should hold only stocks in your portfolio? Zweig discusses new research which makes precisely that argument. But he goes on to offer investors this clear-eyed advice: “​You can’t just take an analysis of the past, no matter how careful it is, and assume you can extrapolate it into the future…Let’s say the odds that stocks will outperform bonds in the future—if, but only if, the future resembles the past—are something like five out of six. As investing author William Bernstein points out, ‘That is also how often you win at Russian roulette.’” Farewell Friends by Jonathan Clements - The world lost a kind and decent person this year when Jonathan Clements died at age 62. He was a friend and a mentor to his many followers and was endlessly generous with his time and his wisdom. In this article, published posthumously, Jonathan talks about his family, life and career. His parting words: “I faced the final months not with sorrow, but with great gratitude. I had spent almost my entire adult life doing what I love and surrounded by those that I love. Who could ask for more?” 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 »

Business and Side Hustle Tax Tips

BUSINESS OWNERS HAVE far more control over their tax bill than W-2 employees. But only if you know how the rules actually work.  The tax code is structured to reward self employment, business investment, and retirement saving, yet many business owners leave significant money on the table simply because they are unaware of all the strategies. If you are eligible, a Solo 401(k) plan can be an effective way to lower your taxes or shield your investments from future taxation. The amount you can contribute to a Solo 401(k) depends on your self-employment income, your age, whether you participate in another plan (like having a 401(k) at a W-2 job), the type of contribution, and your business entity. For example, say you are 40 years old and have an S corporation with which you pay yourself $100,000 of wages. You can contribute:
  • $23,500 to a pre-tax account as an employee
  • $25,000 as an employer (up to 25% of your W-2 compensation)
In total, you can contribute $48,500 to your Solo 401(k).However, if your Solo 401(k) plan allows, you may also take advantage of a strategy called the “Mega Backdoor Roth,” also known as the after-tax account. Going back to our example, the maximum 401(k) contribution (employee + employer + after-tax) allowed under the rules is $70,000.  Since we already contributed $48,500, we still have $21,500 of room left (the maximum limit you can contribute to such a plan is $70,000, or $77,500 if age 50+, up to your compensation). You can contribute to an after-tax account and roll it over into a Roth 401(k) or Roth IRA. This strategy is extremely useful for someone with a high-earning W-2 and a side hustle. For example, if someone has $500K per year in W-2 income, already maxed out the employee side ($23,500) at their main job with no match, and has a $100K (net self-employment earnings) consulting gig on Schedule C, they can effectively contribute:
  • $20,000 to an employer pre-tax account
  • $26,500 to an after-tax account, for a total of $70,000 in retirement contributions.
  Having the right entity If you are self-employed, you have to pay self-employment taxes (7.65% as the employee and 7.65% as the employer, for a total of 15.3%) if you are a sole proprietor. However, you could elect your business to be taxed as an S corporation, which could potentially help you save money on self-employment taxes. You would have to pay yourself a reasonable salary and can take the rest of your income as a distribution. As a rule of thumb, an S corporation could help you save once you make $100,000 net from your self-employment activity. But it comes with extra steps, such as:
  • Filing Form 1120-S
  • Filing a W-2 and paying yourself a salary
  • Paying FUTA/SUTA taxes
  • State tax compliance and potential additional fees
So, it’s important to analyze the cost of the additional compliance fees to determine whether it’s worth it for your specific scenario.   Shifting income/expenses Something that not a lot of people think about is how you can be strategic about the timing of your expenses and income. Most self-employed business owners are on a cash basis. This means that they pay taxes on the cash that is constructively received, not when it is earned and services are provided. This provides an opportunity to shift income depending on when you invoice and receive the money. For example, say you are going to retire next year and your income will drop. In that case, it could make sense to bill a customer (for services provided) next year (the year of retirement) rather than in the current year. Similarly, if you are experiencing incredible growth where you will make, say, $200K this year but are expecting $300K next year, it may make sense to postpone some of your expenses to the next year. For example, instead of upgrading your computer in 2025 and using bonus depreciation to write off 100% of the cost, you could buy it in 2026 instead and save money. So it all depends on your current income and your projected income next year. If income will be higher next year, try to postpone expenses to next year. If income will be higher next year, try to realize as much income as you can this year.   Hiring your child Hiring your child could be a legitimate tax and wealth-building strategy for business owners, but it must be done correctly. And it’s one of those strategies that is often abused or incorrectly set up. Here are some tips:
  • The work must be legitimate. Your business must have age appropriate, reasonable tasks your child can actually perform (e.g. admin work)
  • Pay reasonable wages. Pay what you would pay an unrelated worker for the same job. Document how you determined the wage.
  • Track everything. Hours worked, duties performed, and proof of work.
  • Have your child complete and sign time logs.
  • Run payroll and file forms. Issue a W-2, file required payroll reports (941, 940, state filings), and tax return
  • Actually pay your child
  • Follow child labor laws. Comply with federal, state, and local rules (e.g. work permit for minors).
The tax savings would depend on your circumstances (e.g. are you in a 37% tax bracket?) Just have to make sure you do it legitimately and document (!). Have you used any of these strategies? Let me know in the comments!   Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.
Read more »

Free Newsletter

Get Educated

Manifesto

NO. 39: WE SHOULD worry less about dying early in retirement—and more about living longer than we ever imagined. Faced with that risk, we might delay Social Security and buy lifetime income annuities.

think

RISK-FREE RATE. This is the return you can earn with little or no risk of loss. If you buy anything riskier, the expected return needs to be higher to compensate for the chance you’ll lose money. Experts point to Treasury bonds as the ultra-safe option. But if you have debt, arguably your risk-free rate is the interest cost you could avoid by paying down that debt.

act

BUNCH CHARITABLE contributions. The 2017 tax law’s higher standard deduction, coupled with the $10,000 cap on deducting state and local taxes, means you may get no tax benefit from charitable gifts. One possibility: Bunch, say, three years of contributions into a single tax year. You might even set up a donor advised fund and spoon out gifts from there.

think

COST-BENEFIT analysis. Before committing to a goal or a purchase, we should ponder alternative uses for our time and money. As we weigh our various options, it’s often easy to visualize the benefits. But what about the costs? Those will likely be paid by our future self, who might have to deal with, say, the resulting credit card bill or the ongoing hassles involved.

Plan your estate

Manifesto

NO. 39: WE SHOULD worry less about dying early in retirement—and more about living longer than we ever imagined. Faced with that risk, we might delay Social Security and buy lifetime income annuities.

Spotlight: Borrowing

Debtors’ Prison

IT’S BEEN MORE THAN three years since my wife and I paid off the last of our consumer debt. Since then, we’ve enjoyed the benefits of a debt-free life: less stress, no interest payments and a lower cost of living.
While these reasons alone make a strong case for paying off credit card balances, car loans and other consumer debt, the true cost of borrowing goes beyond the obvious. Here are five drawbacks that I wish I’d considered before taking on debt:
1.

Read more »

Reverse Engineering

WHAT IF I SAID YOU could borrow to buy a home and have no mortgage payment? Would you think I was nuts?
Trust me, I’m not. If you’re age 62 or older, it’s possible to finance a home purchase and have no ongoing mortgage payments. How? By taking advantage of a home equity conversion mortgage, or HECM. The federally insured HECM is the most popular reverse mortgage in America today.
Now, I know what you’re thinking.

Read more »

Debtor’s Dozen

THE GREAT RECESSION highlighted the frightening amount of debt—especially mortgage debt—that had been taken on by many American families.
A decade later, the picture is far brighter, with one exception: student loans. Since 2008’s third quarter, education debt has ballooned 144%, according to data just released by the Federal Reserve Bank of New York. But the total of all other debt—mortgages, car loans and credit card balances—is up less than 1% over the same period.

Read more »

Refinancing—Again

I HAD A NEW HOME built in 2017. I financed it with a 30-year mortgage at a 3.875% interest rate.
Early last year, when interest rates dropped due to the pandemic, I suggested that readers refinance. I took my own advice, replacing my 30-year loan with a 15-year mortgage at 2.99%. The cost of refinancing seemed well worth the reduction in my loan interest rate.
Two months ago, I saw that mortgage rates had continued to decline,

Read more »

Smarter But Homeless

SOARING STUDENT DEBT is putting the kibosh on another major financial goal: buying a home. According to a study by researchers at the Federal Reserve Bank of Cleveland, 40% of those age 18 to 30 have student debt, up from 27% in 2005. For these borrowers, the debt burden is staggering, with student loan payments estimated to devour more than 20% of their income in 2015.
With so much of their income devoted to servicing student loans,

Read more »

Credit Card Debt.

American credit card debt just broke the trillion dollar level.  Taking on  debt, “ bad” debt, credit cards , auto loans and similar, is a like attending a raucous party ,  taking in too much alcohol , etc.
The aftermath , paying off high interest loans, is like the worst hangover, ever. It can take decades to recover from it.
Often,  too much alcohol can kill you, quickly or long term, * alas , debt can kill you,

Read more »

Spotlight: Rodriguez

Did you retire in or around year 2000? If so, how’s it going?

I see this new Forum as akin to the Bogleheads forum.  I have some problems with that site, and I (obviously) like this one better.  But one very interesting post I saw related to retirees from 2000. The idea is that, theoretically, 2000 was just about the "worst time" someone could retire because it was shortly before the 9/11/2001 drop in stocks, followed by the 2008-09 plunge. As a mid-career investor, I'd be interested to hear how retirees from that time period fared.
Read more »

Me and the Dow

WHEN I WROTE ABOUT the Dow Jones Industrial Average reaching 35,000 in 2021, it’ll surprise few to hear that I—like the stock market—was euphoric. I’ll confess that in 2022, as stocks plunged, I felt silly for having written the article. But here I am again, writing about the latest milestone for our old friend. After flirting with the number in mid-March, the Dow hit an intraday high topping 40,000 on May 16 for the first time in its history. The next day, it closed above that level for an all-time high. I agree with a recent Wall Street Journal article that the Dow is a “terrible” index. That’s mostly because it’s a price-weighted index, as opposed to its cousin, the Standard & Poor's 500, which weights companies according to their total stock market value. Nevertheless, I—perhaps like many of you—have followed the Dow almost my entire life, even when I didn’t really know what it was. The reason for my Dow 35,000 article: I was trying to gauge at what Dow level I’d have enough to retire. I was using an admittedly unscientific approach to come up with that figure. Three years ago, I mentioned that my wife and I wanted to retire in 10 to 15 years. We’re still on track for that goal, which is now nine to 12 years’ away. I postulated that at Dow 50,000 we might have reached our goal. Our magic Dow number is still a bit tricky and unclear. Let’s assume our investment nest egg is half of what I’d like it to be at retirement. In other words, I need it to double to retire. Using the rule of 72, if the Dow notched 7.2% a year, including dividends, the nest egg would double in 10 years. At 10%, it would double in 7.2 years. Reinvested dividends, of course, aren’t reflected in the headline Dow number. What if folks don’t think market returns will be so high, and want to use less rosy projections? And what about dividends? With the Dow companies’ dividend yield at roughly 2%, if the Dow’s index level increased by 4% a year, that would result in a 6% compound growth rate. What then? At that rate, a nest egg would double in roughly 12 years, right on track for yours truly. Because dividends accounted for a third of that growth, we know that the Dow won’t have gained another 40,000 points, landing at 80,000. So, if we discount the 40,000-point gain by one-third—the amount that dividends would account for—that would leave us at Dow 66,667. What this analysis doesn’t reflect is any additional savings added along the way. The last time I was roughing out this math, I guessed that Dow 50,000 might be the magic number for my wife and me. Given that we continue to invest considerable sums each month, that 50,000 figure is still probably about right. Much of this, of course, will depend on how quickly the Dow reaches 50,000. If it happens in 20 years, that will not be very satisfying for me or many investors. If it happens in 10 years, I’ll likely be celebrating. But again, the Dow number is not really the key to our investment success. Rather, it’s the annual compound growth rate. Because our youngest child won’t graduate high school for 12 years, my wife and I will likely continue working at least through then before enjoying an “early” retirement starting in our mid-50s. While Mr. Dow and I still have a little way to go before we reach that magic number, I can’t help feeling a little excitement at the most recent milestone. And even if the market takes a hit after this record high, I’m confident that we’ll continue with our investment plan of steadily buying into the market every month. If the Dow does plummet over the next year or so, I’ll try not to feel too sheepish this time—and at least I’ll have the comfort of knowing our new savings are buying at cheaper prices. Licensed in both Ohio and Kentucky, Ben Rodriguez practices real estate law in Cincinnati, where he lives with his wife and daughters. Since 2009, Ben's made a hobby out of personal finance by reading books and articles on the subject, and also listening to podcasts. Check out his earlier articles.
Read more »

The Long View Podcast: Jonathan Clements: ‘Life Is Full of Small Pleasures’

Jonathan was interviewed by Christine Benz on The Long View podcast produced by Morningstar which can be found anywhere podcast are found or here: Jonathan Clements: 'Life Is Full of Small Pleasures' | Morningstar
Read more »

Should all Americans pay federal income tax?

RDQ's recent post about seniors paying taxes reminded me that presently only 53% of Americans pay federal income tax.  Many of the remaining 47% are net recipients of money from the treasury.  We all know that everyone working pays payroll taxes, but should everyone pay income tax? On the Yea side, having all citizens paying income tax would give everyone "skin in the game" when it comes to voting on tax policy and expenditures.  As it is, it is very easy to see why the 53% would ask why the 47% gets to vote on how much the 53% is taxed and where those funds go.  If the percentages flip just a little more there will be more non-payors than payors, creating a potentially perverse situation. On the Nea side, one must wonder if we're asking for blood from a turnip?  As it is, if the 47% are net zero or net takers and are barely making ends meet as it is, where does this tax money come from?
Read more »

No 401 Way

MY WIFE AND I ARE super-savers. For us, that means we save as much as permitted each year in the retirement plans available to us. Once we’ve done that, we invest in our regular taxable accounts, where there’s no limit on the amount we can contribute. We’re under age 50. That meant that, in 2022, the maximum contribution was $6,000 each to our IRAs and $20,500 each to our 401(k)s. Because the contribution limits increase with inflation, the 2023 limits are $6,500 for IRAs and $22,500 for 401(k)s. My wife is considered a highly compensated employee—I know, a nice problem to have—so her company reduces the amount she can contribute to her 401(k). That makes me even more motivated to contribute all that I can. I also have a high-deductible health insurance plan with an accompanying health savings account, which allowed me to sock away $3,650 in 2022, then the maximum allowed. This year’s max is $3,850. In recent years, it’s become fashionable to bash 401(k)s for reasons I don’t entirely understand. While I enjoy contributing to all my accounts, I view the 401(k) as the primary vehicle for ordinary Americans to build wealth. I still believe it’s possible for regular people to get rich in this country, and to do so they should contribute to their retirement plans—even if they don’t or can’t save the maximum allowed. Which, surprisingly, recently happened to me. In March 2022, I was enjoying both my job and my journey toward maxing out my firm’s 401(k). Quite unexpectedly, I received a job offer from another firm, one that was too good to refuse. My new employer also has a 401(k). But the firm’s policy is that new employees couldn’t begin contributing until they worked there for six months. Because I started the new job on April 11, that would mean that I, Mr. Super Saver, would have to cool my jets until October, when I could then resume my 401(k) contributions and max out that year’s contribution limit. No problem, I thought. I dutifully calculated the difference between the maximum contribution for 2022 and the amount I had contributed at my previous employer. I then plotted the exact percentage of my income I’d need to have deducted each pay period to hit the maximum for the year with my new 401(k). When the pay period following Oct. 11 arrived, I eagerly checked my paystub for confirmation of my 401(k) contribution. Nothing was deducted. Obviously, there was a mistake in the processing, either with my firm or its 401(k) provider. I immediately contacted human resources. HR informed me that there was no mistake. The firm’s policy, it turns out, states that a new employee can begin making 401(k) contributions on the first day of the next quarter that follows his or her six-month anniversary. Because I began work on April 11, that date was Jan. 1, 2023. In other words, I was 11 days too late to contribute anything more for 2022. Acting as my own counsel, I objected to the rule. I begged that an exception be made so that I could super-save. The objection was overruled, and no exception was granted for little old me. In addition to fine print like this, there’s another important point for employees to understand: The individual annual 401(k) contribution limit applies, no matter how many jobs or 401(k) plans they may have. If you’re under 50, you may not under any circumstances contribute more than $22,500 to all of your 401(k)s in 2023. Workers 50 or older can contribute another $7,500 in catch-up contributions, or $30,000 maximum from all jobs they have. Because I only had one job at a time in 2022—which was enough for me, thank you very much—that meant I was effectively unable to contribute anything further to my 401(k), beyond what I’d already saved in my previous employer’s plan. Although disappointed, I made extra contributions to taxable brokerage accounts and also saved some cash. As it happens, that extra cash came in handy—when our home was damaged by a tornado. But that’s another story. Licensed in both Ohio and Kentucky, Ben Rodriguez practices real estate law in Cincinnati, where he lives with his wife and daughters. Since 2009, Ben's made a hobby out of personal finance by reading books and articles on the subject, and also listening to podcasts. Check out his earlier articles. [xyz-ihs snippet="Donate"]
Read more »

Ever heard Down the Middle?

I'm betting that a large number of fellow HumbleDollarians have never heard of a podcast called Down the Middle (Down the Middle Archives | Creative Planning).  It is a pod hosted by our fearless founder Jonathan Clements and co-hosted by Peter Mallouk of Creative Planning. You can find it on Apple or anywhere podcasts are found. It's released only once a month at the beginning of the month. It's one of the pods I most look forward to.  Each episode is only about 10 or 15 minutes long, so the good news is if you've never heard of it, you can catch up on a year's worth of episodes in little time. In the past, Jonathan has been reluctant to promote (or allow promotion) of this pod, but I'm hoping he'll let this one through. I find the content very edifying, and I think it's great to hear his voice.  If you're into podcasts, check it out.
Read more »