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Looking Back On My Hard Luck Days

"Thanks Dan. I've had a very fortunate life, but inevitably we've had our challenges along the way. And I'm sure I'm all the better for having to get through rough patches. In an odd way, looking back on tough times can be pretty satisfying, feeling a bit of pride for hanging in there and making it out the other end."
- greg_j_tomamichel
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Jonathan’s Parting Thoughts: No. 8

"Thank you JC as you continue to read, write and listen to everything from above. I recently read two fascinating books: Knowing Enough by John Bogle and William Bernstein, Bogleheads' Guide to the Three-Fund Portfolio by Taylor Larimore. In both the books, there are many references to Jonathan Clements' timeless quotes, wisdom and tips."
- Senthil Nathan
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Taxing Social Security benefits

"Sorry, you lost me on this comment."
- R Quinn
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“Gerontocracy” in America

"Part of the solution isn't stripping away benefits from seniors—it's making it easier for them to share their wealth while they're still around. And I mean seniors at all income levels. You don't need to give $500K or more to a younger person to make a difference in their life. If we actually want intergenerational equity, one clear path is fixing the tax code's hoarding incentive. Right now, the 'step-up in basis' rule means if older folks give assets to their kids while alive, those assets carry a heavy future capital gains tax bill. But if they hold them until they die? Poof—the capital gains taxes vanish entirely. The tax code literally penalizes passing wealth down early, rewards hoarding it until death, and undermines intergenerational equity."
- John Katz
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For most retirees, the greatest fear is not death—it is running out of money before they die.

"reminds me of Wimpy asking Popeye for money: "I will gladly pay you Tuesday for a hamburger today." Maybe one alternative would be to sit on that $100k (or whatever you would turn over) in a TIPS or a total stock fund for 20 years, then buy the annuity, if we're still around to need it..."
- Catherine
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Before Someone Else Decides

"Excellent booklet Kathleen. The chart for comparing alternatives is excellent. Thanks for sharing."
- DavidHLancaster
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Inflation, prices, COLAs, retirement and the last 16 years

"I suspect the posts you read from seniors are those that do not really have adequate funds built up in IRAs (or other investment orientated savings) to act as the buffer on top of SS. The world has however changed and anyone who has retired in the past 10 years (or is coming up to retirement) should be aware of the utility in maintaining equity market exposure as a key part of managing inflation (and other life event) risks. As has been discussed before SWR is only a tool not the entire answer. If you're asking how much can I draw from $1m capital then 40k pa (rising with inflation) is a reasonable answer for a 30 year lifespan etc. That does nothing to tell you whether $40k will support your lifestyle and/or leave enough surplus for unexpected needs. Hence why you also need a budget or alternately the discipline to live within the income. I'd suggest it is wise to at least think about financial strategy in weathering unexpected needs. But it doesn't need to negate the overall drawdown strategy - for some it might be drawing at only 3.5%, for others maintaining a cash-like emergency fund or being prepared to sell a second home or whatever. My approach is to have a notional "when it's gone, it's gone" pot to cover lumpy one-off spend. Then I top it up from excess from my planned drawings or if it goes, replenish by paring back lifestyle spending a bit. Some people might need to see that as a physically separate fund/account. That's personal choice (possibly for those allergic to spreadsheets/budgeting ;) ) and largely just accounting presentation."
- bbbobbins
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When your 401(k) excludes target date funds

"What are the lowest fee funds? Maybe there's actually a good one."
- Randy Dobkin
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Short term and long term Social Security planning

"My statement,”If there are going to be further cuts in benefits and raises in taxation let younger people who have time to adapt their financial plans be the people to sacrifice to ensure their future beyond, just like we were asked to do in the past.”, is that the above changes would secure our promised benefits and those of younger generations. We had to sacrifice a significant amount from when we first started, so why not younger generations?"
- DavidHLancaster
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Yet-Another Social Security Spreadsheet Analysis on what Age to Start taking Benefits

"When the most important value in the equation is unknowable, any decision is simply a roll of the dice."
- Mike A
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Beware the CFP Designation?

"I wouldn’t count on any three letters behind a name to ensure moral or ethical behavior."
- Mike A
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One Piece Of Paper

"Thanks, Winston. I really like your phrase, “the birth lottery.” We all begin life’s journey from different starting points, and it’s easy to underestimate how much that shapes the opportunities available to us. I also smiled at your comment about computers. It’s wonderful when something that begins as simple curiosity or enjoyment turns into a rewarding career. Like you, the older I get, the more I find myself focusing less on achievement and more on gratitude for family, opportunities, and the unexpected turns that made life richer than I ever imagined."
- Andrew Clements
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Looking Back On My Hard Luck Days

"Thanks Dan. I've had a very fortunate life, but inevitably we've had our challenges along the way. And I'm sure I'm all the better for having to get through rough patches. In an odd way, looking back on tough times can be pretty satisfying, feeling a bit of pride for hanging in there and making it out the other end."
- greg_j_tomamichel
Read more »

Jonathan’s Parting Thoughts: No. 8

"Thank you JC as you continue to read, write and listen to everything from above. I recently read two fascinating books: Knowing Enough by John Bogle and William Bernstein, Bogleheads' Guide to the Three-Fund Portfolio by Taylor Larimore. In both the books, there are many references to Jonathan Clements' timeless quotes, wisdom and tips."
- Senthil Nathan
Read more »

Taxing Social Security benefits

"Sorry, you lost me on this comment."
- R Quinn
Read more »

“Gerontocracy” in America

"Part of the solution isn't stripping away benefits from seniors—it's making it easier for them to share their wealth while they're still around. And I mean seniors at all income levels. You don't need to give $500K or more to a younger person to make a difference in their life. If we actually want intergenerational equity, one clear path is fixing the tax code's hoarding incentive. Right now, the 'step-up in basis' rule means if older folks give assets to their kids while alive, those assets carry a heavy future capital gains tax bill. But if they hold them until they die? Poof—the capital gains taxes vanish entirely. The tax code literally penalizes passing wealth down early, rewards hoarding it until death, and undermines intergenerational equity."
- John Katz
Read more »

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

"reminds me of Wimpy asking Popeye for money: "I will gladly pay you Tuesday for a hamburger today." Maybe one alternative would be to sit on that $100k (or whatever you would turn over) in a TIPS or a total stock fund for 20 years, then buy the annuity, if we're still around to need it..."
- Catherine
Read more »

Before Someone Else Decides

"Excellent booklet Kathleen. The chart for comparing alternatives is excellent. Thanks for sharing."
- DavidHLancaster
Read more »

Inflation, prices, COLAs, retirement and the last 16 years

"I suspect the posts you read from seniors are those that do not really have adequate funds built up in IRAs (or other investment orientated savings) to act as the buffer on top of SS. The world has however changed and anyone who has retired in the past 10 years (or is coming up to retirement) should be aware of the utility in maintaining equity market exposure as a key part of managing inflation (and other life event) risks. As has been discussed before SWR is only a tool not the entire answer. If you're asking how much can I draw from $1m capital then 40k pa (rising with inflation) is a reasonable answer for a 30 year lifespan etc. That does nothing to tell you whether $40k will support your lifestyle and/or leave enough surplus for unexpected needs. Hence why you also need a budget or alternately the discipline to live within the income. I'd suggest it is wise to at least think about financial strategy in weathering unexpected needs. But it doesn't need to negate the overall drawdown strategy - for some it might be drawing at only 3.5%, for others maintaining a cash-like emergency fund or being prepared to sell a second home or whatever. My approach is to have a notional "when it's gone, it's gone" pot to cover lumpy one-off spend. Then I top it up from excess from my planned drawings or if it goes, replenish by paring back lifestyle spending a bit. Some people might need to see that as a physically separate fund/account. That's personal choice (possibly for those allergic to spreadsheets/budgeting ;) ) and largely just accounting presentation."
- bbbobbins
Read more »

When your 401(k) excludes target date funds

"What are the lowest fee funds? Maybe there's actually a good one."
- Randy Dobkin
Read more »

Short term and long term Social Security planning

"My statement,”If there are going to be further cuts in benefits and raises in taxation let younger people who have time to adapt their financial plans be the people to sacrifice to ensure their future beyond, just like we were asked to do in the past.”, is that the above changes would secure our promised benefits and those of younger generations. We had to sacrifice a significant amount from when we first started, so why not younger generations?"
- DavidHLancaster
Read more »

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Manifesto

NO. 4: GOOD SAVINGS habits are the greatest of the financial virtues. If we aren’t good savers, it’s all but impossible to grow wealthy. What if we are? We’ll likely prosper, even if we’re mediocre investors.

Truths

NO. 15: WE FAVOR the familiar. We suffer from home bias, meaning we’re drawn to our employer’s shares, local corporations and stocks of companies whose products we use. We also favor U.S. stocks and shy away from foreign shares. These familiar investments create a portfolio we’re comfortable with—but maybe not one that’s well diversified.

think

INTRINSIC VALUE. It’s easy to get caught up in the stock market’s wild price swings. Feeling unnerved? Never forget that behind those price swings are companies of great value. While we can’t put a precise figure on their intrinsic value, we can get a sense by examining the profits they earn, the dividends they pay and the value of the assets they own.

act

CHECK YOUR Social Security statement to get an estimate of benefits and make sure your earnings record is correct. The easiest way to do this: Set up a “my Social Security” account, preferably adding two-factor authentication. This will also preempt scammers, who might otherwise try to set up an account in your name—and claim your benefits.

How we make money

Manifesto

NO. 4: GOOD SAVINGS habits are the greatest of the financial virtues. If we aren’t good savers, it’s all but impossible to grow wealthy. What if we are? We’ll likely prosper, even if we’re mediocre investors.

Spotlight: Saving

LLC Tax Benefits

I WAS RANDOMLY scrolling on social media and saw this post:

“Can you just open an LLC and write things off?”
That’s a real question someone asked, and I’ve seen this question asked many times.
There are a lot of misconceptions around LLCs, their purpose, and how LLC changes your tax structure. With TikTok, there are “tax experts” sharing terrible advice, so let me clarify how it could be useful.
 
First, what is an LLC?

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Secure Act 2.0 Reflections From Across the Pond

Almost half of working-age adults are not paying into a private or workplace pension, the government revealed this week. This headline caught my attention while browsing the BBC News website the other day, and it really made me think!
This is an awful lot of people imperiling their future lives, and with the UK’s pension auto-enrollment system, now in its tenth year of operation, seeming to be pretty successful, it would suggest people are actively going out of their way to opt out of the system.

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Slow on the Draw

RETIREMENT IS LIFE’S most expensive purchase. During our working years, we deprive our present selves of immediate pleasure by refusing to spend money for nicer cars, a bigger house or a vacation to boast about. Instead, we squirrel away those saved dollars with an eye toward keeping the future us fed, clothed and living indoors. 
At age 64, after decades of choosing to save and invest a large chunk of each paycheck, rather than spend it,

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401(k) Savings Limits

When I was working, I saved the maximum to my 401(k) account. So, I always kept up with the plan’s savings limits. If you haven’t heard, there are higher savings limits for 401(k) plans in 2025, plus a new “super catch-up” category. And it’s still early enough in the year for salaried workers to take advantage of them.
Thanks to an inflation adjustment, the maximum regular contribution to a 401(k) plan has increased by $500 to $23,500 in 2025.

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Social Security

AT FIRST GLANCE, Social Security appears straightforward. During our working years, we pay into it, and in retirement, it sends us a monthly check, guaranteed for life. Unfortunately, it isn’t always so simple. Below are five aspects of the system that are frequently misunderstood.
Benefits estimates. Look at a Social Security statement, and an easy-to-read chart provides estimates of the benefits available at various ages. The heading above the chart reads, “Personalized Monthly Retirement Benefit Estimates Depending on the Age You Start.” That seems clear.

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What is your definition of a millionaire?

I recently heard a fascinating discussion about millionaires.  A financial advisor was speaking to an audience and made the comment that billionaires have jets and millionaires have two used Toyota Camrys in the garage.  His point was that millionaires become millionaires by living below their means and that most millionaires whom he has met live modestly.
He went on to say that there are an estimated 24 million people in the United States who are millionaires. 

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Spotlight: Quinn

Quinn ponders taxes, laws, freebies and the future of retirement. Logic need not apply.

If I save on an after-tax basis in a 401k, (plan permitting) the earnings, upon distribution, are taxed as ordinary income and subject to RMDs. However, withdrawing my after-tax contributions only count toward the RMD until they are exhausted. If I save after-tax in a Roth account, the earnings are tax-free with no required withdrawals. There are earnings limits on contributing to a Roth, but no income or account balance limits on Roth conversions.  Roth distributions are excluded from MAGI and thus substantial income may not count toward IRMAA premiums, but that’s not the case for tax-exempt Muni bond interest also purchased with after-tax money. In theory you could have a $1 million in Roth income and avoid IRMAA. What a deal! Pre-tax 401k contributions are subject to FICA taxes, but pre-tax cafeteria plan contributions (IRC Section 125) are not. Generally, there are no income limits using a Section 125 plan. Such plans could modestly lower future Social Security benefits or some workers.  If there is any logic here, it escapes me.  My first thought was some rules are to prevent extra benefits for high income workers, but that is not case, especially for Roth conversions.  The goal is to encourage retirement savings and make it more feasible - I assume. Is it working? Not to the extent hoped. How much is all this encouragement costing? All this may be moot for most Americans if Congress doesn’t get cracking on making both Social Security and Medicare sustainable.  Then there is the possibility that the lost revenue from tax-free programs like Roth get the attention of the current wave of cost cutters. If health insurance premium subsidies get discussed - and they are - why not Roth freebies? 
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HD readers – “a cut above” as Jersey Mike the new billionaire says

When you compare HD readers on subjects like Social Security, health care, retirement, saving and investing, 401k, managing money and all that goes with those topics, with the general public, well, there is no comparison. HD readers know their stuff or know when to ask when they aren’t sure of the facts.  And, of course, discussions, even disagreements remain civil - except maybe when I write about my theory of retirement income replacement. 😎. I scan several social media sites each day. The comments about the subjects I mentioned are startling. They are uninformed to the max, perhaps intentionally misleading and display a frightening ignorance on the subjects, especially Social Security, health care and saving for retirement in general.  Did you know Social Security would be fine except Congress stole the money? I bet you didn’t realize health insurance companies intentionally deny claims so their CEO can have a private jet.  Very sad indeed. Social media has a high content tone lamenting that things are too tough, unfair and the wealthy take it all - everything would be fine, if we just taxed the wealthy more.  I wonder how these people function today, let alone in future retirement.  All this babble would be harmless except for the fact policymakers are influenced by mass media, right or wrong. Future changes to SS, retirement plans, health benefits, even taxes may be affected.  I’m guessing many in the HD community are the prudent savers, investors and planners with above average incomes and net worth who may be most affected in the future by poorly designed changes - based on ignorance. 
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How do you feel about accepting money, etc. from your children?

You faced no financial disasters through life, you were not disabled, you simply went through life with no specific financial plans for the future and now you are old, retired with minimal income or resources. How would you feel accepting money or substantial gifts (car) from adult children? Glad, embarrassed, ashamed, entitled, grateful?
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You’re on Your Own

A WRITER RECENTLY asked my opinion of gig economy jobs and how they could benefit retirees looking for extra income. I looked up the term to be sure my understanding was correct. It was—except we used to call the jobs “temporaries,” “part-time,” “project work” or “consulting.” As I told the writer, a gig economy job sounds pretty good for us retirees who want to keep active or supplement our income, especially if it doesn’t involve being a crossing guard. But I’m not sure the whole gig thing is great for younger workers. I realize I’m a dinosaur when it comes to the workplace and my work experience has long been buried beneath the remains of the last Ice Age. Still, right or wrong, society must come to grips with the employment changes it’s wrought. Gig work has helped sever the old relationship between employer and worker. Gigs provide flexibility, but they also place far greater responsibility on the individual. Gig economy workers need constantly to find new work, while also planning and taking action to safeguard their financial future, including retirement. My experience could hardly be more different: I worked for the same company from 1961 to 2010. I have a pension and 401(k) plan. I have retiree life insurance and health insurance. In 2019, finding such a job is virtually impossible, except perhaps in the public sector. In fact, such jobs don’t even exist at my former employer. Companies have all but abandoned pensions and benefits that encourage long-term employment. At the same time, it’s near impossible to find workers who want to spend most of their life at one company. Given what you now know about me, it’s no shock to learn that my retirement planning was minimal, because that’s all that was required. I checked the progress…
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Despite Myself

I OFTEN BLOG ABOUT mistakes I’ve made. Why change now? Looking back over my 76 years and the many poor money decisions I’ve made, it’s a wonder I’m in better financial shape than the Social Security trust fund—and yet I am. Here are 10 of my more memorable decisions: In 1961, when I started working at age 18, I got hooked on the stock market. With little money and earning a bit more than minimum wage, I focused on penny stocks, hoping for that big killing. I’m still hoping. College was never mentioned in my family. Around 1964 and still an office clerk, I realized I was going nowhere without a degree, so I enrolled in night courses. Before earning credits, I was required to take two years of courses I hadn’t had in high school. After one semester, I quit. I enrolled again in 1969, after a stint in the army. It took me nine years at night, while my wife and I raised four children—with her doing most of the work. Not the best way to get an important piece of paper. College was paid for by the Department of Veterans Affairs, employer benefits and me. My wife and I married 10 months after our first date, much to the consternation of my parents. During eight of those months, I was away in the army. The following year—with me still in the army—was one of significant financial stress. I was based in Alabama and my wife was on her own in New Jersey. I was trying to send home a little money each month, which meant I barely had enough to telephone my new wife every few days. We became pregnant a month after I got out of the army. My wife stopped working and didn’t return to part-time…
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Buying a house yesteryear and today – a long journey.

I have written several times that I don’t use spreadsheets or budgets. However, once when buying our first home I spent endless hours with paper and pencil trying to determine if we could afford a house and for how much? It was 1971. I had gotten out of the army 18 months before and we had one child. Connie stopped working in July 1970. Mortgage interest rates were about 7.5% and you needed a 20% down payment.  I drew a grid on a piece of paper. One side had monthly mortgage payments and the other monthly property taxes. The idea was to look where the two intersected to see what we could afford. We agonized over the grid for months regularly concluding there was nothing we could afford.  Our income that year was $12,575. The current median household income is estimated at $78,171. Nevertheless we kept looking for a house. We found one that seemed ideal. The ad said it was $25,000. When we called we were told it was a typo, the price was actually $35,000 - the grid didn’t work.  The current median home value in the US is $318,124. Where I live it’s about $580,000. The next house we found in the same town was $29,000. The grid was close so we took a chance and bought it, struggling a bit each month with the payments and wiping out our cash for the $5,800 down payment.   Actually we were helped by Veterans college benefits. They were based on my number of dependents and the VA benefits exceeded the cost of my night courses so the tax-free difference helped pay the mortgage for a few years. The house was built in 1918 as attested to by the newspapers stuffed into the walls for insulation. The furnace was…
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