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A long bear market is a retirement saver’s best friend—and a retiree’s worst nightmare.

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Wealth: A Short List on How to Recognize It

"Mark, you had me at “meaningful relationships”. When Chrissy didn't immediately throw me out of the house, after hearing me sing for the first time, I felt like I struck gold. "
- DAN SMITH
Read more »

Feeling Secure

"Hearing about your adventures is inspiring!"
- Cecilia Beverly
Read more »

Affordable? Healthcare? How do you spread your risk?

"Come on folks. Let’s have an estimate. What percentage of your gross income do you think is affordable/fair to spend on healthcare- premiums and out of pocket costs, but mostly premiums. If your income is $50,000 would you be comfortable spending $4,000? Or if you earn $100,000 how about $8000 or $666 per month? Not easy to commit to is it? Not even something we like to think about because we really think about so many better uses for that money."
- R Quinn
Read more »

Discussing money matters with friends- a slippery slope

"Knowing where you stand in the pack, I agree, but you don’t need to make it personal to do that."
- R Quinn
Read more »

Tax Gain Harvesting

MANY PEOPLE ARE familiar with tax loss harvesting, where you sell a losing security/ETF and rebuy a similar, not identical, security/ETF. But often we don’t really think about the opposite side of the coin: sell a winning security/ETF and rebuy the exact same, or a different, security/ETF. That strategy is called tax gain harvesting, and because it’s a gain, the wash sale rule doesn’t apply.   Execution Long-term capital gains can be taxed at 0% depending on your income. That’s how this strategy is executed. The main benefit isn’t paying 0% tax, it's resetting your cost basis higher, so future gains are smaller when your income (and hopefully the tax bracket) rises. For 2025, if your filing status is single and your taxable income is up to $48,350, the long-term gains are taxed at 0% on the federal level. If your filing status is married filing jointly and your taxable income is up to $96,700, the long-term gains are taxed at 0% on the federal level. The taxable income part is important because it means that the amount is after the standard deduction was applied, which means that your gross income can be ~$64,100 ($15,750 standard deduction for single in 2025) or $128,200 ($31,500 standard deduction for married in 2025). For example, say that you just started your career and bought $1,000 worth of VTI in your brokerage account. The VTI is now worth $2,000 after 4 years. Since this individual is early in their career, the W-2 income is $50,000. If this individual sold VTI for $2,000 ($1,000 of long-term gain), and automatically re-bought it, the total gross income for the year would be $51,000. After the standard deduction is applied, the taxable income is $35,250, which means that $1,000 of long-term gains will be taxed at 0% on the federal level. Note: the gains must be long-term, which means that you’ve held for longer than a year. Otherwise, the short-term gain will apply and will be taxed at your ordinary income tax rates. Because we rebought, the cost basis increased to $2,000, which means that in the future when we do have to sell it again and cash out, our gain will be calculated using the $2,000 cost, and not the $1,000 as it would’ve originally without doing the strategy. This could be helpful once you are in the 15% or 20% capital gains tax bracket. Generally, for tax gain harvesting you want to sell specific shares. You can set your cost method to specific identification within the brokerage account to sell specific lots and correctly calculate the amount of gain that would apply to your sale. It’s also generally better to harvest gains on the shares with the lowest gains (highest cost basis). This strategy applies only to taxable brokerage accounts. It doesn’t apply to tax-advantaged accounts such as IRAs or 401(k)s. If you have capital loss carryforwards, tax gain harvesting can also be used to “use up” those losses in a low-income year without actually paying any tax. For example, if you have $3,000 of capital loss carryforwards, you can realize $3,000 of long-term gains tax-free and effectively “refresh” your cost basis.  When executing, remember that you’re still selling a security, which means there’s a small risk of market movement between the sale and repurchase. If you sell and rebuy the same ETF immediately, you’re exposed to short-term price changes during that brief window, so consider doing it asap. The thresholds for 0% long-term capital gains are indexed for inflation, so they typically rise each year. Your brokerage will report the sale on Form 1099-B, so make sure your cost basis is all correct and is updated for the purchase.   Further considerations: State/local taxes Typically, if the state and local taxes will apply to your situation, it’s not recommended to do the gain harvesting strategy. This is because on $1,000 of gain you may have to pay $50-100 of state taxes, and the opportunity cost associated with the tax payment could outweigh the benefit. This strategy is best for people who don’t have state taxes and/or live in states that don’t tax capital gains. The 0% rate applies only on the federal level.   Tax credits In our example, the extra $1,000 long-term capital gain increased your income. Tax credits generally depend on your modified adjusted gross income and they could be phased out or completely eliminated depending on your income. This means that tax gain harvesting could result in some credits being unavailable (for example, the Earned Income Tax Credit or Saver’s Credit). You have to analyze your specific scenario and attributes to see whether this makes sense. The easiest way would be to enter information into a tax software with before and after scenarios to analyze the impact.   Taxability of other items There are certain taxability rules that are dependent upon your income. For example, Social Security benefits could be taxed at 0% depending on your provisional income. Harvesting gains could result in increasing your provisional income, which could push how much of your Social Security benefits are taxed. This is another area that needs careful consideration. In addition, ACA credits also have to be taken into account, if they apply to you.   Is the juice worth the squeeze? It depends on how much you can harvest and on your income. If you are a married couple making $100,000 of total W-2 income, you can harvest a lot of gains, which could result in substantial savings if state taxes and other rules aren’t applicable to your scenario. But if you are harvesting a few hundred every year, it will likely make a minimal impact. The strategy itself isn’t too complicated if you can correctly analyze your income and potential credits. The challenge could come where you receive a bonus on 12/25 that you didn’t think through, or some spot bonuses that could push your income higher. If you have to pay state taxes or sacrifice credits, it’s generally not advisable to harvest your gains. Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.
Read more »

Heads-up for TurboTax Desktop Users (& 2025 Tax Planning)

"Thanks for information on "What-if" scenario planning using the "Info Wks" form. I was not aware of this form. I'm using a PC and don't see the 2025 updates in 2024 TT but am able to fudge enough for planning purposes. Seems the increase in SALT may be the biggest item that will change in 2025? Thanks!!"
- Suzee
Read more »

I Don’t Like to Judge…But.

"As I never quizzed the two women about their intentions, your interpretation is certainly just as valid as mine. The only concrete part of the article is the expression of my thoughts during the encounter. Everything else is open to speculation."
- Mark Crothers
Read more »

Another IRMAA Question

"Oops I see you fixed it. 😁"
- R Quinn
Read more »

Logic Check: 401(k) Loan – Paying Taxes Twice?

"The thing is it is too easy to get the 401k loan. Participants see it as borrowing from themselves when as you know they are borrowing from the plan trust."
- R Quinn
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AI Rally Market Risks

LAST WEEK, OPENAI founder Sam Altman sat down for an interview with venture capitalist Brad Gerstner and Microsoft CEO Satya Nadella. Both are investors in OpenAI, so it seemed like a friendly audience. But Gerstner posed a question that seemed to make Altman uncomfortable. Since introducing ChatGPT three years ago, OpenAI has posted impressive growth, but Gerstner wondered whether the company was, nonetheless, getting ahead of itself. “How can a company with $13 billion in revenues make $1.4 trillion of spend commitments?” Gerstner asked. The commitments in question are OpenAI’s agreements to purchase computing resources. In total, they’d cost more than 100 times its current revenue. Commitments that top $1 trillion would be significant for any company, but they’re of particular concern because OpenAI has yet to turn a profit. Altman was quick to debate Gerstner. First, he said, “we’re doing well more revenue than that.” He dismissed what he called “breathless concern” over OpenAI’s finances, and he expressed frustration at Gerstner—who is himself an OpenAI investor—for even asking the question. “Brad, if you want to sell your shares, I’ll find you a buyer…I think there’s a lot of people that would love to buy OpenAI shares.” In recent months, investors have been asking questions like this with increasing frequency, concerned about the economics underpinning the AI economy.  For everyday investors, these questions are important because many of the largest public companies are now heavily dependent on AI spending. At the top of the list: Nvidia. Its graphics processing unit (GPU) chips power most AI-based computers. Last week, it became the first company ever to reach a market capitalization of $5 trillion. It now accounts for 8% of the total value of the S&P 500. As a point of reference, it’s now worth more than the total value of the UK stock market. As a result, this debate has taken on more importance, so it’s worth looking at both sides. Concerns about the AI ecosystem start with the worry that there’s a circularity to the profits these companies are generating. A little while back, Nvidia announced an investment of as much as $100 billion into OpenAI, at the same time that OpenAI is spending billions on Nvidia’s chips. Nvidia has invested in more than 100 other AI-related companies over the past two years, helping further drive demand for its own chips. OpenAI also signed a deal with AMD, another chip maker, to buy tens of billions of dollars of AMD chips. As part of that deal, OpenAI will become a shareholder in AMD. Those are just some of the very sizable deals that have happened this year. Other complicated and interrelated deals involve Elon Musk’s xAI and a newly-public company called CoreWeave. Beyond the potential circularity of these arrangements, there’s a more fundamental question: Sensing a parallel to the technology bubble of the 1990s, some are asking whether today’s AI spending is all being put to good use. A key feature of the 1990s bubble was the over-building of fiber optic networks, with the result that much of it went unused and billions were wasted. In the 1990s, those miles of unused fiber came to be known as “dark fiber,” leading some to ask whether today there are “dark GPUs.” In other words, are there Nvidia chips that have been sold but that are sitting dormant in a data center somewhere? On this question, opinions differ. At a recent conference hosted by the venture firm Andreessen Horowitz, the consensus was that the notion of dark GPUs is off the mark. The speakers felt that there’s actually a shortage of GPUs. But this is an open question.  Satya Nadella has acknowledged that Microsoft does have Nvidia GPUs “sitting in inventory that I can’t plug in,” due to other constraints. It’s not clear how many, but this is another data point to consider. If there are too many surplus chips out there, it means Nvidia’s future sales may come in lower than expected. A sales shortfall would pose a risk to any stock but would pose a very significant risk to a highflier like Nvidia. What would be the impact on everyday investors? In the past, there was the expression that, “if General Motors sneezes, the country catches a cold.” That is the concern with these deals, and it isn’t limited to Nvidia. The so-called Magnificent Seven stocks—Nvidia, Microsoft, Apple, Alphabet, Amazon, Meta and Tesla—now account for more than a third of the S&P 500’s total market value, up from less than 10% a decade ago. So if they stumble, the overall market will stumble. That’s the risk, and that’s why it’s fair that investors want to better understand these companies’ finances. That said, some see these concerns as overblown. While AI is hardly perfect, it’s delivering tangible productivity improvements across many industries. Among other things, AI can now create video, build spreadsheets and write computer code. New AI “agents” can even be scheduled to take actions autonomously. I’ve tried this myself and found the results remarkable. These capabilities are expanding rapidly. How will things turn out? The reality is that no one knows for sure. Partisans on both sides of this debate make valid points. But as always, risk management should be paramount. Nvidia and its peers have helped drive the stock market up over the past two years. But because of the resulting top-heavy nature of the market, now is a good time for investors to review their portfolios. Look to see how diversified you are beyond these big tech stocks. Do you own mid- and small-cap stocks, which carry much less exposure to these AI risks? Do you hold international stocks? Most importantly, do you hold bonds or cash which could meet your expenses in the event of a market downturn? While stocks are still doing very well, this is a good time to take inventory.   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 »

The Best Money We Almost Didn’t Spend

"Thanks Michael. Barrons must have been having difficulty finding content that day lol"
- Mark Crothers
Read more »

Wealth: A Short List on How to Recognize It

"Mark, you had me at “meaningful relationships”. When Chrissy didn't immediately throw me out of the house, after hearing me sing for the first time, I felt like I struck gold. "
- DAN SMITH
Read more »

Feeling Secure

"Hearing about your adventures is inspiring!"
- Cecilia Beverly
Read more »

Affordable? Healthcare? How do you spread your risk?

"Come on folks. Let’s have an estimate. What percentage of your gross income do you think is affordable/fair to spend on healthcare- premiums and out of pocket costs, but mostly premiums. If your income is $50,000 would you be comfortable spending $4,000? Or if you earn $100,000 how about $8000 or $666 per month? Not easy to commit to is it? Not even something we like to think about because we really think about so many better uses for that money."
- R Quinn
Read more »

Discussing money matters with friends- a slippery slope

"Knowing where you stand in the pack, I agree, but you don’t need to make it personal to do that."
- R Quinn
Read more »

Tax Gain Harvesting

MANY PEOPLE ARE familiar with tax loss harvesting, where you sell a losing security/ETF and rebuy a similar, not identical, security/ETF. But often we don’t really think about the opposite side of the coin: sell a winning security/ETF and rebuy the exact same, or a different, security/ETF. That strategy is called tax gain harvesting, and because it’s a gain, the wash sale rule doesn’t apply.   Execution Long-term capital gains can be taxed at 0% depending on your income. That’s how this strategy is executed. The main benefit isn’t paying 0% tax, it's resetting your cost basis higher, so future gains are smaller when your income (and hopefully the tax bracket) rises. For 2025, if your filing status is single and your taxable income is up to $48,350, the long-term gains are taxed at 0% on the federal level. If your filing status is married filing jointly and your taxable income is up to $96,700, the long-term gains are taxed at 0% on the federal level. The taxable income part is important because it means that the amount is after the standard deduction was applied, which means that your gross income can be ~$64,100 ($15,750 standard deduction for single in 2025) or $128,200 ($31,500 standard deduction for married in 2025). For example, say that you just started your career and bought $1,000 worth of VTI in your brokerage account. The VTI is now worth $2,000 after 4 years. Since this individual is early in their career, the W-2 income is $50,000. If this individual sold VTI for $2,000 ($1,000 of long-term gain), and automatically re-bought it, the total gross income for the year would be $51,000. After the standard deduction is applied, the taxable income is $35,250, which means that $1,000 of long-term gains will be taxed at 0% on the federal level. Note: the gains must be long-term, which means that you’ve held for longer than a year. Otherwise, the short-term gain will apply and will be taxed at your ordinary income tax rates. Because we rebought, the cost basis increased to $2,000, which means that in the future when we do have to sell it again and cash out, our gain will be calculated using the $2,000 cost, and not the $1,000 as it would’ve originally without doing the strategy. This could be helpful once you are in the 15% or 20% capital gains tax bracket. Generally, for tax gain harvesting you want to sell specific shares. You can set your cost method to specific identification within the brokerage account to sell specific lots and correctly calculate the amount of gain that would apply to your sale. It’s also generally better to harvest gains on the shares with the lowest gains (highest cost basis). This strategy applies only to taxable brokerage accounts. It doesn’t apply to tax-advantaged accounts such as IRAs or 401(k)s. If you have capital loss carryforwards, tax gain harvesting can also be used to “use up” those losses in a low-income year without actually paying any tax. For example, if you have $3,000 of capital loss carryforwards, you can realize $3,000 of long-term gains tax-free and effectively “refresh” your cost basis.  When executing, remember that you’re still selling a security, which means there’s a small risk of market movement between the sale and repurchase. If you sell and rebuy the same ETF immediately, you’re exposed to short-term price changes during that brief window, so consider doing it asap. The thresholds for 0% long-term capital gains are indexed for inflation, so they typically rise each year. Your brokerage will report the sale on Form 1099-B, so make sure your cost basis is all correct and is updated for the purchase.   Further considerations: State/local taxes Typically, if the state and local taxes will apply to your situation, it’s not recommended to do the gain harvesting strategy. This is because on $1,000 of gain you may have to pay $50-100 of state taxes, and the opportunity cost associated with the tax payment could outweigh the benefit. This strategy is best for people who don’t have state taxes and/or live in states that don’t tax capital gains. The 0% rate applies only on the federal level.   Tax credits In our example, the extra $1,000 long-term capital gain increased your income. Tax credits generally depend on your modified adjusted gross income and they could be phased out or completely eliminated depending on your income. This means that tax gain harvesting could result in some credits being unavailable (for example, the Earned Income Tax Credit or Saver’s Credit). You have to analyze your specific scenario and attributes to see whether this makes sense. The easiest way would be to enter information into a tax software with before and after scenarios to analyze the impact.   Taxability of other items There are certain taxability rules that are dependent upon your income. For example, Social Security benefits could be taxed at 0% depending on your provisional income. Harvesting gains could result in increasing your provisional income, which could push how much of your Social Security benefits are taxed. This is another area that needs careful consideration. In addition, ACA credits also have to be taken into account, if they apply to you.   Is the juice worth the squeeze? It depends on how much you can harvest and on your income. If you are a married couple making $100,000 of total W-2 income, you can harvest a lot of gains, which could result in substantial savings if state taxes and other rules aren’t applicable to your scenario. But if you are harvesting a few hundred every year, it will likely make a minimal impact. The strategy itself isn’t too complicated if you can correctly analyze your income and potential credits. The challenge could come where you receive a bonus on 12/25 that you didn’t think through, or some spot bonuses that could push your income higher. If you have to pay state taxes or sacrifice credits, it’s generally not advisable to harvest your gains. Bogdan Sheremeta is a licensed CPA based in Illinois with experience at Deloitte and a Fortune 200 multinational.
Read more »

Heads-up for TurboTax Desktop Users (& 2025 Tax Planning)

"Thanks for information on "What-if" scenario planning using the "Info Wks" form. I was not aware of this form. I'm using a PC and don't see the 2025 updates in 2024 TT but am able to fudge enough for planning purposes. Seems the increase in SALT may be the biggest item that will change in 2025? Thanks!!"
- Suzee
Read more »

I Don’t Like to Judge…But.

"As I never quizzed the two women about their intentions, your interpretation is certainly just as valid as mine. The only concrete part of the article is the expression of my thoughts during the encounter. Everything else is open to speculation."
- Mark Crothers
Read more »

Another IRMAA Question

"Oops I see you fixed it. 😁"
- R Quinn
Read more »

AI Rally Market Risks

LAST WEEK, OPENAI founder Sam Altman sat down for an interview with venture capitalist Brad Gerstner and Microsoft CEO Satya Nadella. Both are investors in OpenAI, so it seemed like a friendly audience. But Gerstner posed a question that seemed to make Altman uncomfortable. Since introducing ChatGPT three years ago, OpenAI has posted impressive growth, but Gerstner wondered whether the company was, nonetheless, getting ahead of itself. “How can a company with $13 billion in revenues make $1.4 trillion of spend commitments?” Gerstner asked. The commitments in question are OpenAI’s agreements to purchase computing resources. In total, they’d cost more than 100 times its current revenue. Commitments that top $1 trillion would be significant for any company, but they’re of particular concern because OpenAI has yet to turn a profit. Altman was quick to debate Gerstner. First, he said, “we’re doing well more revenue than that.” He dismissed what he called “breathless concern” over OpenAI’s finances, and he expressed frustration at Gerstner—who is himself an OpenAI investor—for even asking the question. “Brad, if you want to sell your shares, I’ll find you a buyer…I think there’s a lot of people that would love to buy OpenAI shares.” In recent months, investors have been asking questions like this with increasing frequency, concerned about the economics underpinning the AI economy.  For everyday investors, these questions are important because many of the largest public companies are now heavily dependent on AI spending. At the top of the list: Nvidia. Its graphics processing unit (GPU) chips power most AI-based computers. Last week, it became the first company ever to reach a market capitalization of $5 trillion. It now accounts for 8% of the total value of the S&P 500. As a point of reference, it’s now worth more than the total value of the UK stock market. As a result, this debate has taken on more importance, so it’s worth looking at both sides. Concerns about the AI ecosystem start with the worry that there’s a circularity to the profits these companies are generating. A little while back, Nvidia announced an investment of as much as $100 billion into OpenAI, at the same time that OpenAI is spending billions on Nvidia’s chips. Nvidia has invested in more than 100 other AI-related companies over the past two years, helping further drive demand for its own chips. OpenAI also signed a deal with AMD, another chip maker, to buy tens of billions of dollars of AMD chips. As part of that deal, OpenAI will become a shareholder in AMD. Those are just some of the very sizable deals that have happened this year. Other complicated and interrelated deals involve Elon Musk’s xAI and a newly-public company called CoreWeave. Beyond the potential circularity of these arrangements, there’s a more fundamental question: Sensing a parallel to the technology bubble of the 1990s, some are asking whether today’s AI spending is all being put to good use. A key feature of the 1990s bubble was the over-building of fiber optic networks, with the result that much of it went unused and billions were wasted. In the 1990s, those miles of unused fiber came to be known as “dark fiber,” leading some to ask whether today there are “dark GPUs.” In other words, are there Nvidia chips that have been sold but that are sitting dormant in a data center somewhere? On this question, opinions differ. At a recent conference hosted by the venture firm Andreessen Horowitz, the consensus was that the notion of dark GPUs is off the mark. The speakers felt that there’s actually a shortage of GPUs. But this is an open question.  Satya Nadella has acknowledged that Microsoft does have Nvidia GPUs “sitting in inventory that I can’t plug in,” due to other constraints. It’s not clear how many, but this is another data point to consider. If there are too many surplus chips out there, it means Nvidia’s future sales may come in lower than expected. A sales shortfall would pose a risk to any stock but would pose a very significant risk to a highflier like Nvidia. What would be the impact on everyday investors? In the past, there was the expression that, “if General Motors sneezes, the country catches a cold.” That is the concern with these deals, and it isn’t limited to Nvidia. The so-called Magnificent Seven stocks—Nvidia, Microsoft, Apple, Alphabet, Amazon, Meta and Tesla—now account for more than a third of the S&P 500’s total market value, up from less than 10% a decade ago. So if they stumble, the overall market will stumble. That’s the risk, and that’s why it’s fair that investors want to better understand these companies’ finances. That said, some see these concerns as overblown. While AI is hardly perfect, it’s delivering tangible productivity improvements across many industries. Among other things, AI can now create video, build spreadsheets and write computer code. New AI “agents” can even be scheduled to take actions autonomously. I’ve tried this myself and found the results remarkable. These capabilities are expanding rapidly. How will things turn out? The reality is that no one knows for sure. Partisans on both sides of this debate make valid points. But as always, risk management should be paramount. Nvidia and its peers have helped drive the stock market up over the past two years. But because of the resulting top-heavy nature of the market, now is a good time for investors to review their portfolios. Look to see how diversified you are beyond these big tech stocks. Do you own mid- and small-cap stocks, which carry much less exposure to these AI risks? Do you hold international stocks? Most importantly, do you hold bonds or cash which could meet your expenses in the event of a market downturn? While stocks are still doing very well, this is a good time to take inventory.   Adam M. Grossman is the founder of Mayport, a fixed-fee wealth management firm. Sign up for Adam's Daily Ideas email, follow him on X @AdamMGrossman and check out his earlier articles.
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Get Educated

Manifesto

NO. 52: WE SHOULD aim to become homeowners—not because homes deliver handsome capital gains, but because owning locks in our housing costs and, with every mortgage payment, forces us to save.

Truths

NO. 122: IT’S HARD to make money on a house unless we stay put for at least five years, and preferably seven years or longer. Why? It costs so much to buy and especially sell real estate. Add up title insurance, mortgage-application fees, the commission when selling, local transfer taxes, legal fees and other expenses, and the roundtrip cost could total 10% of a home’s value.

think

DURATION. This is a measure of a bond or bond fund’s sensitivity to interest rate changes. A bond fund with a duration of five years would fall 5% in price if interest rates rose by one percentage point and climb 5% if rates declined by one percentage point. A rule of thumb: Avoid owning bonds whose duration is longer than your investment time horizon.

act

MAKE QUALIFIED charitable distributions. In your 70s or older and want to give to charity? Consider donating directly from your IRA. You won’t get a tax deduction. But you also won’t owe taxes on the distribution, which will likely mean a smaller tax bill and lower Medicare premiums, plus the sum counts toward your required minimum distribution.

Life events

Manifesto

NO. 52: WE SHOULD aim to become homeowners—not because homes deliver handsome capital gains, but because owning locks in our housing costs and, with every mortgage payment, forces us to save.

Spotlight: Retirement

Save ’Til It Hurts

I FREQUENTLY FIND myself criticized when I state my fiscally conservative views on saving and spending in retirement. One fellow recently said I had no compassion and I was scaring people.

If folks are frightened by my urging them to retire with the ability to replace most of their preretirement income, then perhaps they should be scared.

I’m also criticized because I have a pension, and so don’t rely on investments for my income.

Read more »

Today’s the Day!

Well, I tried to stay up until midnight to pop a cork, but it just wasn’t happening. So today I woke up as a retired person!  If you’ve read my articles from 2024 on the topic, you know this didn’t sneak up on me.
My road through the logistics of retiring from two university systems and applying for Medicare went…somewhat smoothly. I was pretty meticulous in my preparation. I attended webinars for both systems last year and put the application dates on my calendar.

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My Four Goals

I’M PROBABLY A YEAR or two away from regularly tapping my portfolio for income. That prospect—coupled with this year’s market turmoil—has led me to tinker with my investment mix and ponder how I’ll generate cash once I’m retired. One surprising result: I have more in stocks today than I’ve had at any time in the past three years, and I’m thinking of increasing my allocation even further.
Since 2014, I’ve thought of myself as semi-retired.

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Brace Yourself

PARTICIPANTS IN 401(K) plans will soon be getting estimates of how much income they might receive in retirement if their plan savings were spent purchasing an annuity. Under a new rule, plan providers are required to provide participants with at least two annuity estimates annually on their account statements. One would project the lifetime income from the purchase of a single-life annuity and the other from a joint-and-survivor annuity. A joint-and-survivor annuity extends payments over two lives,

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New 2025 Tax Deductions

THE IRS JUST released a new form called Schedule 1-A, which includes all the new tax bill deductions.
I wanted to quickly go through some of it, so that you are more aware of the new potential savings opportunities.
I’ve previously discussed some portions of the bill, but this is the first time we have a peek of the new lines.
All of these deductions are in addition to the standard deduction or itemized deduction.

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Dream Inflation

AS PART OF OUR retirement strategy, my husband and I plan on using the money we make from the sale of our home in Oregon to help cover part of our retirement expenses. We already own a second home in Arizona, which we’ll move into once I leave my job. We’ve played around with different ideas for how best to use the money, including making a large, onetime payment against our Arizona home’s mortgage.

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Spotlight: Saha

Inflation Bites

FINANCIAL PLANNERS often ask new clients about their first money memory. Mine was about an early encounter with inflation. It involved a favorite childhood snack named fuchka, a popular street food in Kolkata, where I grew up. The snack is a ball-shaped flatbread, filled with spicy potato mash and topped with tamarind water. As you crunch its crispy shell, the magical flavors burst in your mouth and take your tastebuds on a rollercoaster ride. As a child, this occasional savory treat was my main motivation for earning pocket money. In my elementary school days, our neighborhood street-food vendor used to sell three pieces for 10 paisa—roughly one cent at that time. I rarely had more than five paisa, for which the vendor gave me just one piece. I challenged his math and demanded fairness. Pestered by this argumentative little boy, he agreed to give me an extra piece with every other purchase. I felt proud of my negotiation skills. My joy didn’t last long. Out of nowhere, the vendor raised the price to two pieces for 10 paisa. No more extra pieces for me. This came as a surprise. My little mind couldn’t comprehend how and why prices could increase overnight. Angry and frustrated, I ran home to my mother and drew her attention to this injustice. To my disappointment, my mother seemed more sympathetic toward the vendor than her own son. She told me that prices go up over time but couldn’t explain why. Her advice: Sign up for more chores to boost my pocket money. My childhood snack is 100 times pricier these days, compared with a threefold rise in U.S. hot dog prices over the same period, reflecting India’s far higher inflation rate in recent decades. Today, inflation doesn’t surprise me. What does is the realization that my mother isn’t the only one who’s clueless about its causes.
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A Rich Life

I'M FRUGAL AND FEEL fortunate to be so. Indeed, among all the financial skills I’ve learned, frugality stands out as the most powerful. But at the same time, I also feel affluent. This might seem like a contradiction, but the mindset of frugality and the feeling of affluence strike me as two sides of the same coin. Frugality is often associated with being cheap. Frequently, “affluent” is used interchangeably with “wealthy.” I beg to differ. Frugality is about avoiding spending on things that have little value, while affluence is about having things that truly matter. I believe it’s possible to strike a balance, so you’re frugal and affluent at the same time. My family’s frugality is evident in our spending. When I compare our average household expenses to those in the same income decile, our numbers are much lower. In fact, our annual expenses are closest to the income group that’s two deciles below ours. Meanwhile, we rank in the top quartile for household income in our city, and yet the value of our single-family home is below the city median. All but one of the cars we’ve ever owned, including the two we bought in the past year, were purchased preowned. We use them for as long as they're safe and comfortable to drive. We are frugal. But we are affluent, too, in the sense that money has never constrained us from having and doing the things we care about. We vacation a lot, often abroad and never on a shoestring. Each of us freely pursues our interests, despite some being somewhat expensive. My lovely wife has a fascination with luxury German-built sport sedans and SUVs, while I’m a minivan person. We own one of each. We have both been able to take long, unpaid time off from work to care for our ailing parents, without worrying about the financial impact. We strive to be generous with those we care about. Most important, we earned our financial independence a few years ago, so my wife and I now have the freedom to retire early or scale back our work. This is what our frugality has bought us. While frugality is a struggle for many, it came naturally to me. Growing up in a middle class, single-earner family, the good habits of budgeting and responsible spending were ingrained in me. After I finished my education and started living on my own, I religiously followed the “save first” mantra and fought every urge to be extravagant. While my self-discipline was great for my financial future, it also led to occasional feelings of being deprived. I was frugal, but I didn’t yet feel affluent. To prepare for new management responsibilities at work, I was compelled to learn new skills and get broader exposure to business problems. Three key insights from this training came in handy for my personal life. First, the 80/20 rule helped me to relax my self-imposed tight spending rules. I discovered that by increasing my spending just a little, I was able to boost my satisfaction with life significantly. The feeling of deprivation was gone. Second, the “do more with less” paradigm helped me to focus on my family’s top priorities. I identified our most important financial goals and channeled most of our money there. Third, the KISS—keep it simple, stupid—philosophy helped me unclutter our finances and put our money management on autopilot. All these lessons transformed me from being overly cautious about spending to a more balanced lifestyle. Today, we are affluent because we are frugal. Like that idea? Try benchmarking your income and expenses using survey data. If your annual expenses are the same or higher than your income group, the chances are you can reduce your spending without any perceptible impact on your lifestyle. Track your expenses, ruthlessly reducing or eliminating spending that has little meaningful value. This will help you spend more on things you find truly rewarding. It doesn’t take a supersized income, financial windfalls, unsustainable self-deprivation, extraordinary luck or investment genius to become affluent. Even if you have none of these, but you have frugality, financial success is all but inevitable. A software engineer by profession, Sanjib Saha is transitioning to early retirement. His previous article was Cost of Living. Self-taught in investment and financial planning, Sanjib is passionate about raising financial literacy and enjoys helping others with their finances. Earlier this year, he passed the Series 65 licensing exam as a non-industry candidate.  [xyz-ihs snippet="Donate"]
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Marginal Benefit

I'M A BIT EMBARRASSED to admit that, until I started toying with the idea of early retirement a few years ago, I was pretty ignorant about how Social Security worked. I didn’t even pay much attention to the FICA payroll taxes that were deducted from my paycheck. As I looked into it some more, the prospect of receiving lifelong monthly checks from the government came as a pleasant surprise. I started researching how much I might get. I learned that my retirement benefit depended primarily on two factors. First, the system would calculate a monthly benefit—called my primary insurance amount—based on my taxed Social Security earnings. The second factor would be when I decided to start benefits. I could claim Social Security as early as age 62, and take a permanent haircut on my benefits, or wait until as late as 70 to juice up my monthly payments. Based on my birth year, the system designated 67 as my normal retirement age. That’s when I would get 100% of my primary insurance amount—the benefit I’d earned by paying Social Security taxes. I was still unclear, though, exactly how my benefit would be calculated and whether early retirement might affect it. Should I plan to work longer to boost my monthly benefit? How much longer? Would my benefit grow substantially because of those extra years of toil? I’d already paid the maximum Social Security payroll taxes for 15 years, thanks to the steady paychecks from my software engineering job. In my naïve thinking, if 15 years of payroll taxes got my primary insurance amount to, say, $1,500 a month, then each additional working year would proportionately increase the monthly amount by another $100 or so. As with most things, the answer turned out to be more nuanced. To illustrate, imagine a hypothetical worker named Fred who was born in 1960 and started his career at age 22. Throughout his working years, he earned enough to contribute the maximum annual Social Security tax. The accompanying chart shows Fred’s monthly primary insurance amounts if he stopped working at different ages. Notice that Fred gets nothing if he stops working before turning 32. That’s because it takes 10 years, or 40 quarters, of payroll tax contributions to be eligible for Social Security benefits. Also note the diminishing effect of Fred’s contributions on his benefits during the second half of his career. His benefit’s growth decelerates in his early 40s, and almost stops after age 57, even though he works five more years. Why are Fred’s later contributions less valuable—or outright ineffective—compared to those earlier in his career? The devil is in the details of the timing and amounts of Fred’s Social Security contributions. Fred’s annual contributions are indexed, or adjusted, to factor in wage growth over his working life. These indexed earnings are then combined over 35 years to calculate Fred’s average indexed monthly earnings. Think of this as Fred’s Social Security earnings averaged over 420 months, or 35 years of work. What if Fred worked fewer than 35 years? His earnings would still be averaged over 35 years, but with zeroes for the idle years when no taxes were paid. And if Fred worked for, say, 40 years, his lowest-paid five years would be dropped from the equation. This explains why Fred’s benefit barely budges after 57. If he keeps working, he’d be replacing lower-earning years with higher-earning years—but he’s credited with 35 years of work in either case. The difference between the two rates of pay isn’t significant enough to bump up his benefit much, particularly after the lower-earning years have been indexed for wage inflation. [xyz-ihs snippet="Mobile-Subscribe"] Once Social Security computes Fred’s average indexed monthly earnings, it then plugs that number into a three bracket system to calculate his benefit payment. In the first bracket, each dollar of his credited monthly earnings adds 90 cents to his benefit, up to $1,115. The second bracket adds 32 cents for each dollar of credited earnings between $1,115 and $6,721. The third bracket adds 15 cents for each dollar of credited earnings over $6,721. The idea behind these brackets is to favor the folks who’d probably need the benefits the most due to their lower lifetime income. For example, if Fred had a much lower-paying job, his benefits would be lower—but it would represent a much higher percentage of his working years’ wages. In my case, starting my benefits at my full retirement age of 67 would provide me with 100% of the primary insurance amount to which I’m entitled. I’d receive a monthly payment for the rest of my life, which could be passed along to my wife if she survives me, plus it’s increased annually to keep up with the cost of living. As sweet as all this sounds, 67 is not the age when I plan to claim. Waiting for my maximum benefit at age 70 seems like the wiser choice. My benefit would increase by 8% each year I delay claiming, plus annual cost-of-living adjustments will be added on top of that. I won’t be working until I’m 70, though. Like Fred, working longer would increase my benefits only marginally—certainly not the $100-a-month boost that I’d imagined. Grinding beyond a few more years for the sake of a minimally higher Social Security payout doesn’t seem appetizing. Waiting a little longer to claim, though, does seem palatable given the big gain in benefits that would result. Want to know where you stand? You can get an estimate of your benefits from Social Security’s online calculator. Sanjib Saha is a software engineer by profession, but he's now transitioning to early retirement. Self-taught in investments, he passed the Series 65 licensing exam as a non-industry candidate. Sanjib is passionate about raising financial literacy and enjoys helping others with their finances. Check out his earlier articles. [xyz-ihs snippet="Donate"]
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The Poor Millionaire

HOW WE SPEND DEPENDS on how we feel about money. To be sure, we’re supposed to spend according to our financial situation and needs. But life experiences can so badly distort our attitude toward money that our financial decisions end up being ruled by fear and insecurity rather than questions of affordability. Such is the case with an acquaintance—let’s call her Satee—whose money habits are at odds with her financial standing. Satee grew up in a typical Indian family of four. Her working dad was the family’s primary breadwinner and financial decision-maker. Her homemaker mom put most of her energy into raising their two kids and taking care of the house. In their family, the financial and nonfinancial responsibilities were clearly divided between husband and wife. When Satee got married, she envisioned becoming a homemaker instead of a moneymaker. She wanted to be a supportive wife, a loving mother and a responsible daughter. Handling money was neither appealing to her nor on her list of responsibilities. Satee’s husband was professionally successful and financially savvy. They moved to the U.S. and had two children. They bought a house, saved for retirement and set aside money for the kids’ education. Everything was falling into place, just as Satee had hoped, except for one problem: Relationship and trust issues soured their marriage. Long story short, Satee went through a messy and conflict-ridden divorce that dragged on for months and turned her world upside down. A property settlement was eventually reached, but the bitter memories and fear of uncertainty remained. Satee took a while to accept her new role as head of a household with two school-age children. To get through the rough patch, she turned to the local community for emotional support. She met my wife through a mutual friend and quickly formed a bond with her. A few years later, she connected with my wife again. This time, she seemed happy and settled. She had some money questions and my wife asked me to help. Satee and I chatted a few times, going over some financial basics. She was keen to learn more. Satee focused a lot on ad hoc, short-term money decisions. She had no clear long-term financial picture. Instead, she was consumed with keeping a tight lid on her spending. Her modest lifestyle left no room for indulgences or even small niceties. I couldn’t tell if the scrimping and excessive penny-pinching were out of necessity or insecurity. Her financial situation didn’t seem so dire. She owned a paid-off single-family house in a good neighborhood, had a decent job with a six-figure salary, and the kids had fully funded education accounts. On my insistence, Satee figured out her actual annual expenses for the past few years. It took her a lot of time to come up with the numbers—not because she was unwilling or shirking, but because her finances were overly complicated with multiple accounts. It was no wonder she lacked a clear picture of where she stood financially. With some help and handholding, Satee finally managed to get the numbers. Her actual spending in each of the past three years turned out to be far smaller than the number she’d fabricated in her head. I wasn’t too surprised. She behaved financially as if she was in poverty, and I knew that wasn’t the case. [xyz-ihs snippet="Mobile-Subscribe"] Evidently, Satee was underspending and over-saving. The next question I asked: Did she need to save so much? To answer that, she needed to take stock of all her financial assets. Once again, this simple step took longer than it would for most people. As with her spending accounts, Satee had too many financial accounts, including savings accounts with several local banks and credit unions, high-yield money-market accounts and certificates of deposits with various online banks, a couple of brokerage accounts, retirement accounts from current and past employers, and so on. Once she located all her financial accounts and reestablished online access, she gave me a call. I asked Satee to go through each account and enter the balance on a spreadsheet—a step she’d never done before. I then asked her to add the numbers up. At first, Satee didn’t believe the result. Per the spreadsheet, she was already a millionaire in her early 40s, without including her home equity, kids’ education funds and other assets. She double-checked each account. She was hoping to get a different answer, but the numbers didn’t lie. It was clear she didn’t need to save so aggressively. Will the revelation change anything? Will Satee allow herself and her family occasional splurges? Or will she continue to let money rule her life and continue to get worked up about every unexpected expense, no matter how small? I certainly hope Satee strikes a better balance between spending and saving, but I wouldn’t bet money on it. Her profound financial insecurity took root during the years of emotional turmoil and uncertainty that followed her marriage’s collapse. It will likely take more than a household balance sheet to overcome her fear of spending. Sanjib Saha is a software engineer by profession, but he's now transitioning to early retirement. Self-taught in investments, he passed the Series 65 licensing exam as a non-industry candidate. Sanjib is passionate about raising financial literacy and enjoys helping others with their finances. Check out his earlier articles. [xyz-ihs snippet="Donate"]
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Six Seasons

AS A CHILD GROWING up in India, I was taught about the six seasons of Bengal: summer, monsoons, autumn, late autumn, winter and spring. From my recollection, some seasons felt distinct, while others were subtle and transitory. Still, each season had unique characteristics, making it different from the others. A HumbleDollar Voices question—if you could live your financial life again, what would you do differently?—reminded me of the six seasons. How so? Our financial life can also pass through as many as six seasons. I started my financial life with the idea that there were only two seasons: working years and retirement. If I’d recognized the six seasons beforehand and acted accordingly, I could’ve done much better with my most valuable asset—time. What are the six seasons of our financial life? 1. Summer: Financial learning. Bengali New Year starts with summer, arguably the most unpleasant season. Yet the hope of a new beginning overshadows the discomfort from heat and humidity. Similarly, we often start our adult financial life with an occasional stumble and fall. But the thrill of independence trumps any hardships. This is a period to make financial mistakes and learn from them. To explore and settle on a career path. To find a partner and plan a family. The shorter this season, the better. Those who manage to jumpstart their wealth building—saving for housing and retirement—have better odds of enjoying the seasons that follow. 2. Monsoons: Full-throttle saving. The rainy season in Bengal is disruptive. Growing up, I used to hate getting stranded at home because of heavy rain or waterlogging. Instead of playing outside or being with my friends, I had to study or do chores. On the bright side, the extra focus on studies lightened the academic pressure for the rest of the year. The second season in our financial life comes almost as abruptly. We focus mostly on career advancement and earning money, rather than recreation and personal enjoyment. Overwhelming financial responsibilities—for family and housing—force us to reduce waste and streamline spending. Our savings rate rises sharply. 3. Autumn: Slower accumulation. The autumn is highlighted by the festival of Durga Puja, the most enjoyable time of the year for most Bengalis. People slow down to soak up the celebratory mood. [xyz-ihs snippet="Mobile-Subscribe"] The third season in financial life feels the same way. A lifestyle of all work and no play seems unappealing. Our focus tilts away from the career rat race and toward family and other priorities. It isn’t uncommon to scale back career aspirations and make more time for children, or to give up a job altogether to care for an elderly family member. We still earn enough to save a bit toward future financial goals. But we also make a conscious choice to value life outside of work, even when it means less income. 4. Late Autumn: Financial security. Depending on how the prior seasons have turned out, there’s a good chance we can dial back work even further and earn just enough for ongoing living expenses. When can we do this? First, near-term financial needs, such as college education for the kids, must be funded by now. Second, enough must already be saved toward our future financial goals for compounding to take care of the rest. For instance, retirement accounts must have a reasonable balance and enough time to grow before they are tapped. To be clear, we’d still be financially dependent on our jobs during this season, even if we don’t especially like our work. Though we don’t care much about saving anymore, we still need a minimum income to pay the bills. Getting to this stage is when we begin to feel financially secure. How? We know that we have enough for the future, and thus we can choose to spend more time on personal and family interests. 5. Winter: Financial independence. My childhood friends and I used to look forward to the winter months. It was not only the time for school holidays, but also for the seasonal savors. Similarly, we all look forward to financial independence. We may not be wealthy, but we’ve met our financial obligations to others and ourselves. Debts are either paid off or accounted for. Our nest egg is larger and we no longer fear tapping it. We can now choose either to stop working or to work only for enjoyment and supplemental income. From now on, our time is ours. 6. Spring: Conventional retirement. The king of seasons is aptly called the golden age of financial life. Withdrawals from our nest egg may fall as we become eligible for Social Security, Medicare and any other retirement benefits. On the flip side, this final season involves some unique uncertainties. There’s longevity risk, unexpected health issues, and the possible loss of a partner and dependence on others. Still, it’s the season to reflect and be thankful for life’s diverse experiences. Sanjib Saha is a software engineer by profession, but he's now transitioning to early retirement. Self-taught in investments, he passed the Series 65 licensing exam as a non-industry candidate. Sanjib is passionate about raising financial literacy and enjoys helping others with their finances. Check out his earlier articles. [xyz-ihs snippet="Donate"]
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Money Misconceptions

AS I'VE TRIED TO HELP folks understand financial issues, I’ve come across numerous money misconceptions. I wasn’t surprised—because, before I learned better, I too misunderstood some of these issues. Here are the top eight misconceptions I’ve encountered: Misconception No. 8: Consumer prices drop when inflation falls. Inflation measures the pace of price increases. Declining inflation simply means that prices aren’t rising as fast, but they’re still going up, albeit at a slower rate. Furthermore, the effect of inflation remains, with prices stuck at higher levels. Inflation is calculated based on price fluctuations for a variety of goods and services. While specific items might slip in price, a positive inflation number—even if it’s smaller than before—still signifies an overall upward trend in prices, rather than a reversal to lower costs. Misconception No. 7: Investing requires professional help. Investing can seem intimidating to beginners, leading many to conclude that professional guidance is the only way to go. But technological advances and a wealth of free educational resources, including HumbleDollar’s money guide, have transformed the landscape. Unlike years ago, today’s investors have access to user-friendly investment platforms and simple, evidence-based strategies like target-date funds and index funds, eliminating the need to rely on professional money managers and stock brokers. Indeed, arguably, investing has become as straightforward as everyday tasks like grocery shopping. Moreover, after learning the basics and gaining confidence, managing investments—especially low-cost diversified investment products—requires surprisingly little time and effort, and there’s no need for extensive knowledge of the financial markets or the economy. There’s nothing wrong with using an advisory service when the cost is reasonable and conflicts of interest are minimized. But doing so is no longer the only way to achieve your investment goals. Misconception No. 6: Buying a home is always financially better than renting. Homeownership carries numerous benefits—emotional fulfillment, lifestyle upgrade, and a sense of stability and belonging. It still symbolizes the American dream. Buying a house for these reasons is fine, assuming it’s affordable. But whether it’s a better financial decision than renting is another story. The cost of homeownership goes well beyond mortgage payments. You need to account for things like property taxes, homeowner’s insurance, regular upkeep, periodic renovations to maintain a home’s market value, and the opportunity cost of the tied-up home equity. All this money could potentially earn higher returns if it was invested elsewhere. To figure out whether buying a specific property at its current price makes sense, you need to do an objective analysis, devoid of social pressure and realtors’ marketing tactics. Misconception No. 5: Social Security won’t be there when we need it. While the Social Security system faces financial challenges, it’s grossly misleading to suggest that the system is insolvent and that benefits could disappear. Projections indicate that the system’s financial deficit would potentially impact less than a quarter of scheduled benefits. Social Security remains the financial cornerstone for millions of American retirees, with most of the funding coming from the payroll taxes paid by current workers. There’s a trust fund to cover the system’s funding shortfall and, without any changes to the system, the fund could be empty in roughly a decade. Even so, the current system would still be able to pay three-quarters of scheduled benefits. Multiple proposals exist to improve the long-term sustainability of Social Security and avoid benefit cuts. Given Social Security’s pivotal role for citizens, failing to fix the system’s finances is almost inconceivable. Misconception No. 4: Estate planning is for the wealthy. Estate planning encompasses a host of possible steps, many geared toward the wealthy, like creating complicated trusts, sidestepping probate and minimizing estate taxes. But contrary to common belief, there are some estate-planning steps that should be taken by everybody. An estate plan addresses how we want medical, financial and legal decisions handled if we become ill or incapacitated and can’t make those decisions ourselves. A will safeguards our family, designating guardians for minors and outlining how we want our wealth distributed. Naming beneficiaries for financial assets—bank accounts, retirement accounts, life insurance and so on—streamlines the transfer of our assets after our death. Such basic estate-planning steps are essential for every adult. Misconception No. 3: Everyone needs life insurance. Insurance—property, health, disability, life and so on—is crucial for limiting the risks in our financial life. But not everyone needs every type of insurance. Sometimes, the cost would be a waste of money because the financial risk involved isn’t significant. For instance, term-life insurance is vital for those without substantial savings who have folks who depend on their income-earning ability. But if your death wouldn’t cause financial hardship to anyone, life insurance becomes an expensive product with minimal benefits. Misconception No. 2: To save for college, it’s essential to fund 529 plans. Faced with steep college costs, parents often prioritize saving for their children’s education. But while 529 plans offer tax-free growth and many have reasonable investment costs, these plans also come with significant drawbacks. If the money isn’t used for education purposes, parents could face steep tax bills, including tax penalties. That’s why parents might want to consider other strategies that offer greater flexibility, such as stashing college savings in a regular taxable account or funding a Roth IRA, where contributions can be withdrawn at any time for any reason. Misconception No. 1: A higher income guarantees faster financial independence. Sure, a big paycheck makes it easier to save. But in the end, what matters is your savings rate as a percentage of your income, rather than the size of your paycheck. In other words, a modest earner could potentially achieve financial freedom faster than a high-income individual with undisciplined spending and savings habits. Moreover, high living costs mean you need a proportionately larger nest egg to sustain that lifestyle in retirement, making financial freedom even harder to achieve. By contrast, modest earners—who save a significant portion of their income and live well within their means—will need a much smaller nest egg to be financially independent. For instance, assuming historical stock market returns, it might take 36 years to achieve financial independence if you save 15% of your income. But if you save 25%, that cuts this timeline to 26 years, while a super-saver with a 35% savings rate might get there in as little as 20 years. These projections don’t hinge on your annual income. Rather, they depend on your investment returns—and your willingness to save. Sanjib Saha is a software engineer by profession, but he's now transitioning to early retirement. Self-taught in investments, he passed the Series 65 licensing exam as a non-industry candidate. Sanjib is passionate about raising financial literacy and enjoys helping others with their finances. Check out his earlier articles. [xyz-ihs snippet="Donate"]
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