Many folks lead lives of turmoil and pain and yet, ever resilient, they get up the next morning and go to work.
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. NO. 31: WE SHOULD plan for returns below the historical averages. Today’s rich stock valuations and modest bond yields don’t guarantee low returns—but it’s prudent to assume that’s what we’ll get.
TRACKING ERROR. Even if our portfolio makes money in any given year, we may be disappointed if our results lag behind the market averages. Indeed, the less diversified we are, the less our portfolio’s performance will look like the market indexes—for better or worse. Want to reduce this tracking error? Favor funds that offer broad diversification.
NO. 31: WE'RE OFTEN overly optimistic. Entrepreneurs will be bullish about their own prospects, even as they doubt the chances of others in the same business. Investors will declare great hope for their investments, and yet express grave concerns about the market in general. Optimists may be more likable—but pessimists often have a better grip on reality.
NO. 24: MANY financial mistakes can be traced to instincts we inherited from our hunter-gatherer ancestors, who survived because they worked hard, hunted for patterns, consumed whenever they could and greatly feared losses. Today, these instincts can lead us to trade too much, try to beat the market, overspend and panic during market declines.
NO. 31: WE SHOULD plan for returns below the historical averages. Today’s rich stock valuations and modest bond yields don’t guarantee low returns—but it’s prudent to assume that’s what we’ll get.
“Hi, I’m Chris”. That’s how it all began in early 2002. My friend Dave and I were hanging out of a hole in the wall of my duplex, installing a new window. Chris was the good looking neighbor girl. She thought Dave and I were a couple, he was actually my best bud, living with me and providing his carpenter skills in lieu of rent during some hard times.
By the end of the year I and Chris were a couple,
I am a Baptist pastor. Significant moment #1. One day I was in a leadership meeting and a fellow pastor commented that he had just met with his financial advisor and was told he would have to work to age 81 to retire. I didn’t laugh. I was his age and had just lost 40% of my retirement from the economic downturn that began in October, 2007. After that meeting I did some serious soul searching and decided I would become a student of understanding “money”
AT 75 YEARS OLD, I find myself living paycheck-to-paycheck. I now understand how that feels and how it can happen. But you can put away the violin: It’s only temporary.
Being fiscally conservative, I don’t like being in debt or having unpaid bills. I even pay credit cards before they are due—or I used to. Until a month ago, I paid all my bills, with considerable money left over at the end of each month.
Looking up at the ceiling recovering from major surgery has this 70+ boomer rethinking life. Everyone on here has an intense interest in personal finance. Most of us are boomers. Our parents were the Greatest Generation who lived the Depression and fought the war then shared their stories of sacrifice. We’ve read the Wall Street Journal, especially when Jonathan was there, financial papers, magazines and websites galore. My guess is that our playbook is pretty much the same: get an education,
SELLING A HOUSE should be easy. Hire a realtor, find a buyer, the realtor takes a percentage and it’s a done deal. If only.
Try this version instead. Before we could sell our house in 2020, we had to fix a list of defects, including power washing the roof, having a dead tree removed, digging up an already drained oil tank and tearing up the pavers in the driveway to get at the tank.
WHEN WE MOVED to California from India in spring 2014, it was a culture shock—and not just because of the much higher standard of living. Financial life in the U.S. is very different. Here are just some of the surprises that my husband and I have encountered over the past seven years:
Health care. I remember walking into my first U.S. doctor’s appointment. I froze—unaware that I had to pay a $50 copay for each visit,
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- Standard deduction
For single taxpayers, the standard deduction rises to $16,100 for 2026, an increase of $350 from 2025. For married couples filing jointly, the standard deduction rises to $32,200, an increase of $700 from tax year 2025.- Capital Gains Rates
For single taxpayers, long-term capital gains are taxed at 0% if the taxable income is up to $49,450 ($98,900 for married couples filing jointly). Note: Brackets are based on taxable income, not gross. Tax planning with capital gains Using the 0% long-term capital gains rate can be a good way to minimize your tax bill and retire early. For an investment to qualify as long-term, you must hold it for more than a year. For example, say Bob is single, did fairly well financially in his early years, and decided to retire at 50. He paid off his home and needs $65,000 per year to live on. He sells $65,000 worth of Vanguard ETFs (say $5,000 was the basis he originally bought it for). Here’s how his tax return would look: $60,000 of long-term capital gains ($5,000 is the cost basis for his original investment) -$16,100 standard deduction = $43,900 taxable income Since the taxable income is below $49,450, all of this income will be taxed at 0% on the federal level (assuming no other income sources). Using the 0% tax rate on capital gains could be a great strategy to sustain your early retirement until age 59 ½. Additionally, these brackets are adjusted for inflation each year, so if you need $62,000 due to inflation next year, it will likely match the new brackets. Importantly, the $16,100 standard deduction amount (or $32,200 if married filing jointly) can come from any income source. In most cases, it’s actually better to utilize something like an IRA withdrawal or pre-tax 401k to “fill” that income. For example, Bob could use a Section 72(t), series of substantially equal periodic payments, to withdraw $16,100 from his IRA without a 10% penalty. Then, he can withdraw less from a brokerage account to fill the remaining income. However, by using a 72(t) plan, Bob will need to continue withdrawing this amount until age 59. Note that tax law could change the numbers. While the OBBBA just made the standard permanent, another law could change that. Also, capital gains tax brackets could technically change too. Additional opportunities to lower tax A good friend of mine is going back to school to get his MBA. He did very well financially, so he will live off savings with no income. This is a perfect opportunity for him to sell stocks in his brokerage account, pay $0 in federal taxes, and immediately buy back the exact same stocks. Why? Say he bought 100 shares of VTI 10 years ago for $100 per share. Total cost basis is $10,000. Now, it’s worth $335 per share. If he sells 100 VTI shares, he will have ($335 - $100) * 100 = $25,500 in capital gains. Now, my friend will pay $0 in federal taxes on these gains and will buy back those same VTI shares for $335 per share. What this allows him to do is increase the cost basis on those shares from $100 per share to $335 per share, so the next time he sells, his cost basis is much higher (lower capital gains). Note: there is no wash sale on a gain. It only applies to a loss. This only works if you qualify for the 0% long-term capital gains rate on that initial sale. So, any time you have a low-income year or take extended time off from work, it could be a good time to analyze your portfolio. Additionally, he can also use Roth conversions instead, but amounts will be smaller if he wants to stay in the 0% tax bracket. Additional consideration: 1. State Tax It’s important to take state taxes into consideration. For example, that $25,500 of capital gains could cost $1,275 in state taxes (assuming a 5% tax rate). It’s generally not worth harvesting gains if state tax applies. This is because you may lose more by not being able to invest the state tax than you save by avoiding federal tax, especially if you plan it right in the long term. However, some states have no tax on capital gains. For example, Texas and Florida are among the states with no income tax (and no capital gains tax) 2. Increased Income Sometimes a higher income can reduce available itemized deductions (e.g. medical expense deductions are based on AGI) or impact other credits (e.g. the Retirement Savings Credit). It’s important to analyze the full impact based on your unique situation. Have you used the 0% long-term capital gains bracket to retire early? Share your thoughts in the comments!Distance from family: inconvenience…or a financial planning blind spot?
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