If we spend our days doing what we love and our evenings with those we love, we have a rich life—even if we aren’t rich.
NO. 19: WE SHOULD make future spending as exciting as possible, so we’re less tempted to spend today. That means visualizing our goals and imagining how great it’ll be to achieve them.
PLAN NEXT SUMMER’S vacation. By starting now, you’ll have a long stretch of eager anticipation—which may prove to be the best part of the vacation. Let your imagination roam, pondering lots of possible trips to numerous destinations. In the end, you might take just one summer vacation, but in your daydreams you can visit all kinds of places—at no cost.
PARADOX OF CHOICE. We like the idea of having more choice. Yet, if presented with too many options, we can become overwhelmed, leading to unhappiness and greater indecision. A classic example: When investors in 401(k) retirement plans are faced with a slew of investment options, they often become paralyzed and make no choice at all.
NO. 132: DIFFERENCES in investment costs are the biggest driver of differences in money manager performance. Take the mutual funds in any particular category, such as large-cap growth funds or short-term corporate bond funds. Over five years, a category’s best performers are typically those with the lowest annual expenses.
NO. 19: WE SHOULD make future spending as exciting as possible, so we’re less tempted to spend today. That means visualizing our goals and imagining how great it’ll be to achieve them.
As a compulsive list maker, I’m updating my list of finance-related
action items and analysis to do around year-end. Here are a few things on my list:
– Estimate taxes
– Consider year-end contributions
– Target income levels to maximize ACA credits
– Consider Roth conversions
– Assess prior year’s returns
– Analyze last year’s spending
– Project “safe spending” for the coming year
– Re-balance investments if needed
What’s on your list?
IT SEEMS THE WORST of this economic crisis may have passed, though the health risks will be with us for some time. What have we learned? For many people, long-discussed financial risks became all too real in 2020.
There are two words that should always be part of our thinking: what if. Those two words aren’t always associated with bad things. What if I win the lottery? I have a plan for that, which varies depending on how much I win and whether it triggers estate taxes.
IF YOU WANT TO SEE your fellow citizens at their least appealing, look no further than online discussion forums. All too often, they’re a repugnant cesspool of anger, bullying and boastfulness. The comments posted on HumbleDollar are typically fairly civil, though even they occasionally veer toward the unnecessary nastiness that’s rampant everywhere else.
But here’s what these virulent commenters miss: Their postings reveal far more about themselves than about the subject they’re opining upon.
SOCIAL SECURITY HAS come under political attack over the years. With the federal deficit ballooning, will there be another round of attacks in the run-up to 2020’s election?
I hope not. Here are 15 reasons we should all want to preserve Social Security benefits, no matter which political party we favor:
It helps many. About 63 million people get a Social Security check each month. That’s one out of six Americans.
It provides insurance.
THIS IS MY 150TH article for HumbleDollar. My first appeared on Aug. 12, 2019. I’m not sure when I became aware of the site, but it’s become an important part of my life. I’ve truly enjoyed the writing, along with reading the work of others and interacting with the editor, other contributors and readers.
For my 150th, I thought about looking back over the past five years and compiling a list of 150 observations.
BAD INVESTMENT AND personal finance books get cranked out every year with catchy titles and celebrity authors. But skip such pulp fiction. Instead, give yourself or someone you know the gift of timeless investment wisdom with one—or all—of the following classics.
Why? Perhaps you’ve heard that indexing is the way to go. Or that you should insist on low-cost funds. Or that stocks are the best asset class, and should be bought and held.
Hitting the Pause Button
Mark Crothers | Dec 31, 2025
Real vs. Imaginary Returns – Part I
Langston Holland | Dec 31, 2025
What Age Did You Retire—and What Made You Decide It Was Time?
Jeff Peck | Dec 27, 2025
Who cares if Social Security benefits are cut?
R Quinn | Dec 27, 2025
Lump sum Vs Monthly Payment – Which pension option is better?
smr1082 | Jun 21, 2024
Enough with IRMAA complaining
R Quinn | Dec 29, 2025
Seeking the Wisdom of the Ages
quan nguyen | Dec 31, 2025
AI or Black Eye: Choose Your Weapons Steve Abramowitz
steve abramowitz | Dec 30, 2025
If You Could Rewind 5 Years Before Retirement… What Would You Change?
Jeff Peck | Dec 27, 2025
Filing Status and IRMMA
DAN SMITH | Dec 28, 2025
Well: That’s Just Inconvenient!
Mark Crothers | Dec 29, 2025
Tax Loss Harvesting
Bogdan Sheremeta | Dec 27, 2025
- VTI holds 3,000+ stocks vs. 505 of VOO
- They track different indexes (VTI tracks the US Market Index vs. VOO tracking the S&P 500)
He believes that while their performance is similar, it's not substantially identical. Of course, if the IRS audited John, they could argue that John lacked an economic move that had risk, since the transaction could not be primarily motivated by tax rules. To which John could technically answer, "I decided to rebalance into VTI to gain exposure to small market cap companies." Some CPAs make arguments that if two funds have 70% or less overlap, they aren't substantially identical. Others argue that as long as it's 90% or less, it's not substantially identical. While I'm not your CPA and can't advise you on the specifics of your case, here are some facts I do believe:- Two stocks of two different companies are not considered substantially identical
- In terms of funds, if they track an identical index (e.g., S&P 500), even though they are different companies managing the funds (e.g. VOO, Vanguard’s S&P 500 fund, vs. SPY, State Street's S&P 500 fund), I believe an argument could be made that they are substantially identical, even though some robo-advisor companies may disagree
Benefits The best time to engage in tax-loss harvesting is when your tax rate is the highest. For example, if your marginal tax rate is 37%, you would essentially save 37% on taxes for every $1 of loss (up to $3,000) on the federal side. There could be savings on the state side too. In our example, John's move saved him $1,500 * 37%, or around $550 on federal taxes. Another benefit related to tax-loss harvesting is the opportunity cost. When you save money on taxes and invest that savings instead of spending it (or paying it), that money can start earning returns too. Over time, your tax savings can earn more returns. So $550 of tax savings now could grow into a substantial amount over time. Note that the tax-loss harvesting strategy "resets" the cost basis. So if you sell VOO at $534 per share after originally buying it at $634 per share, the next ETF or stock you purchase will have a cost basis that is $100 lower. This could result in higher capital gains later on when you sell the "re-purchased" stock or ETF. However, generally, it can be managed if:- You pass down the brokerage account to your children. They will inherit the account, receive a step-up in basis, and eliminate any capital gains.
- You sell during retirement when you ideally would have a lower income and can harvest these gains at a 0% long-term capital gains bracket (~$48k of taxable income for single filers, or ~$96k for married filing jointly).
Rules Practically, you also need to understand your method, account, and timing when executing tax-loss harvesting. 1. Cost basis method Before you sell, you need to understand your cost basis method. The options include FIFO (First In, First Out), LIFO (Last In, First Out), and specific identification. This is especially important if you’ve been buying the same stock for many years and want to sell only the most recently purchased shares. The best cost basis method for tax-loss harvesting purposes is specific identification, as it allows you to select exactly which shares you want to sell. 2. Account & timing It will be considered a wash sale if you buy any shares of the same ETF in a taxable account or IRA within the 30 days before or after the sale. You can always repurchase the exact same ETF on the 31st day, even if it's substantially identical, because the wash sale rule wouldn't apply after that period. You cannot buy the same fund you sold in any of your accounts. For example, you cannot sell VOO in your taxable account and then buy VOO in your IRA the next day; otherwise, the loss will also be subject to a wash sale. A good way to avoid this is to buy different funds across your accounts so there is no risk of triggering the rule. This also applies across different brokers you might have (e.g. Vanguard, Fidelity). 3. Dividend reinvesting Lastly, it's generally recommended to turn off automatic dividend reinvestment. Dividend reinvestment will trigger a purchase of the fund, and the newly purchased shares will be subject to the wash sale rule unless you sell them as well. Another thing to mention about this topic is that cryptocurrencies are not part of the "wash sale" rules since they are not securities, and the IRS treats cryptocurrency as property. This means that you can sell at a loss and rebuy coins without impacting your wash sale rules, if that fits into your overall asset allocation strategy. Have you done any tax loss harvesting? Let me know in the comments!