Dollar-cost averaging is for wimps. You’d be amazed how many rich wimps there are.
NO. 15: WE SHOULD retire our debts before we retire from our job. Paying off debt cuts our living expenses, plus that debt is likely costing us more than we’re earning on our bonds.
ADVERSE SELECTION. We are—unsurprisingly—more likely to buy insurance products that we think we’ll need. Those in ill-health often opt to buy trip-cancellation insurance. Those who think they’ll live to a ripe old age are more likely to buy lifetime income annuities. Insurers are aware of this adverse selection—and price their products accordingly.
WRITE IT DOWN. Want to spend less, drink less coffee or booze, eat less or exercise more? Keep a diary devoted to one or more of these things. For instance, if you write down every dollar you spend, you won’t just have a better idea of where your money goes. You’ll also be more conscious of when you’re spending—and that by itself will prompt you to cut back.
NO. 92: WE THINK of a mortgage as leveraging our home—but, in truth, it leverages our entire financial life. Imagine we have $300,000 in stocks, a $300,000 home and a $250,000 mortgage. If stocks drop 50%, our total assets fall 25%, from $600,000 to $450,000. But factor in the mortgage and our net worth drops 43%, from $350,000 to $200,000.
NO. 15: WE SHOULD retire our debts before we retire from our job. Paying off debt cuts our living expenses, plus that debt is likely costing us more than we’re earning on our bonds.
I TURNED AGE 64 over the Labor Day weekend. One of my goals for my 65th orbit of the sun is to really dig into Medicare.
Luckily, I have a few friends and relatives who have blazed the trail before me. I’ve also studied Medicare as part of some financial planning courses I took a few years ago. Still, one topic I’ve never researched in detail is Medicare’s income-related monthly adjustment amount, otherwise known as IRMAA.
IS IT JUST ME OR HAS dealing with health insurance companies become more confusing and frustrating? Trying to figure out who to speak to feels like that classic Abbott and Costello comedy routine, “Who’s on first?”
My wife retired last July. For the previous four years, we’d used her employer-provided medical benefits and now we needed to shop for coverage. Under my old employer’s pension plan, pension-eligible employees like me—who retired prior to beginning Medicare—were eligible to sign up for one of the company’s medical plans.
MY WIFE AND I JUST finished watching the Netflix documentary Live to 100, which I highly recommend. The four-part series focuses on Dan Buettner’s study of pockets of people around the world who achieve amazing longevity, including many residents who live to age 100 and beyond.
The seven longevity locations include Okinawa, Japan; Sardinia, Italy; Ikaria, Greece; Nicoya, Costa Rica; and Loma Linda, California. These locations of long-lived people have been labeled “blue zones” based on the seminal demographic work on Sardinia by Giovanni Mario Pes,
For us Medicare types, it’s that Part D time of year again. In mid-September I received an email from our Part D insurer, Aetna Silverscript, saying I could see the Annual Notice of Change online. I did so and got a shock. My wife’s and my monthly premiums were going from $9.80 each to $44.80 each beginning in January 2025.
I did a little reading online, and contacted our broker, and learned that due to some recent legislation Part D plans were in for some big changes in 2025.
One of the most well known advocates for elder care, who worked for a prominent national health center, was talking with me about a year ago. When I asked him what his plan was for he and his wife, as they aged, he replied “ I have four daughters”.
This was pretty shocking to me, given that he worked in this industry, and specialized in helping adult children and their parents to talk about future health care planning.
I QUIT MY JOB last year and then found I needed medical care. My old employer was required to offer me health insurance—but it was expensive. Luckily, I found a loophole that allowed me to obtain the coverage I wanted at a bargain price. I got the treatment I needed, and saved almost $1,000.
First, a bit of background. More than half of the U.S. adult population gets health insurance through their employer. Indeed,
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- 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!Plan for a Pay Cut
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