Don’t miss an episode of our podcast, Personal Finance for Long-Term Investors. Available on all podcast players. Here’s the latest episode: Podcast listener Wes wrote to me: Jesse – I appreciate the great podcast and blog content that goes beyond personal finance 101. I have a question about generating investment losses to offset appreciated assets and/or the income from a Roth conversion. My advisor has been talking about a long/short strategy that I’m researching. However, I was thinking I could either short a stock I think that will go up (risky) or simply buy a leveraged ETF (less risky) that is say the inverse of the S&P500 like SSO. Seems like a simple strategy but I don’t see much content out there about this so I’m guessing I’m missing some pitfalls. Can you give me some input? Hi Wes, thanks for the question. Very interesting. Now…I’d like to paint a little picture for you. You have $10,000 in gains, all of which will be subject to a 15% capital gains tax. So, you’d owe $1500 in tax. You then pursue a strategy that creates $10,000 in losses. This offsets the ENTIRE gain and ELIMINATES the tax. Ok – nice! So, you eliminated that $1500 tax. BUT… You also have $10,000 in losses. You no longer actually profited. The losses totally offset and wipe out your gains. Would you rather have $10,000 in gains and pay $1,500 in taxes? Or have no gains whatsoever? I’d take the first scenario every day. Why lose $10,000 to save $1,500? Now, I’ve painted a very, very simple scenario. Most of the strategies that professionals might use will *attempt* to be more nuanced and complex than this. What they hope to do is create some losses and some gains. The losses will be realized. The gains will be unrealized. Your realized losses can be used to lower this year’s tax bill. And those new, unrealized gains? We kick them down the road to a future tax year. We don’t have to pay taxes on unrealized gains (yet). The question becomes…will we ever have to pay taxes on unrealized gains? I hope you see that you can never “outrun” this tax problem EXCEPT by dying. When you die, your taxable estate goes to your heirs at a stepped-up basis, wiping out the capital gains. Is “Death” Considered a Big Win?! This brings about a funny little pattern in financial planning circles where we have to balance two competing ideas: The first idea is that everyone will die someday. We MUST treat death as a reality. But the second idea is that we need to be a little cautious about treating death as a “win” and living as a “loss.” This scenario is one example. Sweet! You die with unrealized capital gains, and your heirs get a big win!! It’s true. You’re still dead, though. And you didn’t get to spend your money. Another example: you claimed Social Security at 62,

Temporary Lodging Allowance (TLA) is an allowance to offset the cost of staying in temporary lodging when moving to and from an overseas. This is the allowance you get on the overseas side of the move. (You get TLE on the CONUS side of the move.) When a military person or family is executing Permanent… | Read More… The post Everything About Temporary Lodging Allowance (TLA) appeared first on KateHorrell.

Welcome to “Thank God I’m FI” Friday, Volume #172 Here are some things I really like and that you might too! **Note To My Readers – I sometimes get complaints about ads on my blog (too many). I’m kind of… The post T.G.I.F. Friday: Volume 172 appeared first on Accidental Fire.

Harry Styles concert not as described This week saw the start of the Harry Styles Together, Together tour. After the first two shows at Amsterdam’s Johan Cruijff Arena over the weekend (May 16–17), clips on social media showed some concertgoers struggling to see the performance due to a large production set-up, prompting a lot of criticism across social media about the tour’s staging design. The Jeremy Vine Show on BBC Radio 2 invited me to […]

The Roth IRA is 28 years old as of 2026 (its birthday was January 1st). Yet there is still confusion about the rules applicable whenever someone withdraws money from a Roth IRA prior to turning 59 ½. This blog post attempts to correct some misconceptions on the taxation of nonqualified Roth IRA withdrawals. Roth IRA […]

I’ve gone pretty quiet on the Darwinian Doctor blog for most of 2025, although life behind the scenes has been anything but quiet. Between locum tenens work, Cereus Real Estate,… The post Behind the Scenes: Why I Went Quiet in 2025 appeared first on The Darwinian Doctor.

Wondering, “What should my asset allocation be?” The 2025 market performance data can inform sensible asset allocation ETF portfolios. Key Points: The Recency Bias Trap: It’s easy to chase the latest high-performing assets, but recent winners rarely remain at the top indefinitely. The Power of Reversals: After years of underperforming US markets, developed international stocks (VEA) surged by 35.2% in 2025—proving why you shouldn’t drop an asset class just because it had a few quiet years. Consistency in Bonds: While 3-year bond returns hover at 4.3% annualized , they nearly doubled to 7.1% last year, underscoring their role in stabilizing a portfolio. The Low-Fee Solution: Because predicting year-to-year winners is nearly impossible, the most reliable way to maximize long-term returns is by building your core asset allocation around low-fee, total-market ETFs. This article may contain affiliate links which means that – at zero cost to you – I might earn a commission if you sign up or buy through the affiliate link. While it’s easy to get caught up in the year-to-year drama of the stock market, historical data proves that a steady hand beats a chasing strategy every time. Let’s look at the foundational principles of Asset Allocation 101 to see how this plays out in the real world. If you need help with your investments, we’ve partnered with WiserAdvisor to provide you with access to three vetted Financial Advisors – in your area. Click the image below to sign up. (no obligation when signing up) 10 Year Asset Class Returns Source: AAII.com Investing 101 Most investors understand that diversification can temper the volatility of your investment portfolio, smoothing out the losses, and gains. Yet, it can be difficult to diversify when you’re watching the best-performing stocks dominate the US investment market growth. Younger investors might be tempted to hop on the winners, and assume they have the recipe for investment success. And, in some cases, that can be true – but only for the shorter-term. But, for the rest of us, who lack perfect luck, stock and asset picking genius, and perfect timing, there’s another way to investment success. Similar to Ecclesiastes 3: “To every thing there is a season, and a time to every purpose under heaven…” every investment asset has its time to shine. Developed market international stocks returned 35.2% in 2025, tripling its 5-year average of 9.5% and delivering the highest return in 19 years. During the previous 3 to 5 years, international stocks were largely underperforming US Stocks (VTI was at 22.2% for the 3-year, while VEA was at 17.9%). This is the ultimate textbook example of why we don’t drop an asset class just because it had a few quiet years. If you avoided investing internationally due to recent moderate returns, you would have missed out on superior growth in 2025. If you need help with your investments, we’ve partnered with WiserAdvisor to provide you with access to three vetted Financial Advisors – in your area. Click the image

The US tax code was written by wealthy people for wealthy people. I’ve heard that many times. You probly have, too. I used to roll my eyes at the notion. Figgering that the person expressing it really just hated paying taxes and thought that wealthy people avoided taxes by using obscure tactics unknown to us riff raff. I later learned that those folks were right. . . . With the caveats that they probably did […]

Muse is less than a decade old as a comic book character but is one of the most popular and deadliest Daredevil villains. Image source: Amazon Comic book superheroes are defined by their villains. The motivations and actions of the villain can make the hero go to heroic or dark places to reach their goal. Sometimes the villain is so silly and goofy its hard for the hero to them them seriously. Daredevil villains usually […]

We hit the turps last night with some of our fellow travellers, so this post is a day late. This magnificent hall was built in Budapest in 1896, then a few years later it was pulled apart and transported here. This was the starting point of our walking tour of Zagreb, the capital of Croatia, […] The post The Balkans: Day 14 – Zagreb, Croatia. appeared first on Burning Desire For FIRE.

It’s that time of year again. In 10 days, we’ll be pulling out of our driveway for a month-long RV adventure through the Midwest, visiting State Parks and family along the way. Long-time followers know that my wife and I like to take an extended RV trip each summer, with an occasional curveball thrown in for fun (a cross-country train trip, a cruise to the Arctic). We bought our 2018 Reflection 5th wheel and 2017 […]

There is a question I hear often from women who have been saving for decades, doing everything right, maxing out their 401(k), watching the balance climb, and then suddenly, somewhere in their late 40s or early 50s, they start to wonder: is this actually enough? And more importantly, do I actually know how this turns out? The number in the account is not what keeps them up at night. What keeps them up is not […]

Kids birthday freebies can save you $50 to $150 during your child’s birthday month, depending on which rewards you stack. Many restaurants,… The post 63 Birthday Freebies for Kids: Where Kids Get Free Meals, Gifts & Fun in 2026 appeared first on MoneyPantry.com.