Susan's ScoopA Hedge Against Risky Bets Caitlin and I generally encourage setting up a buy-and-hold portfolio of diversified low-cost index funds. And yes, sometimes this can often seem ‘boring’. So what do you do if you want the excitement of investing a small amount of your money in riskier stocks, such as start-ups, but don’t have the risk tolerance to lose it all? This is where stop losses come in. A stop loss is an automatic sell order you can set on a stock through your brokerage. You choose a price point - say, 20% below what you paid - and if the stock falls to that level, your brokerage sells it for you. The idea is to limit your downside without having to watch the market every day. It’s easy to set up in most brokerage accounts: just look for the “sell” order type and select stop loss instead of market or limit. Now you typically don’t want to use these for diversified index funds or companies that you believe in for the long haul, because stocks can often dip and bounce back immediately after. How sad would you be if you bought a stock for $10,000, had a 20% stop loss sale trigger, then the stock immediately jumps back up to the original price a few hours later? You’d be left with only $8000 of your original investment and no stock. 😭 That’s the problem with stop losses for long-term investments. Markets don’t move in straight lines. They dip, they pop, they recover. If you’re investing in index funds or companies you believe in, stop losses usually hurt more than they help. BUT – there are times when they make sense. If you’re dabbling in risky plays like a speculative biotech or a small startup, you may decide you only want to risk so much. In that case, a stop loss can help you draw your line in the sand. Take Rivian, for example. The electric truck startup hit a high around $130 per share and has since fallen to under $15. That’s an 85% wipeout. Firefly Aerospace is another recent case; it reached a high over $70 shortly after its recent IPO, but now has dropped to around $28/share. For someone who bought into the hype early, a stop loss could have been the difference between taking a manageable loss and watching their investment mostly disappear. Most of my portfolio sits in diversified index funds, so I rarely use stop losses. But for the handful of speculative investments I own - where the risk runs a bit higher - a stop loss gives me a way to hedge against major losses. Think of it as just one more tool in your investor toolbox, there to pull out when the situation calls for it. 🔧 What I'm Reading 📕 Jonathan Clements, In Memoriam (WSJ) As many of you may already know, the personal finance world lost an important voice last week with the passing of Jonathan Clements. As the personal finance columnist for the Wall Street Journal, he was one of the first writers to take a stand against retail investors being viewed as “dumb money” and a target for high fees. “In his nearly two decades at the Journal, Jonathan wrote more than 1,000 columns in which he crusaded against high fees, lousy financial advice and mediocre investment management—and explored even bigger topics, like how to raise financially responsible children and how to use money to find happiness. His pen was sharp as a needle, but he wielded it with humor, grace and a confessional, personal touch. Readers felt they knew him—because they did. More than any commentator before or since, Jonathan made personal finance personal.” Join us for free the first Wednesday of each month for an informative money conversation! Next Up: Nov. 5th at 1pm CT- Open Enrollment Edition: Your Benefit and Healthcare Questions Answered A 3-month on-demand course with live community calls designed to guide you through creating your 10-year wealth plan, one practical and powerful step at a time. If you’ve been looking for the right moment to take control of your financial future - this is it. 👉 Click here to explore the Wealth by Design course and get started today. |
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Caitlin's Corner What Our First “Santaless” Christmas is Teaching Us So Far As the holidays approach, I know that not everyone in our community celebrates Christmas, and those who do, celebrate in different ways. Our family’s version is a very secular, winter-marking ritual: a way to bring light into the dark season by connecting with people we love, and celebrating the joys that lift our spirits during these cold months. Of course, if you ask our kids, they’d tell you it’s about one thing:...
Susan's Scoop When Should You Donate? A 2025–2026 Tax Timing Hack I hope everyone who celebrates is enjoying a cozy and restful Thanksgiving! My older son is home from school for the first time in three months, and I’m so grateful to have our family feeling “complete” again. I’m also celebrating a big professional milestone - I passed my final Enrolled Agent certification exam, which means I can now support clients with more advanced tax strategy and represent them directly in front of the...
Caitlin's Corner Tax Jargon, Clarified Every year around this time, it feels like the air gets thick with tax terms. They float around in headlines, in HR emails, in conversations we didn’t ask to be part of: "Brackets! Deductions! Credits! Limits…" If hearing all of that makes your eyes glaze over, you’re in good company. I remember when these terms made me want to bury my head in the sand. It so often felt like the tax language itself was weaponized, like- the sheer amount of jargon and...