My dad is the greatest stock picker the world never knew about. Dare I say he’s even better than Warren Buffett. He’s identified countless companies whose stock prices would later skyrocket. More importantly, he’s never lost a single cent on any of his picks. His secret? He never invested any money in any of the stocks he was so sure about because the risk of losing money terrified him. Instead, I’ve had to listen to him react to news of his countless stock picks: “I knew tha

Over the weekend, I spent some time looking for money I may have forgotten about. And while I was at it, I checked for money some friends and family members may have forgotten about, too.. It's something I like to do about once a year. I'm not talking about the loose change that's sometimes accompanied by the rogue Cheerio hiding between the sofa cushions. I'm talking about unclaimed money. And this time, I didn't find any for us. But I did find several hundred dollars for so

Last week, I explained why my wife and I decided an Health Savings Account (HSA) paired with a high-deductible health plan made sense for our early retirement strategy. Once we made that decision, though, I realized I still had a long list of questions. Some were simple. Others sent me down rabbit holes through IRS publications and insurance websites. I wanted one place that answered everything. If you're considering opening your first HSA, these are the exact questions I res

The end of October marks a big milestone in our early retirement—the expiration of our COBRA coverage. COBRA can be a great healthcare option in early retirement, but it only lasts up to 18 months. After that, you’re on your own. So I started shopping for insurance on the ACA Health Insurance Marketplace recently—the logical next step. And that’s when I realized there was a major flaw in our early retirement plan. We knew buying insurance on the ACA Marketplace could get pric

Last week, I explained how my wife and I can use a Roth conversion ladder to access retirement savings before age 59½ without paying the 10% early withdrawal penalty. The downside? You have to wait five years before touching the converted money. Then I discovered another early retirement income strategy that skips the waiting period entirely. With Rule 72(t), you can begin withdrawing money directly from a traditional IRA immediately—without converting anything to a Roth IRA

One of the biggest questions in early retirement is simple: How do you pay the bills before you're old enough to collect Social Security and access retirement accounts without penalties? Before retiring, we intentionally built our high-yield savings account (HYSA) to cover roughly five years of living expenses. That cash serves two important purposes. First, it lets us take advantage of capital gains harvesting, a tax-saving strategy I covered in a previous post. Second, it g

A year ago, I started seeing ads for Kalshi, a prediction market platform, all over social media. At first I ignored them. Then they started appearing during commercial breaks while I was watching the World Cup. Apparently, I wasn't clicking "Not Interested" aggressively enough. The ads claimed prediction markets were a smarter way to make money by predicting current events. Some influencers even described them as investing. That immediately raised a question: Are prediction

I get an email every time my FICO credit score changes. This week, I finally checked it for the first time in months. 847. After years of hovering around 835, I was suddenly three points away from perfection. Naturally, I ran to tell my wife because we're just competitive enough to compare credit scores. Unfortunately for me, she's one of the fewer than 2% of Americans with a perfect 850, so I never win. Apparently an 847 credit score still loses in my house. When I look at o

Here’s a story that has stuck with me for over 30 years. When I was still in college, my best friend, who was majoring in Finance, once asked me what Annual Percentage Yield (APY) I was getting on my savings account with the local bank. “About four percent,” I confidently told him. There was just one problem. I had absolutely no idea what APY I was earning. At some point, someone had told me it was around 4%, and I assumed it stayed there forever. Because that's how banks wor

I recently received a Gallup survey regarding the cost of healthcare where I live. One question asked whether I'd ever been unable to afford a prescription medication. That question got me thinking. Picking up a prescription often feels like pulling the lever on a slot machine. You don't know what you'll pay until the pharmacist scans the order and the number appears on the register. Luckily, I’ve never been unable to afford my prescriptions, even when the price was more than

Let’s return to the topic of stock investing, shall we? We previously covered how to uncover great companies by identifying those with economic moats and fantastic leaders. Many of these companies are behind the products and services you love. But finding these companies can feel overwhelming, especially if you're a beginner investor. When I first started researching stocks, I had absolutely no idea where to begin. Sometimes I would randomly come across ticker symbols online

After putting together our FIRE plan in 2009, my wife and I adopted several frugal habits—not because we enjoyed deprivation, but because we wanted to spend more intentionally. Those habits helped us reach financial independence in 2019 and eventually retire early in 2025. What surprised me is that even after FIRE, we never stopped doing them. Some habits stick around long after reaching FIRE. Sure, we occasionally splurge on business-class airplane seats or a ridiculously ex

Nine months into early retirement , managing healthcare costs is still top of mind. Health insurance options in early retirement are limited—and expensive. The bigger worry, though, has always been what happens if we have an expensive medical procedure. A single medical episode can derail even a solid FIRE plan . It gets scarier when the safety net of a steady paycheck is no longer there. That’s why maintaining and improving our health has been such a big focus for us. But

I’m so excited to share a new spreadsheet I recently created to estimate tax liability and optimize long-term capital gains (LTCG)! I know this sounds like an odd thing to get excited about—but hear me out. Since retiring earlier this year, early retirement tax planning has become a major focus for us. We have more than a decade before we begin to collect Social Security. And without steady paychecks, we’ll be relying solely on our savings and investments. Of course, we’d li

When I first heard about the zero percent tax bracket for long-term capital gains, I didn’t believe it. Mind you, I’m not talking about Roth IRA withdrawals, which are always tax-free. I’m talking about capital gains from stocks held in a taxable brokerage account . The IRS not taxing this money sounded too good to be true. But it is true—the IRS really does let some of your investment gains be taxed at zero percent. Long-term capital gains actually have their own set of tax

(and why getting bumped into a higher tax bracket isn’t the disaster people think it is) In my previous post , I mentioned that capital gains and dividends can fall within a zero percent tax bracket if you hold your investments long enough. Imagine: legally not having to pay taxes on thousands of dollars of income. Cha-ching! But before we get that fun part—we need to clear up one thing: how our progressive income tax system works. Many people misunderstand how ordinary incom

In my previous post , we talked about capital gains—the money you make when you sell stocks for more than you paid. But that’s only one way stocks can make you money. In this post, we’ll take a look at the second way of making money with stocks: dividends . We’ll break down key dates to know about dividends and how to minimize tax liability. And we’ll also answer the big question every dividend investor wants to know—Is it possible to live off of dividends only? WHAT ARE DIVI

When I first started buying and selling stocks, I never held any shares for longer than a few months. Then tax season rolled around, and I found myself staring blankly at a Schedule D tax form, thinking, “What the heck are capital gains , and why did my tax liability jump?” If you’re new to investing, there are two ways to make money through stocks: capital gains and dividends. In this post, we’ll break down what capital gains are, how they’re taxed, and why your holding per

So you have health insurance. But do you know what you’re actually paying for? If the words premium, deductible, coinsurance, and co-pay sound like gibberish, keep scrolling. I’ll break down the most common health insurance terminology you’ll come across—without the jargon. Trying to understand your health plan can be as painful as hemorrhoids UNDERSTANDING THE COSTS BEHIND YOUR HEALTH PLAN Before diving into the alphabet soup of plan types, it helps to understand the basic

Health insurance is one of the biggest puzzles of early retirement—right up there with "what day is it again?" Six months into early retirement, I wish I could say health insurance isn't on my mind. But it is—a lot. It’s hard not to with health care costs being so high in the U.S. compared to other countries. It is a lot easier when you receive health insurance through your employer. They do all the legwork—they find the best plan and negotiate the best rates. All you have to