We'd just returned from a two-week trip to Peru. After dropping our luggage at home, we headed straight out again to pick up our dogs. Unfortunately, none of our friends can watch both dogs while we're away, so we've always relied on pet boarding services. And boarding two dogs isn't exactly cheap. As happy as we are to see them again, getting the final bill at checkout is another story. Nothing says "Welcome home!" quite like a bill that dropkicks you out of your post-vacati

Since retiring early, we’ve been traveling a lot more, but it sure gets expensive. Naturally, we’d like to keep costs as low as possible without giving up too much convenience or comfort. I’ve looked into popular travel hacks such as credit card point churning and searching for alternative airports. But a lot of them remind me of extreme couponing: They might save us money, but they also sound like a lot of work. And that's not exactly what I had in mind when I retired early.

You'd think achieving FIRE would mean we’d stop worrying about saving money and simply spend freely. Nope. Reaching financial independence doesn't mean you suddenly start ignoring price tags. If anything, FIRE changes the way you think about spending. We don't avoid spending money because we're afraid we'll run out. We avoid wasting money because we'd rather spend it on things we actually value. It goes back to thinking like a CEO and putting our money to work where it genera

Our COBRA coverage expires this year. And next year, we plan to switch to an ACA insurance plan. As mentioned in an earlier post about ACA health insurance in early retirement, we're hoping to qualify for ACA subsidies. Doing so could dramatically lower our insurance premiums. The catch? We need to manage our household MAGI (Modified Adjusted Gross Income). It’s a major factor in determining whether we qualify for subsidies and how much we can receive. How ironic is it that w

Recently, I met with one of my best friends, who is trying to follow in my footsteps and retire before 50. Our conversation eventually turned to mortgages. Because apparently this is what happens when you get older. She was considering making extra payments toward her mortgage principal. You've probably heard the advice before: Make one extra mortgage payment a year, and you'll shave years off your loan. I'd heard an even more impressive version a few years ago on YouTube. An

Investing primarily in individual stocks helped us get the high returns that allowed us to retire early. And even today, individual stocks make up the majority of our portfolio. But it didn’t start out like that. Like many people, our first foray into investing began with mutual funds. Back then, we knew nothing about analyzing companies or even how to go about buying and selling stocks. Mutual funds were less intimidating, but I still remember not really understanding what w

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

In one of my first blog posts, I wrote about the five things everyone needs to plan for before retiring. I focused on big-picture items: money, health insurance, social connections, how you’ll spend time, and identity. But there’s another part of retirement planning that doesn’t get nearly as much attention: the things you need to do just before actually leaving your job. Some of it’s financial. Some of it’s administrative. And some is making sure you don’t leave behind any m

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'm currently watching the FIFA World Cup—my favorite sporting event. A friend and I have even placed a few bets on the matches. We couldn't approach gambling more differently. He'll happily throw hundreds of dollars on long shots. I stick to "sure things," and even then, I rarely bet more than $20. Gambling makes me nervous. But here’s the strange part. That same person who hesitates to bet $20 won't think twice about investing $20,000 in a stock. You might be thinking, “But

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

CostPal alerts shoppers when Costco purchases drop in price, making it easy to claim refunds through Costco's price adjustment program. Costco can save you a lot of money—as long as you don't leave with a kayak, a giant teddy bear, and a 72-pound wheel of Parmesan cheese you never intended to buy. What many Costco shoppers don't realize, though, is that Costco has a 30-day price adjustment policy. If something you buy goes on sale within 30 days, Costco will refund the differ

Last week, I shared how you can tap into Morningstar’s investment research database to unearth investment ideas for free. In this post, I’ll show you how I use Morningstar to quickly check a company’s financial numbers before spending hours researching a company. And definitely before buying a stock. Because finding a company with an economic moat and a great CEO is only part of the equation. Eventually, the numbers have to prove the company isn’t all hype. Learning how to re