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.

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

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

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

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

Last week, I talked about why healthy lifespan matters more than just living longer. But that got me thinking… What if the real problem isn’t how long we live— but when we’re actually able to enjoy it? Because three things determine how good life feels at any moment: Your health Your money Your time And here’s the problem: They peak at completely different times. This is the health, wealth, and time tradeoff most people never think about THE HEALTH CURVE (WHY YOUR BODY PEA

I got really excited when I finished filing our 2025 tax return last week. You might assume it’s because we’re getting a huge refund. Nope. The real reason I was excited? My tax optimization spreadsheet actually worked. Last year, I shared a spreadsheet I built to estimate how much long-term capital gains we could realize while staying in the 0% capital gains tax bracket . I had tested the math every way I could think of. But until you actually file a tax return, you never

As part of our year-end tradition , my wife and I reviewed our Goals Bingo cards and reminisced about the places we visited and the things we did throughout the year. For fun, we also voted on our personal “Best of 2025” across a few categories—including Best New App. This year, we both chose an app that saves us money, helps the environment and businesses—and creates a little excitement. Our Best New App of 2025 is Too Good To Go. Note: I am not affiliated with Too Good To G

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

In my last post , we talked about how long-term capital gains stack on top of ordinary income when calculating your federal taxes. We also looked at the magical unicorn of tax brackets: the 0% long-term capital gains bracket. This “stacking” concept doesn’t just help reduce your taxes today—it can also shrink your tax bill years from now by intentionally using the 0% tax bracket. And that’s where capital gains harvesting comes in. Yes, “harvesting,” as if we’re out in a fiel