How to Retire Early (Without Winning the Lottery)

I’ll admit it—when I first heard people talking about retiring early, I thought, “Sure, right after I invent a money tree.” But as it turns out, early retirement isn’t just for tech bros or eccentric millionaires. It’s something regular folks like me (and you) can actually pull off – with a little planning, a little patience, and, okay, maybe cutting out the daily $6 cappuccino habit. Here are some ideas on how to retire early you can truly benefit from.

Now, when I say “retire early,” I’m not talking about quitting work at 35 and spending the next 50 years trying to beat Netflix. I’m talking about getting to a place where I no longer have to work by my early 60s, or for some folks, even 50s if you’re really strategic. That’s what I set out to do, and let me tell you, it’s been an eye-opening journey. So, here’s how I tackled the dream of retiring early, and how you might just be able to do the same—even if you’re starting later than you’d like.

First off, I had to get real with myself about money. And that meant tracking every dollar like it was a toddler running through a toy store. I didn’t need a fancy financial advisor for this (though one doesn’t hurt). I just used a simple spreadsheet and some free apps to figure out exactly how much I was spending—and, more importantly, where I could start trimming the fat. Spoiler alert: I didn’t need three streaming services or the gym membership I never used but kept “just in case I got inspired.”

One of the biggest mindset shifts I made was to stop thinking of saving as a punishment. I stopped saying, “I can’t spend money on this,” and started asking, “Would future retired me thank present me for this purchase?” If the answer was no, then sorry Amazon—maybe next time. This can be a really detrimental habit to get into, so don’t fall down that rabbit hole.

Maxing out my retirement accounts was another huge step. I took advantage of every tax-advantaged account I could get my hands on: IRAs, 401(k)s, and later on, an HSA—which, by the way, is like a secret retirement account disguised as a health fund. I also got very cozy with index funds. Warren Buffett himself says the average investor is better off putting their money in low-cost index funds, and I figured if it’s good enough for the Oracle of Omaha, it’s good enough for me. Besides, this is a plan that will have you sleeping much better at night not worrying about how the market is doing.

Now, let’s talk about side income. You know what’s better than saving money? Making more of it. I started picking up little side gigs in my spare time—not the “ride around all day delivering tacos” kind, but things I actually enjoyed. I did some freelance writing, taught a few online classes, and even sold some handmade walking sticks online (yes, I know how that sounds). It wasn’t a fortune, but it all added up. If you know any skill that you can teach to others, it’s pretty easy to find a way to make money from it either on Youtube.com or Udemy.com by creating tutorials.

And that brings me to the big secret weapon of early retirement: passive income. If you want to stop working sooner, your money has to keep working after you do. For me, that meant investing in dividend-paying stocks and a couple of rental properties. I’ll be honest, landlording isn’t always glamorous (especially when a toilet explodes at 2 a.m.), but the monthly checks sure help soothe the pain. Is everyone cut out for this type of investment? Not by a longshot, but it’s one of the best long-term investments you can find in my opinion.

I also lived below my means. Not off the grid in a van by the river below my means, but smart enough to keep my expenses lower than my income. I moved to a more affordable area, shopped around for insurance like it was a competitive sport, and learned to cook meals that didn’t come out of a box labeled “ready in 3 minutes.” I mean, who knew lentils could taste that good?

Now, here’s something I don’t hear enough people say: retiring early isn’t about depriving yourself. It’s about choosing freedom over fluff. I still traveled, ate out now and then, and spoiled my grandkids on their birthdays. I just did it all with intention. And yes, I still splurged on good coffee—life’s too short for the cheap stuff, retired or not.

Health care was a big concern for me, too. Before Medicare kicks in at 65, I had to think creatively. That meant exploring high-deductible health plans paired with an HSA, checking out ACA marketplace options, and making sure I had a decent emergency fund just in case my body decided to throw a surprise party. And let’s be honest, once you hit 50, everything starts making noises it never used to. This can be a very big roadblock for some people, I get it. It’s scary wondering how you might pay for medical expenses if you have any type of physical problems that need attention.

So, when did I actually feel ready to retire early? It wasn’t just about hitting a number. It was about feeling secure. I had enough saved to cover 25 to 30 times my anticipated annual expenses, which is based on the 4% rule, a rule of thumb suggesting you can safely withdraw 4% of your portfolio each year in retirement. I tested it out with a trial run, living as if I were retired while still working. Turns out, I liked it so much I made it permanent.

Of course, I didn’t just sit on the couch once I retired. I found purpose in other things—volunteering, mentoring young folks, learning how to play the ukulele (still not great, but improving). That’s something I tell everyone who dreams of retiring early: make sure you know what you’re retiring to. It’s not just about stopping work—it’s about starting something better.

And hey, don’t think you’ve missed the boat if you’re reading this in your 50s or even early 60s. It’s never too late to retire a little earlier than you expected. Maybe that means scaling down your lifestyle a bit, or working part-time while drawing from investments. Every step you take toward financial independence puts more control in your hands.

For me, early retirement wasn’t about escaping work. It was about designing a life where I had more time, more freedom, and more mornings without an alarm clock blaring in my ear. It took effort and discipline, but I never once regretted it. I had the chance to spend more time with family, chase a few dreams I’d put on the shelf, and even get a little better at baking (still haven’t nailed sourdough, but I’m trying). There are endless activities you can pursue in life, so don’t think you won’t have anything to do once you quit working full time.

So if you’re dreaming about early retirement, I say go for it. Get your finances in order, create a plan, and stick with it. Don’t let fear—or that one cousin who swears you’ll “just get bored”—hold you back. If I can do it, so can you. Just remember, it’s not about being rich – it’s about being free. And there is nothing better than the feeling of being free!

Planning for your retirement can be tricky, and there are questions you have like everyone else. If you want to learn and explore more ideas for yourself, check out my book here for more information:

Happy retirement planning!


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