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If retirement is the dessert at the end of life’s banquet, then “pre-tirement” is the cheeky appetizer you sneak when no one’s looking—except in this case, it’s encouraged, delicious, and smart. The “pre-tirement” strategy flips the traditional script of nose-to-the-grindstone-until-sixty-five and offers a juicy alternative: build wealth steadily while living a little now. It’s not just about sipping umbrella drinks on a Tuesday (though that does sound fabulous), it’s about designing a life that lets you enjoy today while still preparing for tomorrow. And no, it doesn’t require lottery winnings or influencer-level income—just a clear-eyed look at your money, priorities, and a sprinkle of rebellious financial spirit.
Let’s be real—most retirement advice reads like a sleep aid. It often starts with “defer gratification” and ends with “maybe you’ll be able to walk the Amalfi Coast when your knees no longer work.” That’s not exactly inspiring. But pre-tirement invites you to ask a different question: what if I didn’t have to wait? What if I could enjoy parts of retirement now, in bite-sized, life-affirming chunks, while still being responsible with my future? The answer lies in a mashup of sound personal finance, intentional living, and just enough YOLO to keep things interesting.
So how do you build wealth while also refusing to delay joy? First, you’ve got to get surgical with your expenses. And no, I don’t mean clipping coupons for sport or debating the ethics of reusing dental floss. I mean real alignment between your spending and your values. Pre-tirement starts by cutting what doesn’t matter so you can fund what does. That might mean ditching the oversized house you never use for a smaller place in a vibrant neighborhood where you can walk to everything and sip overpriced-but-worth-it lattes in peace. It might mean skipping the constant tech upgrades and instead investing in a camper van to travel on weekends. The point is, pre-tirement is personal. Your version won’t look like your neighbor’s—and that’s the magic.
Now, let’s talk about income. A key pillar of pre-tirement is diversifying where your money comes from. It’s hard to live a little if your paycheck is a jealous ex—controlling, clingy, and vanishing when you need freedom. This is where side hustles, remote gigs, freelance work, and passive income streams come into play. You don’t need to launch the next Airbnb, but if you can teach piano lessons on weekends, rent out your garage on Neighbor.com, or build a modest dividend portfolio, you’re creating space. Space equals choice. And choice is the currency of pre-tirement.
You’ll also want to reconsider how you define “wealth.” Because if wealth only means hitting a certain number in a retirement account, you might be missing out on the richness of life. Wealth can also mean having Tuesdays off, the flexibility to travel in shoulder season, or the ability to say “no thanks” to toxic bosses. True wealth is a hybrid of financial security and lifestyle autonomy—and pre-tirement aims for both.
Let’s get into some examples. A teacher who takes every summer off and spends two months living abroad each year? That’s pre-tirement. A software engineer who saves aggressively, then drops to part-time at 40 to start a small vineyard? Pre-tirement. A couple who downsized and took on house-sitting gigs in different cities to explore before choosing where to retire? Textbook pre-tirement. In each case, people are reclaiming pieces of their lives without giving up on long-term goals.
The magic of this strategy lies in smart financial planning, but not the kind that demands martyrdom. Think more “savvy monk with a passport” and less “financial ascetic eating canned beans in the dark.” It’s about crafting a sustainable savings plan that includes investing wisely, taking advantage of tax-advantaged accounts like a Roth IRA or HSA, and automating enough to stay on track without obsessing. One of the best resources for understanding this kind of planning is the ChooseFI community, which blends frugality with intentional living in a way that complements pre-tirement perfectly. You can check them out at https://www.choosefi.com, which is packed with podcast episodes, calculators, and ideas for lifestyle optimization.
Let’s not skip over the fact that health insurance is the eternal party crasher in any early retirement plan. But pre-tirement doesn't always mean quitting your job entirely. It might mean going part-time with benefits, consulting for a company that still offers a group plan, or using marketplace subsidies wisely if your income qualifies. For a deep dive into this, visit https://www.healthcare.gov for details about available plans, subsidies, and coverage calculators. It’s not as scary as it sounds—especially when weighed against the value of getting your time back.
Housing is another lever in the pre-tirement playbook. Many folks are house-poor by default. But in a pre-tirement strategy, the goal is to house-smart. That could mean house hacking (living in one unit of a duplex while renting the other), relocating to a lower cost-of-living area, or even trying geographic arbitrage—where you earn in dollars and spend in pesos, baht, or złoty. Entire Facebook groups and subreddits like https://www.reddit.com/r/digitalnomad or https://www.reddit.com/r/geographicarbitrage are devoted to the art of living well for less around the globe.
You’ll also need to get cozy with a budget—not the rigid, joyless kind, but one that actually reflects your lifestyle. Apps like YNAB (You Need A Budget) allow you to create a spending plan that rolls with the punches. Visit https://www.youneedabudget.com for free trial options and budgeting advice. Think of it like a money GPS, helping you reroute when life happens but keeping you headed toward freedom.
And speaking of rerouting—pre-tirement is flexible by design. It's not a fixed destination but a moving target shaped by your needs, your health, your family, and your weird obsession with restoring vintage campers or taking improv classes. It allows for pivoting. You might work a lot some years, then hardly at all the next. You might pursue passion projects that pay pennies—or build a small business that surprises you with six figures. The point is, you’re not on autopilot. You’re steering.
Of course, living a little now does mean resisting the tidal pull of lifestyle inflation. You’ll need to get good at distinguishing pleasure from pressure. Do you want the artisanal cheese board because it delights your soul or because your coworker posted hers on Instagram? That difference is everything. Pre-tirement works best when you spend money on things that genuinely improve your quality of life—not things that just drain your bank account and clog your closet.
Here’s the truth: retirement isn’t a magical event. It’s not when your soul suddenly becomes whole or when your Instagram becomes inspirational. If you’re not careful, you’ll arrive at retirement and realize you spent decades building a future you don’t even want. Pre-tirement helps you sanity-check your dreams in real time. By living parts of your ideal life now, you get feedback. Maybe you think you want to live on a sailboat. Cool—rent one for a week first and discover you get seasick. Maybe you fantasize about homesteading, but it turns out you like grocery stores and Wi-Fi. Better to know now than after you’ve invested your 401(k) in goats.
We’re entering an era where the lines between working and not working, retirement and real life, career and calling are blurrier than ever. That’s not a crisis—it’s an opportunity. Pre-tirement is a mindset shift. It tells you that your life has value beyond the paycheck, that your time matters now, and that with a little creativity and a lot of intentionality, you can carve out a rich, meaningful existence before you’re “officially” done working.
There’s also something deeply human—and dare I say fun—about not putting all your joy eggs in the retirement basket. A “live for today” attitude doesn’t mean financial recklessness; it just means being awake to your life as it’s happening. Maybe it’s slowing down, maybe it’s traveling more, maybe it’s building something you care about. But it’s always about choosing presence over postponement.
In the end, the pre-tirement strategy is about agency. You’re reclaiming your calendar, your goals, your vision of what success looks like. And in doing so, you’re rewriting a narrative that has too long told us to grind, hoard, then rest. You don’t have to live by the default script. With a well-managed plan and the courage to live a little now, you can create a life that’s not just financially sustainable—but joyful, spacious, and full of good stories along the way.
So, can you really build wealth while enjoying life now? You bet your lunch-hour mimosa you can.
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