I grew up thinking life was simpler. My parents say the same. Now it feels like we’re solving equations written on a moving chalkboard while the classroom is strapped to a rocket, hurtling through the Milky Way. Too heavy? Buckle up anyway. There’s a lighter way to ride this thing, scenic route preferred.
The information age has handed us more awareness than any generation before us, and at the same time we’re late in a much bigger macro cycle. Ray Dalio’s line, “Learn how reality works and act accordingly,” keeps ringing in my ears. Bob Dylan warned us plainly, “The times they are a-changin’.” Mo Gawdat keeps reminding us that AI is accelerating the change whether we like it or not. However you slice it, the map most of us were handed in high school doesn’t match the terrain we’re walking on today.
So maybe it’s time to redraw it.
The American Dream, at least the version most of us inherited, sounds reasonable enough: work hard, buy a house, get a new car, maybe start a business or land the “good job,” and start a family. That’s freedom, right?
Except the modern version of that dream looks a lot like a cleverly branded installment plan.
A “starter” house usually comes with a 30-year IOU; add taxes, insurance, maintenance, upgrades, surprises, and interest. A “freedom” car quietly pulls a payment out of your account every month, then follows up with insurance, registration, and repairs. A “career” increasingly starts with financed credentials. Somewhere along the way, subscriptions begin owning your attention, and your attention quietly rents out your future.
On paper, the typical debt stack isn’t hard to recognize: a mortgage in the mid-$200Ks, auto loans in the mid-$20Ks, student loans in the $30Ks, a few thousand on credit cards, all riding on a median income in the low-$60Ks. The exact numbers aren’t the point. The ratio is. More obligation than optionality. Debt sold as destiny.
We were told ownership equals freedom. But freedom isn’t “I own a thing.” Freedom is “I own my time.” If the thing owns your time, it owns you.
Homeownership can be a beautiful thing. Community, roots, control; those are real benefits. But when you run an honest, all-in calculation that includes taxes, insurance, maintenance, improvements, interest, and transaction costs, the “investment” story often turns out to be a comforting narrative that doesn’t always hold up under the math. Renting gets framed as “throwing money away,” even though for many people it’s actually a way to buy back flexibility and quietly build wealth the boring way, by owning equities directly. No lawnmower required.
I’m not anti-home. I’m pro-math. Ideally, whether you rent or own, total housing costs stay under about 28% of gross income. Once that number creeps higher, the tradeoffs usually show up somewhere else in your life. If the outcome is less freedom in exchange for more square footage you barely use, that’s not really a home—it’s a very polite jail with granite countertops.
Cars deserve the same honesty. Buying new can be reasonable; it just doesn’t have to mean the most expensive model or the fully loaded trim. Used can work just as well. So can finding a good local mechanic you trust, especially one who specializes in a few makes you could see yourself driving for a long time. The goal isn’t deprivation, it’s reducing drag. Consumer auto loan debt is at all-time highs, which is a pretty clear signal that people are stretched thin just trying to get from point A to point B.
That’s the backdrop for a bigger reality check: the rules have shifted.
Blue-collar trades often out-earn desk jobs now, without the same debt minefield and with far less risk of automation. The cost of life has outrun wages, which means the traditional timeline—house, kids, SUV by 30—now collides with basic arithmetic. At the same time, we’re more connected than ever, which means geography, skills, and time are more flexible than they used to be, if we’re willing to stop following scripts written for a different economy.
Thriving in this environment doesn’t require being reckless. It requires being quietly contrarian in small, repeatable ways. The goal isn’t austerity. It’s optionality; not the Instagram version of freedom, but the balance-sheet kind.
That might mean redefining freedom as lower fixed costs, a higher savings rate, and more than one way to earn. It might mean choosing housing and transportation that leave room to breathe, then banking and investing the difference instead of upgrading on autopilot. It might mean renting smart or owning smart, building a second income stream, choosing skills over credentials, or using geography more intentionally. Most of the time it just means letting the math, not the narrative, make the decision.
The version of the Dream worth keeping isn’t flashy. It’s quieter.
A life that feels more like the scenic route and less like the express lane to burnout.
You don’t have to burn down the old Dream. You just have to stop letting it mortgage your future. Reality changed. Acting accordingly is the real upgrade.
And if you want to start small, that’s fine too. Cancel a few subscriptions. Sell some things you don’t use. Set up automatic investing, even if it’s modest. Re-price your next car before you upgrade. Block a couple of hours to explore a complementary path you’ve always been curious about.
Small moves compound. That’s the quiet math of freedom.
Nicholas Ockenga, AIF®, CFP®, CBDA
Financial Planner
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