I bought my first car the second year of college with money I’d earned myself. It was a 1998 Ford Escort — used, nothing fancy, $5,000 cash. I bought it in 2004 and drove it for eight years. When we finally sold it in 2012, we got $3,000 back. That is either a great deal or a sign that I have a very high tolerance for driving an aging compact car. Probably both.

Cars are one of the more interesting categories in our spending history, because they reveal something beyond just numbers. The choices we’ve made — when to buy, how to pay, what to drive — reflect a financial philosophy that we didn’t necessarily sit down and write out, but one that’s been pretty consistent over 20 years: keep required payments low, own things outright, and don’t let a car payment be the reason you can’t do something else with your money.

With one notable — and surprisingly instructive — exception.

The Cars, In Order

Before we get into the numbers, here’s the full fleet history. Between the two of us, we’ve owned five cars over the course of our marriage, with one lease thrown in for good measure.

The Accident That Changed Our Fleet

In 2010, my husband was driving us to visit our parents — about a three-hour trip we’d made many times. He saw a car appear in his blind spot, overcorrected, and we rolled. The Focus went over several times before landing on its side. It was one of the scariest moments of our lives.

We walked away without serious injuries. Our dog, who was in the car with us, miraculously emerged fine. The Focus was totaled.

The insurance company paid us $4,200 for a car my husband had bought new in 2003 for $13,000. That’s the reality of car depreciation — seven years and it was worth less than a third of its purchase price. We added the insurance payout and our own savings, and financed $14,600 of the $23,900 purchase price of a 2010 Honda CR-V. It was a reasonable, practical choice — bottom trim, nothing fancy. Technically it was my husband who had the first car payment in our household (he financed his Focus back in 2003), but this was my first, and I was not thrilled about it.

We paid it off fast. That part felt very much like us.

The Two-Car Problem (And the Escort’s Final Chapter)

After the accident, I inherited the CR-V and my husband started driving my old Escort. Picture a grown man folding himself into a 1998 Ford Escort every morning and you’ll understand why, less than two years later, in February 2012, we bought a 2012 Chevy Equinox.

We financed $16,450 of the $26,800 purchase price and paid it off in 23 months — roughly $715 a month until it was gone. Done. Ours.

The Escort, meanwhile, soldiered on until 2012 — 14 years old and still running well — when we finally sold it for $3,000. I had paid $5,000 for it in 2004. Over its entire life with me, that car cost less per year than most people spend on a single car payment.

October 2017: A Very Expensive Month

By 2017 our second child was six months old and we were a family of four with a CR-V and an Equinox. Both cars were paid off. Both were getting older. And car shopping — I cannot stress this enough — is not our idea of a good time.

So we did it all at once.

We traded in both cars at the Honda dealer and bought a 2017 Honda Pilot Elite for $43,715. The CR-V fetched $9,700 and the Equinox $8,500 in trade-in value — and we’d been strategic about it, getting quotes from the Audi dealer first so we walked into Honda knowing exactly what our cars were worth and could negotiate accordingly. No monthly payment. Exactly how we like it. The Elite trim came loaded: adaptive cruise control, lane keep assist, all the features that make a long family road trip survivable.

At the same time, we started a three-year lease on a brand new 2018 Audi Q5. This was my husband’s idea. I was not immediately on board.

The Lease Experiment: Were We Right to Be Skeptical?

I’ll be honest: I’ve read enough personal finance material to know that leasing is rarely the mathematically optimal choice. You’re paying to use something you don’t own, you can’t make extra payments to pay it down faster, and at the end you have nothing to show for it unless you buy it out. Everything about it runs counter to how I think about money.

But the lease did solve a real problem: it let us get two cars at the same time without draining our savings completely. The Audi Q5 was valued at $52,404 on the lease agreement. A monthly payment of $805.90 made it manageable. We paid the signing costs in cash — we had actually gotten trade-in quotes from the Audi dealer on both our cars, but that was a negotiating tactic, not an actual trade. We used those quotes to put pressure on the Honda dealer when buying the Pilot. It worked. We knew going in that in three years, we’d have the lump sum ready to either buy it out at the pre-negotiated residual of $30,838.50, or buy something else with cash.

The part that quietly drove me crazy? I couldn’t make extra payments. With every other debt we’ve ever had, we’ve thrown extra money at it to get it gone faster. A lease doesn’t work that way. So instead, I channeled that instinct into a savings account — building up the buyout fund month by month, watching it grow while the lease payments went out the door. Not ideal. But it worked.

Then September 2020 arrived, the lease ended — and the used car market had gone completely sideways. Cars that should have been worth $20,000 were selling for $30,000. Buying the Audi out at the pre-negotiated residual value of $30,838.50 was genuinely the smartest financial move available. We bought it.

So was the lease worth it? Here’s the full math:

My husband’s verdict? He still doesn’t really have strong feelings about lease vs. buy either way. He hates car shopping so much that “whatever gets this over with fastest” has always been a significant factor in his decision-making. He now works from home most of the time and drives maybe twice a week — so the Audi’s appeal is mostly about the occasions he does drive it, which, fair enough. It’s a genuinely fun car. The heads-up display, the smooth acceleration, the way everything just works. I’ll admit I enjoy driving it when I get the chance.

My verdict? The lease served its purpose. I’m still not a lease convert. I still despise monthly payments on principle. But I’ll give this one a grudging pass.

The Numbers, All Together

What Twenty Years of Car Decisions Taught Me

The cheapest car is usually the one you already own. The 1998 Escort is my Exhibit A. I bought it in 2004 for $5,000 and sold it in 2012 for $3,000 — eight years of ownership for a net cost of $2,000. It never gave me serious trouble. Every year I didn’t replace it was a year without a car payment, without a depreciation hit, and without an afternoon at a dealership. Those are real savings, even if they don’t show up in a spending tracker.

Fuel costs are remarkably stable — if your habits are. Looking at our annual fuel spending over 18 years, the number barely moved: $2,861 in 2007, $2,332 in 2025. That’s despite gas prices swinging wildly in that time — $4 a gallon in 2008, near-record highs again in 2022. Because our driving habits and our cars’ fuel efficiency stayed consistent, the price swings mostly washed out in our annual total. The one real exception is 2020, when my husband shifted to working from home and our gas bill dropped 40% almost overnight. His commute disappeared and the pump knew it immediately.

Car payments are the enemy of financial flexibility. My philosophy on debt is simple: keep required monthly payments as low as possible. Every dollar you’re committed to paying every month is a dollar you can’t redirect somewhere else — toward savings, toward experiences, toward whatever matters to you. When both our cars are paid off, as they are right now, that freedom is tangible. We can feel it.

Even a “bad” decision can work out with good planning. The lease wasn’t my preference. But we went in with eyes open, saved the buyout funds in parallel, and when the market conditions made the buyout a clear win, we were ready. You can survive a financial decision you don’t love if you plan around it thoughtfully.

Paying cash doesn’t mean paying less attention. We’ve made plenty of deliberate choices — trading in both cars at once to negotiate from a position of strength, timing the Equinox payoff aggressively, walking away from the Audi lease with a pre-negotiated buyout price we knew we could meet. Cash buyers can be just as strategic as anyone else. Maybe more so, because we have to be ready when the moment comes.

As for what’s next — both cars are paid off and running well. We have no plans to replace either one anytime soon. My husband works from home now and barely puts miles on the Audi. I can see a future where his next car practically drives itself.

Knowing him, he’ll probably keep it until it stops running. Which, honestly, sounds about right.