Regret at 70 rarely comes from buying sturdy things you use constantly; regrets at this age come from buying futures you never cash.
Crafting a life you won’t side-eye at 70 is mostly about what you say yes to today.
Money choices have a way of echoing.
Some echo like a song you love, others feel like that ringtone you regret buying in 2008.
Here are the six purchases I see people regret the most when the later decades arrive.
I’m keeping this practical, conversational, and rooted in what psychology tells us about memory, identity, and how we adapt to stuff we once wanted:
1) Oversized homes
A big house can feel like arrival—space for guests, hobbies, celebrations—but then, somewhere around 70, it starts feeling like stairs, maintenance, and rooms you apologize to for never using.
I’ve watched friends hit retirement with a five-bedroom they bought for the family phase, only to realize they’re cleaning for ghosts.
The yard takes a toll and every repair is a decision tax.
Why the regret? We confuse peak moments with everyday reality.
We picture the best holidays in a big kitchen, not the daily upkeep, property taxes, and the fact that walking up two flights isn’t as breezy anymore.
Our brains love the highlight reel and skip the blooper reel.
If you’re younger and reading this, pressure test the fantasy: How often will you use every room in a normal week, not a party week? Would a smaller home near people you love make life richer, not just larger?
If you’re already in the big house and feeling the drag, there’s no shame in right-sizing.
The word downsizing sounds negative, so I prefer 'resizing'.
You’re aligning the container to the life you actually want now.
2) Timeshares
Timeshares are expert storytellers.
They sell belonging, tradition, and guaranteed vacations.
On paper, it looks like smart prepaying; in practice, many people end up battling fees, rigid schedules, and resale headaches that feel like a second job.
A couple I met while shooting street photos in Palm Springs joked that their true family tradition was arguing with their timeshare company.
They loved the idea of bringing grandkids back to the same place.
Life just didn’t cooperate.
Weddings, illnesses, school calendars; vacation windows rarely matched their points.
The psychology here is commitment bias.
Once we’ve sunk money into something, we defend it.
Then we hit 70 and ask a simpler question: Do I still want this?
Often, the honest answer is no, especially when mobility, health, or travel preferences change.
There are exceptions; some people genuinely use and love them.
However, if you’re buying one because the presentation felt warm and the free lunch was decent, pause.
Rent where you want—when you want—without the fine print hangover.
3) Brand-new cars
Cars are freedom.
New cars smell like dopamine, then the depreciation curve shows up like gravity.
By 70, a lot of folks tell me they wish they hadn’t burned so much cash on new models every few years.
Not because cars are bad, but because chasing the latest trim rarely changed their day-to-day happiness.
The premium went to status and novelty, not meaningful utility.
I learned this the expensive way in my 30s; I grabbed a car that looked great in photos and reflected some version of me I thought I wanted.
The thrill lasted a few months, yet the payments lasted a lot longer.
When I finally sold it and went with a reliable used hybrid, my shoulders dropped an inch.
I spent more on travel and cameras, two things that still pay me back with memories and creativity.
Ask yourself a blunt question: Do I want a new car, or do I want transportation plus a story about myself?
4) Trendy gadgets
“Technology is a word that describes something that doesn’t work yet.”
I love that line from Douglas Adams because it explains a drawer most of us have.
Inside: Smart devices, fitness gear, and specialty kitchen tools that promised transformation and delivered clutter.
I’m vegan—I cook a ton—and I’ve also bought gadgets that made three meals and then retired to a shelf.
The truth is, a great knife, a solid pan, and a decent blender see 95 percent of the action; the sous-vide that requires a four-step setup on a Tuesday night at 8 p.m. does not.
At 70, the regret is the cognitive load: More cables, more updates, and more learning curves.
The older adults I admire keep a streamlined arsenal.
Fewer things, better chosen, used often.
If a device requires you to become a slightly different person to see the benefit, you probably won’t stick with it.
Buy for your real routines, not your aspirational Sunday self.
5) Extended warranties
Here’s the pattern: You’re about to check out and you feel a whisper of insecurity because the thing you’re buying might break, then the extended warranty swoops in like a safety net and your nervous system says yes before your math brain wakes up.
Many add-ons are engineered for the moment you’re least rational.
You’re tired, you’ve anchored to a price, and an extra percentage feels small.
Decades later, people tally up those add-ons and see they paid for coverage that overlapped with manufacturer warranties, credit card protections, or was so restrictive it rarely paid out.
A reader once wrote me from her 70s to say she wished she had kept a “self-insurance” fund instead.
Every time she was offered a plan, she’d throw that money into a savings bucket.
By the time she stopped buying electronics altogether, that bucket could cover more than a few repairs.
There are edge cases where extended coverage makes sense, especially for high-risk items you truly can’t afford to replace.
But defaulting to decline and revisiting only when the stakes are high will save most people a surprising amount over a lifetime.
6) Luxury goods with high upkeep
I’m not anti-nice things.
A well-made watch, a beautifully engineered bike, or a timeless jacket can bring pleasure for years.
The regrets pile up around luxury items that cost more to maintain, store, insure, or clean than to enjoy.
Think boats that spend more time in the shop than on the water.
High-end handbags that live in dust bags and anxiety.
Rugs so precious that guests tiptoe around them.
Even jewelry that wants a safe and a separate rider on your insurance.
At 70, that mental overhead feels heavier than it did at 40.
On a trip through Kyoto, I noticed something about the items I envied most.
They were simple, durable, and easy to integrate into daily life.
A cup you use every morning beats an art object you worry about.
The older friends I learn from say the same.
They wish they had spent less on status and more on experiences, education, and health.
One test I use: Will this thing require a spreadsheet? If the answer is yes, it is probably a lifestyle, not a purchase.
Be honest about whether you want that lifestyle.
The bottom line
Regret at 70 rarely comes from buying sturdy things you use constantly as it comes from buying futures you never cash.
Keep asking better questions before you buy.
Choose the version of your life that will feel light and flexible later.
Spend on access, skills, and relationships.
Let your money buy time, not stress.
That way, the echoes you hear in your 70s will sound like music you still love.
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