9 Things Retirees Often Regret Spending Money on in Their First Year

Many new retirees treat year one like a reward for decades of work. That mindset, paired with a lot of free time and a portfolio that finally feels "available," can lead to purchases that feel great in the moment and painful a year later.

In the 2026 Retirement Confidence Survey from EBRI and Greenwald Research, two in five retirees said their expenses in retirement turned out higher than they expected when they first retired. Here are nine things retirees commonly say they wish they'd skipped buying, or at least waited on.

An oversized home or a rushed relocation

Moving somewhere new feels like the ultimate retirement reward. But buying before renting, or sizing up before downsizing, often backfires.

Retirees sometimes relocate based on a vacation impression rather than what year-round life actually looks like. A place that's perfect in February can feel isolating in August. It can also feel expensive once property taxes and homeowners association fees show up. Selling and moving again adds real costs, too: closing fees, moving costs, and the time lost settling in twice.

A boat or RV bought for a dream that didn't stick

Boats and RVs represent freedom on the showroom floor. In practice, many sit in a driveway or a storage lot and get used only a handful of times a year.

There's an active debate about how bad RV depreciation really is. Some RV fans argue the "instant regret" story is overblown. Critics point to maintenance, storage, insurance, and fuel costs that add up fast whether the vehicle gets used or not. Renting or borrowing a similar model first can be a cheap way to test whether the lifestyle fits.

A big trip paid for by selling investments in a down market

A bucket-list trip in year one feels earned. But pulling a large chunk of money out of investments during a downturn can lock in losses. That stings most early in retirement, when the portfolio has the longest time left to recover from the hit.

Interestingly, newer research suggests the bigger problem for many older adults is the opposite of overspending. Prudential's 2026 Retirement Pulse survey, fielded in the summer of 2026, reached more than 3,000 U.S. adults age 50 and older. It found that 61% feel guilty about spending on big trips, and 86% don't feel free to spend their savings on things they enjoy.

Leib Litman, discussing the findings on a Prudential podcast, said the reluctance to spend is as much a psychological hurdle as a financial one. The lesson isn't to skip travel. It's to plan for it with cash set aside in advance, instead of selling investments when markets happen to be down.

A new vehicle bought right after retiring

Trading in a reliable car for a new one is a classic first-year splurge. It feels like a fresh start, but a new vehicle loses value quickly. It can also add a payment right as income shifts from steady paychecks to withdrawals and Social Security.

Home renovations that don't pay for themselves

Many retirees use part of their first year to finally renovate the kitchen or add a sunroom. Some projects make sense for comfort and accessibility. Others cost far more than they add to a home's resale value, which matters if a move is possible down the road.

Timeshares and vacation properties

Timeshares are pitched hard to people with new free time and a travel itch. The ongoing costs often outlast the enthusiasm.

Maintenance fees are billed every year whether the owner shows up or not, and they tend to climb over time. Reselling a timeshare is also notoriously difficult. That combination is how some owners end up paying year after year for a place they rarely visit.

Skipping estimated tax payments

This one is easy to miss. While working, an employer automatically withholds taxes from every paycheck. In retirement, that stops, even though money from a 401(k) or traditional IRA may be taxable, and part of a Social Security benefit can be, too.

For 2026, the IRS generally expects quarterly estimated payments if someone will owe at least $1,000 for the year after withholding and credits. There's a second part to the test: it also applies if withholding and credits will cover less than 90% of this year's tax or 100% of last year's.

Retirees can also ask the company holding their IRA, or Social Security, to withhold taxes for them. Those who do neither can get hit with a surprise bill plus a penalty the following spring.

Claiming Social Security early without running the numbers

Claiming Social Security as soon as it's available, at age 62, is tempting after decades of working. But Social Security permanently lowers the monthly benefit for every month claimed before full retirement age.

For people born in 1960 or later, full retirement age is 67. Claiming at 62 cuts the monthly benefit by about 30%, according to the Social Security Administration. That cut isn't temporary. It lasts for life, and it can also reduce what a surviving spouse receives later.

None of that makes claiming early automatically wrong. It just means the choice deserves a real calculation rather than a reflex. Social Security's own online planning tools are free, and some retirees also run the numbers with a financial advisor before deciding.

Keeping insurance that no longer fits

Life insurance, disability coverage, and even some auto or home policies are often set up for a working life that no longer matches reality. A policy bought to replace a paycheck for a young family may not serve the same purpose once the kids are grown and the mortgage is paid off. Reviewing coverage once a year, instead of letting old policies auto-renew out of habit, can turn up both gaps and premiums that aren't buying much.

The habit that prevents most of this

The common thread in nearly every regret above is speed. Big, hard-to-undo purchases made in month two or three of retirement are based on guesses about future spending, not actual experience.

Many financial advisors suggest living through a full year of real retirement spending before locking in a major decision like relocating, buying a vacation property, or claiming Social Security. A year of bank statements shows what retirement actually costs, not what it was expected to cost on the last day of work.

That pause is free, and the numbers suggest spending often settles down on its own. In Transamerica Institute's retiree report, based on its 25th annual retirement survey fielded in late 2024, 46% of retirees said their spending had decreased since retiring, and only 13% said it had increased. Giving that pattern time to show up before making big moves may be the cheapest insurance policy in retirement.

Bottom line

Year one is the window when a stopped paycheck meets unchanged habits, and that's where the expensive mistakes cluster. Most of the regrets on this list aren't about the money itself. They're about buying something irreversible before anyone knows what retirement really costs.

Waiting a year before a big, permanent purchase costs nothing. It also buys the one thing a retirement calculator can't provide: a real record of how the money actually gets spent.

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