What Retirees Regret Most About Money?

Ask a room of retirees what they'd do differently with money and you will not hear a single word about Nvidia.

No one says "I should have timed the 2008 bottom." Nobody mourns a fund they didn't pick.

What they actually say is duller, and much more expensive: I should have started sooner. I should have kept going. I had no idea how any of this worked.

Three large U.S. surveys — TIAA Institute, Transamerica, EBRI — keep landing in the same place. And buried in the data is one regret almost nobody warns you about, which is that a meaningful share of retirees are sitting on money they're too scared to spend.

Let's go through the list. 👇

Notice what's missing from that entire list: investment performance. Not one line is about returns.

Every single regret is a planning regret — timing, habits, knowledge, contingency. Which is good news, because those are the only parts you actually control.

(A caveat worth keeping: TIAA's own release of the same study reported 76% regretting not starting earlier and 71% wishing they'd saved more. Different question wording, different numbers. Treat the themes as the signal, not the decimals.)

Everyone nods at this one and nobody feels it, because compounding is invisible until it isn't.

So here's the feeling, in numbers. Two people, both investing $500/month at a 7% return, both retiring at 65:

Twice the contributions bought five times the outcome. The late starter would need to put in roughly $2,500 a month to catch up — five times the savings rate to buy back twenty years.

That's the whole regret. The first decade of saving isn't 25% of the work; it's most of the result.

This one is sneakier, and it's the biggest number in the whole dataset: 69% of Transamerica's retirees wished they'd saved more consistently.

The typical pattern: 3% in your thirties, a pause during a rough stretch, a bump in your forties, a hardship withdrawal, a restart at fifty. Money went in. It just kept leaving, and the clock kept running.

The fix is structural, not motivational. Auto-escalation — the setting that raises your contribution 1% a year automatically — works because it removes the monthly decision.

And then there's the raise. You get $5,000 more a year. Two options:

That $2,500/year, invested at 7% for 25 years, is roughly $158,000. Split two raises that way across your career and you've added a quarter million dollars without a single month that felt like sacrifice.

65% wished they'd been more knowledgeable about retirement saving and investing.

That's not "I wish I'd day-traded better." The missing knowledge is almost always basic:

Here's the uncomfortable version: you can spend 40 years successfully accumulating a large balance and arrive at retirement with no idea how to convert it into income. Accumulation and distribution are different sports, and almost nobody trains for the second one.

It handles a lot. It does not handle everything, and it costs money on day one.

2026: standard Part B premium is $202.90/month (more for higher incomes) with a $283 deductible. For a couple that's roughly $4,870/year before a single prescription.

Fidelity's 2026 estimate projects a 65-year-old retiring this year could spend an average of $185,500 on healthcare across retirement. That's up from $172,500 in last year's version — the number keeps climbing.

And the asterisk is the whole story: that figure excludes long-term care. Medicare states plainly that it doesn't pay for long-term custodial care — the ongoing daily-living help that is, for most families, the single largest bill in the entire retirement.

So the regret isn't usually "healthcare was expensive." It's "I budgeted for premiums and copays, and then the thing that actually happened wasn't on the list."

This is the one that should genuinely change how you plan, and almost nobody builds for it.

EBRI's 2024 study: 58% of retirees left work earlier than they expected. Why?

TIAA found 51% had left the workforce for more than a year due to an unplanned event, and 49% regretted not planning for late-life events like illness, job loss and caregiving.

Read that as a coin flip. Your "I'll work until 67" plan has roughly even odds of being overruled — by your body, your employer, or a parent who needs care.

And retiring three years early is a triple hit: three fewer years of contributions, three fewer years of compounding, three extra years the portfolio has to fund. It's not a 5% adjustment. It can be a 20–30% swing.

43% of Transamerica's retirees said debt interfered with their ability to save (earlier waves put it as high as 48%).

And it follows people in. EBRI found that among retirees carrying debt, 68% had outstanding credit-card debt.

Credit-card debt in retirement is a uniquely bad trade: you're paying ~20%+ interest out of a portfolio you hope earns 7%. You can have $800,000 saved and still feel broke every month if enough of the cash flow is pre-committed to debt and housing.

Which is why a portfolio balance alone tells you nothing about how retirement will actually feel.

People treat the claiming age like a birthday. It's one of the largest financial decisions of your life.

For anyone born in 1960 or later, full retirement age is 67. Wait until 70 and you receive 124% of your full benefit — because delayed retirement credits run about 8% per year past FRA.

Claim at 62 instead and you lock in a permanently reduced check. On a $2,500 full benefit, that's roughly the difference between $1,750/month at 62 and $3,100/month at 70 — inflation-adjusted, for life, with survivor implications for a spouse.

That doesn't make 70 the right answer. Health, marital status, cash needs, taxes and other income all matter. But it does mean claiming is a lifetime income decision, not a paperwork milestone — and it's one of the few here you can't redo.

Here's the finding that reframes the entire article.

EBRI found 38% of retirees describe themselves as having a "savings mindset" — versus only 11% with a "spending mindset."

Read that ratio again. Roughly three and a half times as many retirees are still in saving mode as are comfortable spending.

Think about what that means. You spend forty years training yourself to defer, accumulate and not touch it. Then one Friday you're supposed to flip the switch and start dismantling the thing you spent your whole life building.

Most people can't. So they don't. They eat the cheap dinner, skip the trip, decline the flight to see the grandkids — sitting on a portfolio that could easily cover all of it.

(The other tail is real too: EBRI found 31% of retirees said they were spending somewhat or much more than they could afford, up from 17% in 2020. Both failure modes exist.)

But underspending is the quiet one, because it never looks like a crisis. It just looks like a careful person.

And retirement has a second currency besides money:

Money you never spend wasn't saved. It was just never used.

Underneath everything above sits one gap: people accumulate a number and never build the machine that turns it into income.

Retiree with $1 million, Social Security, a paid-off house and no pension. Great. Now answer:

Morningstar's research put a 3.9% starting withdrawal rate on a 30-year, inflation-adjusted retirement with a 90% success probability — not a rule, an illustration of how sensitive the answer is to assumptions.

And taxes don't retire when you do. Traditional 401(k) and IRA withdrawals create ordinary income. Up to 85% of Social Security can become taxable depending on your other income. RMDs generally begin at 73 (75 for those turning 74 after 2032) whether you want the money or not.

Which is why $500,000 in a Roth is not economically the same as $500,000 in a traditional IRA. Same headline. Very different spendable amount.

Every regret on this list is boring, and that's exactly the point. Retirement isn't lost in one dramatic decision. It's lost in a hundred small deferrals.

Save later. Save irregularly. Never learn the rules. Assume the schedule holds. Ignore the debt. Claim Social Security on autopilot. Build a balance without building an income plan. And then, after all that, be too frightened to spend what you've got.

Notice that none of it requires bad luck. It just requires waiting.

The cruel arithmetic: at 25 these are cheap to fix. At 35, easy. At 45, urgent. At 55, tight. At 65, several of them are simply closed.

Retirement is thirty years long. Plan for the whole thing — and then, please, actually spend some of it.

See you next issue. 🪙

Penny Brief is for informational and educational purposes only and is not individualized investment, tax or financial advice. Survey figures come from the TIAA Institute (2026 retiree research), Transamerica Center for Retirement Studies (2025 Retirement Realities and earlier waves) and EBRI (2024 Spending in Retirement Study); percentages are not directly comparable across studies because samples, dates and question wording differ, and the same TIAA study has been reported with materially different figures depending on the question asked. Other figures: 2026 Medicare Part B premium of $202.90 and $283 deductible (CMS); Fidelity 2026 Retiree Health Care Cost Estimate of $185,500, which excludes long-term care; Social Security full retirement age of 67 for those born 1960 or later, 124% of the full benefit at age 70 and roughly 8% annual delayed retirement credits (SSA); Morningstar's 3.9% base-case starting withdrawal rate; IRS rules on Social Security taxability and RMD ages 73/75. Compounding examples assume a constant 7% annual return with no fees or taxes and are illustrations, not projections. Confirm your own situation with a qualified professional.

Sources: TIAA Institute; Transamerica Center for Retirement Studies; Employee Benefit Research Institute; Fidelity; CMS/Medicare; Social Security Administration; Morningstar; IRS; U.S. Bureau of Labor Statistics.