People most often leave money on the table when they retire in four places: employer benefits, tax breaks, Social Security choices, and low-income years. Most of these come with deadlines or age windows. Miss one, and you can’t go back for it.
It’s an easy list to overlook, since most of it comes due while you’re busy wrapping up a career. The 10 places below follow the order you’ll meet them, from your last working years to your first years retired.
Where Do You Leave Money on the Table Before You Retire?
Before you retire, money slips away through a missed match, unused catch-up room, a thin HSA, and forgotten accounts. These are the last years you can add to tax-advantaged accounts from a paycheck.
1. Are You Getting Your Full Employer Match and Catch-Up Contributions?
An employer match is part of your pay, and any match you don’t collect is gone for good. If your plan matches half of what you contribute up to 6% of salary, contributing 4% leaves part of the match behind.
Check your vesting schedule before you set a retirement date. If you leave before you’re fully vested, you forfeit the unvested part of your employer’s contributions.
At 50 and older, you can save more. For 2026, the 401(k) limit is $24,500, and catch-up contributions add $8,000. People 60 to 63 can add $11,250 instead. IRAs allow $7,500, plus $1,100 at 50 and older.
If you earned more than $150,000 from your employer in 2025, your 2026 401(k) catch-ups must go in as Roth contributions.
2. Have You Filled Your HSA Before Medicare Starts?
A health savings account lets money go in, grow, and come out for medical costs without federal tax. You need a high-deductible health plan to contribute, and contributions stop once you enroll in any part of Medicare.
For 2027, you can contribute $4,500 with self-only coverage or $9,000 with family coverage, plus $1,000 at 55 and older. If you sign up for Medicare after 65, stop contributing six months before you enroll. Premium-free Part A coverage reaches back up to six months, and contributions made in those months can draw a penalty.
Save your medical receipts. You can reimburse yourself tax-free later for qualified expenses you paid out of pocket after you opened the HSA.
3. Do You Have an Old 401(k) or Pension You’ve Lost Track Of?
Accounts left at past employers are easy to lose after a merger, a plan change, or a move. The Labor Department’s Retirement Savings Lost and Found and state unclaimed property sites can help you track down a lost 401(k) or pension.
Once you find one, roll it over into an IRA or your current plan so it sits with your other savings.
What Money Is at Stake When You Leave Work?
Leaving work sets three things: your employer’s final payout, your household’s Social Security income, and how you use the low-income years after. Several of these choices are hard to reverse.
4. What Does Your Employer Owe You When You Leave?
Your last paycheck can carry more than salary. Before you give notice, find out how your employer handles each of these:
- Unused vacation: Some states require employers to pay it out, and some companies pay it by policy.
- Bonuses: Many plans pay only if you’re on the payroll on the payout date.
- Stock awards and ESPP shares: Unvested grants often end when you leave, and purchase periods can close early.
- Deferred compensation: The payout schedule you chose years ago decides when that income lands on your tax return.
A few weeks’ difference in your last day can decide whether you collect a bonus or reach another vesting date.
If you have a pension, the choice between a lump sum and monthly payments is permanent in most plans. Lump sums are figured from interest rates. The same pension can pay a bigger or smaller lump sum depending on the year you retire. Check when your plan pays a full pension before you pick a date.
5. Is Your Household Getting Every Social Security Benefit It Can?
Married couples leave Social Security money on the table when they plan each benefit alone. A spouse can collect a spousal benefit of up to 50% of the other’s full retirement age benefit, if that’s more than their own.
Delay matters most for the higher earner. Each year past full retirement age adds 8% to a benefit, up to age 70. When one spouse dies, the survivor keeps the larger of the two benefits. The higher earner’s delay raises the income the surviving spouse lives on.
Divorced spouses can also claim on an ex’s record if the marriage lasted at least 10 years and they haven’t remarried.
The Social Security Explorer in the Boldin Planner compares claiming ages for you and your spouse. You’ll see how each pair of ages changes your lifetime benefits.
6. Are You Using Your Low-Income Years Before RMDs?
The years between retiring and the start of Social Security and required minimum distributions can carry your lowest taxable income in decades. Leave them empty, and you waste room in the lowest tax brackets.
Two moves use that room:
- Capital gains at 0%: For 2026, long-term gains are taxed at 0% up to $49,450 of taxable income, or $98,900 for joint filers. For 2027, those limits rise to $51,050 and $102,100. You can sell appreciated shares, owe no federal tax on the gain, and buy back in at a higher cost basis.
- Roth conversions: Converting part of a traditional IRA to a Roth in these years means paying tax at a low rate now. It also shrinks the RMDs you’ll take later.
Both moves raise your income for the year. That can raise Medicare premiums two years later and cut ACA subsidies before 65, so size each one with the side effects in view.
Where Do You Leave Money on the Table After You Retire?
After you retire, money goes unclaimed in new tax breaks, Medicare surcharges you can appeal, idle cash, and home equity.
7. Are You Claiming the $6,000 Senior Deduction?
Taxpayers 65 and older can deduct an extra $6,000 each for tax years 2025 through 2028. A married couple who both qualify can deduct $12,000. You can claim it whether you itemize or not. It comes on top of the extra standard deduction people 65 and older already get.
The deduction shrinks by 6% of modified adjusted gross income above $75,000 for single filers or $150,000 for joint filers. Married couples must file jointly to claim it, and each qualifying person needs a valid Social Security number. A smaller Roth conversion or IRA withdrawal in a given year can keep more of the deduction. The One Big Beautiful Bill Act created the deduction along with other changes for retirees.
8. Can You Lower Your Medicare Premiums After You Stop Working?
Medicare sets its income-related surcharges, called IRMAA, on Part B and Part D from your tax return two years back. A high salary in your last working years can bring a surcharge on income you no longer have.
Retirement counts as a life-changing event. You can file Form SSA-44 with Social Security and ask it to base the surcharge on your current income. Marriage, divorce, a spouse’s death, and the loss of a pension also qualify.
9. Is Your Cash Earning Anything?
Cash sitting in a checking account can earn close to nothing while inflation shrinks what it buys. Keep enough there for monthly bills, and move the rest of your emergency fund or spending reserve to an account that pays interest.
High-yield savings accounts, money market funds, CDs, and Treasury bills all pay more than most checking accounts. Interest on Treasury bills is exempt from state and local income tax, which helps in high-tax states.
10. Is Your Home Equity Part of Your Plan?
For many retirees, home equity is the largest asset they own, and it’s often left out of the retirement plan. You can turn equity into income in three main ways:
- Downsize: Moving to a smaller or cheaper home frees cash and can cut property tax, insurance, and upkeep. The first $500,000 of gain is tax-free for couples, or $250,000 for single filers, if you’ve lived there two of the past five years.
- Rent out space: A spare room or an accessory unit can bring in monthly income.
- Use a reverse mortgage: A reverse mortgage lets homeowners 62 and older draw on their equity with no monthly loan payments. You still pay property tax, insurance, and upkeep, and falling behind on them can make the loan come due. It also carries fees and reduces what your heirs inherit.
Where Is Your Plan Leaving Money on the Table?
Most of the money on this list depends on timing, from your last day at work to the year you sell your home. Each choice moves the others. A Roth conversion can use up your 0% capital gains room, shrink your senior deduction, and push up Medicare premiums in two years.
In the Boldin Planner, you can test your retirement date, claiming ages, Roth conversions, and home equity side by side. Each scenario shows how your taxes and the life of your savings change. Timing also drives the most common retirement mistakes, from claiming Social Security early to drawing down accounts in the wrong order.
Leaving Money on the Table FAQ
What does leaving money on the table mean in retirement planning?
Leaving money on the table in retirement planning means missing money you could have collected or kept. Common examples include an unclaimed employer match, an unfunded HSA, and Social Security claimed without a household plan. Low-income years left unused for Roth conversions or 0% capital gains also count.
What can you max out in the years before you retire?
In the years before you retire, collect your full employer match first, then max out your 401(k) and IRA, including catch-up contributions. For 2026, the 401(k) catch-up is $8,000 at 50 and older, rising to $11,250 for those 60 to 63. HSAs take an extra $1,000 once you turn 55.
Who qualifies for the $6,000 senior deduction?
The $6,000 senior deduction covers taxpayers who are 65 or older by the end of the tax year, from 2025 through 2028. Itemizers and non-itemizers both qualify, and joint filers can claim $12,000 when both spouses qualify. It phases out above $75,000 of MAGI, or $150,000 on a joint return.
Can you contribute to an HSA after 65?
You can contribute to an HSA after 65 only while you’re covered by an HSA-eligible plan and not enrolled in Medicare. Enrolling ends new contributions. The balance stays yours to spend tax-free on qualified medical costs, and that includes premiums for Medicare Part B and Part D.
How do I find money from an old 401(k)?
To find money from an old 401(k), contact your former employer’s plan administrator first. If the company merged or closed, search the Labor Department’s Retirement Savings Lost and Found and your state’s unclaimed property site. The National Registry of Unclaimed Retirement Benefits offers another free search.
