Most retirement planning focuses on when to stop working. The bigger question is what closes the day you do. Some of the things to buy before you retire are only available while you still have a paycheck, and the rest get sharply more expensive the moment that paycheck ends. Here are five, with the numbers behind each one.
Health insurance, if you're retiring before 65
Medicare doesn't start until 65. Retire at 60 and you have a five-year gap you have to cover yourself. People don't feel this one until they've already left the job.
While you're employed, your employer covers most or all of the premium. You might pay $200 a month and never think about it. The day you leave, you're buying your own coverage on the market at full price. The ACA subsidies that made that manageable expired at the end of 2025, which affects about 22 million people.
A couple in Atlanta went from $162 a month to $483 a month for the same plan with the same benefits. That's nearly $3,900 more per year for nothing extra. COBRA is the usual fallback, and it runs $650 to $750 a month for an individual and lasts only 18 months.
Run the math on five years, ages 60 to 65, and you're looking at somewhere between $42,000 and $114,000 in premiums alone, depending on your coverage and where you live. That's a real money problem that needs a real plan. Price out what your coverage will actually cost before you set a retirement date, while you still have options.
Long-term care insurance, before a diagnosis closes the door
70% of people aged 65 and older will need some form of long-term care before they die. That covers a nursing home, an in-home aide, memory care, assisted living. And 70% of baby boomers believe Medicare pays for it. It doesn't. Medicare covers short-term skilled nursing after a hospitalization, and that's it. It does not cover custodial care, which is someone helping you get dressed and eat. Custodial care is what most long-term care actually is.
Without a policy, that money comes out of your retirement accounts or it comes from your kids.
A policy bought at 55 costs a man about $950 a year and a woman about $1,500 a year. Wait until 65 and it's about $1,750 a year for a man and $2,200 a year for a woman. Nearly double in ten years, and that assumes you can still qualify at all. One major health event, one diagnosis, and the carriers will not cover you. It's a window that closes and does not reopen.
Most traditional long-term care policies have left the market. Carriers stopped offering them when people lived longer than projected and the math stopped working. What's available now is mostly hybrid coverage, usually a life insurance policy with a long-term care rider. If you need care, it pays for the care. If you never need it, the death benefit passes to your heirs. That answers the "what if I never use it" problem.
Life insurance, at your current age and health
The logic here is simple. If you have a spouse who depends on your income, or a mortgage you want covered, lock in your rate before you retire.
A healthy non-smoking man buying a $500,000 20-year term policy at age 50 pays about $75 a month. The same man with the same policy at 60 pays roughly $300 a month, nearly four times as much for identical coverage. At 65, traditional term coverage either gets very expensive or isn't available. The hybrid policies work the same way, priced on both age and health. Every year you wait costs you real money.
Disability insurance, for the years right before you stop
This one works differently. It protects the stretch of years leading into retirement, when your earnings peak.
Income is usually highest in your fifties. The mortgage is paid down, the kids are done with college, and you can finally save aggressively. Those are the years your portfolio grows fastest. A disability in that window costs you the income, the savings you would have built, the employer match you would have gotten, and the compound growth on top of all of it. You may also have to pull from retirement accounts early, triggering taxes and penalties.
The Social Security Administration says 25% of workers become disabled before retirement age. You're three times more likely to become disabled than to die before you retire. If you file for Social Security disability benefits, the average payout is about $1,582 a month, with a 68% denial rate. Disability causes nearly half of all foreclosures in this country. It can unwind years of building in a very short time.
People carry life insurance because they're thinking about death, and disability is statistically the more likely event. If you don't have long-term disability coverage, look into it. Once you're retired you no longer need it, since it only has value while a paycheck is coming in.
A house, a mortgage, or a HELOC
Banks want W2 income. That's how they verify you can make the payments. Once you're retired and drawing from investment accounts, the math looks different to a lender. You might have $1.2 million in a brokerage account, but if your W2 income says zero, qualifying gets difficult. Plenty of retirees with solid net worth get turned down for a home loan because their income is too low on paper. The bank doesn't care about your portfolio balance the way it cares about your pay stub.
If you're planning to downsize, relocate, or buy a retirement home, it's usually best to do it while you're still working. Same with a HELOC. You can qualify in your last working year and never touch it until you need it. Wait until after you've retired and your chances of getting one are very low.
Everything on this list needs income
Health insurance premiums, long-term care coverage, life insurance, a mortgage payment or a HELOC. All of it requires income while you're retired, and the quality of your retirement depends heavily on where that income comes from.
Most people default to the same two answers, Social Security and selling stocks out of the retirement portfolio. The problem with the second one is that the market doesn't care about the timing of your retirement. A bad crash at 63 or 64 that forces you to sell can permanently damage the portfolio, because the money you sold can't participate in the recovery. That's sequence of returns risk, and it's the thing most retirement plans don't account for adequately.
There are ways to produce income in retirement that don't depend on stock prices. Dividends are one, though a dividend can be cut and the share price still moves. There are bonds, including treasuries, high yield corporate bonds, and municipal bonds. A high yield savings account is useful for liquidity. And there are secured mortgage notes, where you sit in the bank's seat. A homeowner or a real estate investor wants to buy a property, you fund the loan, and you're in first position, secured by the property. That's the same position a bank holds on a conventional mortgage. You receive fixed monthly payments of principal and interest for the term of the loan, usually five to seven years, and it can be done inside a retirement account. A solo 401(k) and a self-directed IRA both allow it.
Most regular investors never hear about that last one from an advisor, and the reason is structural. There's no brokerage fee and no fund management fee in it for Wall Street. Some of the wealthiest financial institutions in the world make their money exactly this way.