Retirement Retirement Planning

Don't Retire in 2027 if Any of These 6 Things Apply to You

The financial hurdles to address before you retire next year.

By Josh Koebert , Edited by Laura Hohenstein

Updated Nov. 15, 2026

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Having the perfect retirement date in mind and having the means to commit to it are two very different scenarios. An otherwise reasonable retirement plan you made years ago can seem uncertain when your paychecks stop.

These six conditions aren't, individually, a total deal-breaker for diving into retirement. But since they can leave you with less financial security in your senior years, they're worth addressing first.

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Many successful investors eventually reach the same moment. The saving is done, the portfolio is built, and the question quietly changes from how much can I grow this to how much can I take out? Get that second question wrong and decades of good investing can come apart in a handful of years.

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You have high-interest debt

Credit card balances and other expensive loans add two stressors to a retirement budget. First, they add additional monthly payments, and that money can't be used for food, healthcare, or other essentials. They also come with interest charges that take away from your wealth instead of helping it grow.

Not all debt is the same, and manageable, lower-rate mortgages may still be affordable enough to pay while retired. But if credit cards or other loans take a significant part of your monthly budget, one more year of working could help you pay down those balances.

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You have no reserve for your first retirement withdrawals

What happens if you need emergency house repairs or have to replace a vehicle? If your cash cushion isn't adequate, you may turn to your investments for relief. But if you need to sell investments during a market downturn, this brings sequence-of-returns risk into the equation. It works like this: Selling investments at depressed prices early in your retirement leaves less in those accounts to grow when the market rebounds.

Schwab says to keep roughly one year of spending not covered by other income in cash, with another two to four years of that spending in high-quality short-term bonds or bond funds. This can help you avoid selling stocks during a downturn and give them time to recover for your later years.

You have no health coverage before 65

Leaving the workplace before 65 can leave you without more than a paycheck; for some, it also means losing their health insurance. If you're not yet eligible for Medicare, you'll need another source of coverage, such as COBRA, a Marketplace plan, or another employer's plan through a spouse. Losing job-based coverage qualifies you for a Marketplace Special Enrollment Period.

Marketplace financial assistance depends on income and household size, and subsidies and plan prices change every year. If premiums seem out of budget, working a bit longer can buy you time until you become Medicare eligible.

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Most people spend their entire working lives focusing on one thing: growing a pile of money. Then they retire and discover the skill they actually need is close to the opposite. Turning that pile into steady income, year after year, through good markets and bad, without ever running out. It may be the least discussed and most consequential transition in personal finance, and plenty of otherwise careful investors walk into it with no real plan.

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You have many years left on your mortgage

Not all mortgage payments put a big strain on a retirement budget. If yours is affordable, retiring may not make much of a difference. For those with bigger housing costs, including taxes and insurance, the loss of income can bring them dangerously close to being 'house poor.'

Look at your payoff date and the number of retirement years that require payments. If your anticipated Social Security payments and other retirement income aren't enough, it's worth looking at extending employment or downsizing to better meet your new income reality.

Others still depend on your paycheck

A stable retirement plan assumes you're taking care of yourself, but it may not consider support for children, an adult child, or another relative. If you're still paying recurring transfers, tuition, insurance, housing, cell phone, or child care for a loved one, this may not stop just because you retire.

Develop a plan for reducing these costs while you continue working, or consider an affordable ongoing support amount that works for everyone. You don't have to stop helping out; just be sure you budget for it.

Claiming benefits now would permanently reduce them

Claiming Social Security before full retirement age reduces the monthly benefit. For those born in 1960 or later, full retirement age is 67, and claiming at 62 reduces the retirement benefit by 30% compared with claiming at 67. Wages from another year of working could let some people postpone claiming and reduce the early-claiming reduction. You can also retire and delay claiming if you have other income or savings to cover the gap.

This isn't an option for everyone. But since early claiming generally means a permanently lower monthly benefit, it's a legitimate consideration.

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The counterpoint: Working has a cost, too

No good argument for working longer would be complete without acknowledging the drawbacks. Working can prevent you from spending time with family, traveling, or caregiving for a sick loved one. The extra cash or benefits from a physically demanding or highly stressful job may not be worth the toll, making 'one more year' a poor trade.

In the end, working longer or retiring now is a very personal decision that's dependent on too many factors to leave to someone else.

Bottom line

If you haven't planned for a mortgage, the loss of work-based health insurance, a reduction in senior benefits, credit card debt, or any of the other factors on our list, retirement could be further off than you had hoped for.

Your income gap may be filled by working just a few more months. Or you may be able to coordinate with a spouse for an ideal compromise that lets you both retire sooner. With many older adults continuing to work, at least part-time, into their late 60s and 70s, you'll at least be in good company.

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