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Let’s say you’re sitting where a lot of our clients sit: about five years out from retirement, watching your accounts, and wondering if you’re actually ready.
Nobody knows exactly what the next five years will bring.
We didn’t know five years ago what the last five would look like, and we don’t know what’s coming in Washington, in the markets, or anywhere else.
But we don’t need a crystal ball to retire well. Stress-testing the plan and using history as a guide can better serve us than trying to predict what life will look like in 2031.
Here’s what that plan should include.
Build Your War Chest Before You Need It
If you’re planning a 25 or 30-year retirement, you’re planning through inflation, through market drops, and through stretches where equities just don’t cooperate. That means the “right” portfolio probably isn’t sitting at 100% stocks anymore, specifically if you’re planning to turn the assets you’ve saved into income.
Five years from retirement, our hypothetical friend Mark doesn’t need to touch a dime of his portfolio yet, but he knows that when the market drops (not if, when) he doesn’t want to be forced into selling stocks at the bottom to cover his bills.
So instead of scrambling in the moment, Mark builds a war chest now: a few years of anticipated income sitting in cash and bonds, ready to tap when the market is down instead of when he needs it.
Not everyone needs this. If you’ve got a strong pension, Social Security that covers your basics, a working spouse, or you plan to keep earning part-time income, your allocation can look very different.
But if you’re planning to lean on your portfolio for income, a war chest gives you options instead of panic.
The market will drop. Bake that into the plan now, while you have the luxury of time, instead of figuring it out mid-crisis.
Max Out Your Catch-Up Contributions
If you’re over 50, you get access to catch-up contributions on top of the standard retirement account limits. It’s one of the simplest ways to supercharge your savings in these final working years.
It’s worth noting there’s a notable change for 2026: if you’re 50 or older and earned more than $150,000 in FICA wages last year, your catch-up contributions can no longer go in pre-tax.
Under SECURE 2.0, they have to go into a Roth account instead. It’s worth a conversation with your planner about how it fits your overall strategy, especially if you were counting on that pre-tax deduction.
Either way, don’t leave the extra room on the table. This is one of the few places where the tax code hands you more space to save.
Update Your Beneficiaries
Take an annual snapshot. It sounds small, but this one gets skipped constantly.
Whatever the account, whatever the reason, an out-of-date beneficiary form can override your will entirely. And this isn’t only about your own accounts. If your spouse’s retirement plan has stale paperwork, they could unintentionally be disinherited too.
Review this every year, or any time there’s a major life change: marriage, divorce, a new grandchild, a death in the family.
Revisit Your Legal Documents
While you’re at it, pull out three more documents:
Your will. Your healthcare power of attorney (sometimes called a medical power of attorney or healthcare proxy) and your durable, or financial, power of attorney.
Five years out is the right window to get these current, because you don’t want to be updating your entire legal and financial life the month before you retire, and the risks associated with not having these documents are present even before you retire.
Solve for Health Insurance Before Medicare Kicks In
If you’re planning to retire before 65, you need an answer for health insurance before you hand in your notice. Medicare doesn’t start until 65, and the gap between “I retired” and “I’m covered” is why many people who want to retire cannot.
Depending on your health, your former employer, and where you live, you’ll have options: COBRA, a marketplace plan, or a spouse’s coverage.
But figure out which one applies to you and price it out before you commit to an early retirement date, not after.
The Bottom Line
Five years from now, you’ll look back at this stretch and know exactly what you did with it. You can’t control what the market or Washington does between now and then.
But you can control whether you built a war chest, maxed your catch-up contributions, kept your beneficiaries current, updated your legal documents, and solved for healthcare before you needed to.
Do that, and retirement stops being something you brace for. It becomes something you walk into.
If you’re approaching retirement or already there and want help building the structure that supports real financial peace, we can help. At Hyperion Financial, we work with our clients to build plans that reflect their actual lives – not just their balance sheets. Because the numbers matter, but the peace matters more. Click Here to schedule a conversation.