6 Silent Killers of a Great Retirement

You can do everything “right” on paper. Save diligently. Invest responsibly. Retire with more than enough money.

And still have your retirement quietly undermined by a few loose ends.

These aren’t dramatic mistakes. They don’t usually show up as a crisis on day one. Instead, they create stress, bad decisions, and unnecessary taxes over time. I see them constantly, even among well-prepared retirees.

Below are six of the most common retirement loose ends I see. All of them matter. The last three are the most dangerous.

1. No Plan for Long-Term Care

When most retirees think about long-term care, they think about insurance. Or more often, they think about avoiding the topic altogether.

But the real issue isn’t whether you buy a policy. It’s whether you have a plan at all.

Most people know long-term care is a possibility. Few have decided how it would actually be paid for. They are hoping it never becomes an issue. That hope is risky. A majority of people over age 65 will need some form of care, and Medicare does not cover it.

In reality, there are only three ways long-term care gets handled:

• Medicaid, which requires spending assets down and gives you less control

• Long-term care insurance, which has become more expensive and harder to qualify for

• Self-insuring, which is how many retirees end up paying for care whether they planned to or not

The biggest problem is not the cost itself. It’s the uncertainty.

If long-term care is not modeled into your retirement plan, it can disrupt your tax strategy, change how aggressive you should be with Roth conversions, and force large distributions at the worst possible time. For married couples, when the first spouse needs care, the surviving spouse is often left wondering whether there will still be enough money when it’s over.

You don’t need a perfect answer. You do need a decision.

Leaving long-term care as an unanswered question is one of the most dangerous loose ends in retirement.

I’ve gone deeper on this in my video: How to Plan for Long-Term Care Expenses in Retirement.

2. Only One Spouse Understands the Plan

In many households, one person handles the big picture. The investments. The tax strategy. The withdrawal plan.

The other spouse trusts that it’s being handled.

That arrangement works fine, until it doesn’t.

Retirement plans often work beautifully right up until the primary planner dies early or can no longer manage things. That’s when complexity becomes the enemy. Accounts are scattered. Decisions feel overwhelming. The surviving spouse is forced to learn everything while dealing with grief, stress, and pressure from people who may not have their best interests at heart.

This has nothing to do with intelligence or capability. It’s about preparation.

A great retirement plan is only great if the surviving spouse knows how to carry it forward. They don’t need to understand it at the same level. But they do need to know the basics, or at least know exactly who to call and what questions to ask.

If you are the only one who understands how your retirement works, your plan is fragile by definition.

I’ve addressed this more deeply in my article What Retirees Should Fear Most. 

3. Outdated Risk Assumptions

One of the most common things I see is retirees holding a 60/40 portfolio simply because they think that’s what they’re supposed to do.

For decades, that mix has been treated as the default retirement allocation. But retirement is not the place for rules of thumb.

There is no single “right” stock-to-bond mix that fits everyone. If your allocation is wrong for your situation, it can hurt you in two ways. You can take more risk than your retirement income can withstand, or you can be so conservative that you miss growth you still need.

Most people choose an allocation first and hope it works.

It should be the opposite.

Your investment mix should come from the plan. When you model your spending and income, you can see in real dollars how much volatility your plan can absorb. That is your risk capacity, and it is often very different from how aggressive you feel.

When risk is not aligned with the plan, markets stop being a math problem and start becoming an emotional one.

4. No Plan for Downturns, Just a Plan Built on Hope

This is where many retirement plans quietly fall apart under normal market conditions.

On paper, they look fine. But they are built on average returns and a lot of hope. Hope that markets cooperate. Hope that downturns are short. Hope that you do not have to sell at the wrong time.

Hope is not a strategy.

If your plan requires you to sell investments every month regardless of what the market is doing, a normal bear market becomes a real problem. That is when people panic, abandon good plans, or lock in losses they did not need to take.

This is why we use a spending bucket approach.

By separating near-term spending from long-term growth, your income does not depend on what the market is doing right now. For our clients, we typically set aside about five years of spending, structured based on what the plan shows they will need each year.

Historically, most bear markets recover within that window. Some take longer, many are shorter, but five years provides breathing room to avoid forced decisions.

The biggest benefit is behavioral. When markets are down, you are not forced to sell growth assets to pay the bills. When markets recover, you refill the spending bucket intentionally.

If your retirement income strategy does not change how you spend during downturns, it is not really a strategy at all.

5. No Coordinated Tax Planning

This is where a lot of damage happens quietly over time, especially in the early years of retirement.

When you first retire, before Social Security and required minimum distributions begin, you often have a window where your income is lower and your flexibility is higher. I call this the Golden Runway.

That window does not last forever. And once it closes, you do not get a do-over.

Roth conversions without guardrails can trigger higher Medicare premiums, increase how much of your Social Security gets taxed, or create regret later when flexibility is gone. On the other hand, doing nothing during this window can leave you with higher taxes later simply because the IRS is forcing income on you.

IRMAA surprises are another example. Medicare premiums are based on your income from two years prior, so decisions you make today can quietly raise healthcare costs down the road.

Charitable giving can also work against you if it is not coordinated. Writing checks instead of using strategies like qualified charitable distributions or donor-advised funds often means paying more tax than necessary while still giving the same amount.

None of these mistakes feel dramatic in the moment. But over time, they compound.

A real retirement plan coordinates income, taxes, healthcare, and giving while you still have control.

I’ve gone deeper on this in my article The Retirement Tax Sweet Spot: Use It or Lose It

6. No Written Income Plan

This is the most dangerous loose end I see in retirement.

Many retirees know how much they can spend. Far fewer know exactly where that money should come from each year.

There is a big difference between a spending number and a written income plan.

When should Social Security start? Which accounts should be used first, and why? How do you handle irregular expenses like cars, home repairs, or travel? What happens if spending is higher in the early years?

When those decisions are made in advance, you are not guessing. You are simply following the plan.

That is what allows retirees to spend with confidence instead of second-guessing every decision.

If you do not have a written income plan, you should.

If you would like help building one, you can schedule a Retirement Clarity Meeting. This is not a sales call. There is no pressure. It is simply a conversation where we look at the big picture of your retirement and see whether there is any value I can add.