The 5 Biggest Retirement Planning Mistakes (and How to Avoid Them)

For many people approaching retirement, the transition brings both excitement and uncertainty. After years of saving and working toward a goal, the question becomes: How do I turn what I’ve built into lasting income and peace of mind?

That’s where the real work of retirement planning begins.

In my experience as a fee-only financial planner, most mistakes don’t happen because people are careless or uninformed. They happen because retirement involves so many moving parts—taxes, investments, healthcare, and lifestyle—that it’s easy to overlook how interconnected everything really is.

Here are five of the most common mistakes I see as a fiduciary financial advisor—and how to avoid them.

1. Not Having a Written Plan

This is by far the most common gap I see when meeting new clients. Most people approaching retirement have done a good job saving—they might have a 401(k), an IRA, maybe a pension or brokerage account. But when I ask how all those pieces fit together, the answer is often a pause.

Having accounts isn’t the same as having a plan.

A written retirement plan connects the dots between your income, investments, taxes, and goals. It helps you see where your money will come from, how long it’s likely to last, and how to adapt when life changes.

One couple I worked with had plenty saved but couldn’t shake a lingering anxiety about whether it would really be enough. Once we mapped out their plan—including income sources, spending, and taxes—they could finally see how the pieces worked together. That sense of clarity changed everything.

2. Overlooking Taxes

Taxes don’t stop when you retire; they simply shift form. I often see retirees surprised by how withdrawals, Social Security benefits, and required minimum distributions interact in ways that can push them into higher tax brackets.

For example, drawing too much from a traditional IRA early in retirement can unintentionally increase how much of your Social Security income is taxed. Small details like that can add up over the years.

Coordinating your income and withdrawal strategy as part of a holistic retirement plan can help manage taxes over time—not just year to year. It’s one of the most overlooked but impactful ways a financial advisor can add value.

3. Mismanaging Risk or Cash Flow

Once paychecks stop, your portfolio becomes your income source—and that shift can make market volatility feel more personal. Some people get too conservative, parking most of their savings in cash and watching inflation quietly erode their purchasing power. Others stay too aggressive, riding out every market swing with unnecessary stress.

The best approach is balance. For many retirees I work with, that means keeping enough cash or short-term bonds to fund a few years of spending needs while letting the rest of their portfolio continue working for the long term.

That kind of structure helps take emotion out of investing—and keeps your plan grounded, not reactive.

4. Underestimating Healthcare Costs

Healthcare is often one of the biggest blind spots in retirement. Medicare helps, but it doesn’t cover everything. Premiums, supplemental policies, and out-of-pocket costs can all add up, especially if you retire before 65.

Building these costs into your retirement plan early allows for flexibility later. Whether that means funding an HSA while you’re still working or reviewing long-term care options before you need them, planning ahead makes a big difference.

As a financial planner, I’ve found that clients feel most at ease when we’ve accounted for the unpredictable—not because we can control it, but because we’ve prepared for it.

5. Trying to Do It All Alone

There’s more financial information available today than ever before—and that’s part of the challenge. Between online articles, calculators, and “expert” opinions on TV, it’s easy to get conflicting guidance.

Working with a fiduciary, fee-only financial planner can help cut through the noise. My role isn’t to predict markets or sell products—it’s to help clients make confident, informed decisions that align with their goals and values.

Even if you enjoy managing things yourself, an outside perspective can reveal blind spots and bring peace of mind.

Bringing It All Together

Retirement isn’t just about making your money last. It’s about using what you’ve built to live with clarity, purpose, and contentment.

Avoiding these five mistakes won’t make retirement “perfect,” but it can help you approach this next season with a stronger foundation and less uncertainty.

If you’re approaching retirement and want a clearer picture of where you stand—or simply want to know whether your current plan is truly working for you—I’d be glad to have a conversation.

You’ve worked hard to build your future—now let’s make sure it supports the life you want to live.
Schedule a short Discovery Call with Stillwater Financial Planning to explore how a planning-first, fiduciary approach can bring more clarity and confidence to your retirement.

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