7 Retirement Mistakes High Achievers Make After They’ve Already “Won”

By most conventional measures, you’ve already won.

Your retirement accounts are well funded. Your portfolio is diversified. Perhaps you’ve even worked with a financial advisor and determined your savings have a high probability of sustaining a long, fulfilling retirement. According to the spreadsheets, you’re ready.

Yet, for many near retirees, this is the stage where the most consequential retirement planning mistakes are made.

And they tend to be subtle, considering they’re rooted in assumptions from a career-driven life that no longer fully applies. They can limit purchasing power, flexibility, and peace of mind, even if your nest egg itself remains intact.

Let’s explore seven common retirement mistakes we see among successful professionals after they’ve already “won” financially and how recognizing them can meaningfully improve not only your retirement lifestyle, but also your family’s financial future as well.

Mistake #1: Treating Retirement as a Permanent State Instead of a Flexible Phase

Many high achievers approach retirement the same way they approached their careers: as a binary decision.

You’re either working or you’re not. Accumulating or withdrawing. In or out.

These days, retirement isn’t a single, permanent state. It’s a phase that unfolds over time, potentially with multiple transition points. Even so, one of the most common mistakes we see among successful retirees is assuming they must “get it right” on day one.

It’s a mindset that creates unnecessary pressure around questions like:

What if I retire and regret it?

What if I want to work again?

What if my interests change?

So instead of experimenting, many people delay. Or they retire abruptly, only to feel boxed into a version of retirement that they don’t find fulfilling only a year or two later.

That’s why we encourage soon-to-be retirees to view retirement as a sequence of decisions, not a single irreversible move.

For example, retirement might look like:

• Stepping away from full-time work while consulting part-time
• Taking a planned sabbatical before deciding what comes next
• Working fewer hours or pivoting into an advisory role
• Pausing work entirely, then re-engaging selectively

Each of these paths preserves optionality financially, professionally, and psychologically.

And this optionality is important, because your needs and preferences will likely evolve across your years of retirement. Energy, interests, family dynamics — all can change. What feels fulfilling at 62 may not feel the same at 68 or 75.

Your retirement plan supports this flexibility. It allows you to test different versions of Life After Work, adjust your retirement income strategy as needed, and revisit decisions as circumstances change, rather than forcing you into an all-or-nothing outcome.

Winning financially gives you the freedom to choose. Treating retirement as a phase ensures you actually use it.

Mistake #2: Being an Exceptional Saver but an Inexperienced Spender

Most high achievers are excellent at building wealth.

They’ve spent decades saving consistently, maximizing retirement accounts, investing prudently, and letting compounding do its work. For many, the mechanics of accumulation (contribute, invest, reinvest) are second nature.

What’s far less familiar is the opposite process.

Very few people spend 30 or 40 years practicing how to draw down a portfolio.

So it’s natural that many retirees enter this phase assuming that a sufficiently large balance will simply sustain itself.

But retirement spending is not simply accumulation in reverse.

Once paychecks stop, your portfolio becomes the primary source of retirement income. And unlike a salary, it doesn’t arrive automatically, predictably, or tax-efficiently unless it’s structured to do so.

Retirement introduces questions most savers have never had to answer before:

• Which accounts should fund spending first?
• How do withdrawals affect taxes and future flexibility?
• How should income adjust during down markets?
• What role should guaranteed income sources play alongside portfolio withdrawals?

Building wealth gets you to retirement. Learning how to spend it, deliberately and sustainably, allows you to enjoy the years that follow.

Mistake #3: Underestimating Healthcare and Long-Term Care Costs

It’s easy to underestimate just how much medical care can cost you. A 65-year-old couple retiring today is estimated to need around $345,000 in savings just to cover health care expenses in retirement, according to Fidelity.

Medicare helps, but it doesn’t cover everything — and it offers limited protection against long-term care needs. This can lead to two common planning gaps.

First, healthcare costs are often modeled too optimistically. People assume “average” expenses without accounting for longevity, chronic conditions, or inflation specific to medical care, which has historically outpaced general inflation.

Second, long-term care is frequently treated as a distant concern or avoided altogether. Not because it’s unimportant, but because it’s uncomfortable to acknowledge our life expectancy (and not to mention difficult to predict). 

Only 27% of pre-retirees believe they’ll need long-term care. Realistically though, 70% of retirees will require long-term care at some point in their lives.

To avoid unpleasant and expensive surprises, consider:

• Stress-testing retirement income against higher healthcare costs
• Coordinating HSAs, taxable accounts, and IRAs to fund medical expenses tax-efficiently
• Evaluating long-term care insurance, hybrid policies, or self-funding strategies
• Planning how care decisions would affect a spouse or loved ones

Healthcare planning is as imperative as your investment and withdrawal strategies. 

Mistake #4: Claiming Social Security Benefits Without a Coordinated Strategy

With a substantial portfolio, strong retirement savings, and multiple accounts to draw from, Social Security can feel secondary. Almost like a supplement. Something that will cover “some” expenses while the portfolio does the lion’s share of the work.

And that’s an oversight. Social Security is the closest thing most retirees have to a pension — a guaranteed, inflation-adjusted payment that lasts as long as you do.

In other words, it sets your retirement income floor.

Unlike portfolio withdrawals, Social Security’s monthly benefits don’t fluctuate with markets. They don’t depend on asset allocation, sequence of returns, or interest rates. And they don’t require you to sell assets in down markets to generate cash flow. This reduces pressure on your portfolio and creates stability during market volatility or unpredictable healthcare costs.

But retirement benefits don’t exist in a vacuum. They affect (and are affected by) your tax strategy, withdrawal sequencing, healthcare costs, and even estate planning. Without proper planning, you could inadvertently expose yourself to higher taxes or leave a sizable amount of money on the table. 

Mistake #5: Underestimating Tax Complexity

During your career, taxes are largely automatic.

Income is withheld. Contributions reduce taxable income. Equity comp may add a wrinkle or two, but nothing proactive planning can’t handle. 

Retirement changes that dynamic.

Once paychecks stop, taxes become self-directed. You decide which retirement accounts fund spending, how much income to recognize each year, and when benefits like Social Security begin. Those choices interact in ways that aren’t always obvious. Left unmanaged, they can increase lifetime taxes and reduce flexibility.

A common misconception is that tax planning becomes simpler once work ends. In reality, retirement adds more complexity (and opportunity). For many retirees, the years between leaving the workforce and age 70 represent a unique planning window. Earned income is usually lower, which can create flexibility around withdrawals, Roth conversions, and managing future tax exposure.

That window can be valuable, but only if it’s used intentionally.

Without a coordinated approach, retirees typically default to convenience: pulling from the easiest account, paying taxes as they arise, and revisiting decisions year by year. Over time, this can lead to higher taxes later in retirement, larger mandatory withdrawals, and fewer options later on.

Mistake #6: Delaying Estate and Legacy Planning Because “There’s Time”

It’s natural to assume you’ll revisit these decisions later. You’re healthy. Your net worth is solid. And compared to questions about retirement income or healthcare, estate planning can feel distant and abstract.

At this stage in life, estate planning is unquestionably consequential. But many people rely on outdated documents or assume a basic will is sufficient “for now.”

The cost of delay leads to misaligned beneficiary designations, unnecessary legal complexity for loved ones, or missed opportunities to transfer wealth thoughtfully and tax-efficiently. More often than not, it creates inordinate stress for family members at highly emotional moments.

Estate planning ensures that your wealth supports the people and causes you care about, reduces uncertainty for loved ones, and aligns your financial plan with your broader life values. Addressed early, it reinforces peace of mind and allows you to focus less on administrative loose ends and more on enjoying the years ahead.

Mistake #7: Assuming Peace of Mind Is Driven by an Account Balance

Money answers some questions — but not all of them.

Having “enough” doesn’t automatically clarify:

• How you’ll spend your time day to day
• What gives your weeks structure
• Where your sense of contribution comes from now
• How you’ll stay connected, challenged, and engaged

Without answers to these questions, retirement can feel disorienting. This is where many retirement plans stop short.

They prove financial viability, but they don’t address how retirement feels. And peace of mind isn’t created by numbers alone. It comes from alignment between your finances, your time, your relationships, and your values.

At BEW, we call this phase Life After Work, when financial independence enables you to live a more flexible, intentional life. That could mean still working in some capacity or pivoting to something entirely new. 

If you’re beginning to explore what that could look like for you, our guide, Retirement Redefined: Your Guide to Life After Work, offers a deeper look at how to align your personal finances and retirement goals, whatever the next chapter holds in store for you.