Top Retirement Planning Mistakes Pre-Retirees Make in Mid-Year Reviews
A mid-year review catches six critical issues that a year-end review catches too late: spending that has outpaced the plan, portfolio exposure that no longer matches your timeline, withdrawals that will land you in a higher tax bracket, savings gaps from forgotten accounts, healthcare costs that were never budgeted, and Social Security timing that locks in permanently once you claim.
June and July offer the sweet spot: you have six months of actual spending data to review, plus enough runway to make tax-year adjustments that still count for this year.
Here’s what you need to look at:
- Post-retirement expenses: Several categories actually climb once you stop working.
- Sequence-of-returns risk: This does the most damage during your first few years of withdrawals.
- Your withdrawal order: How you pull from taxable, tax-deferred, and tax-free accounts.
- Savings pace and forgotten accounts: Especially those left behind at former employers.
- Healthcare and long-term care costs: Medicare only covers a portion of these expenses.
- Age-based milestones: Your Social Security claiming age and the year your required minimum distributions (RMDs) begin.
The data shows that most people reach retirement wishing they had taken these steps earlier. According to Nationwide’s 2026 Advisor Authority study, 55% of people who retired in the last five years have regrets about how they saved, with 28% wishing they had started earlier and 13% wishing they had contributed more each year. The same study found that only 40% are still on track with the budget and withdrawal plan they originally set, and 21% have had to spend more conservatively than they expected.
I’m Michael Ginsberg, JD, CFP®, founder of Ginsberg Financial Strategies. Over my 25 years working across estate planning law, commercial lending, and financial planning, and since founding this firm in 2012, I’ve watched these same six items surface in mid-year reviews time and time again. Each one responds well to a few decisions made in July.
This guide walks through all six mistakes and what to do about each. For more on how we build withdrawal sequences that hold up over a long retirement, see our retirement income strategy guide. For our full planning process, visit our financial advisory services page.
Why the Mid-Year Mark Is the Right Time to Review
Most pre-retirees treat the mid-year checkup as a quick glance at their account balances. The real value lies in the two things June and July give you that January and December do not.
First, you have six months of actual spending data, which turns your retirement budget from a loose estimate into a precise measurement. Second, you have five months left to act on what you find. This lead time is crucial for anything with a December 31 deadline: Roth conversions, charitable giving, tax-loss harvesting, and additional portfolio contributions. A December review tells you what happened. A July review still gives you the power to change it.
The Retirement Planning Mistakes Worth Catching Now
As retirement gets closer, your primary job shifts from growing your balance to protecting it and turning it into reliable income. That shift is the common thread running through all six items below.
1. Underestimating Post-Work Expenses
It is a common myth that your spending will automatically drop 20% to 30% the day you stop working. Commuting costs and work-wardrobe budgets do go away. Several other categories move in the opposite direction.
Early retirement often brings higher spending on travel, hobbies, and dining, because forty hours a week suddenly open up. Fixed costs hold steady or climb, particularly housing, property taxes, and home maintenance. This combination is why so few recent retirees manage to stick to their original budgets.
Your mid-year data solves this. Pull six months of your actual spending and sort it into what you need, what you want, and what you would wish for if the plan allows. Our Needs, Wants, Wishes Calculator does this sorting for you, and our guide to calculating how much you need to retire covers what to do with that number once you have it. The goal is simple: essential needs covered by dependable income, leaving plenty of room above that for the rest of your lifestyle.
2. Overlooking Sequence-of-Returns Risk
The order of your investment returns matters far more once you start withdrawing than it ever did while you were saving. During your working years, contributions continue on a set schedule regardless of which direction the market moves, so a decline changes your balance without changing the fact that you are still adding shares. Once you are living off the portfolio, that same decline forces you to sell depreciated assets to cover expenses. This locks in your losses and leaves you with fewer shares in the account if and when markets do recover.
Morningstar put a number on it. As reported by CNBC, a portfolio that drops at least 15% in the first year of retirement while the retiree withdraws 3.3% of the balance is roughly six times more likely to run dry within 30 years than one that starts with a positive year.
The mid-year review is where you check your exposure to this risk. The point is not to forecast what markets will do, since nobody can. It is to structure the portfolio so the forecast stops mattering. Holding several years of planned expenses in stable, liquid vehicles means a down year gets funded from that cash reserve instead of from your equity positions, whatever the market happens to be doing that year. Our page on sequence-of-returns risk walks through how we size that reserve, which is one of the core mechanics behind our Lifetime Wealth Blueprint℠.
3. Skipping a Tax-Aware Withdrawal Strategy
What you keep matters more than what you earn. Many pre-retirees expect their tax bracket to fall automatically in retirement, and that holds true only when your savings are diversified across different account types. If the bulk of your wealth sits in a traditional 401(k) or IRA, every dollar you withdraw is taxed as ordinary income.
Without diversification across taxable, tax-deferred, and tax-free accounts, a single large withdrawal (like buying a car or funding a major trip) can push you into a higher tax bracket. It can also raise your Medicare premiums through IRMAA and increase the taxable portion of your Social Security benefits. Because all three effects happen in the same tax year, the combined impact is often larger than people expect.
Mid-year is the right window for partial Roth conversions, because you can size the conversion to fill up the remainder of your current tax bracket while you still have time to adjust. Converting pre-tax dollars during lower-income years builds a tax-free bucket you can draw from later. Our approach to tax-efficient retirement planning calculates how much to convert and when.
4. Delaying Savings or Leaving Accounts Behind
Compounding rewards time far more than it rewards the principal amount. Postponing contributions by just a few years in your forties or fifties means you have to save considerably more later to reach the same goal. Pulling money out early removes both the balance and every year of future growth it would have produced.
Forgotten accounts are a widespread version of this mistake. Capitalize, working in partnership with the Center for Retirement Research, estimates that 31.9 million left-behind 401(k) accounts held roughly $2.1 trillion in assets as of July 2025, with an average balance of about $66,700. Those accounts often sit in default investments with outdated contact details and nobody keeping an eye on the fees.
If you have changed jobs more than once, spend twenty minutes of your mid-year review listing every employer you have had and confirming where each retirement plan ended up. It is arguably the highest return-per-minute task on this list.
5. Underplanning for Healthcare and Long-Term Care
Medicare starts at age 65 and covers a great deal, leaving deductibles, copays, Part B and Part D premiums, and income-related surcharges on the table. Those out-of-pocket costs add up over a retirement that could last 25 or 30 years.
Fidelity has published an annual estimate of these costs since 2002. Its 2026 estimate projects that a 65-year-old retiring this year will need $185,500 to cover lifetime health and medical expenses, up 7.5% from the previous year, assuming enrollment in Medicare Parts A, B, and D. Keep in mind that this figure covers just one person and excludes long-term care entirely.
Long-term care is an even larger financial exposure, because Medicare and standard health insurance do not cover custodial care such as assisted living or nursing homes. According to the U.S. Department of Health and Human Services, someone turning 65 today has close to a 70% chance of needing some form of long-term care in their lifetime, and about 1 in 5 will need it for longer than five years.
Your mid-year review is an excellent moment to price out long-term care coverage, look at hybrid policies that combine life insurance with a long-term care benefit, and decide how much of this risk you plan to self-fund. Pricing improves the earlier you start looking.
6. Uncoordinated Social Security and RMD Decisions
Your claiming age dictates your monthly Social Security benefit more than any other single decision. According to the Social Security Administration, for anyone with a full retirement age of 67, claiming early at 62 permanently reduces the monthly benefit by 30%. Waiting past full retirement age earns delayed retirement credits of 8% per year, giving you a boost of up to 24% if you wait until age 70. These percentages vary for other birth years, so run the math against your own earnings record.
Required minimum distributions (RMDs) are the other half of this decision. Under current law, RMDs begin at age 73, rising to 75 in 2033. Once they begin, the IRS requires you to withdraw a percentage of your tax-deferred accounts every year, whether you need the money or not. For those with large traditional balances, that can produce a bracket-shifting distribution.
These two timelines interact closely. The years between your retirement date and your RMD start date are often your lowest-income years, which makes them the best window for Roth conversions that shrink your future RMDs. Mapping your Social Security claiming age alongside your projected RMDs coordinates the entire sequence, and it sits at the center of the Personal Pension-Like Paycheck we build for our clients.
See Where Your Plan Actually Stands
A mid-year review works because it pairs hard data with time left on the clock. Six months of spending tells you what your retirement actually costs, and five months of runway means you still have time to optimize your strategy for this tax year.
At Ginsberg Financial Strategies, we build retirement plans around dependable lifetime income, so your essentials are covered by sources that keep paying out regardless of what the markets do. If you want a clear look at where your distribution plan sits with five months left in the year, reach out to us or start with the Lifetime Wealth Blueprint℠.
Protect what you have and create lifetime income.
