Retirement planning for executives in the last five working years

How do you pick a retirement date the numbers support?

Start with what you spend, not what you've saved. Take your yearly spending, subtract guaranteed income such as Social Security or a pension, and see what savings must cover. A hypothetical executive spending $200,000 a year with $60,000 of Social Security needs $140,000 from savings, and $140,000 divided by a 4% starting withdrawal is $3.5 million. That is a rule of thumb, not a promise.

Mariner Wealth Advisors tests the date against weaker markets as well as average ones, because a bad first three years hurts more than a bad year twenty. Evidence from long-term research guides the plan. A market forecast doesn't. Investing involves risk, including loss of principal.

When should you claim Social Security?

Claiming later raises the monthly check, and full retirement age is 67 for anyone born in 1960 or later. But waiting only pays if you can cover the years in between from savings without selling at a bad time. If you stop work before claiming, those savings become the bridge.

And if you keep earning before full retirement age, the earnings test applies: $24,480 a year for 2026 (higher in the year you reach 67). Married couples should look at both benefits together, since the survivor keeps the larger one.

Turning a 401(k) into a monthly paycheck

The 401(k) rarely pays you on its own, so you build the paycheck. We would rather hold a cash reserve because selling stock in a down year does the real damage.

Before Mariner Wealth Advisors suggests moving a holding, it estimates the tax bill of the switch. That matters if you hold a large block of company shares, where concentrated stock planning or a 10b5-1 trading plan may spread the sales.

• Keep one to two years of spending in cash or short-term bonds, so a down market doesn't force a sale.
• Decide which accounts pay first: taxable, then tax-deferred, or a mix that smooths the tax bill.
• Set up automatic monthly transfers so retirement feels like a paycheck.
• Review the stock and deferred compensation payout schedule before the last day of work.

What about health insurance before Medicare at 65?

If you retire before 65, you need coverage until Medicare starts, usually through COBRA, a spouse's plan or a marketplace plan. Price it before you set the date, since it can run to many thousands of dollars a year.

Income also drives later costs. Medicare premiums in 2026 rise in steps with income from two years earlier, so a large conversion at 63 can raise the Part B premium of $202.90 a month at 65. Check the income thresholds first.

Are the low-income years before RMDs worth using?

For many retirees, yes. The years between your last paycheck and RMDs (age 73, or 75 if born in 1960 or later) often carry the lowest tax rates you'll see. Converting part of a traditional IRA to Roth in those years pays tax now at a lower rate.

The trade-off is real. Conversions add income, which can lift your bracket and Medicare premiums, and the tax is paid from cash. We model several years of conversions together with deferred compensation payouts, since those can land in the same years.