The fear comes from three gaps a balance sheet does not show: sequence of returns risk in the first years of withdrawals, the health care years before Medicare, and a tax and Social Security strategy nobody built. A plan that turns savings into sequenced income addresses all three without predicting the market.
Why doesn’t a large balance stop the worry?
A balance answers one question: how much money you have. Retirement asks a second one, how much the two of you can spend each year and for how long, and answering it means turning a lump sum into income drawn from the right accounts in the right order, coordinated with taxes and Social Security. Robert sees the same pattern with couples who come in anxious. They saved for decades, they have a healthy balance, and they do not sleep well. The fear is common: 67% of Americans now worry more about running out of money than about death, according to Allianz Life’s 2026 study.
What is sequence of returns risk?
Picture two couples who retire with identical portfolios, the same investments and the same withdrawal rate. One retires into a strong market. The other hits a downturn in year one. Ten years later, all else equal, one couple is fine and the other is in trouble. The investments behaved the same; the order the returns arrived in made the difference. You cannot pick your way out of this with better funds. The fix is a plan for which accounts pay your income in the first five years, the window where the damage happens or does not. The answer on sequence of returns risk runs the numbers.
How big is the health care gap before Medicare?
Medicare starts at 65 for most people, whenever you stop working. Retire at 62 and the two of you fund two to three years of coverage yourselves. Robert says most retirement projections get this wrong: they leave it out, or plug in a placeholder that covers a fraction of the cost. Your options for those years, and how your withdrawal choices change what you pay, are on the page about health insurance if you retire before 65.
What does the third gap look like in a plan?
Robert describes a composite couple in their early 60s with $1 million to $2 million invested. On paper they looked fine. They had no plan for when to claim Social Security, no view on whether Roth conversions made sense, and no answer for the years before Medicare. Their approach had been to grow the number and hope it was enough. Their rebuilt plan sequenced withdrawals, mapped a Roth conversion window before required distributions begin, timed Social Security across both ages and built a health care bridge for the gap years. None of it required beating the market.
What are the six parts of the Retirement Income Roadmap?
Robert uses the same framework with every couple, six parts that work together:
- Income design: your accounts turned into a paycheck sequenced to survive a bad first five years.
- Tax strategy: the order you draw from accounts and the timing of Roth conversions.
- Social Security timing across both spouses, since a married couple’s claim carries survivor consequences.
- Roth conversion ladders in the years before required minimum distributions.
- A health care bridge for the years before Medicare, and a plan for long-term care exposure.
- Legacy planning coordinated with your estate documents instead of default beneficiary forms.
He calls it six pieces and one plan, in place of six separate products. The Retirement Income Roadmap entry explains what the written plan contains.
Why does the timing of the plan matter?
Most pieces of the roadmap have a window that closes. Roth conversion room shrinks as required distributions get closer, claiming options narrow as you approach your target age, and today’s tax brackets may change under future law. Couples who build the plan with three or four years of runway have more options than couples who start a year before they retire. Robert’s 30-minute retirement clarity call is an honest look at where the two of you stand on all three gaps.
Common questions
- When does Medicare eligibility start?
- At 65 for most people, whenever you retire. Someone who retires at 62 needs another source of coverage for about three years, such as COBRA, an ACA marketplace plan or a working spouse’s employer plan.
- What is a Roth conversion ladder?
- A series of Roth conversions made year by year in the window before required minimum distributions begin at 73, or 75 if you were born in 1960 or later, each sized to fill a chosen tax bracket. It moves pre-tax money to Roth while you control your taxable income.
- How do you manage sequence of returns risk?
- By deciding which accounts fund your spending in the first five years of retirement, and how much of that spending sits outside the market when withdrawals begin. Those years matter most, because a loss taken while you withdraw leaves fewer shares to recover.
If the decisions on this page are ahead of you, the two of you can work through them with Robert Boeck before any of them becomes permanent.
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