A corporate executive in his mid-60s at a medical device company came to Rubiq as he approached retirement. He had spent decades earning a strong salary, accumulating a large pool of restricted stock units (RSUs), and building over $10M in qualified retirement assets through company plans. What he didn't have was a plan for turning all of it into reliable, tax-efficient income that would last the rest of his life — without a spouse or children to share the planning burden.

Important Disclosure: This case study is a hypothetical illustration based on a composite of client experiences. Details have been modified to protect confidentiality. The results depicted are not guaranteed, may not be representative of all client experiences, and should not be interpreted as indicative of future performance. Individual outcomes will vary based on market conditions, tax situations, and other factors.

The Situation

The executive's financial life had been structured around a paycheck for over 30 years. His employer-sponsored plans — 401(k), deferred compensation, and RSU grants — had performed well, but they were all concentrated in pre-tax qualified accounts or company stock. He had no pension, no guaranteed income source beyond Social Security, and no clear picture of how to draw down his assets in a way that wouldn't expose him to crushing tax bills as required minimum distributions kicked in.

Several challenges made this situation more complex than a typical retirement plan:

  • Over $10M in qualified retirement accounts meant future RMDs would generate substantial taxable income — potentially pushing him into the highest federal bracket regardless of his actual spending needs
  • A large RSU pool that needed to be managed around vesting schedules, tax withholding, and concentration risk in a single company stock
  • No spouse or dependents to share income-splitting strategies or provide a planning backstop for healthcare decisions
  • Medicare enrollment timing and plan selection needed to be coordinated with his retirement date and existing employer coverage
  • Social Security claiming strategy had to be evaluated against his balance sheet — not just the standard "delay until 70" advice that ignores individual circumstances

Medicare Planning and Social Security Timing

The first priority was getting his healthcare and income foundations right. We worked through Medicare enrollment timing, coordinating the transition from his employer-sponsored health plan to Medicare Parts A and B while avoiding late-enrollment penalties. For someone without a spouse on a separate employer plan, the timing of this transition directly affects coverage gaps and premium costs — details that are easy to get wrong without deliberate planning.

For Social Security, we didn't default to the conventional wisdom. Instead, we modeled multiple claiming scenarios against his complete balance sheet — factoring in his qualified account balances, projected RMDs, anticipated tax brackets, longevity assumptions, and the fact that as a single filer, he had no spousal benefit strategies available to him. The analysis evaluated when drawing Social Security would produce the best after-tax outcome over his projected lifetime, accounting for the interaction between Social Security income, RMD income, and Medicare premium surcharges (IRMAA).

"He'd been on a salary his entire career. Our job was to build the paycheck that would replace it — one that would last, adjust for inflation, and not get eaten alive by taxes." — Rubiq Advisory Team

Getting Ahead of RMDs: Roth Conversions

With over $10M in qualified accounts, the math on required minimum distributions was stark. Once RMDs began, the annual forced distributions would generate hundreds of thousands of dollars in ordinary income — taxed at the highest marginal rates — whether he needed the money or not. Left unaddressed, this would create a compounding tax problem that would only get worse as account balances continued to grow.

We used IncomeLabs' Roth conversion modeling tool to build a multi-year conversion strategy. The analysis projected his tax liability under multiple scenarios: no conversions, partial conversions in the years between retirement and RMD age, and aggressive front-loaded conversions. The tool quantified the net tax savings of each approach over his projected lifetime, factoring in the upfront tax cost of conversions against the long-term benefit of tax-free Roth growth and the elimination of future RMDs on converted balances.

The result was a phased Roth conversion plan designed to systematically move assets from pre-tax accounts into Roth accounts during the lower-income years between retirement and age 73. By paying taxes now at a lower effective rate, he would dramatically reduce the RMD burden later — and every dollar converted would grow tax-free for the rest of his life, with no future required distributions.

Guaranteed Income*: Replacing the Paycheck

After decades of receiving a predictable salary, the executive's biggest concern wasn't investment returns — it was cash flow certainty. He wanted to know that his essential expenses would be covered regardless of what markets did, and that his income would keep pace with inflation over a retirement that could last 25 or 30 years.

We structured a portion of his portfolio into annuities designed to provide guaranteed, inflation-adjusted income for life. This created a reliable income floor — a replacement for the paycheck he'd always had — that covered his core living expenses independent of market performance. The annuity income, combined with Social Security, provided a base layer of certainty that allowed the rest of his portfolio to remain invested for growth without the pressure of forced withdrawals during down markets.

The balance of his portfolio was positioned for long-term growth and flexibility — available for discretionary spending, travel, healthcare costs, and legacy planning on his own terms. By separating guaranteed income* from growth assets, we gave him both the security he needed and the upside he wanted. * Annuity guarantees are subject to the claims-paying ability of the issuing insurance company.

Managing RSU Concentration

The executive's RSU holdings represented a meaningful portion of his net worth, concentrated in a single company's stock. We developed a systematic diversification plan — timed around vesting schedules and coordinated with his broader tax picture — to reduce single-stock risk while minimizing the tax impact of each liquidation event. The proceeds were deployed into the diversified portfolio alongside his other assets, integrated into the overall income and growth strategy.

The Outcome

Within the first year of the engagement, the executive had:

  • A Medicare enrollment plan coordinated with his retirement date, avoiding coverage gaps and late-enrollment penalties
  • A Social Security claiming strategy modeled against his full balance sheet — optimized for after-tax lifetime income as a single filer, not just the highest monthly benefit
  • A multi-year Roth conversion plan designed to reduce future RMD tax exposure — converting pre-tax assets at lower current rates designed to help reduce six-figure forced distributions at the highest brackets
  • Guaranteed (subject to the claims-paying ability of the issuing insurance company), inflation-adjusted income streams through annuities that replaced his salary and covered core living expenses for life
  • A systematic RSU diversification plan coordinated with vesting schedules and his annual tax projections
  • A growth portfolio positioned alongside guaranteed income — providing flexibility for discretionary spending, healthcare, and legacy planning

For the first time in his career, the executive's financial plan wasn't built around earning more — it was built around making what he'd already earned work as hard as possible for the rest of his life. The paycheck stopped. The income didn't.