Case Study 3: Repairing DIY Retirement Plans

In this fictional case study, we walk you through how we repair an outdated, one-time, DIY retirement plan. Marcus & May retired a couple of years ago with a one time plan. But, instead of enjoying retirement, they’ve been stressed over how much they pay in taxes and how volatile the market has become. They aren’t sure how to find confidence in their finances on their own.

Listen to our conversation, or read the case study below!

Breakdown of the Case Study

Meet Marcus & May

Marcus and May are both 68, and recently retired from long careers in corporate leadership and project management. They had worked with a financial advisor years before retirement, receiving a one-time plan they thought would guide their transition into this next phase of life. But now that they’re a few years into retirement, they’ve realized something critical: having a plan is not the same as knowing how to implement it.

Without clear direction, even simple financial decisions started to feel stressful — they were constantly wondering if they were doing the right thing. They’ve been paying more in taxes than expected. Worse, some of the key strategies their one time plan was built on never happened. They came to us not just for answers, but for an ongoing partner to help fix their plan and adjust it as their life unfolds.

Marcus and May’s vision for retirement is centered on freedom and family:

• Travel more frequently, while they’re still healthy and energetic
• Help fund college costs for their grandchildren
• Keep taxes low, especially on RMDs and future investment growth
• Preserve their assets through lower-risk investing that matches their comfort level

Above all, they want flexibility — the ability to pivot financially if the right opportunity comes along.

The Challenges

Their biggest frustration wasn’t that they had made major mistakes — but that they had been operating without guidance in key areas:

• Roth conversions were never started, even though their original plan had recommended them
• Tax drag was rising, as they began drawing from multiple accounts (brokerage, IRA, and Social Security) without a coordinated withdrawal plan
• Low risk tolerance meant their investment portfolio had become too conservative to support long-term needs without some adjustments
• No plan for gifting to grandkids yet, even though they wanted to start while they were alive to see it

Our Approach

We knew Marcus and May didn’t need to start from scratch — their plan simply needed to become dynamic. It needed to evolve as their lifestyle did. Our job was to restore control and simplify their decision-making.

Phase 1: Organization

We started with Marcus and May just as we do with any client. We gathered about every facet of their finances, from insurance to estate planning to portfolio. Then, we place each data point into a visual form, which we call a blueprint. This gave Marcus and May a grounded starting point — not just a snapshot, but a map of where things stood and where they could go next.

• We gathered and reviewed retirement accounts, brokerage assets, real estate holdings, and income sources (including Social Security).
• We clarified their short-term and long-term goals: ongoing income, potential home purchase, travel, and education gifts.
• We built a personalized retirement timeline, aligning their financial resources with each potential goal or decision point.

Phase 2: Strategy

Next, we start playing with the different decisions we could make. For Marcus and May, we narrowed in on identifying their known cash needs (living expenses, annual travel budget) and their “possible goals” (a new home, education gifts). Then we matched each goal to a timeframe and risk-adjusted funding source. This gave them a “financial timeline” to see what they’d likely need, and when — without locking them into fixed decisions.

• We created a coordinated withdrawal plan, prioritizing tax-efficient distributions from brokerage accounts and starting Roth conversions while they were still in lower brackets.
• We evaluated funding options for a new home — comparing selling their lake house vs. using investment assets — while modeling capital gains implications and liquidity needs.
• We discussed gifting strategies for grandchildren’s education, including the use of 529 plans.
• We reviewed their risk tolerance and investment positioning to ensure their assets matched their comfort level — without sacrificing growth where it was needed.

Phase 3: Implementation

With their strategy in place, we helped them put it into motion — step by step.

• Their Roth conversion schedule was launched, lowering future required minimum distributions and managing long-term taxes.
• Their investment portfolio was restructured into clear buckets:
  • A low-volatility cash/bond bucket for near-term needs
  • A conservative growth bucket for mid-term flexibility
  • A legacy bucket aligned with longer-term goals
• They began funding 529 college accounts for their grandchildren.
• And most importantly, they felt empowered to explore a potential home move without rushing into a decision — knowing the financial pieces were already in place.

The Results:

With a team of advisors on their side, Marcus and May don’t need to worry about their retirement plan being on track any more. They have confidence in knowing . . .

• They have a structured, low-tax income plan that adapts each year
• Their investments are aligned with their risk comfort, while still supporting long-term growth
• They’ve begun gifting to their grandchildren’s 529 plans
• They have financial flexibility to buy a new home — without needing to make a rushed or irreversible decision
• Their Roth conversion strategy is already reducing their projected RMDs and tax burden in future years

Marcus and May told us they finally feel “off the sidelines” with their finances again. They’re no longer reacting; they’re proactively shaping their retirement. They’ve let go of the pressure to know everything because now they have a team that walks with them, reviewing and refining their plan every year.

Note: The above case study is hypothetical and does not involve an actual Financial Design Studio client. No portion of the content should be construed by a client or prospective client as a guarantee that he/she will experience the same or certain level of results or satisfaction if Financial Design Studio is engaged to provide investment advisory services.

Are You Considering How to Fix Your DIY Retirement Plan?

Here are some additional resources to help you dive deeper:

• Video: How to Calculate Your Roth Conversions
• Article: Tax Changes from the One Big Beautiful Bill Act
• Article: Estate Planning Checklist
• Podcast: Ep 62: How to Plan for Upcoming RMD Taxes

But if you’re tired of searching the internet for answers and hoping you get retirement right, what’s stopping you from taking the next step towards financial confidence? Our team specializes in using executive compensation to build tax efficient retirement plans.

Schedule your free zoom consultation with our advisors by clicking “get started.” Let’s build a plan that’s designed for your life, together.

Bonus: Our Retirement Planning Guide