Estate Planning Case Study: Choosing Smart Growth Over a Roth Conversion Gimmick

Greg DuPont
Dec 11
3 min read

The Estate Planning Clients

Brian and Lisa Carter (names anonymized) are old estate planning clients that came to us with a common concern: Were they really on track for retirement, or were hidden risks lurking in their plan?

On the surface, they looked strong. Brian was still working and contributing to his 401(k). Lisa was preparing for retirement. Their expenses were modest, and when we ran the numbers, their projected income needs were very closely aligned with their expected Social Security income. Even factoring in inflation, their plan kept them in the lower tax brackets for the foreseeable future.

What they didn’t have was an abundance of savings outside retirement accounts. That made every dollar of capital precious.

The Pitch They Heard From Their Financial Advisor

Like many in their shoes, they had been pitched a Roth conversion strategy paired with a bonus annuity product. The salesperson framed it as “using Other People’s Money (OPM)”—the bonus would supposedly help cover the taxes due on the conversions. They wanted a second opinion.

The problem?

Brian was still working, so Roth conversions now would push their taxable income higher, driving them into unnecessarily high brackets.
The “bonus” wasn’t free — it came with strings attached in the form of product constraints, vesting schedules, liquidity restrictions and reduced flexibility.
With limited liquid savings, using current dollars to pay conversion taxes would drain capital they needed for resilience.

Our Diagnostic Approach with The Wealth Solutions Network

We looked at the Carters’ plan holistically:

Income vs. expenses showed their needs were largely covered by Social Security, with only a small gap.
Tax analysis revealed that forcing conversions while Brian was still working would reduce the value of the conversion.
Savings gap made it clear that building more secure capital, not pre-paying taxes, should be the priority.

The Financial Plan We Designed

Instead of chasing the Roth conversion “bonus pitch,” we flipped the strategy:

1. Protect and Grow Core Capital

We used the bonus not to offset taxes, but to increase their contract value base inside a protected growth vehicle.
This approach effectively let them use “Other People’s Money” to grow their savings and secure an asset floor — not to prepay taxes they didn’t need to accelerate.

2. Shift Future Contributions to Roth

Brian’s employer plan offered a Roth 401(k) option.
By switching his ongoing contributions from traditional to Roth, we began building a future tax-free bucket without creating today’s bracket creep.
These contributions were directed into the plan’s low-cost equity index options, giving their Roth balance room to grow efficiently.

Tax Bracket Management

By avoiding unnecessary conversions during Brian’s working years, we kept them in their current low bracket.
The plan allows for revisiting measured Roth conversions later — once Brian retires, income drops, and their bracket window opens up more favorably.

4. Income Alignment

With Social Security covering most of their needs, the annuity growth plus conservative assets in the 401(k) created a secure retirement cushion without added tax strain.

The Outcome

By reframing the bonus from a tax gimmick into a capital booster, the Carters achieved:

Secured retirement savings that grow with protection.
No unnecessary tax acceleration during high-income years.
A clear path to build a future Roth bucket through contributions, not forced conversions.
Greater peace of mind that their modest savings will stretch further.

Key Takeaway for Attorneys

Not every Roth conversion is the right move. In this case, the smarter play was:

Protect what you have.
Grow what you can.
Time your tax moves wisely.

By resisting the product-driven sales pitch, the Carters walked away with a retirement plan built for stability, growth, and clarity — without draining their capital or overpaying taxes.

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