He just wanted to understand what his next move should be - and whether he was missing something important.

When we first spoke with Gary, he was outside in 95-degree heat, digging a garden by hand… cocktail nearby. That detail matters. It tells you something about how he approaches life: thoughtful, hands-on, not afraid of effort - but not interested in unnecessary complexity either.

When “Good Advice” Still Leaves You Guessing

Gary’s questions started when another advisor mentioned annuities in passing. Not to sell one outright - just enough to plant the seed. Curious, Gary asked for clarification.

What he got instead was dismissal.

He described feeling like the advisor assumed he “didn’t know anything,” and when Gary pushed for real explanations - fees, mechanics, tradeoffs - the follow-up never came. That experience stuck with him. Not because he wanted an annuity, but because he wanted understanding.

So Gary did what many retirees do next: he started researching on his own.

That’s when the fog really rolled in.

Annuities came with caps, floors, riders, guarantees, surrender periods, tax treatment differences - and every explanation seemed to introduce three new variables. Roth conversions were no better. Some sources warned of massive tax bills. Others insisted “now is the perfect time.” None of it felt grounded in his situation.

What Gary wasn’t missing was intelligence or discipline.

What he was missing was context.

The Well-and-Bucket Problem in Retirement

At one point, Gary shared an analogy that perfectly captured his frustration.

Growing up, his family used a water well. You didn’t just pull water endlessly. You had to know where the pump was, how deep the well ran, and how much the bucket could hold. Pull too fast or without understanding, and you’d create problems.

That’s how retirement accounts work - but almost no one explains them that way.

Many retirees unknowingly rely on a single “well” for income: their traditional IRA or 401(k). It worked beautifully during accumulation. But in retirement, that same account becomes the source of required minimum distributions, rising tax exposure, and reduced flexibility.

Gary realized his real question wasn’t “Should I buy an annuity?” or “Should I do a Roth conversion?”

It was: "How do I create options so I’m not trapped later by taxes I can’t control?"

Why Product Decisions Miss the Bigger Picture

One of the most common retirement planning mistakes is treating each decision in isolation.

Annuity conversations happen without tax modeling. Roth conversions are discussed without considering future RMD pressure. Income planning ignores how withdrawals affect Medicare premiums and marginal tax brackets.

Gary didn’t want another product pitch. He wanted to understand how different buckets of money interact over time.

That’s when he was introduced to a framework some retirees use that focuses less on products and more on account layering:

- A traditional IRA for tax-deferred growth

- A Roth IRA for tax-free flexibility

- And a third, tax-refunded private asset designed to offset future tax exposure

This approach isn’t about replacing everything Gary already has. It’s about adding flexibility - so income later in life can be drawn from different sources depending on tax rules, required distributions, and lifestyle needs.

The Real “Ah-Ha” Moment

Gary’s breakthrough wasn’t technical. It was conceptual.

He realized retirement planning isn’t about finding the best account. It’s about avoiding the worst-case scenario: being forced to take taxable income at the wrong time, under the wrong rules, with no alternatives.

“If I only have one well,” Gary explained, “I’m stuck with whatever problems it has. But if I have three wells, I can choose which one to draw from.”

That’s the shift many retirees never make.

They focus on returns instead of control. They worry about performance instead of positioning. And they don’t realize that the biggest risks often show up after retirement - not before.

Progress Doesn’t Require Perfection

Gary hasn’t “solved” retirement. And that’s the point.

He’s now doing modest Roth conversions instead of all-or-nothing moves. He’s exploring additional income sources that reduce future RMD stress. Most importantly, he understands why he’s doing each step - and what problem it’s meant to solve.

He’s no longer guessing.

And that’s what separates confident retirees from anxious ones.

Join Gary and download our free retirement checklist here.