And yet, after a lifetime of building systems—actual systems—he found himself stumped by retirement.

“I spent my life solving complex problems,” he said, “but this feels more confusing than anything I ever built.”

The Engineer Who Couldn’t Engineer Retirement

What threw him off wasn’t the accounts or the income. It was the taxes. The RMDs. The way everything suddenly triggered a chain reaction he didn’t anticipate.

“It’s like no one talks about that part,” he told us. “And now my RMDs are here… and I’m getting walloped.”

John wasn’t looking for someone to take over. He just wanted to see the math—to understand the implications, the cause and effect, the why behind the numbers.

When Planning Meets Purpose

The real shift came when we stopped talking about taxes—and started talking about his granddaughter.

“She’s obsessed with space,” he told us, his voice softening for the first time. “Wants to be an aerospace engineer. I’d love to help her with school someday... but I don’t want to just write a check. I want her to earn it.”

That one comment opened a new door.

We talked about values. About guiding wealth, not just distributing it. We introduced the idea of a legacy trust—one that could provide for his granddaughter if she met certain criteria. Maintain her GPA. Volunteer. Show character. Not just be smart—but be grounded.

John lit up.

That was his ah-hah moment. Not when we showed him a clever tax strategy. Not when we mapped out the perfect asset withdrawal sequence. But when he realized that he could align his money with his meaning.

He said, “I didn’t just want to leave money. I wanted to guide it.”

More Than a Plan—A Compass

That’s the part most retirement advice misses. It focuses on optimization, but not orientation. It tells you how to save, how to invest, how to withdraw. But it rarely asks: What do you want this to mean?

John had the money. What he didn’t have was a compass. A framework that connected the dots between accounts and intention.

Once that clicked, everything else came into focus. He began researching charitable strategies. A living trust. Using specific accounts for targeted legacy gifts—tax efficiently.

And he said something I’ll never forget:
“This is the first time I’ve actually felt excited about planning.”

What John Taught Us

Retirement isn’t a math problem. It’s a values problem.

If you’re in that same space—where you’ve got the pieces but not the clarity—know that you’re not alone. Retirement isn’t just the end of a working life. It’s the beginning of a different kind of life. One where your choices matter more than your balances.

If you’ve ever looked at your accounts and thought, “Is this it?” — that’s not a flaw. That’s the beginning of a better question. One worth answering. Because when your money starts to reflect what you actually believe, retirement becomes more than sustainable.

It becomes meaningful.

Want to see how your retirement pieces fit together?

Check out our Retirement Readiness Checklist or just give us a call at (872) 266-3015.