Retirement Planning Lessons Learned from a “Heart Attack”

“Devin, you’ve had a heart attack.”

Those are not easy words to hear. Thankfully, I didn’t actually have a heart attack, but a doctor once told me I did after looking at the printout from an EKG. Hearing those words shook me in a way I’ll never forget, and the experience taught me a valuable lesson that applies directly to retirement planning.

And no, it is not the usual “life is short, smell the roses” advice. That is certainly true, but we have all heard that before. This lesson is different, and one I believe is crucial if you are serious about building a retirement plan that actually works.

The “Heart Attack” That Wasn’t

Years ago, I woke up with abdominal pressure, a slight fever, and a higher-than-normal heart rate. By the afternoon, I felt awful and went to see a doctor. After running an EKG, he looked at the paper strip and said, “Devin, you’ve had a heart attack.”

Seconds later, he backtracked: “Well, hang on, I don’t know.” But I never really heard the second part. Those first words had already lodged deep in my mind.

At the hospital, I went through a full workup. Every test came back clean. My heart was perfectly fine. But the damage had been done. I carried that scare with me for years.

What I eventually learned is that my EKG will always show something called Q waves, which can look like the sign of a prior heart attack. The machine’s software will always flag it. But as one cardiologist explained, in my case those Q waves are actually normal and indicate a healthy heart.

Here is the key: the machine only provided raw data. It took a trained expert to interpret it correctly.

The Same Problem in Retirement Planning

The connection to retirement planning might not be obvious at first, but the parallel is striking.

Not long after, I hired a CFP on a contract basis to help with overflow work. He had about ten years of experience and delivered a plan for a client interested in Roth conversions. The output was an 80-page PDF full of charts, graphs, and pictures of happy couples walking on the beach.

But when I reviewed it, something was missing. The report did not clearly explain why Roth conversions were beneficial. It just showed the client converting up to a certain bracket. Even worse, when I asked, “Where are the taxes being paid from?” the planner replied, “I don’t know. The software doesn’t tell me that.”

That is when it hit me, just like the EKG. The software had produced data, but the planner could not interpret it deeply enough to explain what was really happening.

And this is all too common. Many advisors rely on planning software to generate glossy reports that look impressive on the surface. But if they are only reading the machine without digging deeper, you can end up with flawed conclusions that do real harm to your retirement.

How to Tell If an Advisor Is Reading the Machine

If you are working with an advisor, or considering hiring one, do not be afraid to ask questions that get beneath the surface. A good advisor should be able to explain not just what the plan says, but why it makes sense.

Here are some powerful questions you can ask:

• How does my overall plan drive the asset allocation you recommend?
  A thoughtful answer will tie your expected distributions to your true capacity for risk, not just default to a 60/40 split.

• Why would I draw from taxable accounts first instead of my IRA or the other way around?
  The right answer depends on your asset mix, income needs, and tax picture, not just a default software setting.

• Why do you recommend this Social Security strategy over the alternatives?
  Good planning compares multiple filing strategies to show the long-term impact on benefits, portfolio balances, and taxes.

• What assumptions are you using in my Monte Carlo analysis, and why?
  Assumptions drive results. A good advisor should explain them clearly so you know the plan is grounded in reality.

• Why do Roth conversions make sense in my case?
  Conversions should be explained in terms of cumulative lifetime taxes, future flexibility, and trade-offs, not just “filling a bracket.”

• How will we know when I have converted enough?
  The right balance depends on your lifetime tax picture, charitable giving, and even long-term care considerations.

If your advisor can answer these clearly and confidently with data, not rules of thumb, you are probably in good hands. If they stumble, or just recite conventional wisdom, that is a red flag.

The Real Retirement Planning Lesson

Whether it is an EKG machine or retirement planning software, the output is only as good as the person interpreting it. The machine gives you data. It takes expertise to explain what that data really means for your life and future.

Your retirement deserves more than “planning-lite.” It deserves clarity, depth, and an advisor who can dig beneath the surface.