Why Even the Best Retirement Calculator is Wrong
Retirement Answer Man
Roger Whitney, CFP®, CIMA®, RMA, CPWA®
4.6 • 1.2K Ratings
🗓️ 25 March 2026
⏱️ 60 minutes
🧾️ Download transcript
Summary
Roger Whitney explores why retirement planning software—especially Monte Carlo simulations—can give a false sense of confidence if misunderstood. He explains what these tools actually measure, the hidden assumptions behind them, and why retirement is a complex problem that requires judgment, flexibility, and resilience—not just a high “success rate.” Roger shares how to properly interpret results, avoid common traps, and use software as a guide rather than a decision-maker so you can build a retirement plan that supports a great life.
OUTLINE OF THIS EPISODE OF THE RETIREMENT ANSWER MAN
- (00:00) This show is dedicated to helping you not just survive retirement, but have the confidence to lean in and rock it.
- (00:30) Roger introduces the episode topic—why your retirement calculator’s success rate can be misleading.
PRACTICAL PLANNING SEGMENT
- (02:50) Roger explains his perspective as a long-time practitioner and outlines his experience using Monte Carlo-based retirement tools.
- (05:05) Complicated vs. complex problems: why retirement can’t be “solved” like a math equation and must instead be managed over time.
- (09:30) Concerns about overreliance on software—from advisors scaling businesses to individuals misinterpreting results.
- (11:30) What retirement software actually measures.
- (13:25) What software does NOT measure.
- (14:18) Best uses of planning software.
- (17:40) What software should NOT be used for.
- (19:40) Key dangers of using retirement software.
- (23:00) Feasibility vs. resilience: why a plan that “works” on paper may still be fragile in real life.
- (24:20) The real risk:
- Overspending early and jeopardizing later years
- Underspending and missing out on life
- (26:20) The massive number of assumptions behind every plan—and how small changes can dramatically alter outcomes over time.
- (38:20) How to interpret results properly.
- (40:55) Looking beyond the number: evaluating the distribution of outcomes and plan sensitivity.
- (44:43) Understanding failures:
- Timing (early vs. late failures)
- Severity (minor shortfall vs. major gap)
- (48:27) Best practices:
- Hold success rates lightly
- Keep plans simple
- Regularly review assumptions
- Avoid over-planning and constant tweaking
- Define what success actually means for your life
SMART SPRINT
- (56:04) Schedule time to review the assumptions in your retirement planning software—focus on understanding the inputs rather than optimizing the output.
CLOSING THOUGHTS
- (56:50) Roger shares an update on the merger of his firm with Tanya Nichols’ firm and the creation of a new company, Retire Agile.
REFERENCES
- livewithroger.com — Register for Noodle Live on March 28!
- Submit a Question for Roger
- Sign up for The Noodle
Transcript
Click on a timestamp to play from that location
| 0:00.0 | your retirement calculator gave you a 90% success rate. Today we'll talk about why that number |
| 0:06.0 | might be the most dangerous thing in your retirement plan. Hey there, welcome to the show |
| 0:15.0 | dedicated to helping you not just survive retirement, but to have the confidence, because you're |
| 0:19.6 | doing the right work, to lean in and |
| 0:22.0 | rock it. My name is Roger Whitney. Welcome to the show. Today, we're going to dive into |
| 0:27.9 | retirement planning software. These things are amazing. They're getting better and better and better. |
| 0:33.0 | We even got to AI yet. We'll do an AI theme at some point when I've finished my research on that. |
| 0:40.1 | I think we're actually still early on that one. But retirement planning software is everywhere. |
| 0:44.2 | Your advisor is using it if you work with an advisor. If you're not, you're doing this on your own. |
| 0:49.0 | My guess is you're using retirement planning software that's available through Bolden or |
| 0:53.6 | Fidelity or all the firms that |
| 0:55.0 | offer it. And it's really important that we understand what this software is good for, what it's |
| 0:59.7 | not good for, and some of the dangers of how they're built. If we interpret them incorrectly, |
| 1:06.1 | it can literally cause a lot of problems if we don't use them properly. So that's what we're going to dive in |
| 1:11.5 | today. Now, before we get to that, two housekeeping things. One is this Saturday, March 28th at 10 a.m. |
| 1:18.3 | Central, I'm going to hang out with listeners live for about an hour so. We're calling it the noodle |
| 1:24.2 | live where anybody that wants to hop on, grab your cup of coffee, |
| 1:27.8 | we're just going to talk about maybe the recent episodes. We'll talk about retirement in general |
| 1:32.9 | and spend an hour or so just enjoying each other's company and talking about how to create |
| 1:37.7 | a great retirement. So you can learn more about that at live with roger.com. And then if you are signed up for our weekly email, the noodle, |
| 1:46.3 | so this is the noodle live, but if you're signed up for our weekly email, you're going to receive |
| 1:51.3 | an exclusive interview with Paul Merriman, a wonderful man who has done Yoman's work on |
... |
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