Paul Merriman Newsletter

“Every age has its peculiar folly: some scheme, project, or fantasy into which it plunges, spurred on by the love of gain, the necessity of excitement, or the force of imitation.”

— Charles Mackay, Extraordinary Popular Delusions and the Madness of Crowds

In This Issue

1. Do I Have Enough to Retire?
2. What If This Turns Out to Be a Terrible Time to Retire?
3. Truth Teller of the Week — Mike Piper
4. Podcast — Mike Piper on the Decisions That Shape Retirement
5. Testimonial

From Paul

Do I Have Enough to Retire?

Do I have enough to retire? Will my savings be able to survive the spending we have planned in retirement? Are we prepared for the possibility that the market will take a nose dive the day we retire? These are questions our Truth Tellers spend a lot of time helping pre-retirees address.

What If This Turns Out to Be a Terrible Time to Retire?

Sources referenced in the article:
· Employee Benefits Research Institute — Retirement Confidence Survey
· 2012 University of Missouri study (SSRN)
· Sequence-of-returns risk explainer (Morningstar)

Workers are feeling pretty confident about their nest eggs, according to the latest survey from the Employee Benefits Research Institute. Roughly two-thirds of workers in the 2025 survey said they were at least somewhat confident that their funds would last through their retirement years. That’s down from the 2025 result, but still a pretty good number.

But the same forces that have fueled retirement confidence have the potential to work against new retirees in the years ahead. A 2012 study conducted by researchers at the University of Missouri found that workers often retire when the market is cresting. Somewhat counterintuitively, that has the effect of reducing a portfolio’s durability, unless the new retiree steers most of their assets out of the market and into an annuity.

Of course, bumps in the road are inevitable in any investing horizon of 25 or 30 years: Indeed, the past 30 years have been pockmarked by two major bear markets. But for new retirees, those downturns can prove especially painful and even lethal. The reason is what retirement researchers call “sequencing risk” or “sequence of return risk.” That means that encountering big losses early in retirement while simultaneously spending from a portfolio reduces the amount of assets in place for the market’s eventual recovery. Retirees who encounter a weak market environment later in their retirement years—say, when they’re in their late 70s or 80s—are much less at risk for this problem than are early retirees. They’ve made it through the danger zone of their early retirement years, and their now shorter life expectancies mean their portfolios don’t have to last as long.

Christine Benz also produces a weekly podcast, The Long View, and in this episode she interviews another of our Truth Tellers, Mike Piper, on how having sufficient assets for one’s own lifetime affects decision-making for investments, charitable giving, estate planning, and taxes. All of these are topics that should be part of the decision, “Do I have enough to retire?”

Listen: Mike Piper on financial considerations for people who have “enough” →

Recently, Truth Teller Rob Berger spoke to the subject in a Q&A podcast:

YouTube · Rob Berger

How many years of “safe funds” should you hold beyond guaranteed income? (FQF)

▶ Watch on YouTube

Truth Teller of the Week

Mike Piper

Mike Piper is a CPA and Personal Financial Specialist, and the voice behind the Oblivious Investor blog and the free Open Social Security calculator. He has a rare gift for taking the topics that intimidate most investors and making them feel obvious — from which dollars to spend first in retirement to why delaying Social Security is best understood as insurance, not a gamble.

obliviousinvestor.com · opensocialsecurity.com

Independently vetted by Paul Merriman. No compensation received.

This Week’s Podcast

Mike Piper on the Decisions That Shape Retirement

Session 3 — 2026 Bainbridge Community Foundation Spring Financial Education Series

In Session 3 of the 2026 Bainbridge Community Foundation Spring Financial Education Series, Paul talks with Mike Piper — CPA, Personal Financial Specialist, and the voice behind the Oblivious Investor blog and the free Open Social Security calculator — about the handful of decisions that genuinely shape a retirement. Mike’s quietly radical starting point: if you’ve prepared well, “more than enough” isn’t the exception — it’s the most likely outcome. From there he covers which dollars to spend first each year, how to guide a couple when one spouse is aggressive and the other can’t stand the market, the case for matching a young person’s Roth IRA, and why delaying Social Security is best understood as insurance against a very long life, not a gamble.

Throughout, he and Paul return to the same theme — simple, low-cost, broadly diversified portfolios keep beating the clever alternatives. Stick around for the closing exchange on using AI to learn from the “Truth Tellers” — and Mike’s cautionary tale about a chatbot that invented an entire tax-code provision, word for word and completely convincingly, that simply does not exist.

▶ Listen on Paul’s Site

▶ Watch the Video

Links & Resources From This Episode

Mike Piper’s blog — obliviousinvestor.com
Open Social Security — opensocialsecurity.com
Mike’s books on Amazon — bit.ly/49BQugd
Oblivious Investor — bit.ly/4oeIacs
We’re Talking Millions! (free PDF & audio) — paulmerriman.com/free-books
If You Can by Bill Bernstein (free PDF) — paulmerriman.com/free-books
PlanVision — Mark Zoril — planvisionmn.com
The Bessembinder study — “Do Stocks Outperform Treasury Bills?” — read on Morningstar

From a Reader

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From Paul Merriman

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Do You Have Enough to Retire?