Real Planning

The Most Dangerous Moment in Your Retirement

The Most Dangerous Moment in Your Retirement

June 1, 2026

Market Update

Markets hit new record highs last week. The S&P 500 is up 8% year-to-date. But things cooled off a bit as tech stumbled. (We are seeing portfolios overweighed in tech, if you are not sure where you stand, we can check it for you)

The 10-year Treasury yield climbed above 4.5%. (This is providing great opportunities for fixed rates and principal protection. We are seeing 8-10% returns in CD-like investments. If you’d like to learn more, give us a shout!)

We also saw a significant leadership change at the Federal Reserve last week. Kevin Warsh was confirmed as the new Fed chair, replacing Jerome Powell. Warsh is inheriting a messy

situation.

Overall, most people are feeling good. Portfolio statements look great. Nobody’s asking hard questions right now.

Here’s what most advisors won’t say out loud: the most dangerous moment in a retiree’s financial life isn’t when markets are crashing. It’s right now — when everything feels fine, and nobody’s thinking about protection.

You’ve worked for years to build that account value. A bad sequence of returns in the first 5–10 years of taking income can undo decades of discipline.

When you’re accumulating, a down market is a buying opportunity. When you’re distributing, a down market is a permanent loss (this is true for passive strategies, which most retirement plans are in). Same event. Completely different outcome.

In The News

Market volatility and retirement: Sequence of returns risk explained

CNBC | April 2026

  • Fidelity CFP Frank Maltais explains it plainly: retire into a poor market and keep pulling the same withdrawal, and you’re selling low at the worst possible time — permanently shrinking what’s left to recover.
  • According to Fidelity data, a $1M portfolio withdrawing $50K/year with negative returns early gets depleted by year 27. Flip the sequence — positive returns early — and the math changes entirely.
  • The 1973–74 bear market (S&P down 48%) is the textbook example: retirees who hit that window with high withdrawal rates ran out of money. Those with diversified portfolios drawing 4% survived.

Why the First 5 Years of Retirement Are the Most Dangerous for Your Portfolio

24/7 Wall St. | March 2026

  • Morningstar’s 2026 State of Retirement Income research found roughly 70% of simulated portfolio failures were tied directly to losses taken in the first five years of retirement.
  • A Schwab analysis shows: a $1M portfolio with 15% early losses is depleted by year 18. The same portfolio with those losses occurring later — year 30 instead.
  • After strong equity returns in late 2025, portfolio balances are elevated — which means the dollar impact of a correction is larger than it would have been two years ago.

3 Ways Baby Boomers Are Setting Themselves Up for Retirement Disaster

24/7 Wall St. | Updated May 2026

  • Boomers are retiring earlier than planned — average actual retirement age is 65 for men, 63 for women — often forced out by health or caregiving, not choice. That compresses the accumulation window and starts the sequence risk clock sooner.
  • Social Security only replaces about 40% of pre-retirement income. The 2026 COLA of 2.8% is being largely offset by a 9.7% jump in Medicare Part B premiums (now $202.90/month).
  • Median Boomer retirement savings sits at $194,000. At the safer 3.7% withdrawal rate, that generates just $7,178/year — nearly $600 less than the old 4% rule suggested.

“Where do you land relative to these numbers?”

Market Volatility in 2026: Why Retirement Income Planning Matters More Than Ever

Skybox Financial Group | March 2026

  • Growth-focused strategies assume time and flexibility. Income strategies assume the opposite — they require structure, intentional coordination between income sources, withdrawal sequencing, and liquidity.
  • Once withdrawals begin, the sequence of returns matters just as much — if not more — than the returns themselves. A down market early in retirement doesn’t just test patience; it quietly reshapes portfolio longevity.
  • Done well, income planning creates distance between market movement and spending needs. That distance is the advisor’s job to build.

Do you see a trend? We have talked about Sequence of Return Risk forever. Here is where the industry gets it wrong. It’s not about a product; it’s about creating structural distance between your lifestyle and market risk. It’s about portfolio architecture. Have questions? Let’s talk! Reply to this email or book a call here.

Just for Fun

Dad Joke of the Week:

What do you call a belt made of watches? A waist of time!

Say What?

How 2 men claimed an absurd record by driving an old 3-wheel car the length of Africa.

Englishman Ollie Jenks remembers when his friend first pitched the idea to him.

“It was so ridiculous I couldn’t say no,” Jenks said.

The proposal by his Canadian buddy Seth Scott, a fellow lover of cars and crazy adventures, was for them to drive a decades-old British-made Reliant Robin car from London to the southern tip of Africa — a 14,000-mile (22,500-kilometer) journey through 22 countries — to set a record for the longest trip in a three-wheeled vehicle.

Reliant Robins have cultlike status in the U.K. as humble three-wheelers that, in Jenks’ words, were designed to go to the shops and back in 1970s Britain. They went out of production in the early 2000s but remain loved in British culture, especially after a Reliant appeared as the Trotter brothers’ trusty but battered yellow van in the hugely popular sitcom “Only Fools and Horses.”

Yet you couldn’t find a less suitable vehicle to take thousands of miles through tropical jungles, mountain ranges and deserts down the west side of Africa. And that’s precisely why Jenks went for the absurd plan.

This Week in History

1859 – Big Ben starts ticking over London for the first time

1917 – Future President John F. Kennedy is born

1937 – Golden Gate Bridge Opens

1953 – Edmund Hillary and Tenzing Norgay reach Everest summit

1977 – Star Wars opens in theaters

What Did it Cost? (toaster)

1975: $10.99

2005: $24.99

2025: $49.99

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