Good morning, Retirement Starts Today Community. Welcome to "Every Day is Saturday," the newsletter reminding us that in retirement, every day is Saturday (including Thursday mornings).​​​

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This week, we’re talking about one of the biggest fears retirees face: a stock market crash—especially one that hits right after you retire.

Losing your paycheck and becoming fully reliant on Social Security, pensions, or your investment portfolio? That’s already a big shift. Add market volatility to the mix, and the stress levels can rise fast.

But here’s the good news: every crash in history has ended the same way—with a recovery. That’s not just hopeful thinking—it’s backed by 150 years of market history.

In today’s episode, we break down a Morningstar article by Amelia F. Fredrickson titled “What We’ve Learned from 150 Years of Stock Market Crashes.” You’ll learn:

• How long some of the worst downturns actually took to recover
• Why every decade brings a crash (and that’s totally normal)
• How to prepare your retirement portfolio to weather the storm

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After that, we tackle a great listener question:

We explore strategies like giving cash, appreciated stock, and the philosophy behind “giving with warm hands.” Plus, a book recommendation that might just change how you think about money in retirement. Click here to listen​

Outline of This Episode​
(0:00) Welcome: Crash anxiety and paycheck-free living
(1:50) Retirement Headline: 150 years of stock market crash history
(2:30) Lesson #1: We can’t predict recovery times
(6:40) Lesson #2: Every decade brings a crash
(11:20) Diversification: Why bonds and cash still matter
(15:10) Lesson #3: Staying invested is the only winning strategy
(20:50) Listener question: How to gift money to adult children
(27:30) Book recommendation: Die With Zero by Bill Perkins

What 150 Years of Market Crashes Teach Us

Lesson #1: Recovery is always uncertain—but it always happens.​
From the 2020 COVID crash (which rebounded in just 4 months) to the drawn-out 2000–2013 “lost decade,” history tells us that we can’t predict when a crash will end—but we can count on recovery.

Lesson #2: Every decade brings a crash.​
Nineteen major crashes over the last 150 years… that’s about one every 8–10 years. Which means: downturns aren’t anomaly events—they’re part of the plan.
That’s why we diversify and hold bonds and cash—even when they feel “boring.”

Lesson #3: Staying invested is the only winning strategy.​
If you had invested $1 in 1870 (adjusted for inflation), you’d have over $30,000 today. If you invested $100 in 2000—even with two major crashes—you’d have tripled your money.
Why? Because markets recover. But only if you don’t sell.

Want to stay invested without panic?

• Count how many months of retirement income are held in bonds and cash
• Pre-plan withdrawal guardrails or temporary spending cuts
• Trust your diversified, well-constructed plan

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The biggest mistake isn’t experiencing a crash. It’s missing the recovery.

Listener Question of the Week

I love this question—because it speaks to the real goal of financial independence: helping others while we’re still around to enjoy the impact.

Three Ways to Gift Money (Without Breaking the Bank)

1. Direct Giving (Cash or Checks)

• Simple and flexible
• No paperwork up to the annual gift tax exclusion ($18,000 in 2024)
• You and your spouse can each give to multiple recipients
• Great for milestone moments: home purchases, weddings, new babies

2. Appreciated Stock

• Avoids capital gains on your end
• Lets your children potentially realize gains at lower tax rates
• Ideal if you have concentrated positions or big winners like NVIDIA

3. Give With Purpose

• Want to give more than the exclusion? Just file a simple gift tax form—it’s not taxable unless you exceed the lifetime exemption
• Not sure how much to give? Start small and build a pattern
• Want to inspire generosity or legacy thinking in your kids? Share the “why,” not just the dollars

Pro Tip: Read Die With Zero by Bill Perkins. It’s one of the best retirement books I’ve read in years. You don’t have to follow every suggestion (like annuitizing everything), but the mindset shift it offers is gold.

Resources & Mentions

• ​Morningstar: “What We’ve Learned from 150 Years of Stock Market Crashes” by Amelia F. Fredrickson
• Book: Die With Zero by Bill Perkins​

Resources & Mentions​

• My new book, Retirement Starts Today: Your non-financial guide to an even better retirement, is available! To order click here​

That's it for our three hundred and seventy-fifth installment of "Every Day is Saturday." As always, reply to this email with your retirement questions and you might hear them featured on the show! I read and respond to (almost) every email.

Have a great "Saturday",
- Benjamin Brandt (your humble host)