Every Day is Saturday: May 1st, 2025


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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With volatility dominating the headlines—tariffs, global tensions, and your portfolio playing hopscotch—this week’s episode is about regaining clarity when the market feels like chaos.

We’re looking at an article by Cullen Roche titled “Finding Certainty in a Sea of Uncertainty,” and breaking down nine practical moves you can make today to stay on track with your retirement plan—even when nothing else seems predictable.

After that, we answer a listener question:

“Should I keep paying premiums on a $500,000 term life insurance policy when I don’t really need it anymore?”

We’ll walk through how to weigh the emotional and financial trade-offs of a policy that’s more “legacy gift” than lifeline.


Outline of This Episode
(0:00) Market volatility check-in + why bonds are your best friend right now
(3:05) Retirement Headline: 9 smart steps to stay calm in chaos
(15:45) Listener question: Should I keep my term life policy?
(24:10) The opportunity cost of insurance vs. legacy giving

Listen on Spotify. Listen on Apple Music.


Retirement Headline: 9 Ways to Find Calm in Market Chaos
From: Finding Certainty in a Sea of Uncertainty by Cullen Roche (Discipline Funds)

If the market's recent behavior has you gripping your coffee mug a little tighter, you’re not alone. But as Cullen wisely reminds us, volatility is the price of admission for long-term growth.

Here's how to regain your footing and focus on what you can control:

  1. Revisit Your Retirement Plan
    Haven’t checked in lately? Now’s the time. Consider holding 2 years of expenses in T-bills, cash, or short-term bonds to avoid panic-selling your stocks during downturns.
  2. Update Your Estate Plan
    Big swings in the market get us thinking about the big picture. Let that prompt you to review your will, POAs, beneficiaries, and overall estate structure.
  3. Consider Tax Loss Harvesting
    Have losses in your brokerage account? Selling and locking in those losses could reduce future tax bills—just mind the wash-sale rule.
  4. Cost Average Excess Cash
    Got moldy money sitting on the sidelines? Consider dollar-cost averaging into the market gradually to reduce timing risk.
  5. Match Time Horizons to Assets
    Short-term money = bonds and cash. Long-term money = stocks. Viewing your portfolio in this way helps stomach red numbers and avoid rash decisions.
  6. Stick to Your Plan (Unless You Had No Plan)
    If you already had a risk strategy and rebalancing schedule, follow it. Don’t adjust just because the market got loud.
  7. Talk to Someone
    Spouse, advisor, friend—just don’t bottle it up. Investing in isolation breeds anxiety.
  8. Control What You Can
    Your taxes, your spending, your risk exposure. The market? Not so much. Don’t let CNBC or daily headlines hijack your peace of mind.
  9. Go Do Leg Day
    Seriously. Physical activity is a mindset reset button. Go for a walk, hit the gym, or do something that gets you back in your body—not stuck in your browser tabs.

Serenity Prayer Energy:
“Grant me the serenity to accept the things I cannot change, courage to change the things I can, and the wisdom to know the difference.”
That’s not just recovery wisdom—it’s retirement planning gold.


Listener Question of the Week

“I’m 67, retired, widowed, and financially independent. I’ve got a $500k level term life insurance policy that costs me $1,600/year and runs until 2031. My adult kids (and grandkids) are financially sound. Should I keep paying for it—or let it lapse?”

Fantastic question. Let’s break it down into a few core considerations:

1. Do You Need Life Insurance?
Probably not. Life insurance protects against financial hardship after death. But you’re financially independent, and your beneficiaries are doing well.

2. Probability of Payout
At age 67 and in good health, your life expectancy is 84+. That means there’s a high chance the policy won’t pay out before it expires at age 74. Statistically, you’ll outlive it—which is good news!

3. Cost vs. Benefit
You’ll pay ~$11,200 over 7 years for a benefit that likely won’t be used. From a strict ROI standpoint, that’s not a great trade.

4. Legacy Intentions
If $500k tax-free sounds like a meaningful gift to your kids or grandkids—and the premiums aren’t a burden—then sure, keep it. But this is more of a gift than a need.

5. Opportunity Cost
That $1,600/year could fund:

  • Roth conversions (and long-term tax savings)
  • 529 plans for grandkids
  • A donor-advised fund for charitable giving
  • Your own bucket-list experiences

Bottom Line: If it brings you peace of mind and joy to keep it—great. But from a numbers perspective, it sounds like you’ve graduated from needing term insurance.


Resources & Mentions

  • Finding Certainty in a Sea of Uncertainty by Cullen Roche (Discipline Funds). To read click here
  • 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-seventh 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)

Benjamin Brandt

Want to spend more money & pay less taxes on your way to an even better retirement? Then you'll definitely want to check out our newsletter and podcast! Our weekly newsletter helps to remind us that in retirement, every day is Saturday (even Thursday mornings).

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