Every Day is Saturday: February 20th, 2024


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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Most people plan for retirement by focusing on their finances—building up a nest egg, securing passive income, and minimizing taxes. But what if that’s only part of the equation? Many retirees find themselves financially secure yet feeling unexpectedly lost, disengaged, or even unhappy. The truth is, money alone doesn’t guarantee a fulfilling retirement.

Dr. Daniel Crosby explains how work naturally provides purpose, engagement, relationships, and growth—key elements we often lose in retirement without realizing it. Without a plan to replace them, retirees risk dissatisfaction, depression, and even health issues.

The good news? By proactively designing your retirement around these five pillars—positive experiences, engagement, relationships, meaning, and growth—you can create a life that is just as rich in purpose as it is in financial security.

Whether it’s through hobbies, social groups, volunteering, or personal growth, Dr. Crosby shares how to build a retirement that keeps you mentally, emotionally, and socially fulfilled for decades to come. Click here to listen

Outline of This Episode

  • (0:00) Introduction
  • (1:30) The unexpected struggles of retirement
  • (2:40) The five facets of a meaningful life
  • (6:23) How to intentionally rebuild purpose after retiring
  • (9:50) The hidden danger of loneliness in retirement
  • (14:30) Why purpose-driven money decisions matter
  • (22:50) A hilarious twist: How Elon Musk “stole” from Dr. Crosby!

Why Retirement Happiness Isn’t Guaranteed

Many retirees expect that financial independence will bring automatic happiness, but research shows a different reality. Depression, dissatisfaction, and even health risks spike in the years after leaving work. The missing piece? Work naturally provides more than just a paycheck—it fulfills deeper human needs.

Dr. Daniel Crosby breaks down why so many retirees struggle with this transition and why traditional retirement planning often overlooks the real drivers of a fulfilling life. It’s not just about having enough money; it’s about having a plan for meaning and engagement.

The Five Facets of a Meaningful Retirement

Retirement isn’t just about money—it’s about designing a life that keeps you engaged, connected, and growing. Dr. Crosby shares the five core elements of a fulfilling retirement: positive experiences, engagement, relationships, meaning, and growth.

Most of these are naturally built into our careers, but once we retire, they don’t just continue on their own. Without realizing it, many retirees lose the very things that made their lives fulfilling. The key to avoiding this? Intentionally rebuilding these elements in a way that fits your new stage of life.

The Dangerous Cost of Loneliness in Retirement

Loneliness isn’t just an emotional struggle—it’s a serious health risk. Studies show that chronic loneliness has the same impact on life expectancy as smoking 15 cigarettes a day and is twice as deadly as obesity. Yet, many retirees unintentionally isolate themselves, losing the relationships that work once provided.

The best solution? Actively planning for connection. Whether it’s through social clubs, volunteering, or simply prioritizing friendships, staying socially engaged is one of the most powerful ways to ensure a long and fulfilling retirement.

How to Align Your Money with Meaning

Money alone doesn’t create fulfillment, but the way you use it can. Dr. Crosby shares fascinating research on how tying financial decisions to meaningful goals leads to smarter spending, better saving habits, and long-term financial confidence.

Something as simple as naming your financial accounts—like “Grandkids’ College Fund” instead of “Savings”—can make a dramatic difference. By shifting your mindset from numbers to purpose, you create a financial plan that keeps you grounded, focused, and less likely to make emotional decisions in uncertain times.

Resources & People Mentioned

Connect with Dr. Daniel Crosby


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That's it for our three hundred and sixty-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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