A Legacy That Doesn’t Collect Dust: Teaching Grandkids to Save with the 100 Envelope Challenge
When we think about the legacy grandparents leave behind, we often picture handwritten recipes, cherished heirlooms, or family stories passed down over generations. But some of the most powerful gifts aren’t tangible at all—they’re the values and habits that shape how future generations think.
What if your legacy wasn’t something that sat on a shelf… but something that changed how your grandchild approached life?
Introducing the 100 Envelope Challenge
A creative, hands-on way to teach kids the power of saving—with purpose.
The 100 Envelope Challenge has gained popularity for its simplicity and effectiveness, but beyond the trend lies an opportunity: a chance to create meaningful, money-related memories with your grandchild that can shape their financial habits for life.
How It Works
Start with 100 envelopes labeled 1 through 100. Each time your grandchild selects an envelope, they save that amount in cash or digitally. For example, envelope #67 means saving $67. Over time, and with consistency, completing the full challenge could result in $5,050 saved—and a powerful lesson in discipline, patience, and progress.
Note: Savings outcomes are not guaranteed. Results will depend on your grandchild’s commitment, timeline, and ability to follow through.
Why Kids Love It—and Learn From It
- Tangible Progress: Each envelope represents a clear, achievable goal. Seeing the stack grow builds confidence—and motivation.
- Delayed Gratification: By spreading the savings over time, kids learn that worthwhile goals require patience and discipline.
- Open Family Conversations: The process naturally opens the door to conversations about money, budgeting, and values.
- Ownership and Motivation: There’s something exciting about seeing your own money grow, especially when it’s tied to effort.
Make It a Shared Memory
You don’t have to just hand them a stack of envelopes and hope for the best. This is an opportunity to be hands-on—and heart-forward.
- Decorate the envelopes together
- Match their savings occasionally to reward consistency
- Share your own stories about earning, spending, and saving
- Talk about goals—what they’re saving for and why it matters
Moments like these have staying power. More than just helping them build a savings habit, you’re showing them that financial awareness is part of their family legacy.
From Envelopes to Long-Term Impact
At Whalen Financial, we believe true financial education doesn’t begin with spreadsheets—it starts with simple conversations, lived experiences, and shared values.
If you’re a grandparent who wants to pass down more than money—like mindset, wisdom, and strategic thinking—we invite you to join us for the Retirement Money Prism™ Webinar.
This free, educational session is designed to help retirees and multigenerational families think about wealth with purpose. Learn how to translate your life experiences into financial principles that your children and grandchildren can carry with them.
Click the button below to register.
It’s free. It’s educational. And it could be the most meaningful financial conversation you start this year.
Disclosures
Whalen Financial is an SEC-registered investment adviser. Registration does not imply a certain level of skill or training. The content of this blog post is for informational and educational purposes only and should not be construed as personalized financial advice.
The 100 Envelope Challenge is presented as a behavioral finance concept and is not intended to be a recommendation of any specific investment or savings strategy. Outcomes are not guaranteed and will vary based on individual participation and personal circumstances.
For more about our services and regulatory disclosures, please refer to our Form ADV and Form CRS.
