The topic of this article and the accompanying podcast was sparked by a recent visit with our Uncle Jess—who, at ninety-four years young, is still teaching us about legacy. He’s lived in the same simple house for nearly 75–80 years and, though he’s shared some of his wishes for what happens next, he’s only now putting together a formal trust. He has never married and has no children. What’s remarkable is the impact he’s already made, not through wealth, but through the heartfelt poems he sends to family for every occasion.
It was a timely reminder: investing in the future isn’t just about finances. It’s about intentional living—how we use our time, share our wisdom, and build something that lasts. In this article, we’ll unpack some practical ways to plan ahead with purpose and make the kind of impact that truly matters.

Why Thinking and Planning Ahead Matters
Don't Facilitate Consumption, but Impact
That last story is why Greg and I have begun to think more intentionally about how we "invest" in the next generation—especially our own kids. Not just financially, but in ways that help them grow, take ownership, and develop into capable, resilient adults.
With a background as a certified financial planner, Greg has seen this play out countless times. Parents, after working hard and sacrificing for decades, want to spare their children the same struggle. But giving too freely, too soon, often leads to entitlement rather than empowerment. It’s the classic gym metaphor: you can pay for your kid’s membership, but you can’t buy them muscles. They still have to show up and do the reps. And in life, it’s the reps—those challenges and efforts—that build real strength.
That’s why instead of simply handing our kids money, we created a system that mirrors real-life business. If they want to pursue a venture—buying a rental property, expanding a business—they first need to pitch it. Convince us it's viable, and if it passes the test, we offer support through a structured loan. It’s interest-only until they’ve built equity, at which point they can refinance and pay us back. It’s supportive, but it’s not a free ride. And more importantly, it teaches responsibility, resourcefulness, and the kind of grit that lasts. The true value of investing in our kids, as well as others, isn’t in the dollars—it’s in the wisdom, the work ethic, and the ability to steward opportunity with character.
Paying Off and Managing Debt
Most of us remember what it was like trying to qualify for that very first loan—it felt like they wanted your firstborn child, a quart of blood, and a promise to come back in three years once you’d somehow become "worthy." That experience taught us the value of hard-earned credit and responsible borrowing. When it comes to supporting our kids, we've tried to apply those same principles. We don’t offer loans to bail them out of credit card debt or fund overspending.

Helping to pay off consumer debt only reinforces bad habits. Instead, we believe they need to wrestle through the discomfort, make lifestyle changes, and dig their way out—just like we all had to at some point. As difficult as it is to watch them struggle, especially knowing we’ve already walked that path, it's a crucial part of their financial maturity.
However, once they’ve proven they can manage their money—by getting out of debt, increasing their income, and showing fiscal responsibility—we’re open to stepping in, not with a handout, but with a business-minded partnership. We’ve accumulated assets not just to hoard, but to steward. Rather than grow our portfolio alone, we’d rather see our kids bring their energy, ideas, and sweat to the table. That might mean offering a loan for a smart business investment or real estate project, but only if they come to us with a clear, convincing plan. It’s a way of passing on more than money—we’re passing on responsibility, opportunity, and trust. We didn’t have this kind of chance in our forties; it was mostly survival mode. But if our kids are ready and willing to build something meaningful, we’re ready to come alongside them—not to carry them, but to run alongside them as they create something of their own.
This principle of earned trust through responsibility extends well beyond our families—it holds value for individuals, teams, and entire organizations. We’ve witnessed firsthand how easily resources can be squandered when there's a lack of ownership or clear expectations. Whether it's time, funding, or people power, when there’s no accountability, waste becomes the norm. However, when accountability is woven into the culture—when people know they must steward what they’ve been given and answer for how it's used—trust grows. And with that trust comes better decisions, smarter investments, and often, significantly greater outcomes.Write Down Stories and Memories
One of the most powerful investments we can make in others doesn’t cost a dime—just a little time and thought. Writing down your stories and memories is a priceless gift, not only to your family, but to generations you may never meet. These aren’t just tales of the past; they’re threads of legacy, connection, and identity. Whether it’s a handwritten journal, a collection of emails, or even recorded voice memos, preserving your perspective allows your loved ones to understand where they come from, what values shaped your decisions, and how you weathered life’s toughest storms or celebrated its sweetest moments.
Our Uncle Jess has written poems for nearly every holiday and special occasion, carefully typing them on his typewriter and mailing them out. I’ve collected over 45 years’ worth of these poems in a file—a treasured record of his creativity. It’s a meaningful legacy from this dear 94-year-old man, one I will continue to cherish long after he’s gone.
Capturing your memories is also a way of affirming purpose and possibility. When you reflect on your journey—your challenges, your triumphs, your detours—it reinforces the idea that life isn’t always linear, but it’s rich with meaning. This can be with a journal or even a memoir. Sharing those experiences becomes a way of mentoring from afar, offering encouragement, wisdom, and even humor that might be just what someone needs years down the line. In a world where so much feels fleeting, written stories ground us. They remind us who we are and inspire others to dream boldly, act with intention, and live with heart.
Value of Trust vs. Probate
When it comes to preparing for the future, understanding the difference between a trust and probate can be one of the smartest moves you make for your loved ones. A trust is a legal arrangement that allows you to transfer your assets directly to your beneficiaries, often avoiding the lengthy, public, and sometimes costly process of probate. It can be set up while you're still alive (a living trust), giving you control over how and when your assets are distributed. This can be especially important when you want to ensure your estate is handled privately, efficiently, and in accordance with your values and timing.
On the other hand, if you don’t have a trust in place, your estate may go through probate—a court-supervised process that verifies your will (if one exists), settles debts, and distributes assets. Probate can take months, or even years, and often incurs legal and administrative fees that eat away at what you’ve worked hard to build. More importantly, it can create emotional stress for family members during an already difficult time. Setting up a trust isn't just about asset protection—it's a thoughtful investment in peace of mind. It’s a way of saying, “I’ve thought this through, and I care about making this transition as smooth as possible for you.”
Application: Putting Thought into Action
Plan Ahead with Purpose
- Organize your values, assets, and intentions now.
- Shift from reacting to life’s changes to shaping them with intention.
Impact Over Consumption
- Help others grow by investing in their future, not by funding temporary fixes.
- Encourage responsibility and resilience, not dependence.
Write Down Your Stories
- Share your life lessons, values, and key moments in writing.
- Your words may become your most lasting and meaningful legacy.
Choose a Trust Over Probate (with legal advice)
- A trust provides clarity, privacy, and a smoother transition.
- It ensures your assets fulfill your intentions without unnecessary conflict.
Additional Resources
Angel Investing to Drive Change with Marcia Dawood by Deborah Johnson
Quarterly Reviews and Evaluation with Greg and Deb by Deborah Johnson
Business Models: What Good do They Do? with Greg and Deb by Deborah Johnson
Fast Wins vs. Steady Growth with Greg and Deb by Deborah Johnson
- about Greg & Deb
GREG joins DEBORAH as a co-host on Women at Halftime Podcast once a month.
GREG JOHNSON is a former professional athlete, a triple A relief-pitcher with the Cleveland Indians (now Guardians) He also has years of experience in sales and as an R.I.A. (Registered Investment Advisor), owning his own business. He & Deb met on a blind date and have been married over 40 years.
Investing in the future isn’t just about finances. It’s about intentional living—how we use our time, share our wisdom, and build something that lasts.
deborah johnson
Thought Leader, Keynote Speaker, Author
If you are interested in growing and learning, check out our online courses here: Online Learning
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