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Lessons from My Grandfather: Foundational Integrity in Business and Life

  • Writer: Doug Oosterhart, CFP®
    Doug Oosterhart, CFP®
  • 7 hours ago
  • 3 min read


On October 9th, 2025 my grandfather passed away. He lived a long, meaningful life, and as I’ve reflected on his story over the past few weeks, I’ve realized how much of who I am—and how we approach our work at LifePoint—comes directly from him.


From Humble Beginnings to Foundational Integrity


My grandfather grew up dirt poor in Chicago and slept on the couch. His home life wasn’t easy, but it shaped him. He learned early on what not to do, and he decided that he wanted something better.


He started taking action toward that better life in small, determined ways. As a kid, he’d go to Wrigley Field after games to pick up trash in the stands. The “payment” for that work was a ticket to the next day’s game. That small reward wasn’t just a baseball ticket—it was proof that effort, consistency, and integrity could change your circumstances.


If I had to describe him in one phrase, it would be this: foundational integrity.


A person with foundational integrity is trustworthy, consistent, accountable, principled, respectful, resilient, and authentic. You knew where my grandpa stood, and you could count on him to do what was right—especially when it wasn’t easy.


That’s the same standard we implement in our work with clients. It's not about chasing trends or quick wins; it’s about doing the right thing for each client, even when it’s inconvenient or less profitable. It’s about building trust over time and aligning actions with values.


A Lifelong Commitment to Learning


My grandfather was also deeply curious, well read, and always learning--especially about money, saving, building, and maintaining wealth.


That mindset of continuous learning is something he passed down to me. In financial planning, there’s always more to learn: changes in tax laws, new investment vehicles, shifting client goals, or emerging opportunities to optimize outcomes. Grandpa’s approach to learning reminds me that curiosity and humility are essential in this field.


When we keep learning, we keep serving clients better.


The Art and Science of Planning


Grandpa loved music. He was fascinated by the balance between its structure and its freedom—how there’s a "mathematical" framework behind every song, yet infinite room for creativity within it.


That’s how we think about financial planning. There’s a science to what we do: cash flow modeling, tax projections, investment allocation. But there’s also an art to it—the human side, where each plan is tailored to a person’s life, values, and goals. Just like no two songs sound the same, no two financial plans should look identical.


Loving the Process


One of Grandpa’s quotes, and one I’ll never forget, was this:

“Winning is a goal, but in the pursuit of anything that tests your abilities and demands your best, the real ‘win’ is learning about yourself.”

To me, that means that success—whether in business, golf, or life—isn’t found only in the outcomes. It’s found in the process. The work, the challenges, the adjustments along the way—those are what shape you.


In our work with clients, that philosophy guides everything we do. The “win” isn’t just a perfectly timed Roth conversion or a well-structured withdrawal plan. It’s helping people gain clarity, confidence, and self-understanding as they navigate complex financial decisions. It’s helping them fall in love with the process of planning, not just the end result.


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His Legacy


My grandfather’s life reminds me that where you start doesn’t define where you end up—but how you show up, every day, does. His integrity, curiosity, and love for the process are at the heart of how I live and how we serve clients at LifePoint.


While his physical presence is gone, his influence remains in the foundation of this firm—and in every conversation, plan, and decision that helps people live their version of a better life.

 
 
 
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