Caleb J. Chupp is a Financial Consultant serving the Harrisonburg office. In his work, Caleb works alongside individuals, families, and businesses as they integrate their finances and values in order to achieve their goals. 
“I am proud to be able to help build lasting community impact and create more sustainable futures for people of all backgrounds,” he said. “Through my work, I’m able to pursue my passion of connecting with people and creating holistic, meaningful relationships.” 
Caleb graduated from Eastern Mennonite University, where he received a bachelor’s degree in business administration. He attends Zion Mennonite Church. When he’s not working with clients, Caleb enjoys hiking and backpacking throughout the Shenandoah Valley, playing games and sports with family and friends, and trying new foods. 

One of the most common things people say when they sit down with a financial consultant for the first time is some version of: “I feel like I should already know this.” Whether it’s a recent college grad who hasn’t started saving yet, or someone in their 50s wondering if they’ve already missed their window, the feeling is the same — uncertainty, a little guilt, and honestly, some relief that the conversation is finally happening. 

Here’s what every person should hear, no matter where they are in life: it is never too early to start, and it is never too late to have a conversation. 

For Young Adults: Time Is the Greatest Asset 

For those in their 20s or just entering the workforce, one of the most common myths worth challenging is the idea that there isn’t enough money to start saving. It comes up constantly — “I’ll start when I make more,” or “I’ll get serious about it after my loans are paid off.” Those feelings are understandable, especially in those first years out of school when every dollar seems already spoken for. 

But the truth is this: $10 or $20 a month, starting today, can do more for a financial future than $200 a month starting ten years from now. That’s not an exaggeration — that’s simply how compound growth works over time. More money can always be earned, and the amount being saved can always be increased. 

The practical approach for someone in their 20s is straightforward: think about one meal out each month and redirect that $15 or $20 instead. Build it into the budget like a non-negotiable bill — because in a real sense, it is one. Paying your future self-first is the habit that changes everything. Once it becomes automatic and consistent, it won’t even be noticeable. And ten, twenty, thirty years from now, starting early will be one of the best financial decisions ever made. 

For Growing Families: Intentional Planning in a Season of Change 

Starting a family, buying a first home, changing jobs — these seasons of life are exciting, but they’re also overwhelming. There’s so much demanding attention at once that financial planning can easily become one of those things that keeps getting pushed back. 

But this is actually one of the most critical times to slow down and look at the full picture. 

It’s not just about the immediate numbers. It’s about building habits and patterns that carry a family forward. The financial behaviors modeled for children — how money is talked about, how decisions are made around it, whether it’s treated as a tool or a source of stress — all of that shapes how the next generation will think about money for the rest of their lives. Building good habits now isn’t just an investment in retirement. It’s an investment in the whole household. 

For new and growing families, the recommendation is to map out a clear, intentional strategy — one that accounts for current expenses, short-term goals like building an emergency fund or buying a home, and long-term goals like retirement and education planning. Having a plan doesn’t mean everything goes perfectly. It means when things change, there’s a foundation to come back to. 

For Those Nearing Retirement: Steady Wins the Race 

The closer retirement gets, the louder the questions become: Did I save enough? Is it too late? What if the market drops? These concerns are valid, but they don’t have to lead to panic-driven decisions. 

The key reminder here is that financial planning isn’t about hitting home runs. The goal is singles — consistent, steady, intentional growth over time. Trying to time the market or make bold moves to “catch up” is typically where people get into trouble. Some of the most successful long-term savers rarely check their accounts — not because they’re careless, but because they have a plan, and they trust it. Decisions based on emotion or a bad week on Wall Street rarely serve anyone well. 

This is the marathon mentality. There will be stretches where the numbers don’t look great. That’s normal — that’s investing. What matters is staying the course, continuing to make intentional decisions, and resisting the urge to react out of fear. Even for those who feel behind, the years leading up to retirement still hold real opportunity. The more proactive the approach right now, the more security can be built before that finish line arrives. 

A Plan Built Around What Matters Most 

Good financial planning isn’t one-size-fits-all. At Everence Financial, the process starts with understanding what matters most — values, goals, and the life someone is working toward — and building a personalized strategy from there. 

Whatever stage of life you’re in, the most important step is the same: start the conversation. There’s no need to have all the answers first. That’s what a financial consultant is there for. 

To connect with Caleb Chupp and the team at Everence Financial, reach out to the Harrisonburg office or visit Everence Financial online. 

Listen to Caleb’s full interview with WSVA here.