We recently sat down with a couple in their 50s who had spent decades building. Careers. A portfolio. A family. They funded education, paid down debt, and prepared for a future that always seemed to require one more year of work and one more dollar saved.

For most of that time, every dollar had a job. Pay down the mortgage. Fund college. Max out retirement plans. Set aside cash for taxes. Invest the next business distribution.

Now their cash flow is beginning to look different. Many of the major assignments are covered, which means more of the next dollar comes with a choice.

They like their work and still have goals. They also care deeply about having time for the relationships that matter to them, especially family, friends, and their own parents.

That led us to a more interesting question:

The next dollar could go into the portfolio. It could pay for help that creates breathing room, fund a longer family visit, support a cause, help the kids, or simply wait until the right use becomes clearer.

The right answer depends on the person.

Every client has some mix of assigned dollars and choice dollars, and that mix changes over time. For someone still building, preferences help determine which goals deserve priority. For someone with more room in the plan, those same preferences can help direct that freedom.

Our founder, Rick Hill, offers one example. Rick spent a good solid decade following what we called the “Rick Hill Plan,” slowly walking down from working 40 hours a week to 10. He still keeps his toe in the water, giving him the community, mental engagement, and fun he gets from work while creating more time for family, friends, travel, and hobbies.

That plan fits Rick. Someone else may love working full time. Another person may want to leave work completely and move toward something new. Research on gradual retirement has found benefits to maintaining meaningful work and connection when the arrangement fits the person.

A financial plan tells us what is possible. Knowing the client helps us understand what those possibilities are for.

One family may buy a second home because it becomes the place where everyone gathers. Another may prefer the freedom to travel anywhere. One client may help the kids earlier because they want to see what the money makes possible. Another may value the confidence their children develop by building independently.

Research supports the importance of this fit. One study examining more than 76,000 bank transactions found that people whose spending better matched their personalities reported greater life satisfaction. The fit between the spending and the person mattered more than how much they spent.

The useful question is whether your spending looks like you.

Money can remain invested. Time with parents, children, friends, and our own health has a season. The way we use our resources influences who receives our attention, what receives our energy, and what we have room to experience now.

Understanding our preferences takes its own kind of work and awareness. Clients rarely arrive with perfectly articulated answers, so we help draw them out.

We may notice that a client lights up when talking about traveling with her siblings and grows quiet when discussing a second home. We may learn that “working less” is really about seeing aging parents more often. We may ask whether helping a child is meant to create opportunity, security, or connection.

We ask questions, listen for patterns, and reflect preferences back. Then we put numbers around the choices so clients can decide with confidence.

• Which trips leave you restored and excited?
• What do you hope helping the kids will make possible?
• Who and what do you want more time for?

The couple we met with is still in the gray. They are becoming more aware of their choices and more intentional about what they want their dollars to do.

Good financial planning helps turn wealth into a life well lived. For clients who are building, that means protecting what matters along the way. For clients with more freedom, it means giving more of their lives to what matters most.

For years, your money had a job. Now you may have more freedom to choose its next assignment.

The best part of our work is the relationships we build with our clients. This series celebrates those relationships by highlighting the interesting people behind the portfolios. This spring, several members of our team had the opportunity to visit Larry West at his remarkable Route 66 Museum, Campbell’s Service, in Pacific, Missouri.

What began as Larry’s appreciation for America’s “Mother Road” has grown into an incredible collection of vintage service station memorabilia and Route 66 treasures, all thoughtfully displayed in a restored building along Historic Route 66. The museum is a labor of love, filled with carefully curated signs, gas pumps, and artifacts. Walking through the museum feels less like visiting a collection and more like stepping back into a piece of American history.

That same commitment is evident in their family business, West Contracting. Founded in 1956 by Larry’s parents, Norman and Mary West, the company has grown from a small family business into one of Missouri’s leading paving contractors. For nearly 70 years, the West family has helped build the roads that connect our communities, while earning a reputation for hard work, integrity, and putting relationships first.

This year, West Contracting reached another exciting milestone as the company celebrated its 70th anniversary. As part of the celebration, Larry sat down with his son, Chris, to reflect on the company’s history, the lessons learned over the decades, and what it means to prepare the next generation to carry the business forward. Their conversation wasn’t just about construction—it was about family, leadership, and leaving things better than you found them.

 View Part 1 here. 
 View Part 2 here.

At Hill Investment Group, our motto is Take the Long View. While we often think about that in terms of investing, it’s just as meaningful when we see clients who have spent decades building businesses, preserving history, and investing in future generations.

Larry and Kathleen have done all three.

We’re grateful they welcomed us into a place that’s so personal to them, and we’re even more grateful to know them as clients and friends.

Is your cash working as hard as it could be? Many checking and savings accounts still pay very little interest. That’s why we recommend Flourish, a high-yield cash account for everyday cash and short-term savings (we use it ourselves, too). It keeps your money accessible while earning a competitive rate. 

For a limited time: If you set up direct deposit into Flourish before the end of 2026, you’ll earn a boosted interest rate for your first 90 days. It costs nothing and only takes a few minutes to activate.

After the promotional period ends, your cash will continue to earn Flourish’s competitive standard rate rather than sitting in an account paying little or no interest. 

At Hill, we believe the best financial strategies are often the simplest ones. Small changes like earning more on your cash and automating good financial habits can make a meaningful difference over time.

If you’d like help getting started with Flourish or setting up direct deposit, recurring transfers, and other automations, we’re happy to help. Please reach out to us.