As their summer at Hill came to a close, we asked our interns to reflect on the lessons they’ll carry with them. Their answers touched on investing, leadership, relationships, and a few of the values that shape how we work together every day.

Arriving at Hill, I wanted to prioritize improving my communication to help me become a better leader. Communication channels are more fragmented than ever, and effective leadership increasingly relies on the ability to overcome these obstacles.

At Hill, I learned that candor means more than just vocalizing disagreements. By observing the leaders at Hill, it became obvious that some of the most difficult conversations can be the most fruitful.

The thing I admire most about the leaders at Hill is the way they are able to challenge each other, not to break each other down, but to build each other up. I plan to take this skill with me to help me become a more effective leader, both at work and beyond.

Before this summer, I thought investing was mostly about finding the right answer. At Hill, I learned that the better question is often why.

Every project taught me not to accept something just because that is how it has always been done. At Hill, the focus is on understanding why and asking, “What does the evidence support?”

But the most important lesson I will take away has less to do with investing and more to do with people. The work matters, but the people beside you shape how meaningful and enjoyable that work becomes.

At Hill, fun is not separate from business. It builds the trust, energy, and openness that allow people to do their best work together.

This summer taught me to seek evidence before reaching a conclusion, but it also taught me something even more valuable: when you surround yourself with the right people, meaningful work and fun naturally go together.

A few weeks ago, I heard Morgan Housel speak at a conference for top advisors. Many of you may know Morgan from his book, The Psychology of Money, which we often share with clients. We also had him as a guest on my podcast, Take the Long View.

During his talk, Morgan told a story that reminded me of one of my favorite investing lessons.

Everyone knows Warren Buffett. Most people know Charlie Munger. But far fewer people know Rick Guerin.

That’s interesting because Buffett once said Rick was every bit as smart as he and Charlie were. Yet history remembers Buffett and Munger, while most investors have never heard of Rick.

So what happened?

In the early days, Buffett, Munger, and Guerin invested alongside one another. They shared ideas. By all accounts, Rick was an exceptional investor.

But during the brutal bear market of 1973 and 1974, Rick used leverage. He borrowed money to invest. When markets collapsed, margin calls arrived, and he had to sell.

He sold shares to Warren Buffett.

Years later, Buffett explained the difference between them this way:

That is one of the most important investing lessons there is.

The difference was not intelligence. It was not information. It was not access.

It was patience.

Buffett and Munger built their lives and their portfolios in a way that allowed them to stay in the game. Rick could not, or would not, do the same.

That is why I think this story is bigger than investing. It is really about compounding.

Compounding only works if you give it enough time.

That applies to investing. It also applies to building a business, raising a family, improving your health, and developing meaningful friendships and relationships. The biggest rewards often come from years of steady progress that may not look very exciting in the moment.

I have seen that firsthand.

When we started Hill Investment Group in 2005, there was no shortcut. There was no trick. There was simply a commitment to do the right things repeatedly. Serve clients well. Stay disciplined. Keep learning. Think long-term. Allow time to do what time does best.

Now, 21 years later, one of the things I appreciate most is this:

That is true in investing. It is true in business. And I think it is true in life.

The next time markets get noisy, or life gets noisy, I hope you remember the story of Rick Guerin.

Not because he failed, but because his story reminds us that success is often less about brilliance and more about patience.

That is what Taking the Long View is all about.

A few years ago, a family member transitioned to assisted living. The decision felt difficult for her, like a loss of independence. She fought it hard. But once she settled in, something unexpected happened: she found routine, connection, and purpose again.

Watching that shift reframed how I think about financial planning.

As planners, we often approach aging and retirement through a practical lens. We focus on the details: health care plans, long-term care, estate documents, and whether the financial plan can support the years of spending ahead.

Those things matter. But quality of life matters too. So does preserving a sense of agency as your needs, abilities, and priorities change.

Earlier this year, during a conversation about a client’s transition into assisted living, his daughter suggested I read Being Mortal by Atul Gawande.

I’m glad she did. The book changed how I think about the later stages of life and the role planning should play in them.

1. Independence Matters More Than Perfect Safety
One of the book’s core ideas is that many senior living decisions prioritize safety over autonomy. Safety matters, of course. But losing independence can take a real toll on wellbeing.

The best living environments preserve choice: how you spend your day, who you’re around, and what gives you meaning.

We’ve seen this with clients who explore senior communities early, before they need them. Beginning earlier gives families more agency over the decision. It can also help clients gain more life through social connection, activities, and less stress about home maintenance.

2. Purpose Is Fundamental to Wellbeing
Gawande highlights research showing that even small responsibilities, like caring for a plant, can improve wellbeing and longevity for older adults.

The lesson is simple: people need purpose. They need a reason to get out of bed in the morning.

Financial independence is important. But planning should also ask what replaces the structure and meaning that work once provided. People who thrive in this phase often stay connected to hobbies, community, family, or roles where they still feel needed.

3. Define Quality of Life, Before a Crisis
Being Mortal reminds us that our definition of quality of life changes over time.

When we’re younger, it may mean freedom and adventure. Later, it may mean staying close to family, maintaining familiar routines, or enjoying a favorite meal with people we love.

Many families avoid talking about aging until a crisis forces decisions. The book encourages asking better questions sooner:

• What are your fears and goals as you get older?
• What tradeoffs would you be willing, or unwilling, to make?

In our advisory role, we’ve seen how helpful it is when families have these conversations before a medical event or major transition. When your values are clear, decisions become less about guessing and more about honoring what matters most.

Planning for aging doesn’t mean expecting the worst. It means getting clear about what matters most, so that when decisions come, they reflect your values instead of default choices.

At Hill, we believe financial planning is about more than numbers. Taking the long view means helping people live well across every stage of life, with clarity, confidence, and peace of mind.

If this sparks a conversation about aging, independence, or planning for later life, we’re here to help you or someone you care about talk through it. Reach out any time here.