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The Long View on Estate Planning

After I earned my Certified Financial Planning (CFP(R)) designation, my grandparents were both proud and curious. They asked me to take a look at their finances and see if there was anything they should be doing differently. My grandpa had always managed things on his own and had done well, but one glaring gap stood out: they hadn’t done any estate planning.
They didn’t know what a trust was or where to start. But they did know what mattered most: how they wanted their assets to pass, which of their children they trusted to handle things, and that they wanted to make the process as easy and stress-free as possible for their family one day.
For someone used to doing everything himself, my grandpa recognized that this was one aspect of his life that he needed to delegate. He also saw the value in doing some work now to make life easier for his kids later, a small act of love that will one day make a big difference.
That mindset captures how we typically approach estate planning with our clients at Hill. It can feel complicated and overwhelming, but when you focus on the big picture and surround yourself with the right team, it becomes a powerful way to protect your family and preserve your legacy.
No two estate plans look the same. Some are wonderfully simple, others more complex. There’s no “right” way to do it—only what’s right for you. That’s why we take time to understand each client’s values, family dynamics, and long-term vision before collaborating with their attorneys and CPAs to design a plan that fits.
Here are a few guiding questions we use when helping clients update or establish their plan:
- Is it easy to understand? You should be able to explain the big picture in plain English.
- Does your team collaborate on your behalf? Your attorney, CPA, and Hill advisor should be aligned so your investments, taxes, and estate all work together.
- Are you avoiding probate? The right structure may help your family avoid a lengthy and expensive court process.
- Are your heirs protected? Your plan should clearly state how and by whom assets will be managed.
- Is everything included? It’s easy for accounts or property to be left out due to incorrect titling.
- Who will carry out your plan? Executors, trustees, powers of attorney, and guardians can all play important roles. It’s important to make sure they understand and accept them.
When my grandparents’ plan was complete, my mom (named as executor) told me multiple times how relieved she felt knowing everything was organized and clear. That sense of clarity is exactly what we hope to provide for every Hill family.
Estate planning isn’t one-and-done; it’s an ongoing act of care, and it’s part of Taking the Long View®. We generally recommend our clients to review their plan every five years, or sooner if life or laws change. Families grow, goals evolve, and your plan should, too.
If you’re wondering whether your plan still fits, or if you’ve been meaning to get started, we’d love to help you or a loved one take that next step.
Email us at askanadvisor@hillinvestmentgroup.com to connect with your Hill advisor and start the conversation.
Hey Hill! Help Me Avoid Common Investing Misconceptions

At Hill Investment Group, we spend our days immersed in markets and evidence. We know most people don’t, and our clients rely on us to do that work for them.
Even the most financially literate investors can encounter misconceptions, often picked up from friends, social media, or the financial press. Many of these are rooted more in behavior and emotion than in evidence.
Here are a few we hear regularly, along with an evidence-based perspective on each.
It can be easy to think of dividends as “free money” from an investment, and some even choose funds solely for their dividend yield. The reality is that when a company pays a dividend, the value of its shares is reduced by the same amount. For example, if you hold a $20 share and it pays a $2 dividend, you now have $2 in cash and a share worth $18—the total value is unchanged.
Companies that reinvest profits into their business sometimes create more long-term growth than those that pay them out. At Hill, we view dividends as one element of total return and often as a way to rebalance portfolios in a tax-efficient manner.
For clients who rely on investments for retirement income, we may help design a withdrawal plan by selling shares. This approach allows:
- Investment decisions to be based on total return, not dividend yield alone.
- Greater flexibility to manage tax impact by choosing which holdings to sell.
This can be more tax-efficient than receiving dividends automatically, which are taxable whether you need the income or not.
No one enjoys seeing an investment go down. But in certain cases, realizing a loss can provide a tax benefit while keeping your long-term plan intact.
For example, tax-loss harvesting involves selling an investment that has declined, capturing the loss to reduce taxes today (or in future years), and reinvesting in a similar security to maintain your portfolio’s strategy.
This doesn’t remove the reality of market downturns, but it can turn them into opportunities for tax management. While individual investors may not do this on their own, professional advisors often monitor for these opportunities as part of portfolio management.
Because U.S. companies are most familiar, many investors lean heavily toward them—sometimes without realizing it. Yet the U.S. represents only about half of the global market, which means there is significant opportunity beyond our borders.
Diversifying globally can help manage risk and position a portfolio to benefit from growth wherever it occurs. History has shown that different markets lead at different times. For example, U.S. stocks lagged from 2000 to 2010 while international markets performed better. In other periods, U.S. stocks have led. Since no one can predict which region will outperform next, broad diversification helps reduce reliance on a single market.
Investing comes with complexity, and misconceptions are common. Our role is to help clients cut through the noise and make evidence-based decisions that support a long-term plan.
If you know someone who might be interested in learning more about this approach, we’re glad to share educational resources or have an introductory conversation. They can reach us at askanadvisor@hillinvestmentgroup.com.
The Parable of the Wizard & the Prophet: What It Teaches Us About Money

There’s a well-known idea in the world of big-picture thinking, first introduced by historian Charles Mann, that people tend to fall into one of two camps when it comes to solving problems: wizards and prophets.
The wizard believes in the power of innovation. They chase breakthroughs, trusting that human ingenuity can overcome nearly any obstacle. In their view, the solution is out there. We just haven’t invented it yet.
The prophet, on the other hand, champions restraint. Prophets remind us of our limits, calling for thoughtful stewardship and humility. They believe real progress comes not from racing ahead, but from pausing to reflect, simplify, and align with deeper values.
This tension between wizard and prophet shows up in everything from climate change to technology, and even how we think about investing.
The Wizard
In investing, wizard energy often shows up as the lure of the new:
- A product promising market-beating potential
- A hot stock expected to soar
- An app that promises to automate everything overnight
The wizard pursues complexity and fast results. And in moderation, this mindset has its place. Without it, we wouldn’t have low-cost index funds, digital account access, or the academic breakthroughs that helped shape evidence-based investing.
But unchecked, wizardry can lead to chasing fads, mistaking novelty for progress, and believing the next big thing is always just a click away.
The Prophet
Prophets bring a different mindset to investing. They emphasize what’s within our control: saving consistently, diversifying broadly, and sticking to a long-term plan. They ask deeper questions like: How can I align my money with my values? And what will make this last?
This approach can feel quieter, but over time, it offers clarity, resilience, and connection to what matters most.
Better Together
At Hill, we aim to balance both perspectives. Like the wizard, we embrace smart innovation, leveraging tools and research when they align with long-term evidence. And like the prophet, we build portfolios and plans around timeless principles: patience, discipline, and long-view thinking.
Financial progress isn’t about choosing sides. It’s about responsible stewardship and intentional alignment so that your money supports a life of meaning and purpose.