At Hill Investment Group, we’ve found that when a few clients ask similar questions, many more likely share the same curiosity. To better serve you, we’ll periodically feature this “Hey Hill” segment in our newsletter, addressing common client questions and explaining our perspective. To submit questions for future newsletters, email us at service@hillinvestmentgroup.com.

Tax season always feels like a scramble. Are there things we (or you) can be doing throughout the year to make it easier – and smarter?

At Hill Investment Group, we believe taxes aren’t just a once-a-year concern. They’re a year-round opportunity. While most people only think about taxes in the spring, we’re building strategies into your plan every day—so you’re not just reacting in April, you’re planning ahead with purpose.

Markets move. Headlines shift. But one thing we can control is how efficiently your portfolio is managed from a tax perspective. It’s a key part of Taking the Long View, helping you keep more of what you earn—not just this year, but every year.

How We Build Tax Efficiency into Your Plan

• Strategic Asset Location – Some investments generate more taxes than others, and where you hold them matters. We structure your portfolio to keep tax-inefficient assets in tax-advantaged accounts, reducing unnecessary tax drag.
• Tax-Loss Harvesting – When the opportunity arises, we strategically offset gains with losses—lowering your taxable income without disrupting your investment strategy.
• ETF Investing – ETFs (Exchange-Traded Funds) allow investors to defer most, if not all, capital gains taxes until they sell, helping avoid surprise tax bills.
• Tax-Advantaged Accounts – From IRAs and Roth conversions to HSAs, we help you maximize the long-term tax benefits of these accounts.
• Charitable Giving Strategies – Tools like donor-advised funds, qualified charitable distributions (QCDs), and appreciated stock donations allow you to give while staying tax-smart.
• Estate & Gifting Strategies – Thoughtful wealth transfer planning helps minimize estate taxes and ensures your legacy is passed on efficiently.

Making Tax Season Easier

Beyond these long-term strategies, we make tax season seamless by preparing tax packets with key reports and details your CPA needs. Because we work closely with your tax team, we help ensure that your investment and tax strategies are always aligned.

If you have questions about how tax planning fits into your financial picture, we’re here to help.

Taking the Long View means thinking ahead—about taxes and beyond.

Turbulent times test everyone’s resolve—whether you’ve taken the long view for decades, are just beginning to embrace it, or still find yourself leaning on stock-picking instincts. No matter your background, chances are you’re hearing more chatter lately—around the office, at the gym, or over cocktails—about “the market.” Some are panicked. Others are simply asking, “What should I do now? What are you doing?”

Here’s our suggestion: Pause. Breathe. And consider sharing a copy of Odds On with your friend or colleague. (Just call, email, or click here to send a hard copy or audio version.) If you’re feeling uneasy yourself, revisit the book—or better yet, let’s talk. Need a quick refresher? Start with the Odds On summary of key takeaways.

While there’s no substitute for a real conversation to calm the nerves, not everyone has an advisor on speed dial—or a sleepless night may strike at 2:00 AM. That’s where Odds On comes in. For nearly a decade, it’s helped readers stay grounded, especially when markets feel like a rollercoaster. Yes, the book will turn 10 before we know it—but the philosophy behind it is backed by over a century of evidence and forms the bedrock of how we invest at Hill Investment Group.

Styles may drift in and out of favor, but taking the Long View means committing to a philosophy that consistently puts the odds of long-term success on your side—regardless of today’s headlines.

So, if you’re feeling uneasy, give us a call. Or pick up your copy of Odds On and revisit a few highlighted pages. And if someone you care about could use a steadier hand, let us know where to send their copy. We can’t control the market—but we can help you control how you think about it.

At Hill Investment Group, we often say that real financial planning isn’t about being exactly right today—it’s about being less wrong tomorrow.

That may sound strange coming from a team grounded in evidence, logic, and long-term thinking. But we also know life doesn’t follow a straight line. That’s why we believe the most valuable part of financial planning isn’t the plan itself—it’s the process of ongoing planning.

Carl Richards, a friend and fellow long-term thinker, offers a great analogy we love to share:

Airline pilots prepare a flight plan before every trip. Yet when asked how often the flight goes exactly according to that plan, the answer is: rarely.

Course corrections are built into the process because the unexpected is expected. Weather changes. Winds shift. But the destination remains the same—and they keep adjusting until they land safely.

The same principle applies to your financial life. We build your plan using the best data available—making thoughtful assumptions about returns, taxes, inflation, goals, and more. But the moment the plan is complete, we know one thing for sure: it will be wrong. We just don’t know how yet.

That’s not a flaw. It’s reality.

Real planning is what happens next. It’s the process of revisiting, refining, and adjusting—so you can stay on track, even when the world around you changes.

That’s why our team is here: not just to build your plan, but to keep you flying steady all the way to your destination.

Take the Long View.