When you’re working, the focus is often on what you earn from your investments. But in retirement, what you keep after taxes can matter even more.

That’s why the order in which you withdraw from your investment accounts can have a meaningful impact. It may influence how much you pay in taxes, how long your portfolio lasts, and even what you’ll pay for Medicare premiums.

Here’s a general framework that financial professionals often consider when building tax-aware withdrawal plans:

• Start with taxable accounts. These are brokerage or investment accounts where taxes have already been paid on contributions. Selling investments from these accounts may trigger capital gains, which are often taxed at lower rates than ordinary income.
• Then consider tax-deferred accounts. Withdrawals from traditional IRAs and 401(k)s are taxed as ordinary income. By spreading these distributions over time, you may reduce the chances of being bumped into a higher tax bracket later.
• Preserve Roth IRAs for later. Roth accounts grow tax-free, and withdrawals are generally tax-free in retirement. Plus, Roth IRAs aren’t subject to required minimum distributions (RMDs), making them a valuable tool for later-life needs or legacy planning.

A Hypothetical Example

Imagine a retired couple, Elaine and Bill. They have a mix of taxable, tax-deferred, and Roth accounts. After reviewing their situation and long-term goals, a strategy was developed that began with their taxable assets, incorporated modest distributions from their IRA to manage future tax exposure, and left their Roth IRA intact for later.

This approach helped them create a more predictable tax picture and supported their long-term planning objectives.

Tailored to You

Of course, the best strategy depends on your personal circumstances—things like your income needs, tax bracket, account types, family or charitable goals, and how markets perform over time.

That’s why we take a collaborative and proactive approach. At Hill, we coordinate closely with your tax professionals and use evidence-based planning tools to help ensure your withdrawals are as tax-efficient as your investments are intentional.

Want to explore your retirement income strategy or review your current plan? We’re here to help—and to take the long view with you.

Hill Investment Group does not provide tax or legal advice. You should consult with a qualified tax professional regarding your individual circumstances.

Before joining Hill Investment Group, I spent part of my career at Dimensional Fund Advisors (DFA)—a firm whose investment philosophy has helped shape our own. DFA, like Hill, was founded on a simple but powerful belief: markets work. That foundational idea continues to shape how I view the world and reinforces my deep confidence in evidence-based investing.

It’s easy to think of “the market” as a complex or distant system. But in reality, we all interact with markets more often than we realize. Whether you’re selling a used couch on Facebook Marketplace, comparing mortgage rates, or negotiating with a contractor, you’re participating in a market—exchanging value based on available information, competing options, and mutual agreement. This same principle drives how trillions of dollars are traded globally every day.

What makes markets remarkable is their ability to reflect the collective wisdom, emotion, and activity of millions of participants. In the short term, markets can be unpredictable, reacting to headlines, global conflicts, elections, or economic data. But over time, they’ve proven to reward long-term thinking, discipline, and optimism.

Of course, that doesn’t mean every moment in the market feels good. Volatility can be unnerving, especially when headlines are loud and uncertainty is high. But as our co-founder Matt Hall recently reminded us, “sometimes you need to duck.” In other words, short-term turbulence is a natural part of investing. It’s the price we pay for the opportunity to pursue long-term growth.

If you take a step back, the broader trend is compelling. As David Booth, co-founder of DFA, noted in a recent commentary, markets delivered strong returns in early 2024, even amid geopolitical tensions and economic uncertainty. That’s not magic. That’s markets doing what they do best: translating risk, effort, innovation, and information into forward motion. It’s a reflection of human ingenuity—entrepreneurs solving problems, companies adapting, and people continuing to build and invest in the future.

At Hill, we believe that investing is ultimately an act of faith in global progress. When you invest in a broadly diversified portfolio, you’re investing in the belief that economies will continue to grow, that people will continue to innovate, and that the world will continue to move forward—not just in the U.S., but around the globe.

Yes, markets do go down. Historically, downturns have occurred roughly every six or seven years. But staying invested—despite those temporary declines—has historically been a reliable way to participate in long-term growth. On the other hand, trying to time the market or avoid short-term dips can carry a different risk: missing out on the recoveries that often follow.

There’s also a hidden cost to stepping away from the market: the mental load. The stress of trying to guess when to get in or out, or constantly second-guessing your plan, can be draining. Many investors eventually come to see the value of having a trusted advisor, not just to manage investments, but to help them focus on what matters most in their lives.

If you’re reading this, you’ve likely already embraced that philosophy. You’ve chosen to Take the Long View with us. Our encouragement now is simple: lean into that mindset. Let the markets do their job, while you focus on yours—being present with your family, pursuing your passions, and building a life filled with meaning and intention.

That’s the real return—and the heart of why we Take the Long View.

Disclosures:
This content is for informational and educational purposes only and does not constitute personalized investment advice or a guarantee of future results. Hill Investment Group does not provide legal or tax advice. Please consult your legal or tax professional regarding your individual circumstances. References to third-party firms or individuals do not constitute endorsements or affiliations unless explicitly stated.

At Hill Investment Group, we think long-term—whether we’re helping clients stay the course or cultivating the next generation of talent. One of the ways we live out that mindset is through our summer internship program, which continues to grow in depth and impact each year.

Every spring, we carefully select interns who reflect our values: curiosity, humility, hard work, and a hunger to learn. We look for students who aren’t just academically strong but also thoughtful communicators and team players; people we’d want to work alongside long after the summer ends.

We often share Odds On early in the process to give candidates insight into our philosophy, then host a series of team interviews to ensure mutual fit. We see the internship as a two-way opportunity: a meaningful growth experience for the intern and a chance for us to deepen our bench of future leaders. Once they join us, interns receive a fully immersive experience, learning from every department, working on real projects, and even participating in strategic conversations. And of course, we make time for fun.

Many of our intern alumni have gone on to successful careers in finance, consulting, and even full-time roles with Hill. Their contributions continue to shape who we are. We’re proud to carry that tradition forward this year with three exceptional individuals.

Michael Wanda – Principia College

Hi, my name is Michael Wanda, and I’m a rising senior at Principia College, majoring in Business and Economics. I was born and raised in the suburbs of Nairobi, Kenya. Though I had been accepted to the top law school in the country, I followed a different calling—finance—thanks to the influence of my older brother.

When the pandemic changed everything, a chance connection through soccer helped me apply to Principia and begin a new path in the U.S. Earlier this year, I discovered Odds On and was fascinated by Matt and Rick’s journey to build Hill Investment Group. After finishing the book, I knew where I wanted to intern.

Since joining, I’ve had incredible experiences—including a memorable lunch with Matt at his usual lunch spot, Rearn Thai. The people here are kind, smart, and committed to something that feels bigger than just numbers. I’m grateful to be part of it.

Cameron Martin – University of Miami

Hello, my name is Cameron Martin. I grew up in University City, Missouri, where sports like football and wrestling taught me how to embrace adversity and push through challenges. That mindset has carried over to my academic life—I’m a Singer Scholar at the University of Miami, double majoring in Finance and Business Law.

What excites me about Hill is the mission to make the complex simple for the sake of helping others. To me, a smart person doesn’t complicate things—they clarify them. That’s what I want to do in my career, and it’s why this internship is such a great fit.

So far, the people here have been incredibly generous with their time and insight, especially Jonesy and Jack. I’m looking forward to learning more and contributing wherever I can this summer.

Sofia Perez – Washington University in St. Louis

Hi, my name is Sofia Perez. Though I was born in St. Louis, I lived in Mexico for 10 years before returning for college. I’m a rising junior at Washington University in St. Louis, double majoring in Finance and Marketing with a minor in Human-Computer Interaction.

Helping my parents run their small businesses taught me how much heart and effort go into every dollar earned. That experience sparked my interest in business and a desire to help people grow stability and opportunity.

I was drawn to Hill because of the firm’s long-term, evidence-based approach and its focus on relationships. From my first interaction, I felt aligned with the team’s values and supported in my growth. I already know I’ll look back on this experience as a defining step in my career.

We’re proud of Sofia, Cameron, and Michael, and excited to learn from them just as much as they’re learning from us. Their early contributions are already helping us grow stronger as a firm.

Stay tuned for more from the interns in a future newsletter.