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Category: Philosophy
Investing for Upgrades: How the Long View Creates Better Experiences
The beauty and benefit of taking the long view is not just about building wealth. It’s about upgrading your experiences.
Transcript:
Hey everyone, Matt Hall here. You’re going to see more of me like this, not just in writing, but on video. We think it’s a warmer way to stay connected. You can see us, you can hear us, and not just read about us.
So last month I shared some reflections on Hill Investment Group’s 20 year journey. And if you missed it, you can catch it somewhere in the post or the link below. And I left something out that I really want to share with you. It’s likely one of the most important observations over the last 20 years of Hill. And then 25 years of doing evidence-based planning and investing.
When I was coming up in this business, as I wrote in Odds On, I was so struck by how powerful the research was and is patient diversified investing.
It works. The data is and was overwhelming. But here’s the thing, people don’t connect to research alone. Those of us in the industry, we love the logic, the data, and the evidence, but most clients aren’t asking for more charts. You want to know, how does this connect to my life? What will this do for me?
And there, that’s where the difference comes in. We spend our time measuring and managing, running the evidence, monitoring the portfolios, staying disciplined and helping you stay disciplined. And what that does for you, for clients is it frees you up to live.
And here is what I’ve noticed. The payoff rarely shows up in mansions or flash. It shows up in upgrades.
The upgraded hotel room where the view changes the trip, the better seat on the plane that makes travel easier. The bike trip where someone else is helping you with just the right amount of support or the family vacation where you, you don’t just go, you upgrade it by bringing kids and grandkids along. Those moments aren’t about showing off wealth. They’re about upgrading experiences, creating memories, and being more present with the people you love.
One client summed it up perfectly when he told me. Now, Matt, the only thing I think about is which pool toys to get out for the grandkids. I think that’s the beauty of taking the long view. It’s not just about building wealth, it’s about upgrading your experiences, turning patience and discipline into more time, more freedom, and more memories with the people who matter most to you.
We thank you for being with us on this journey. Here’s to the next 20 years and all the upgrades that come with them.
The Long View Library: Books Worth Reading & Sharing
Many of the people we work with tell us they value not just our diligence and professionalism, but also the personal touch and team chemistry that make working together feel special. In that spirit, we’re pulling back the curtain to share what’s been on our bookshelves lately and why these titles resonated with us. Think of it as an open invitation to browse, discover, and maybe even find your next great read or a thoughtful gift.
Let’s start with my suggestion:
Odds On: The Making of an Evidence-Based Investor by our own Matt Hall is a thoughtful overview of our evidence-based approach, how it reflects academic insights, and how it contrasts with more traditional investing methods.
You may have read it at some point over the past decade, but your friends and family—especially the next generation of investors who were too young when it debuted in 2016—may not have had the chance.
If you or someone you know would like to explore our investing philosophy, we’re happy to share a complimentary copy. There’s no cost or obligation. It’s simply a resource we’re proud to pass along. Just email me and we’ll send one your way. Short on time or attention? Email me for a two-page summary. Prefer audio or Kindle? Those versions are available too.
Now, onto more team favorites for you to explore:
I’ve been leaning hard into fiction lately and found some real gems. Pachinko is an epic family story set in Korea and Japan, surprising and moving in how it explores generational identity. Tom Lake is a beautifully written portrait of family and choices that shape a life. The Night Circus—magical realism, stunning imagery, and an immersive mystery—is pure escape. My latest nonfiction read was Good Morning, Monster: powerful real-life stories of resilience that stay with you.
In fiction, I recently reread A Tree Grows in Brooklyn, a timeless favorite. I also enjoyed The Magnificent Lives of Marjorie Post (a great example of someone who took the long view). The Favorites is a story about figure skaters I picked up for nostalgic reasons—think The Cutting Edge. Lady Tan’s Circle of Women scratched my historical fiction itch. On the nonfiction side, The Anxious Generation has been especially helpful as a mom looking to support calm and confidence in my kids.
Going Infinite (by Michael Lewis) offers a fascinating look at Sam Bankman-Fried and the broader crypto narrative. It’s a complex profile of someone who became a central figure in one of the biggest financial stories of the decade. For fiction, Project Hail Mary (by the author of The Martian) was a standout, and Tomorrow, and Tomorrow, and Tomorrow might be one of the best books I’ve read in a while. For a lighter beach read: Nora Goes Off Script.
Good Morning, Monster was a recommendation from Matt, and it’s now one of my top five books. It shares a therapist’s most difficult cases—dark, yes, but incredibly insightful. It helped me appreciate how much childhood experiences shape adult life.
A fiction book I recently loved is Tomorrow, and Tomorrow, and Tomorrow by Gabrielle Zevin. It follows two childhood friends who reconnect in college and begin designing video games together. What stood out most was the deep, complex relationship between the two main characters, intimate without being romantic. It was refreshing and emotionally rich.
My favorite nonfiction book is Endurance: Shackleton’s Incredible Voyage by Alfred Lansing. It tells the gripping true story of Ernest Shackleton’s 1914 Antarctic expedition, where his crew endured an unimaginable struggle for survival after their ship was crushed by ice. It’s an unforgettable story of leadership and perseverance.
We’d love to hear what you’re reading, too. If you have a book you’d recommend, please send it our way, along with a short note about why you loved it. With your permission, we may feature your suggestion in an upcoming issue of the Monthly Journal.
Living the Long View

Coming back from maternity leave after welcoming our daughter this spring has reminded me of what our work at Hill is really about: helping clients use their money as a tool to build lives rich in meaning, not just numbers.
Whether you’re navigating new parenthood, approaching retirement, or somewhere in between, the core questions often remain the same: What matters most? And how can your money support that?
Here are a few reflections that have stayed with me through this milestone.
Time Is Our Most Limited Asset
This season has made it clear: time is precious. As the saying goes, the days are long, but the weeks are short. At Hill, we encourage clients to think of time like any other resource, i.e., something to be used intentionally.
Having a baby sharpened my awareness of how valuable time with all generations can be. We’ve prioritized visits and calls with our parents and grandparents, including Merrill. One visual we often share is Tim Urban’s “Your Life in Weeks,” which maps the average lifespan as a grid of boxes, each one a week. Sam Harris captures the feeling well: “It always is later than you think.”
Experiences That Leave a Lasting Impact
One book that’s prompted meaningful reflection is Die With Zero, which invites readers to think intentionally about how they use time, money, and attention. One key idea is the “memory dividend,” that experiences created now continue to bring joy over time.
During our first family trip with Merrill, we bought matching tracksuits for three generations (thankfully not pictured on the cover of this post!). The laughter that moment created has become part of our family story, which is something we’ll carry forward.
When you “eventize” small moments, making them playful, meaningful, or tradition-worthy, you create experiences that stay with you long after the money is spent.
Freedom Through Planning
Taking the Long View isn’t about deferring joy. It’s about aligning today’s choices with your long-term values. For our family, that included investing in a high-quality caregiver–not only to support our daughter’s development, but to give both Walter and me the capacity to continue doing meaningful work. This single decision had ripple effects across our financial plan and peace of mind.
In our experience, thoughtful planning doesn’t restrict you. Instead it creates more space for the things that matter.
The Time to Act Is Now
Watching our daughter grow has been a reminder that certain windows of opportunity are fleeting. Whether it’s a trip you’ve been considering, a gift you’ve meant to give, or simply time with someone you care about, the moment to act may be now.
At Hill, we aim to help you simplify, clarify, and align your financial life so it supports the life you want to live. With a new rhythm, a deeper commitment to this work, and a fresh perspective, I’m more convinced than ever: the best investments are the ones that help us be present, generous, and fully alive.