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.

Last month, we dedicated an issue of the journal to Odds On. As we were putting that together, I had a realization. The reason I’m actually here at Hill is because of this book I read years ago.

Before Hill, I worked at Dimensional Fund Advisors. That’s how I met Matt Hall, through a study group we were putting together of advisors who had an aptitude for media and marketing. In advance of that meeting, I read Odds On. What initially stuck out to me is how the book reads. It’s not a typical finance book. There’s no jargon. There are no equations. It’s simply a story about someone finding a better way to invest and building a firm that treats clients right.

Hill is a really special place. What is apparent to me now is that the values and the things that drew me into the firm years ago still ring true. The intentionality we put into every interaction. The hospitality we try to show our clients every step along the way.

Making the switch ultimately gave me the ability to use my CFP in a much more meaningful way. Rather than just focusing on investments, now I get to help and guide clients through some of the most important financial decisions of their lives.

Looking back, reading Odds On and meeting Matt felt relatively small at the time. Today it feels more monumental. It led me to where I am now, and it shaped the way I show up for this work and the way we want to treat clients every day here at Hill.

Since my introduction to Odds On many years ago, I’ve always shared the book as a recommendation for people who want to better understand our industry and the way we think about investing. It feels less like a book and more like a note from a friend, or a story passed along by someone you trust. It’s one of the easiest books I’ve ever read, and it’s stuck with me in a way that not many others have.

When I learned we were doing a newsletter issue all about Odds On, I found myself saying to someone on our team, “You know, it’s funny… I hadn’t really thought about this directly, but the book is actually the reason I’m here at HIG today.”

Before Hill, I worked at Dimensional Fund Advisors, a now $1T+ money manager and the pioneer of evidence-based investing. I met Matt Hall through a new study group we were launching, a group of evidence-based advisors we brought together from around the country who all had an interest and aptitude for media and marketing. Odds On put Matt at the top of our list, and he became one of the founding members of that group.

I had read Odds On in preparation for our first meeting, so I had a sense of Hill and its mission. But it was really through getting to know Matt in that group, hearing how he talked about his purpose, the people he works with, and the way Hill cares for clients, that made both him and the firm stand out.

In my role at DFA, I worked with hundreds of advisory firms across the country. It gave me a unique lens into how firms operate; what they prioritize, how they invest, and how they show up for their clients. Hill always felt different. There was a level of care and intentionality behind each decision, a real desire for clients to feel known and taken care of, and a culture of excellence. The kinds of things every firm likely strives for, but not all are able to truly deliver.

All of that made the decision easy when the opportunity to join Hill came along. I get to do work I love, with people I genuinely enjoy, and care for clients in a way that feels meaningful and aligned with who I am (a caring nerd!).

I don’t think I’d be here today without Odds On. So thank you to Matt for writing it. I doubt finding one of your lead advisors 10 years down the road was top of mind when you sat down to write it, but I’m really glad you did.