Reflections of a Spender

When Kristen first suggested our RisingGen Collective group read The Art of Money: Simple Choices for a Richer Life by Morgan Housel I was nervous! I had a fear of being shamed with each chapter for my past lavish spending [I’ve gotten better], so I put it off for a bit. With our call fast approaching, I knew I had to face my fears and read the book.

To my surprise, once I downloaded it on my Kindle, I could not put it down! I was enthralled with each passing chapter. I was shocked at how I was feeling, but guilt was not the word that came to mind. Alignment, justification, and memories resurfaced as I considered how my past spending habits reflected a particular ...

 In over twenty years of working with enterprising families, I often help them navigate issues that arise when love and money become intertwined. Consider the following real-life scenarios (identifying info changed):

A Next Gen family member who is away at university finds himself picking up the tab for his friends, feeling guilty about having more money than they do. But in time his friends begin taking advantage and expect him to pay for everything.

A newly engaged couple finds themselves in gridlock when attempting to negotiate their prenup. She resents feeling like he is being greedy and fears that this relationship may be about her money. He is deeply offended that she doesn’t trust h...

When families steward significant wealth, whether through a formal single-family office (SFO) or a looser, informal “family office” ecosystem, one of the hardest challenges isn’t investment strategy, legal structures, or tax planning. It’s people.

Finding advisors who can serve with skill and are aligned with your values - particularly in environments where personal dynamics and long-term family legacy are on the line - is a persistent struggle for families and their advisors alike.

The Human Capital Challenge

In traditional institutional settings, clients interact with clearly defined teams, processes, and performance expectations. In contrast, family offices (including those coordina...

If you’re part of the Leading Generation in a successful family, you’re likely juggling two massive jobs at once.

Job #1: Running the Enterprise
You’re leading the business, the investments, and/or the family office. You’re the operator, the decision-maker, the one everyone counts on to keep the engine running. 

Job #2: Shaping the Future
You’re also the visionary - responsible for preparing the next generation, clarifying the family’s long-term purpose, and imagining what your family enterprise may need 10, 15, or 20 years from now.

Most in the Leading Generation are doing both of these roles simultaneously… and quietly wondering why it feels so heavy.

It is heavy.

Why These Are Two D...

If you haven't tossed this book in your shopping cart yet, it might be the best thing you do today.

Build an Enterprise Family To Last: Proven Strategies to Thrive Across Generations, by Sara Hamilton and Margaret Vaughan Cox, feels like a text book, but in the very best way - not that it will put you to sleep or that it will weigh down your backpack, but rather that is overflowing with practical wisdom and beautifully offers the best of the thinking about family enterprise planning between its covers.

With, eye-catching frameworks and charts on seemingly every single page, the authors have offered readers an easy to use guidebook to help them apply the concepts they've presented so logica...

By Celine Fitzgerald
Inspired by the RisingGen Collective Call – Q3 2025: “Earning Your Influence Before You’re in Charge”

“Are They Just Letting Me Watch… or Am I Welcome to Speak?”

Have you ever found yourself in a meeting with family members, wondering:
Am I here to observe or to participate?
Should I speak up, or just stay quiet until invited?

If you’ve asked yourself these questions, you’re not alone. Many of us in the Rising Generation feel unsure about when (and whether) our voices are welcome - especially when the decisions being made impact our future too.

Echoes of the Past: “Children Should Be Seen and Not Heard”

Does the above quote resonate with you? I remember hearing it qui...

By Lydia Tuthill

Last month I took my daughter to ‘The Happiest Place on Earth’ for a 3rd grade field trip,
Epcot at Disney World. I attended this field trip exactly a year ago with my now 4th-grade son, and I was blown away by the remarkably different (and much better) experience I had this time - all of
which I attribute to my all-encompassing consumption of The Anxious Generation, by Jonathan Haidt.

For those who have not yet encountered this gem of a book, Haidt explores the mental health crisis among young people, linking it to the rise of smartphones and social media. He argues that excessive screen time, especially during formative years, disrupts sleep, reduces face-to-face interacti...

By Kristen Heaney

What’s Holding You Back?

Joining a peer group can feel like a big step, especially when family, identity, and wealth are part of the conversation. At In Three Generations, we see firsthand how transformational these groups can be. But we also know that getting there isn’t always easy.

If you've ever hesitated to join a peer group, you're not alone. Below are some of the most common barriers we hear - and our reflections on how to move past them.

1. “I don’t want to share personal stuff with strangers.”

This is one of the most common concerns we hear - and we get it. Vulnerability isn’t easy, especially in families of wealth where discretion and privacy are often deeply...

By Kristen Heaney

If you’ve ever sat through an estate planning meeting and left feeling like you just left a foreign language class (only to immediately forget half of what you heard) you are not alone.

For people with significant resources, estate planning isn’t just about writing a will. It’s a series of weighty decisions:

• Who should raise your kids if something happens to you? 
• Should your assets be held in individual trusts or one large family trust?
• What powers should your trustee have, and who should that even be?
• How and when should you utilize your lifetime gift and estate tax exemption to pass assets to the next generation?

These are tough, high-stakes choices and unfort...

When we think about legacy, our minds often go to what we’re leaving behind—wealth, businesses, heirlooms. But legacy is just as much about how we live as it is about what we leave.

And for many families, philanthropy plays a central role in that story.

Why Philanthropy Matters in Legacy Conversations

Giving isn’t just a transaction—it’s a reflection of our values, our vision for the world, and our sense of responsibility to others. Whether through a foundation, donor-advised fund, or community involvement, philanthropy offers families a unique opportunity to align their wealth with their purpose.

It’s not just about writing checks. It’s about cultivating compassion, leadership, and l...

“Give a man a fish and you feed him for a day; teach a man to fish and you feed him for a lifetime.” 

While the context may be outdated, the principle remains deeply relevant. Especially with the largest wealth transfer in history underway, families are increasingly focused on how to prepare rising leaders not just to inherit wealth, but to steward and grow it in meaningful ways. 

Entrepreneurship offers one of the best vehicles for this kind of preparation. It equips next generation family members with real-world experience in risk assessment, decision-making, problem-solving, team-building, and value creation - all critical skills whether they eventually take on leadership roles within t...

By: Kristen Heaney

He built an empire, conquered challenges most people can’t even fathom, and yet something still feels just out of reach. The next deal, the next venture, the next milestone, surely that will be the thing that makes it all feel complete. But what if the very drive that got him here is also what’s keeping him from feeling satisfied?

Arthur Brooks calls it the Striver’s Curse - the relentless pursuit of achievement that, while outwardly celebrated, can quietly erode one’s sense of fulfillment. We see this often - those whose success has brought them extraordinary wealth, influence, and responsibility, but who remain tethered to an insatiable drive for more.

For some, t...