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While the context may be outdated, the principle remains deeply relevant.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...

^{Author: Celine Fitzgerald}

"Not all those who wander are lost." J.R.R. Tolkien

In anticipation of facilitating our newest peer group program, RisingGen CORE 20s, I've found myself reflecting on my own twenties era - a roller coaster of emotions!

I learned, in what felt like an "all at once" moment at age 21, that I was a wealth inheritor. An attorney sat across a conference room table from me and shared that I was a beneficiary of a trust. I wasn't sure what that meant, but he made it clear that I had very limited access to the assets. While many would think this kind of moment would leave a girl elated, I left overwhelmed, feeling completely unprepared for the road ahead.

What I d...