In many enterprising families, a familiar pattern emerges over time. The senior generation, often shaped by experiences of scarcity and uncertainty, makes a deliberate choice to create a different life for their children. The comfort and opportunity that follow are not accidental but an expression of care and intention.
What is often less anticipated is the tension that can emerge later. As the rising generation grows within that environment, they are sometimes described as entitled, a characterization that can feel misaligned with their experience. From their perspective, they have simply received what was given; they did not shape the conditions of their upbringing, even as both generations sense a disconnect that is real but understood differently.
What’s Really Happening Beneath the Surface
What the senior generation is often sensing is not ingratitude but something harder to define: a question of readiness. Their capability was shaped through real decisions made under uncertainty, building judgment, resilience, and a lived understanding of risk. These are not easily transferred, even with the best intentions.
The rising generation, in turn, often carries a quieter experience. While they have received education, opportunity, and support, many are still developing a grounded sense of their capability. There is a difference between being told something and testing it. What may be described externally as entitlement can, from within, feel more like uncertainty or a search for confidence.
In seeking to remove hardship, the senior generation created something valuable. At the same time, some of what hardship once developed judgment, resilience, and self-trust now requires more intentional ways to take shape.
How This Shows Up in Families and Decisions
In business transitions, such behaviour tends to become visible during moments of consequence. A rising generation member may hesitate or seek more reassurance than the senior generation expects. They are not disengaged; rather, they have not yet accumulated the experience needed to navigate something uncertain that is genuinely theirs to navigate. The senior generation develops its instinct for making difficult decisions over decades of experiencing exactly those moments.
Family governance conversations often surface the same tension. The senior generation may read the rising generation’s caution as a lack of conviction. The rising generation may read the senior generation’s directness as dismissiveness. Neither reading is entirely wrong, but both tend to miss what’s underneath. What makes these moments harder is that they often happen inside high-stakes settings like transitions, estate conversations, and business decisions, where there isn’t much space for the kind of patient exploration the underlying dynamic would actually need.
Reframing Thought Leadership
The word “entitlement” can quickly narrow these conversations. It places the focus on the rising generation, making it harder to see the broader dynamics at play.
A more constructive lens is to look at conditions. What helped build capability in the senior generation, and how can we create those conditions more intentionally today when material hardship is no longer present? This is not about recreating difficulty, but about fostering genuine agency: real decisions, real responsibility, and meaningful ownership.
This shift moves the conversation from judgment to design. It allows both generations to engage more openly, recognizing that they share the situation and have the opportunity to shape it thoughtfully.
Concluding Thoughts
These conversations rarely resolve all at once. The senior generation holds experiences that have shaped them in lasting ways, while the rising generation often faces measurement against a path they never lived. Both perspectives carry something real.
What matters most is the ability to stay curious about that gap, rather than settling too quickly on conclusions. The conversation often opens in more constructive and meaningful ways when families are able to do so.
ABOUT THE AUTHOR
As the Senior Wealth Advisor at Beacon Family Office at CI Assante Wealth Management Ltd., Cory Gagnon has supported successful family enterprises to preserve, protect and transition their wealth since 2011.
Cory’s personal objective as a Wealth Advisor is simple. He is committed to supporting families to take control of the areas of their lives that truly matter to them. This commitment revolves around using specific tools and strategies that enable families to take action with confidence which will support them through life’s critical transitions.
ABOUT THE AUTHOR
As the Senior Wealth Advisor at Beacon Family Office at CI Assante Wealth Management Ltd., Cory Gagnon has supported successful family enterprises to preserve, protect and transition their wealth since 2011.
Cory’s personal objective as a Wealth Advisor is simple. He is committed to supporting families to take control of the areas of their lives that truly matter to them. This commitment revolves around using specific tools and strategies that enable families to take action with confidence which will support them through life’s critical transitions.
