• Judi Cunningham

Addressing Entitlement in Your Family Enterprise: It’s Only Natural

When we hear the word “entitlement,” most of us have a particular kind of reaction. It is a word we hear a lot, especially in the family enterprise world, but its meaning is not always as precise as we may intend. In fact, it is a term that points at a range of different kinds of expectations or behaviours. When I am working with families, and parents come to me saying “I’m worried my kids are entitled,” I often need to do a lot of exploring to get to the root of the issues that they are trying to identify.


We have a tendency to point at entitlement as though it is a clear problem. But from its source all the way to its manifestation, entitlement is a lot more slippery than it appears at first glance. The most overlooked element of it, and one families need to start with if they hope to address it, is where it comes from.


Contrary to many of our beliefs, entitlement is not a one-directional issue that spontaneously arises. It doesn’t just “show up.” Rather, it grows slowly over time. And it is not an accident or an anomaly: it is only natural. When you raise your children, you want them to be happy, and you want their needs to be met. This naturally leads to a level of expectation. The question is not about what has gone wrong to create entitlement, but what parents can do to shift some of the overused expectations and start supporting and empowering their children to stand on their own.


Once you recognize that entitlement is a natural element of parent-child relationships, you can begin to address it. First, by acknowledging your roles and how they relate, and second by setting boundaries, and sticking to them.



Acknowledging Your Roles

It makes complete sense that parents want to make their children’s lives easier. In fact, a foundational contract of the parent-child relationship is one of providing: love, safety, happiness, and guidance, alongside the essentials like food and shelter. This relationship dynamic naturally leads to expectations. In fact, if you’re doing a good job with your children, they will almost certainly expect things of you.


On the one hand, as children transition into teens and begin to move into the adult world, these expectations can begin to look a lot like entitled demands. On the other, when parents then suddenly turn around and call their children “entitled,” it creates a confusing matrix of mixed messages.


The expectations that children have of their parents develop through patterns of repetition. These are habits that have been built over the course of their lives. For example, each time your child comes to you and asks you for money to buy a new pair of jeans, or go to the movies, etc., and you give it to them every time, this builds this pattern of repetition. To turn around and point the finger of entitlement is not only somewhat unfair, it is also confusing and wholly unproductive.


Explicitly addressing and acknowledging parent-child roles, needs, and desires is a key to beginning to empower your children. The happiness of both parents and children should be an important consideration. But achieving satisfaction and happiness may begin to look different as you equip your children to take on new responsibilities in their transition into a more adult independence. What is more empowering than involving them in these important discussions?



Setting Boundaries, Sticking to Them

Entitlement develops through a dance between generations: it is not created by the younger generations or the senior generations in isolation. There are connections, and systems of push-pull dynamics that lead to the development of tension-points, demands, and unrealistic or undesired expectations. Setting clear boundaries - and sticking to them - may feel uncomfortable, but it will lead to clearer relationships.


If a child grows up with certain “things” provided to them, adjusting their expectations will take time. Boundaries do not have to be harsh, and they absolutely do not have to operate as punishments. If you begin to involve your children in discussions about fostering their independence and encouraging their sense of personal responsibility, then the setting of boundaries can feel logical and encouraging.


A boundary is not necessarily the removal of a luxury, but a clearer way of establishing our relationships with our expectations and demands. So, setting boundaries clearly and reasonably, and making sure everyone understands why they are there can start to clarify relationships and lead to more ease.



At the end of the day, worries about entitlement are pretty common, but rarely managed head-on. They’re also usually accusations levelled at a rising generation by a senior generation in an enterprising family. Moving out of finger-pointing, and toward reflexive conversation is a way out of the entitlement bind. Empowering next generation leaders starts at this level, and can operate as a significant primer for more formal continuity and succession efforts.


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