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What is Entitlement, Anyway?

Updated: Apr 10

Defining “entitlement” is kinda like defining porn.  It’s hard to describe, but you know it when you see it.  Or do you?


I may or may not know an 18-year-old (who will remain anonymous to protect the guilty) who I think demonstrates entitled behavior. Last spring, he forgot to apply for a Senior Parking Pass, and his high school sold out of them.  So, he used his stellar graphic arts skills to replicate the parking pass, and he parks illegally in the Senior parking lot using that fake pass every day.  He just decided he could jump ahead of the other classmates who responsibly applied for, earned and paid for a parking pass.  Because he thinks he can.


Is this egregious entitlement?  Probably not.  To a rule follower like me, it’s just wrong, wrong, wrong.  But my developmental journey has been discerning when it’s ok to break the rules.  So part of me admires him.


What gigs me the most is that he did it last year too, when as a Junior, he wasn’t even eligible for the Senior parking lot.  He got caught.  The principal punished him.  And he just did it again this year.


I’m wrapped around the axle about what’s fair and not fair.  (Cheating is not fair, and he’s cheating!) To me, it’s classic entitlement behavior.  He thinks he can get away with it, and that’s justification enough even though he knows “it’s wrong.”


But to him, it’s not entitlement.  To him, it’s a victimless crime.  It’s simply a risk/reward tradeoff, and he’s decided that the risk is worth the reward.  He’s not wrong.  If he gets caught again, he’ll take his punishment, and it’ll be worth the months of sneaking in the Senior parking lot for free and ahead of everyone else who played by the rules.


What is Entitlement, Anyway?

This is what makes entitlement such a slippery topic.  What’s entitlement to one person isn’t entitlement to another.  Further, what looks like entitlement on the surface can be behavior motivated by something very different than “because I can.”


In my book Hug of War (coming in July!), I describe twin brothers, Maks and Peter, who enjoyed working together in their mother’s business, until Peter started to spend more time golfing than working.  This went on for months, and Maks didn’t say anything for fear of violating their unwritten code that twins don’t judge each other. 


Although Peter’s behavior bothered Maks, it really got to Maks’s wife, Lenore, who also worked in the business and refused to tolerate such flagrantly entitled behavior in Peter.  Knowing her husband Maks wouldn’t say anything, Lenore raised a stink with Peter and insisted he show up at the office for a full workweek.  Instead coming to the office more, however, Peter did the opposite – he showed up even less. 


This pattern went on for a few more months – the more Lenore barked at Peter, the more Peter went golfing – until a consultant interviewed the family members, and eventually the truth came out.


Truth was, Peter couldn’t stand Lenore.  He wanted out from under Lenore’s oppressive judgment, but he didn’t know how to escape.  He couldn’t disappoint his mom by leaving, and he didn’t know how to tell his brother that he couldn’t tolerate Lenore.  So he golfed.  That’s not entitlement.  That’s a coping strategy.


How I Define Entitlement

Because I hold privilege and responsibility as a polarity*, my definition of entitlement is the overuse of privilege.  There’s nothing inherently wrong with privilege – everyone has some form of privilege in their lives. However, what keeps excess privilege from spilling over into entitlement is a healthy dose of responsibility.   Privilege and responsibility pair well together, like dark chocolate and red wine.


(*By polarity I mean, a set of interdependent opposites, each of which represents one half of a whole.  Think inhale and exhale, for example.)

What is entitlement?

What do you call the overuse of responsibility?  Well, as you can guess by my Church Lady tut tut of this 18-year-old’s brazen use of a fraudulent parking pass, I tend to operate in the overuse of responsibility.  (“Isn’t that special?”) There is nothing inherently wrong with responsibility, but when responsibility is overused, it looks like judgment and feels like a burden. 


While my 18-year-old high schooler is learning how to sprinkle some responsibility into his privilege to stay out of its overuse, I’m learning how to sprinkle some privilege into my responsibility to do the same.  And I’m not alone in feeling the pressure of responsibility.  Countless family business leaders I interviewed for Hug of War feel heavily burdened by responsibility in their family business. 


Speaking of Hug of War, to learn more about polarities, especially its privileges and responsibilities in a family businesses, join my mailing list. That should tide you over until Hug of War: Leading a Family Business With both Love and Logic is released in July 2024.


PS: I’m still beta testing the family business polarity assessment so leaders can see how well they are leveraging the most common tensions in family business leadership.  To access the assessment, click here and check the box next to “Please send me the complementary family business assessment.” 

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