How Entitlement is Silently Ruining Your Life

Jason Henry
5 min readAug 8, 2019

Venture capitalist and author Guy Kawasaki once wrote, “Entitlement is the opposite of enchantment.” I’ve lived this so I know it to be true.

For most of my life I’ve been in pretty good situations both socially and financially. But right after I finished my degree in 2010, my family was hit with significant money problems.

We had suffered those before but this was different. Bills went unpaid. Dinners had to be rationed. Water was lunch. Thankfully we had friends and family donate stuff for us.

While this time in my life lasted less than a year, I had to call it like I saw it: we were poor. And yet, I had never felt more alive.

I didn’t feel more alive because I was hungry more often. I didn’t feel more alive because I was worried they’d cut off the light and water. I didn’t feel more alive because I personally had debts to pay and wondered if they’d come for my kneecaps.

I felt more alive because I gave up the chase for more. I was humbled. I knew things could be worse and was more grateful for the little we had.

When the money came back, I had mixed feelings. This life that was flowing through my veins, this enchantment Kawasaki wrote about and my ability to finally embrace the present moment… what would happen to it? Would I be back to being just okay, future-oriented and thinking I deserved more and more? You bet.

I tried to fight it but I eventually lost. I said to myself, “Am I to believe that the only way I can feel truly alive is to be food insecure?” That didn’t make sense. Clearly some people are rich and obnoxious, but there are some that were humble too. How can I be like them? And that leads us to the first way entitlement is ruining your life.

1. Entitlement is Unconscious

When we think of someone being entitled, it’s the person barking at the coffee shop for their order or the person who thinks that because they are nice to another person, that person should do whatever they want, or whenever we put out little effort and expect immediate and/or big results.

And we’re right! Those are great examples of entitlement. But sometimes we fall prey to these tendencies. I for one hate when the…

Jason Henry

Former Edu. Psychologist | Current Writer | Constant Learner | “By your stumbling the world is perfected.”