Grinding Out An Entitlement Mentality

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Every so often I find myself feeling entitled to things. I can’t help it. I tell myself that I deserve this or that and find myself dreaming about what deserving that would look like. Maybe it’s a car or a trip or an expensive bottle of wine. An afternoon spent goofing around, or maybe a whole day off. People treating me the way I want to be treated. Employees loving what they do and wanting to do more. Customers paying on time. Traffic adjusting to my schedule. My family agreeing that whatever I think is the right thought. Bliss.

It’s easier than it should be for me to feel like this. After all, I seem to run into other, entitle-deserving people most everywhere I go. People in my family, people I work with and people who don’t like waiting for a table at a restaurant (“this is ridiculous” I hear them whisper to one another, so as not be overheard by the restaurant staff). So many of the ads we see on TV target our entitlement desires. Whether it’s the personal injury and bankruptcy attorneys, the credit card debt restructurers or the food and drug companies, everyone seems to be telling us what we deserve, what we’re entitled to and how they can help us get it – for a fee of course. Entitlement loves company.

When I was growing my business and trying to be a leader (“trying” being the operative word), I could get frustrated about having to keep working so hard to get ahead, or sometimes even to just stand still. There were days when I thought that what I wanted was to be entitled. When I wanted the world, and time, to stop so I could soak in a bath of ‘leave me alone.’ Not at the beginning, when I was just getting started, but sometime later, when I’d achieved what I thought was a little bit of success.

Was that too much to ask?

Turns out, it was.

“You’ll Get Nothing And Like It” – Judge Smails, Caddyshack

Just when I was getting all comfortable being happy with, and entitled to, where I was, the world would come knocking with a new challenge. Often it was something I hadn’t seen coming (or hadn’t wished to see) that would just blow my entitlement illusions to shreds. Sometimes it was a competitor deciding to cut prices or “stealing” a great customer of ours and others it was a customer demanding more service for less money. Sometimes it was an employee I counted on deciding to leave, or demanding more money, or a regulator showing up for an unannounced inspection that lasted for hours and made me feel dirty and stupid.

While it was always tough for me to recognize in the moment, wallowing in entitlement thinking, like a pig in mud, was a recipe for getting my *ss kicked. And deservedly so.

It occurred to me later in my career (I’m not someone who learns quickly) that feeling entitled was a by-product of me just getting lazy. It was me getting trapped and stuck in my thinking about where I was and forgetting about how far I’d come, or how far I could still go. I was “woe is me-ing” myself when I should have been “what’s next-ing” myself. Grinding myself down, rather than building myself up. Wallowing, rather than showering.

In the imperfect way I do everything in my life, I’ve made not feeling entitled a mission. Yes, I still want things – lots of things (tangible and non-tangible things), but I know that I’m not owed anything. I’m not entitled to any of it. Nobody made me want the things I want – those wants are my property. I have to earn what I want, which means I have to be willing to do what’s needed, day in and day out. I still slip often, probably too often, but I feel it sooner and correct it faster.


Special thanks to Hammerstone Marketing for blog design, SEO and featured image selection.

Mike Malatesta

Mike Malatesta

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