The Ballad of the Perpetually Disappointed ~ Personal Finance Blog

If you sit down for a cup of coffee with a random Baby Boomer (those born 1946 to 1964) and ask them their outlook on the average Gen X'er (born 1961 to 1981) or Millennial (early 1980s to mid 1990's birth years) you're likely to hear how entitled and lazy the youngins are. How back in "their day" kids were grateful...they were polite...they worked hard and they asked for little. 

If you were to sit down with someone who lived through the Depression (a generation that is fast dwindling....sadly), you are likely to hear that the Baby Boomers are selfish, money-obsessed, and wouldn't know a hard day's work if it bit 'em in the ass. They don't know how to go without or make do.

If you were to dig up someone who lived during the turn of the Century, dust 'em off and have some'd hear about these damn Jazz Age kids and their wanton ways.

My point?

Entitlement, disappointment, complaining, and a selfish nature does not have an age attached to it. Every generation believes the generation after them screwed everything up. That they want everything done for them, handed to them, and complain far too much.

They are never. ever. satisfied. 

I've worked in customer service for years....really since the age of 12 when I decided I was going to deliver papers for the Beloit Daily News. So, over the years, I've run across plenty of folks who seemed to find a certain amount of glee in expressing disappointment. 

They've been old. They've been young. But all of them have led me to learn something from my experience with them.

There was the lady I used to wait on at a local drug store who would bring in a stack of coupons every week and argue over pennies....PENNIES. To her, a coupon for Charmin meant she held a coupon for ANY sort of toilet paper. Now, I could have passed this off as pure senility....but something told me after months of dealings with the Coupon Lady that she knew what she was doing. Maybe she just wanted a "cause". The coupons were her cause. 

There were the difficult customers who came into the pizza place where I waited tables and always ordered the same thing....and always complained about it. When I finally asked them WHY they continued to order things that didn't live up to their standards week after week, they didn't really have an answer for me. 

I think they enjoyed being disappointed about SOMETHING. It gave them a purpose. Something to talk about with their friends. "That damn pizza place, they can NEVER get a sandwich right! It's because they're so stupid! I mean, how hard IS it?" 

But week after week they returned. And week after week they ordered the same thing. And week after week they chided me for how terrible the sandwich was.

There was absolutely NOTHING I could do to make them enjoy the sandwich.....believe me I tried. 

"If only you'd make the sandwich right, we would be so happy"

I didn't even MAKE the sandwich. I just delivered it.

Somehow, I doubted they would ever enjoy that stupid sandwich.

Perpetual disappointment in EVERYTHING is not a generational issue. I think it may be a personality glitch. Perhaps it's nurture over nature. Perhaps it is linked to social media and our constant view of everyone's highlight reel. What we see is everyone's perfection: their beautiful children, their lovely homes, their great vacations. So, in return, when reality happens to us we feel it's sub-par. It's not the way things should be. They should be perfect. The internet said so.

This doesn't explain bad-sandwich people, because that all went down prior to Instagrams of perfect meals, but it may help explain current complainers. 

Perhaps it's indicative of a childhood where one was always coddled, always catered to, never told "no". (Just a note, please people....say no to your children)

Perhaps it's indicative of a childhood where one had absolutely nothing, so now they grab at it all, in fear of going without.

There are different schools of thought with a number of theories, but it all comes down to one clear fact: the perpetually disappointed are out there in spades and they are coming to ruin parties, work days, and a whole host of other events. 

Being perpetually disappointed will even destroy your finances. People will go to great lengths purchasing anything they believe will relieve their ongoing dissatisfaction with their life in general. Because that's what it comes down to: a deep seated dissatisfaction with life.

So, if the big disappointments cannot be handled: who you married, where you live, what you do for a living.....then you will adapt: you will nitpick the small stuff to death. Maybe by taking care of all the small disappointments in your "way", the big ones will fall to the wayside and become less "big".

But this never really works, does it? 

Being disappointed all the time usually runs hand in hand with being entitled. And being entitled doesn't necessarily mean you were spoiled as a child, or you have money, or that you're a bad person. It does mean your expectations are skewed. Life is messy, imperfect, not timed well, and....very often...sad. It's rarely exactly what we expect.

Are You Entitled?

According to Psychology Today, there are some basic signs you can look out for to see if you have fallen into the trap of being an entitled person.....and probably impossible to please as well. 

Now, all of this takes, at it's root, a bit of self-reflection. I always wonder if folks who are constantly complaining KNOW what they sound like? Do they KNOW how others view them? 
Do they have an awareness of their entitlement, or is being entitled keeping them from being aware? 

Food for thought.

So ponder a few of these....and see if you can own up :) 

1. Rules that apply to others don't apply to you.
2. Being asked for favors annoys you, but others not doing perceived small favors for you annoys you as well
3. You expect others to be more interested in you than you are in them. Your goals/dreams/plans are more valid than other people's.
4. You disregard rules intended for the comfort of everyone. For example, you smoke in line at the amusement park or pull out your cellphone at the movie theater.
5. You are not respectful of other people's time. You cancel appointments at the last minute, you are frequently late, or you expect people to wait for you. 
6. In environments based on reciprocity, you take without giving. For example, if you are part of a forum of professionals, you consistently ask questions without offering insight or answers to others. 

So, taking these personality traits into consideration, you can see how being entitled easily leads to someone being constantly disappointed.  If someone calls them on breaking rules, they are angered because....duh...rules don't apply to THEM. They are special. They are entitled to breaking the rules. If someone stops inviting a person places because they are always late or blowing them off, it's unlikely the entitled person is going to take personal responsibility for this. It's more likely they will be dissatisfied with the friend and their lack of invites going forward.

So what can you do if you're reading this going "Shit, this is ME."

Well first, kudos for seeing yourself there. I think that's definitely the first step to changing your entitled behavior and not being one of the perpetually disappointed. 

Second, work on really mulling over the WHY behind your dissatisfaction with things. If it's a meal, or customer service, or something of that nature....ask yourself if the average person would complain about what you are finding so wrong....or are you making a mountain out of a molehill?

This takes practice, and a crap-load of self-awareness. I'm fond of asking myself "does it matter"?  I find the older I get, precious little REALLY matters enough to make a stink about.

Like, the other day my kid came home with an assignment that was half finished. The assignment had a note on it from the teacher that said my kid didn't finish her homework because she was playing around in the air conditioning vent (whatever THAT entailed, who the hell knows. Sounds interesting though). Now, my daughter was REALLY upset that her teacher had called her out. She knew she had done wrong and she knew she should have finished the assignment. Her lesson was learned and I didn't need to make some big ass deal about it, right?
Right. Because it doesn't matter. In 5 years we won't even remember what the worksheet was about. But, she will remember that I laughed my tail off at the "Molly was playing in a vent" note. Because it was funny.

When we introduce themes like minimalism, simplicity, and financial awareness into our lives, it means letting go of some of the toxic attributes of our personalities along the way.

Being entitled and perpetually disappointed about everything will never get you far, even if you think you are getting everything you're never happy, and happiness trumps stuff every time.

Last week I was working a wedding on the banks of a lake in Door County. The air was still unseasonably warm, but there was a hint of crispness to it that made it very comfortable. I stepped outside for a moment to retrieve something from my car and, breathing in, caught a hint of burning leaves, lake mist, and pine trees all wrapped up into one and it was absolutely wonderful.

It was a tiny moment but I just stood here and let it kind of waft around me. Now, I could have sat there and thought about the mosquito bite on my knee or God KNOWS what.....but in that moment, everything was PERFECT. I was in awe of the world around me. 

Don't lose that. Don't lose that ability to sense wonder in the little things by focusing on the negative. There will ALWAYS be negative if you seek it out hard enough. But in the meanwhile, the wonderful things will go by unnoticed.