4 Things You Can Learn from Gatsby’s Mistakes

The Great Gatsby (1926 film)

Lobby card for the first screen adaption of The Great Gatsby (1926) (Photo credit: Wikipedia)

88 years ago today one of the greatest pieces of literature ever written was published.  I am speaking, of course, of F. Scott Fitzgerald’s short novel The Great Gatsby.


The novel, set in 1922 Long Island, centers around the mystery and obsessive nature of one man, Jay Gatsby.  He is in love with a rich woman named Daisy Buchanan, whom he met while he was in the service during World War I.

After a brief affair, Daisy dumped him because he did not have the money and security she felt she deserved.  She chose to marry the rich and powerful Tom Buchanan instead.

Her marriage meant nothing to Jay Gatsby.  He set out to do everything he could to win her affection.  All the money he made, all the parties he threw, all the dreams he had—everything—was to impress her and make her fall in love with him.  He even took the blame for the hit and run that killed Tom Buchanan’s mistress, Myrtle Wilson.

Nothing but having Daisy mattered to him. Even if it meant going to jail for a crime she committed.

Unfortunately, he never reaped any benefits from all his hard work.  In the end, after another brief affair with Gatsby, Daisy chose to stay with her husband.  The life they had built together was more than all the money and beautiful dress shirts Gatsby had collected since their first meeting.

All was truly lost.

As Gatsby lay in his pool, feeling the stings of rejection, Myrtle Wilson’s grieving husband George comes in with a gun and shoots Gatsby, killing him instantly.  George then turns the gun on himself.

Poor Gatsby died for a crime he didn’t even commit…for the love of an uptight woman who did not love him back.

What a ripoff….

There are a few lessons we can learn from this tale of obsession, love unrequited, and murder.  The character Jay Gatsby made a few of mistakes in his life that ultimately lead to his death.  And today I am going to talk about those mistakes and how you can avoid making similar ones.

Gatsby Allowed Other People to Define Him

Gatsby lived most of his life wanting to please other people, and make them love him.  He created a life that he thought Daisy Buchanan would be impressed with and not being his own person and doing something for himself.

How you can avoid doing the same thing:  BE YOURSELF, damn it.  It’s been said a hundred and a half gazillion times already by countless people on the internet and elsewhere.  Just do it.  Don’t let other people dictate who and what you are.

Gatsby Capitalized off Illegal Activities

Everything Gatsby owned—the mansion, the clothes, the cars, the lavish lifestyle—was bought and paid for with dirty money.  He made his money by bootlegging and investing in a number of other shady deals. He had to get rich quick to impress his girl, and breaking the law during Prohibition was the easiest way to do that, see.

How you can avoid doing the same thing:  It’s simple, really—don’t become involved in crooked business deals. Even the most honest businesspeople in the world can become involved in illegal activity.  And it winds up costing them a lot of money—and possible jail time.  Bottom line:  don’t cut corners or take on deals that look and feel fishy.  Keeping your fingers crossed isn’t going to keep you out of the clink.

Gatsby Wasted His Life Pining Over Someone He Could Never Have

If you are in any way familiar with F. Scott Fitzgerald’s work, you knew that Jay Gatsby was not going to have a happily ever after with Daisy Buchanan.  Fitzgerald rarely ever gave his readers the happy ending they were looking for.  Like so many other people in this world, Gatsby became obsessed with obtaining the unobtainable.  So it wasn’t any surprise when he not only lost the girl, but his life.  (OK, getting shot to death was probably a HUGE surprise for first-time readers, but you get what I am saying…)

How you can avoid doing the same thing:  Breaking up is tough, but you have to get over it eventually.  It’s for your own good.  Go out and live and forget about the past.  There is nothing you can do to change it.  And becoming obsessed with someone who clearly has other interests won’t do you any good.  You lost.  It is time to accept it is over and move on.

Gatsby Took the Blame for a Hit and Run to Protect Daisy

After a tense little party at a swanky hotel, Gatsby and Daisy speed off in Gatsby’s car, with Daisy behind the wheel. As they make their way through the streets, and speed by the “valley of ashes”, Tom Buchanan’s lover Myrtle Wilson runs in front of the car.  Daisy runs over her, completely dismembering her, and keeps on driving.

Gatsby takes the blame for the horrific accident so Daisy won’t get into trouble.  And he ultimately pays with his life for it…when it wasn’t even worth it since he didn’t get any love in return.

How you can avoid doing the same thing:  I honestly do not understand people who are willing to throw their freedom and their lives away to protect people who have committed something unspeakable.  And the people who are actually responsible let them go ahead and pay for their crimes.  If you really love someone, convince them to do the right thing and do their time, to make things right with whomever they have hurt.  Don’t ever sacrifice yourself for something you did not do.  That is completely stupid.

Can you think of anything else that The Great Gatsby teaches people about life and the terrible mistakes people make?  What advice would you give someone who continues to make the same mistakes over and over again?

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14 thoughts on “4 Things You Can Learn from Gatsby’s Mistakes

    1. Angie Schaffer Post author

      Yes, yes! Indeed. People can have all the “money and glitter” in the world, but are they someone you would admit to knowing and give a reference to? Power has its positive points for sure, but it’s not worth it if it compromises your integrity.

    1. Angie Schaffer Post author

      My friend Chris Long, a historical media researcher, sent me a clipping from an Australian newspaper review from 1925. The critic didn’t understand what the moral of the story was, so assumed there was no point to it at all. That is pretty much what prompted me to write this post.

      There is SO much we can learn from the way other people (fictional or not) act in this life.

    1. Angie Schaffer Post author

      Aye, yes. It will be on the big screen for the 1,058,043 time next month. (slight exaggeration lol) I won’t be seeing it because I find the trailers insulting. But most screen adaptions of Gatsby make me cringe.

  1. Regina Walker

    Advice to people who make the same mistakes over: Just stop it! You are the one that can break the negative cycle in your life. Do it.

    But, I have to add that the greatest sacrifice ever happened on a cross 2000 years ago, by a guy that did nothing wrong. But He paid the price for me. So I get it, even though I don’t really.

    Just my two cents!
    Regina Walker recently posted…Love Your Wife WellMy Profile

    1. Angie Schaffer Post author

      It was. It (and most of F. Scott Fitzgerald’s work) approached subjects that the aging Victorian “polite society” didn’t want people to discuss in public. Sexual references and profane language (words like “hell” and “damn”) had people in an uproar as recently as 25 years ago.

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