Part 4: Lessons From The Great Gatsby – Ambition, Reality, and Stoicism

Part 4 of Book Analysis: The Great Gatsby by F.Scott Fitzgerald

Introduction

Even after 100 years, our era feels a lot like Gatsby’s. Rapid technological advancements, like AI, have sparked an intellectual revolution, creating both opportunities and chaos. It’s hard not to notice the similarities between the Roaring Twenties and today.

Starting a business now seems easier than ever, especially with social media. Scroll through your feeds, and you’ll find countless “How to Make Money” videos and posts. With AI and the internet, the possibilities feel endless. But, just like in Gatsby’s time, the gap between dreams and reality can be painfully wide, often leading to frustration and disappointment.

When I first read The Great Gatsby, I couldn’t help but think of Marcus Aurelius’s Meditations. Gatsby found an opportunity in chaos and relentlessly pursued his version of the American Dream, practicing a form of stoicism by holding firm to his belief that he could achieve it. In a way, Gatsby and Fitzgerald share a similarity—they both chase wealth to gain societal acceptance. The tragic part is that neither truly got what they wanted despite their tireless efforts.

I believe the American Dream is still achievable, especially in chaotic times. But it takes more than relentless effort—you need clarity and balance. Maybe there is something we can learn from this book so that we don’t repeat the same mistake Gatsby did. So, I decided to reflect on Gatsby’s story with Marcus Aurelius’s teachings. Maybe we can uncover insights about ambition, reality, and finding harmony in pursuing our dreams.

Author’s Purpose

Before we dive into Meditations, let’s take a moment to unpack Fitzgerald’s purpose in The Great Gatsby. On the surface, Jay Gatsby seems to have it all—money, a mansion, and parties that would make anyone jealous. But despite all of that, his story doesn’t exactly have a happy ending. So, what went wrong? Let’s dig a little deeper. Gatsby’s dream went south because he was chasing a fantasy—his picture-perfect version of Daisy and the life he thought they could have. He put all his effort into a goal that was, let’s be honest, never going to happen. Turns out, Daisy wasn’t the angel he imagined, and the social barriers? Those weren’t going anywhere either.

Fitzgerald shows us that there are things that can’t be bought with money. Through Tom and Daisy’s shallow relationship and Gatsby’s inability to buy true friendship or social acceptance, the novel highlights how wealth can’t solve more profound issues. Was Gatsby’s relentless chase worth it? Fitzgerald gives us the answer when Nick leaves the East, disillusioned by everything he’s witnessed.

Interestingly, Fitzgerald himself wasn’t so different from Gatsby. He was captivated by the glamour of the Jazz Age but also knew how hollow it could be. Like Gatsby, Fitzgerald worked hard to achieve success, hoping it would validate him. Still, he understood how fleeting and empty that success could feel. Much like Tom and Daisy’s, his marriage to Zelda wasn’t a fairy tale either. This personal connection gives the book’s critique an added depth.

I don’t think Fitzgerald was denying the American Dream entirely. Instead, he was reminding us that money can’t buy everything. Most importantly, sometimes what we’re chasing isn’t what we think it is. It does not matter what dream you can chase. You need to understand what you are after. Dreams tied to love, wealth, or status can be illusions, and blindly chasing them is just a recipe for heartbreak. You can dream big but think carefully about what you’re really pursuing. It’s a lesson worth remembering. 

Personal Reflections

Focus on What’s Real

Marcus repeatedly encourages focusing on the present moment and the reality before us rather than being distracted by unrealistic hopes or illusions. He writes, “You have power over your mind – not outside events. Realize this, and you will find strength.” This reminds us to anchor ourselves in reality rather than chasing unrealistic goals because chasing after such goals can lead to frustration and disappointment. Gatsby wants to be with Daisy, who is from old money. This is how Fitzgerald concluded The Great Gatsby, “So we beat on, boats against the current, borne back ceaselessly into the past.” As Fitzgerald himself experienced, Climbing up the social status is nearly impossible because you cannot escape from your past. So, what Gatsby was chasing after was nothing but his illusion. 

Distinguish Between What You Can and Cannot Control

Marcus emphasizes the importance of understanding what is within your power and letting go of what isn’t. He says, “If you are distressed by anything external, the pain is not due to the thing itself but to your estimate of it, and this you have the power to revoke at any moment.”

Gatsby’s inability to let go of Daisy and his dream of recreating the past reflects a failure to accept what is beyond his control, leading to his ultimate disillusionment. In other words, he failed to distinguish between what you can and cannot control. 

Don’t Be Deceived by Appearances

Marcus Aurelius once said, “How much more grievous are the consequences of anger than the causes of it?” He’s pointing out that the fallout from anger is often worse than whatever made you angry in the first place. Similarly, focusing too much on appearances or superficial things—like wealth, fame, or status—can create even bigger problems. Nick observed this firsthand in The Great Gatsby. Despite their wealth, Tom and Daisy aren’t truly happy. Gatsby’s grand parties attracted crowds, but when he died, only a handful showed up at his funeral.

The saddest part is that Gatsby is so consumed by his illusions—his dream of winning Daisy and being accepted by her world—that he ends up dying because of them. Chasing after such illusions leads to disappointment and unhappiness because they don’t bring the deeper fulfillment people hope for. Gatsby’s story is a cautionary tale: be careful not to lose yourself in an illusion that can never become reality.

Live According to Nature and Reason

Marcus Aurelius talks about how important it is to live in balance with life and think things through logically. He explains that trying to fight against the natural flow of life, like Gatsby trying to recreate the past, will only lead to disappointment. Marcus advises us to “Look at things as they are. Analyze them into their causes, material, and purpose.” This means we should see life clearly and understand why things happen and what they mean. By thinking this way, we can avoid chasing impossible dreams, like Gatsby does, where his emotions and obsession take over instead of reason.

Discussion Questions

So, here is a question for you. 

Do you think Gatsby’s dream was worth pursuing, even though it was doomed? Do you think you can, somehow, make his dream work?

Conclusion

I’ve wanted to do this analysis ever since I read The Great Gatsby. As a big fan of Marcus Aurelius’s Meditations, I couldn’t help but reflect on why Gatsby’s dream didn’t work and how it ties into the stoic lessons from Meditations.

Now that you’ve read my thoughts, take a moment to ask yourself: What did Gatsby do wrong? Could he have made better choices? Here’s my take—Gatsby had the talent, drive, and determination to be successful, but he focused all of it on chasing an illusion. Suppose he had pursued something more grounded, like building a happy family or finding fulfillment in other ways. In that case, his life might have turned out differently.

What about you? Did Gatsby’s dream inspire, frustrate, or maybe leave you feeling a mix of both? I’d love to hear your interpretations and what lessons you took away from the story. Share your thoughts in the comments!

If you enjoyed this analysis, don’t stop here. There’s more to explore, and I hope you’ll come back for future posts. Let’s keep the conversation going and dive deeper into the timeless lessons literature has to offer.

Happy reading!