The Challenges of Ambition

Every life in history happens only once. If you want to do something excellent with yours, you’ve felt ambition. [1] Maybe you see yourself as Toronto's north star, becoming the greatest rapper of the game. Maybe you see yourself on Mars, building out the next civilization. Maybe you see yourself carrying the torch forward in the intersection of humanities and technology.

[1: I don’t think there’s a standard for what excellence looks like. That being said, the greatest work tends to be done by people who set high bars for themselves.]

Whatever it may be, I bet many of you have had these ambitious feelings about what you could do with your lives. While these feelings are very real, I can’t tell you what to do with them. There are two reasons. The first is that I believe there is no one size fits all solution. The second is that better resources exist. [2]

[2: How to Do Great Work by Paul Graham]

While there are great resources on what to do if you’re ambitious, few delve into the challenges of ambition I sought to understand. Therefore, this is me writing the essay I want to read. I try to answer the question,

What are the challenges of ambition?

Before discussing this, it’s good to think through why ambition is challenging in the first place. Ambition can be a good force; it is what leads the hunter to fixate on the prey. But the hunter gets distracted by attractive alternatives: power, politics, fashion, fear, expectations, the environment, and assumptions never questioned. Therefore, ambition can be reframed as the hunter who may or may not get blinded by its prey.

It's dangerous to leave ambition unchecked because life is short. During this period, you can change reality. Once it’s over, all that’s left of you is your work. Will you have fulfilled your ambitions, or will you be another cog in the machine, another gladiator lost in the arena, another restless dreamer? Time will tell, but you can prepare for your death now.

Now that you understand ambition’s shadow, I will discuss the shape it takes. I dive into truths that I have experienced so far in my life. As I learn more, this essay will grow. For now, each lyric introduces a new challenge.

“Told ‘em I finished school and I started my own business. They say ‘Oh, you graduated?’ No, I decided I was finished.” - Kanye West

Evolution shows our modern societies are unlike anything that’s happened for the majority of humanity’s history. For thousands of years, humans coordinated with one another in small hunter gatherer tribes. If you were alive during this time, your ambition was constrained to a few important skills: hunter, toolmaker, storyteller, explorer, ecologist, shaman. You didn’t have the choice between physics and fashion. You had to do what was most important for the survival of the tribe.

Today, young people are introduced to institutions where they choose what to study in exchange for paying a fee. During this time, you are around people who want to do something with their lives. You are free to plunge deeply into whatever you find most interesting. You have access to professors who are experts in what may be your craft.

These institutions were originally designed as a place to pursue truths, cultivate minds, and shape characters. Over time, they evolved into institutions for capitalism, credentials, and technical skills – although some departments get by without ever actually achieving this. The promise of intellectual discovery is still marketed, but the reality can feel hollow for the ambitious.

The universities expect it’s easy to decide what one should do. Life lasts 4000 weeks. These institutions expect you to declare what could be your life’s work in 104 of them. The curriculum exacerbates this: you are placed in a cohort that learns the exact same information, at the exact same pace as you. Much of what you study is abstracted, outdated, or presented without the attention the work deserves.

Meanwhile, adulthood is delayed, political ideologies are branded into curriculums, and at best, fragmented knowledge is conveyed. Worst yet, some departments feel stagnant, as if they’ve stopped participating in the advancement of knowledge.

Ambition thrives on curiosity, but institutions demand answers. This leads to ambition being cornered rather than cultivated. Indeed, ambition is often redirected until the original drive is buried beneath routine achievement. And in a world rushing towards a singularity, nobody can say for certain what knowledge will matter in the future.

So, the challenge of ambition is to treat institutions like a tool, not a path. And if they stop serving you, you may realize, as Kanye did, that graduating isn’t the same as being finished.

“They done stole your dreams, you don’t know who did it.” - Kanye West

In The Matrix (1999), there is a world shaped by illusion; the people believe they are making choices, but their lives are programmed by the Machines. A similar phenomenon can be observed in our context: one thinks their ambition is self-generated, but it’s actually programmed based on what others – peers, leaders, influencers – deem desirable.

This wasn’t always the case: humans tend to have the most esoteric ambitions during youth. I knew people who wanted to become filmmakers, truck drivers, and athletes. But by the time of graduation, a shift occurred. It became fashionable to join in on what everyone else was doing (I saw pivots to cyber, trading, medical).

Imitation is important to understand because ambitious destinations require devoted journeys. When you face a major dip, the only thing that will keep you in the game is how much you care about your goal. [3] If you imitate features without inner drive (which can’t be manufactured), then your ambition will fall like a house of cards encountering gusts of wind.

[3: Some questions for inner drive: What would you do if you could tell only your friends about it? What are you excited to see in the 22nd century? Why do you live?]

The nobodies are most susceptible to imitation. When you’ve done nothing, it’s easiest to start by parroting others. But you can’t keep on doing that to go from zero to one. You have to create your own jutsu to become a great shinobi.

Another dimension of imitation is competition. Historically, competition was necessary if you desired resources such as status, wealth, and power. If you didn’t compete, you risked being conquered. This was true for all kinds of people, from kings to children. Today, the risk competition poses is more subtle.

The things humans compete for are not forces of nature; they are human constructs. Yet inside you, something is natural: a unique seed is planted at birth. This is a one-time phenomenon in the universe. As you grow, the seed has potential to blossom to its full ambition. If the seed doesn’t understand why it’s competing, it risks undergoing mutation. [4] The secret is you can get ahead by adding to what everyone already has. Therefore, the question isn’t “How high can you climb the mountain?” but rather, “What mountain can only you grow?”

[4: You may be inherently wired to do something related to status, wealth, or power. One question worth asking is “would I still want what I want if I had infinite amounts of this?”]

Fans of The Matrix interpret the red pill as a symbol for truth-seeking. In the case of ambition, it represents seeing through imitated desires – how dreams are stolen – and to risk following your own.

“They tell you, ‘read this, eat this, don’t look around. Just peep this, preach this.’” - Kanye West

In the story 1984, Winston Smith is haunted by an authoritarian regime. He seeks the truth through secret writing, love, and reading. However, Winston ultimately fails because he never sees the deeper truth: the Party cares not for facts or belief, but power and control. The experience of Smith shows how without truth, ambition leads to staggering like a drunken sailor. [5]

[5: Richard Hamming said a drunken sailor without a vision (i.e. the truth) ends up about square root n steps from the origin. But if there’s a pretty girl (again, the truth) in one direction, the sailor ends up about n steps from the origin]

You consist of two things: soul and body. Naturally, truths are split into external and internal categories. External truths are the world outside your mind: the nature of animals, the force behind planets, the causes of rain. Internal truths are the world within your mind: your desires, values, loves. To navigate the world well, you need to know both its external order and your internal nature.

Truth is a conformity to reality. It’s not made by us; it’s discovered. Therefore, the most direct path to your destination is the truth. And since you have control over your path, you must be aware of when you encounter non-truths.

You may think truth is binary because reality is grounded in truth. However, you’ll find there’s varying levels of truth to your situation. If you’re trying to do what’s never been done, you’ll have to determine truths for yourself. This sounds straightforward in practice, but it’s not always that easy. When you read about another’s life in reverse, everything seems inevitable. When you live it forward, everything feels uncertain.

There is a dance between ambition and truth: ambition without truth is dangerous. This is when people get so caught in their desires they fail to see what they seek. On the other hand, ambition guided by truth leads to proper aim. In return, ambition gives truth its power in action.

Winston mistook rebellion for truth, thinking that joining the Brotherhood or loving Julia was enough. However, truth did change Winston: he reclaimed his humanity, found a language for what he felt, and had desires to fulfill. The lesson becomes clear: ambition without truth is noise. Ambition with truth is signal.

Steve Jobs once said, “real artists ship.” Despite wanting to cover more challenges of ambition, I need to end this essay here to ship this small experiment. I’m thinking of this essay as a first version product. As my understanding of ambition evolves, this essay will require iterations to fully answer the question, “what are the challenges of ambition?”

I initially thought I'd write this essay for myself, but someone could find this work useful. Even if you didn't, I would still like to discuss. Reach out!