Careers and Ambition

2258 words, 12586 characters

About a year and some time ago, I wrote a piece on careers. It’s the thing I point at whenever someone asks me about careers. But when I revisited the piece, something was off. The concepts were solid but the writing felt stiff and impersonal. So here, with another year of wisdom, are my thoughts around careers, sometimes shaped by ambition but most of the time by ambitiousness.

Last time, I phrased careers as a series of hills that offered different views.

Some people climb a hill and decide they like the view at the top. They settle down, build a house atop the hill and improve upon it year over year, adding trees, gardens, and paths to help others climb the hill.

Sometimes, it’s not even at the top of the hill. They find the right height with the right view and call it a day. Some want to explore the view of taller hills which make for a more arduous climb. Some want to try something new and climb a hill in another area, one that might not be taller but is definitely different. Finally, some reminiscence about their previous views and retreat back to the previous hill.

Allow me to add one more case. Sometimes, people get tired of climbing and get burned out, their desire to work is lower than the amount of work ahead.

Burnout doesn’t only happen to consultants burning the midnight oil, it can happen to average store clerks or engineers at Google. It also happened to me, kinda.

Some background

Around two years ago, I came across a book that changed my life, Harry Potter and the Methods of Rationality. Since I’ve read it, a quote about ambition kept ringing in my head.

“Then again, only a very few folk ever do anything interesting with their lives. What does it matter to you if they are mostly witches or mostly wizards, so long as you are not among them? And I suspect you will not be among them, Miss Davis; for although you are ambitious, you have no ambition.”

“You were sorted into Slytherin, Miss Davis, and I expect that you will grasp at any opportunity for advancement which falls into your hands. But there is no great ambition that you are driven to accomplish, and you will not make your opportunities. At best you will grasp your way upward into Minister of Magic, or some other high position of unimportance, never breaking the bounds of your existence.”

The juxtaposition between ambition and ambitiousness has swirled around in my head for the past two years. Ambition is the act of striving toward a single goal, while ambitiousness is the process of grasping for advancement.


My first existential crisis came in high school.

I went to Montgomery Blair, an average high school with a prestigious magnet program. Unfortunately, I was part of that magnet program.

At Blair, I realized that I was not as smart as I thought I was. It wasn’t the classes, they were hard but manageable. It was the way in which my classmates would breeze through everything. For the first time in my life, I realized I wasn’t special.

To most people, having smart classmates isn’t crisis inducing. For me, I’ve always been a competitive person, the type that would spend hours trying to get better. And try as I might, I just couldn’t see how I could win in academics.

So I started looking around for something that I could win at.

Games? I was a hard stuck bronze League player. Swimming? I was better than average, not great. Making money? Well, I did sell about 10 dollars worth of playground stones when I was in Elementary school. Looking back, I’m pretty sure I traded some pretty stones I found for someone’s lunch money. Not the best look but hey, I’m pretty sure that none of my classmates did anything like that.

And so, I decided that I would try to make money. It helped that I also wanted to buy a new computer and that was the last thing my parents wanted for me. Either way, I realized that I needed to find a way to make some cash.

The first thing I did was sell my assets. It wasn’t much, mostly a League of Legends account that I spent three years on. In a series of rash decisions, I decided to list the account on eBay. The next day, it sold for $30.

I found my ambition staring at my PayPal account, now $28 (net of fees). I couldn’t articulate it well at the time, but I realized that I could make a whole lot more than $30. Maybe, I could buy myself a new computer. Maybe, I could be good at this.

So, rather than do homework, I started researching everything about League accounts. I found a black market for League accounts on EpicNPC, an online forum where hundreds of accounts were listed for sale every day.

Without realizing it, I had stumbled into an arbitrage opportunity. The prices on EpicNPC reflected a lack of trust between buyers and sellers. Whereas my account had sold for $30 on eBay, I found plenty of similar accounts for just $10-15 on EpicNPC.

Over the next few weeks, I started buying accounts on EpicNPC, packaging them up, and reselling them on eBay. On the way to school and back, my head swirled with figures. Rather than math homework, I was calculating account values and how I could cut better deals with EpicNPC sellers.

For the first few weeks, my PayPal balance fluctuated in the double digits, rarely breaking the $100 mark. Each deal would net around $10 after fees. Sometimes, I’d get scammed and lose money. The losses always stung.

Then, one night, I bought a batch of accounts with the King Rammus skin (one of the rarest skins in the game). After listing them on eBay, the accounts sold in hours. Each account sold for $55 and cost me $25.

Skin rarity was the key to success with my bootleg arbitrage operation.

Accounts with highly sought after skins were undervalued in EpicNPC due to the chance for fraud. On the other side, I was the proud owner of an eBay seller account with 13 5-star ratings. I also learned dearly from my previous encounters of scammers. And so, I could focus on rare accounts and flip them for a profit in the $25-50 range.

That brought two new problems. Accounts with rare skins had fewer buyers. So I’d often buy an account and list it for two weeks before finding a buyer. The increased transaction time really cut into my earnings. The other problem was that these accounts were more expensive. They’d tie up my capital as I waited for a buyer.

I don’t think I ever solved these problems - I was just happy seeing my PayPal balance increase. About two months later and $800 richer, eBay wised up to my schemes and suspended my seller account. Annoying, but I had reached my goal - I had enough to buy a great desktop and I could enjoy the new computer with the League accounts I still held.

While fun, the moral of this story isn’t to encourage high schoolers to start underground account trading. The tradeoff to my entrepreneurial journey were my grades. They tanked and never recovered for the rest of my time in high school. I also missed out on having a “normal” high school experience.

That being said, let’s talk about ambition. Ambition, to me, is the decision to prioritize one outcome above all others. Sometimes, it’s explicit - my decision to scour EpicNPC rather than study for exams. Other times, it’s implicit - when I thought about new trading schemes instead of paying attention in class.

In my case, I’m not too sure if a new computer was worth lower grades and later, worse college admission chances.

But, my days as an underground League dealer were probably the happiest days of my whole life. [0]


Shortly after my eBay account was suspended, I had another dilemma. I had SATs coming up and I sucked at writing.

Growing up in Montgomery County, there was one thing that was a given - tutoring. After Chinese school each Saturday, I spent another hour of my afternoon in a classroom where we wrote SAT essays. Over the span of 4 months, I probably wrote 15 different essays on “The Stranger” by Camus to answer questions such as, “Is listening more important than speaking when you are trying to persuade others? Plan and write an essay in which you develop your point of view on this issue.”

I got really good at adapting Camus’ words to answer any essay question that the SAT threw my way.

But for some reason, I could never figure out my way around the Writing section of the SAT (this was before the section was taken out in 2016). Grammar and syntax have never been my strong suite.

Instead of spending my days taking practice SAT problems in a classroom, I decided to take a different tack. I had started two dangerous hobbies after I stopped my underground League dealings, Reddit and Chinese web novels.

After seeing some translations for Chinese web novels pop up on Reddit, I thought that I could do the same exact thing, but better, and earn some quick popularity while also strengthening my writing skills.

It turned out that there were a lot of readers for translated web novels. It also turned out that you could build a business around translating these novels. And it finally turned out that publishers would be willing to acquire a company focused on translations.

And so at the ripe age of 18, I found myself as a founder with an exit. Or in my words, someone who got lucky. At the time though, I didn’t think any of the results were attributed to luck. Instead, I attributed my success to hard work and persistence.

Instead of relaxing, I wanted more. It wasn’t for some noble purpose. It was greed.

I struck at any opportunity for advancement. In my previous careers piece:

Celebrating the acquisition over a fancy meal, my only thoughts were around how I could build the company to be better. Like before, my motivation came from staying one step ahead of others rather than finding some specific view.

And so, I kept climbing. Since the acquisition, I left the company I founded, learned a bit of venture capital, joined another venture-backed startup, and started another company. One after another, I was searching for a view that was always a bit out of reach. Yet, as soon as I found any view, I would realize that I wanted something better, something higher. I was continuously climbing.

It’s really been the past few months where I slowed down both by circumstance and choice that I’ve gotten a chance to really examine what I was searching for and let the question of careers catch up to me. For so much of my life, I had been avoiding the question and simply been ambitious without ambition.

In the moment, it felt like I was competing with a hundred different versions of myself. My first thought after hearing things like someone getting promoted or some startup raising a large round was, “what can I do to be in that position?”

The answers that I came to were of the “work harder” and “look for a better problem” variety.

Ambitiousness is the search for more. There’s no purpose for behind the journey. It’s grasping for a better future without making any opportunities.

I can’t chalk the past few years as a total waste. I learned a lot about business, life, and myself during this time.

But I did feel deeply unhappy during these few years.

And… happiness?

Whenever I come across good writing, I get the impression that the author has his or her life together. Here’s an exception, I’m still trying to figure things out. I didn’t magically become happy by learning the difference between ambition and ambitiousness.

Ambition (and thereby happiness) isn’t something that can be willed into existence. Looking at it from another angle, maybe ambition is only possible from sheer willpower. Confusing right?

In some ways, I’m once again in high school, surrounded by smarter classmates. Try as I might, I’m not too sure what I want to do.

Maybe, one day, I’ll sell my League accounts and find ambition again. [1]

Thanks to Yang and Lauren for reading through early drafts as I tried to understand the weird thing called ambition.


[0] If you’ve finished this post, there’s a pretty big question that I leave unanswered - “Can you find happiness outside of ambition or ambitiousness?”

No. I don’t think you can find sustained happiness without ambition.

I’ve spent thousands of hours on League. I poured through patch notes, read build orders, and watched the professional play the game.

In the moment, I was having fun. Whether it was playing the game at midnight in college or watching LCS with friends, I was happy.

Eventually, things calm down. It’s suddenly 2 AM and I start to regret the series of poor life choices that led me to play League at midnight. I’m certainly not happy anymore.

Perhaps, ambition is just the yardstick we measure ourselves by and we find happiness as we edge our way up.

[1] I no longer play League.

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