Every year, I try to write about what I’ve learned about careers.
I wrote my first essay in 2021 when I felt directionless, unsure of what I wanted to do. By imagining careers as hills, I realized I was chasing after the wrong things. I had been trying to scale Everest when I should have been enjoying the local hills and searching for the right view.
A year or so later, I found myself in another crisis. I was losing motivation to work on new things, reluctant to expend effort when there wasn’t a clear reward. The second essay asked why, and I found a difference between ambition and being ambitious. I was the latter, grasping for advancement with no goal in mind.
I spent the next year studying the idea of ambition, mostly by reading biographies of people who reached the pinnacle of their chosen profession. In the end, I came away with a new definition of ambition, the continued pursuit of a new reality, and a more vivid picture of the toll that ambition takes.
This past year, instead of trying to find my own ambition and then structuring my career around that, I’ve flipped things around. I started with three principles and tried my best to stick to them. Doing so hasn’t been entirely easy, but it’s been a fun journey.
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Be Serious
A while back, I helped draft a commencement speech. I didn’t realize it at the time but that speech was a full-circle moment for me.
At the start of the year, I made a commitment to be serious. To not wander or hedge my bets, and instead give myself fully to a single thing. That was stories — why people like stories, what makes a story good, and how to tell a good story.
A couple of years back, I read a book called Something Incredibly Wonderful Happens. The book follows the life of Frank Oppenheimer, brother of Robert Oppenheimer. Although also a highly accomplished nuclear physicist, Frank mostly languished in obscurity, spending years tending a cattle ranch and teaching at a local high school. But the part of his story that I kept coming back to, again and again, is his speech to the 1960 graduating class of Pagosa Springs High School.
I think that part of the sense of having lived a full and a rich life comes from an ability to continually take things seriously - but not too personally. Of a willingness, even a determination, to become deeply involved in what you are doing, but not obsessed by it.
Frank Oppenheimer
When I took a hard look at my own life, I realized that, ironically, I wasn’t serious about the idea of seriousness until this past year.
I’m a pretty lazy person. I try to look for the easy way out. That, in part, explains a lot of my career as I jumped from industry to industry. I wanted to find the easiest path to success. What ended up happening is that I spent a lot of time doing things that I was lukewarm about. A recipe for unhappiness.
Being serious about stories was perhaps the scariest decision I made in a long time.
For one, I wouldn’t have an excuse if I failed. I was going to give it my all and if I fell short, I couldn’t say, “Well, I wasn’t really trying.” And second, I stopped thinking about what my backup plan would be. Instead of trying to find a narrative for what I was doing, I just started working on stories. Seriously.
And work I did. Since making that decision, I have been either writing or editing stories every single day. On an average day, I work through about ten thousand words, either from writing or editing.
This sounds really simple. It is. Action has never the tough bit of work. The hard part has been ignoring the whispers of an easier path. Waking up at the crack of dawn to work on a story that might never be read by more than a thousand people is sobering. Trying to write the perfect sentence after seven different drafts is exhausting. Reading negative comments is frustrating. There were times when I felt helpless. There were times when I paused halfway through a chapter and questioned everything I was doing. I would look out the window and wonder why I chose a path that involved sitting in front of a computer from sunrise to sunset.
Every time, I would think back to Oppenheimer’s speech. Oppenheimer never promised that things would be easy. He did, however, promise a full and rich life. And that was true.
Ever since the day I took writing seriously, I’ve read thousands and thousands of supportive comments, worked on a commencement speech, and even typed away in dozens of different cafes across the world. It’s honestly still a bit surreal as I write this right now. This past year has been one of the fullest years I lived. All because I made a single choice to be serious.
Happiness of Pursuit
In some ways, all of my essays about careers have been about the idea of happiness.
Like most people, I like being happy. But for a long time, no matter what I did, my work simply wasn’t giving me the happiness. To quote La Guardia, my life was “a squalid succession of days; whereas in fact it can be a great, living, thrilling adventure.”
In February, I decided to drive across the country. Starting in Maryland, I took Route 70 out to San Francisco, then back to Maryland through Route 40. Round trip, east to west and back to east, was around 7,500 miles. For thirty days, I lived on the road, leapfrogging from motel to motel across America.
It was horrible.
Every morning, I would drag my bone-tired body into the car, knock out a couple hundred miles, arrive at a small town in the middle of nowhere, and talk with locals. Each night, I would surrender to the roar of cars outside my unfamiliar motel, wishing that I wasn’t sleeping between off-white blankets and stiff sheets.
I should have been unhappy. But, somehow, I was having fun.
Every time I glanced at the odometer and counted the miles I had driven, I’d get the world’s biggest smile.
Those miles, ticking upwards, became evidence that I was working towards something. It wasn’t just the same day after day. I was on an adventure — all I had to do was look out my window to see great mountains, endless corn fields, and blue lakes. More importantly, my progress was something tangible.
Going back to the idea of ambition, it’s easy to see why I was unhappy when I was just ambitious. I wasn’t working towards something tangible. All that was happening was advancement with no goal in mind. I thought that if I could find ambition, I would be happy.
But happiness is more than just finding ambition.
What made the road trip fulfilling was the fact that I could measure my progress. What makes ambition meaningful is the world changing to a new reality. And happiness sits at the intersection of these two things. It needs both the pursuit of a new reality with some kind of way to track progress.
There’s just one last challenge. As Morgan Housel says, “progress happens too slowly to notice, but setbacks happen too quickly to ignore.” Part of why I went on that road trip was because I felt that I was in Groundhog Day, repeating the same day over and over again. Zooming out, it was easy to see that I was making headway and creating better stories. But, in the moment, it felt like taking one step forward and two backwards. It felt like a squalid succession of days.
In the months after the road trip, I’ve tried to find a way to measure my progress. I counted the number of words, or rated each day with a score from one to five. Most of the time, it felt like I was measuring for the sake of measuring. After a bunch of failed attempts, I’ve come to internalize the idea that professional progress takes the form of days where years happen and years where only days happen. It’s a pretty simple idea, one that I’ve probably written about elsewhere. The difference now is that I don’t just know that, I believe it.
And I still slave away at the grunt work, digging and shoveling through the same tasks for the same result. But I also poke my head up every so often. And, as if by magic, I see my old work and realize that my skills have forever changed for the better. It’s not exactly progress that can be measured by a specific yardstick. But, day by day, I’m gaining more and more conviction that I’m improving. And that’s enough for me. Or at least enough to make me happy, which is what this whole thing is about.
To end with another quote from La Guardia, “I shall not rest until my native city is the first not only in population but also in wholesome housing; not only in commerce but also in public health; until it is not only out of debt but abounding in happiness.”
Find Valhalla
For a long time, I’ve had this uncomfortable feeling in my stomach. It probably started back in college. Whenever I was at a party or playing league, I felt guilty about not doing productive things. Later, when work became a bigger part of my life, that feeling started to seep into the other things. I ate my lunches faster, as if those extra few seconds were the difference between success and failure. I skipped out on museums and parks, opting to spend the time in front of a screen.
Ironically, the time that I spent working wasn’t much better. The rushes I got when we got a new customer or reached a new revenue milestone were short-lived, and I’d daydream about getting to the part of the day when I could relax.
In other words, I had this push and pull between ambition and hedonism.
To explain these two ideas, I’ll borrow the idea of Valhalla. More specifically, I’m going to use the popular culture idea of the ultimate resting place for warriors, where they feast and fight, feast again, and fight some more.
Valhalla’s interesting because the fighting part sounds a lot like ambition, while the feasting part is pretty much a straight line to hedonism. In Valhalla, these two ideas both coexist together and build on each other to deliver a Nordic version of heaven.
For me, it wasn’t very fun trying to find the balance between ambition and hedonism. I eventually settled on a formula with some days being more ambition-focused, where I did a ton of work and went to sleep feeling happy. Enough of those days in a row, and I gave myself permission to let up on the gas pedal and have an entire day of just lounging around. The guilt of that becomes fuel for the next series of productive days.
Enough of those cycles and I fell into what I’ll call the “there’s something better than this” rut. I couldn’t imagine the next twenty years of my life stretching on like that. There had to be a way where I didn’t need to carry around low-grade guilt all the time.
So in August, while watching the 2024 Olympics, I heard the commentators say that Kristen Faulkner (gold medalist for women’s road race cycling) had only learned to cycle seven years ago. An idle thought of “what if I tried to do that?” skirted across my mind. In September, I booked a one-way ticket to China and began training badminton full-time.
A couple of months later, I’m better at badminton. Not Olympic level good yet, but making my way there. More than that, I’ve also began to really embrace traveling, going into the rural parts of China, making new hostel friends in Taiwan, and having the best mango sticky rice in Thailand.
Somewhere along the way, I lost that uncomfortable feeling in my stomach. Now, I don’t think about work while I explore a new city, and I don’t think about the life I’m missing out on while I type away in front of my laptop. And a large part of why is because instead of my work life clashing with my personal life, they now build upon each other.
In Valhalla, warriors feast to become stronger and they fight to enjoy the feasting. The ambition and hedonism come together in a cycle that enhances both. Now, in some ways, that’s my life too. The fighting? Storytelling. The feasting? Playing badminton and traveling. It’s not pure hedonism or ambition, but instead of a balance of the two.
And finding that balance was worth every bit of the struggle along the way.