Over 6 months ago, I quit my dream tech job and went traveling solo through Europe. My family members thought I was crazy. They asked me if I was being mistreated at work — I wasn’t. They were concerned that I was going through a tough time — I wasn’t. They asked, how could I possibly quit the kind of job that most people can only dream of having?
And it’s true. You see, Uber was a dream job in every way. I grew up in a poor immigrant family in NYC. Growing up, nobody ever told me to pursue my dreams. Make money first, dream later. My parents were practical people — well, they were immigrants, so they didn’t have a choice. They worked all their lives, 100-hour weeks in pretty miserable conditions, so that my siblings and I could eat and bathe and live. To them, the “high” standard was whether you can make enough money to support yourself. An intellectually and emotionally fulfilling dream job where you get to build cool products with literally just your mind, working ~40 hour weeks in an air-conditioned office with free food and unlimited vacation days? Unheard of. Unthinkable. It’s actually so far out of their world that they couldn’t even imagine it when I described it.
Uber was, and still is, a dream job. I thoroughly enjoyed it and learned so much from my peers. My career was starting to take off. I felt comfortable, productive, and useful. I made impactful contributions to the business and I was proud of myself. In San Francisco, my friends and acquaintances were like-minded, ambitious, career-oriented, interesting individuals — most of us getting paid a lot of money in cushy jobs. But you see, there was always this nagging feeling. At first, I couldn’t understand it. If I had everything I ever wanted… no, if I had more than I could’ve imagined for myself, then what could I possibly be unfulfilled over?
Even now, I still can’t explain it to most people in a way that makes sense. I just felt a little stuck, a little lost, and a little wistful for something different. Time flew by faster than I could keep track, and whenever I did stop to reflect on it, I felt shock and uncertainty that came from realizing I had changed in a number of ways that I hadn’t intended or even been conscious of.
I was becoming the kind of person who complained about free food, because it wasn’t as good as other companies’ free food and because everyone else did too. The kind of person who didn’t want to appear “too girly” for fear of not fitting in or not taken seriously at work. The kind of person who stayed within a bubble of people I was already comfortable with, because it was easier than trying to understand somebody new and different. The kind of person who subconsciously judged others based on where they worked and what they did.
I’m ashamed of it. At the time, I didn’t understand why I felt this nagging feeling. Maybe it had something to do with my surroundings. Being in San Francisco and in this bubble of extreme privilege where we can all buy away our problems. I was living so far inside this norm that I couldn’t see how it was making me unsatisfied. Was I living the best life that I could? Was I becoming someone that I wanted to be?
So I did what any insane 20-something year old going through an quarter life crisis would do, I quit my job and went traveling. I gave up my apartment, put all my things into storage, bought a 40L traveling backpack and a one-way flight to Europe, and I traveled.
It was truly fantastic, but also, still so so privileged. I recognize that not a lot of people my age would be able to up and quit their job, live off of savings for 6 months, and come back to pick up right where they left off. I guess you can say that I used the result of my privilege to escape that privilege. I see the irony.
At the time, I felt so cool, so brave, so badass, and so free. I lived by nobody’s agenda but my own. I had no obligations to anybody or anything other than myself. I could wake up, eat, shit, and sleep whenever I wanted to. And boy, is it the little things in life! (Just kidding. Kinda.)
In the very beginning of my travels, I was a little at a loss of what to do with that level of freedom. I went from established routine to just, nothing. Do I just… wander? Do I just go to this bar and order a drink by myself? Isn’t that weird? Do I just walk up to these people and start talking to them? By the way, the first time that I racked up the courage to do that was when I approached these two people in Barcelona, all happy and cheerful and hopeful that I was going to make the greatest friends ever (because that’s just what happens when you’re traveling?) and I got a bemused “no hablo ingles” back. Oof. Okay, take two, then.
Then I realized that I was trying too hard to manufacture a good traveling experience. Before, I had always been the type of traveler who went somewhere to see or do something, for a purpose. I used to make itineraries that planned out every hour of my day — and that was good when I only had a week or two of vacation. But I didn’t need to do that during an extended exploration. So I let go of those expectations and the need to get something out of it, and just let it be.
And with that, I experienced some of the most joyful, peaceful, and relaxing times of my life. I spent 5 hours straight sitting in a coffee shop sobbing my eyes out over a particularly emotional book I was reading. I started a conversation with a random German guy in a burger shop about how good his fries looked, and we ended up spending 2.5 hours walking around Berlin talking about what we want out of life. I journaled extensively about my trip, putting words to thoughts and feelings, and shared it with friends who had similar experiences. I went into an art supplies shop on a whim and bought a watercolor paint set that I spent the rest of day painting at a park.
I realized that I was missing those moments — moments when you do something just because you can and because you want to, instead of putting it off for something “more important”. I realized that I was too calculating with how I spent my time — anything that didn’t immediately yield some sort of instant gratification was thrown to the side. Before, I’d think, what would be the point of painting if I could read a systems design book and get better at my job instead? What would be the point of talking to a stranger, if we’re not going to follow up with each other? But it actually made me fulfilled — doing something just because I was in the mood for it with no priorities and no agendas. Fulfillment for the soul, I guess.
I met fun and interesting people from all walks of life. The reality was that I didn’t click with all of them, but the ones that I did click with, I felt so thankful to share a little piece of our lives together for a brief moment while we passed through the same town. Serendipitous encounters. I stayed in hostels, so meeting new people was way easier. What I found most refreshing were people who were interested and interesting. People who greeted you, talked to you, asked you questions, shared their life experiences. The most common questions were, “where did you come from?” and “where are you going next?”
This was a stark contrast to the people I met at home. People in their own heads, going about their daily lives and their routines. People I met for the first time at parties and gatherings who will inevitably ask the same questions: “what do you do” and “where do you work”. Perhaps it’s an SF thing. Perhaps forming meaningful relationships as an adult is just hard. I don’t know. What I did realize, though, was that surface-level conversations drain the introvert in me, while deeper conversations invigorate me. I realized that I wasn’t being intentional about the kind of conversations, and therefore connections, that I wanted to have. After I returned from my trip, I made a pact with myself: when I meet someone new, I won’t ask about their work. Instead, I’ll try to understand who they are as people first.
After a while (for me it was 2 months), I started to genuinely miss my job. Not the cushy free food part of it, but the parts that made me feel productive and intellectually stimulated. Before this adventure, I already knew that I enjoyed my job. (I’ve never, ever dreaded a Monday, which is how I knew.) But I wasn’t sure about it. Did I actually enjoy it? Do I feel bored? Am I learning/growing enough? There are millions of jobs in the world, how do I know that this is the thing that I would enjoy doing the most? And does it matter if it isn’t? I pondered that for a while — my reasoning for studying Computer Science and becoming an engineer. I worried that the benefits, perks, and cushiness clouded my judgment. What if I was meant to be a world class professional glass blower and I never discover that part of myself because I never tried?
But then I got bored of traveling — the one thing that I thought I could never get bored of. And I started to miss my job. So maybe this is just the human condition. Something is exciting because it’s new, out of reach, and novel. And anything, no matter how great, gets routine if you have to do it for a while. You see, I had the incorrect impression, as someone who transitioned from a student to a professional, that it was “correct” or “good” to be under constant change, pressure, stress, and excitement. However, in reality, being in a stable and healthy relationship with my career didn’t mean that it was wrong for me. (You can draw a parallel here on how people treat romantic relationships too, but that’s a different topic.)
So now I’m back in SF. I spent a couple months studying and doing interviews, and got a great new job that I had my eyes on for a while. I would say that overall, the change that I want to incorporate in my day-to-day is to be more intentional with how I am spending my time. That means making an effort to get to know people who seem interesting to me, rather than shying away. That means doing something simply because it might be fun, rather than needing to get something concrete and immediate out of it. That means that I shouldn’t socialize for the sake of socializing, but be more conscious of who I surround myself with. Hopefully, the next time that time flies by, as it tends to do, I can look back and see the ways that I have become someone that I want to be. Maybe I’ll report back.