Lessons from 3 years of work

October 21st, 2023

This is all written with my ~3 years of working experience so far, so take with a grain of salt! I’m still learning a lot about how to work and live well, and how to balance my ambitions with my comfort. So far, I’ve had the opportunity to work at a large publicly traded tech company, a small 30 person startup, and two medium sized unicorn startups around a few hundred people. Each work experience has come with its own set of unique challenges, but I don’t regret for a minute any of my choices thus far — despite many of them inviting more chaos, providing less consistent income, and also being potentially “bad” decisions. For example, joining a company pre-product market fit and working across 5 different timezones was not what I needed 1 year into my career. However, as a result of trying out all these different companies, I feel that I’ve gotten a much better sense of what I value in work and what I’m working towards in my medium term and long term goals. I won’t talk too much about them here, but will instead dive into five main lessons that I’ve learned that also serve as tips!

It’s been easy for me to spend time daydreaming about what a different, easier job or career path could be, or one that I feel more energized by. However, I strongly believe that the goal of early career is to learn how to work and how to get things done -- no matter what profession, passion, or industry we choose. There will always be some element of “work” involved that won’t be fun. I learned this the hard way by joining a company that was, on paper, everything I was looking for at the time. Working in education and gaming, at a high growth startup, with tremendous ownership and scope — these were all things that I really thought I was looking for. It turns out that none of it mattered for me, and that I still had to learn to just do the work — and all my boxes being checked didn’t help. I’ve also heard similar feedback from creative friends who’ve said that needing to turn their passion projects into reliable income killed their passion for it.

One of my favorite pieces of advice on this lesson comes from Obama:

Another tweet about how just reliably getting things done already puts you in the top X decile

I had heard these sayings a million times and thought that it was such a cliche that I never needed to really learn. However, I’ve definitely been on the short end of the stick more times than I want due to ways I’ve presented myself. In asian culture, we’re taught to just work hard and let our results speak for themselves. In many ways, this is a great mindset that doesn’t step on others’ toes and keeps us grounded on our output. However, this mentality ends up falling apart in corporate America and in any group context in which your outward perception shapes the outcome substantially. Whether it be fighting for a promotion or getting a job interview, I’ve noticed how easy it is to get slighted when you don’t fight for your own worth and really sell your accomplishments. I realized that if no one hears about your work, then no one will know how good of a job you did. And no one is going to advocate for you more than yourself.

Another relatively self explanatory lesson about boundaries that took me a long while to really internalize. When I started my first job, I had considered it a “dream” job of sorts. I had read every blog post about the program I was joining, I was a “power user” of the product, and I genuinely considered it to be one of the single best new grad opportunities for me. All this energy going into the job gave me an unreasonable amount of care for doing my job well, to the point of frustration at not learning and delivering more quickly. I was also spending hours outside of work worrying about what else I could be doing. Ironically, all this care made me perform worse — as I would get paralyzed at work about the best way to do things. In my second role, my company worked in Discord and that blurry line between play and work meant that I was exposed to work 24/7, leaving me feeling trapped and uncomfortable. Fortunately, by the time I started my third role — I had figured out how to start separating work from life and made time for things that mattered to me outside of work.

Recently, I wrapped up a 1.5 month job hunt in one of the most challenging tech job markets in the last 10+ years and managed to get a nearly 6-figure raise. This role was the result of a serendipitous friendship I formed over discord with someone whose face I’ve never seen and name I’ve never known. This was a perfect example of what Meg Jay defines as a “weak tie” in “The Defining Decade”. She talks more in the book about the importance of these weak ties and how our personal network of people we’re not close to ends up being far more important than our good friends professionally. On the more day to day side, our work relationships both define our experiences and our ability to get things done. My best work experiences so far have been those where I had strong relationships with my teammates. On the flipside, it becomes hard to ask for favors and support from your team if you isolate yourself from them. Having good relationships with your teammates makes work both more fluid and more enjoyable.

One of the single most common regrets of the dying is: “I wish I hadn't worked so hard.” Work will always be there, and there will always be more work to do. If anything, the reward we usually get for a job well done is just more work. Meanwhile, it’s been easy for me to forget that my parents are aging right alongside me — it’s heartbreaking to see my mom and dad after a long stint away from home and notice how they’ve grown a little older, their faces a little more worn. It’s always a stark reminder of how little time I really have left with my parents, and how precious my time with them truly is — it’s the tail end. Whenever I choose to prioritize with loved ones, I’ve never regretted it whereas the flip-side hasn’t been true with work.