Hindsight’s 2020: What I’d Gotten Wrong About Planning for Happiness

Jennifer Wang
Wangdering Ruminations
5 min readDec 6, 2020

Like the rest of the world, I started 2020 with a very different idea of what my year would look like. By then, I’d generally achieved the objectives I’d set when I came to the US for college — a degree, followed by a well-paying job in the US, getting ready to settle in a city I enjoyed, a robust network of friends…etc. I had a pretty predictable idea of what my freshman year of adulthood would look like. Until the whirlwind of a pandemic scattered my neatly sketched blueprints of life. The disruption, and the months that followed slowly led me to fully realise what I’d gotten wrong the past few years. I’d had my doubts and suspicions while I was in college (see this post), but because it still looked like I was “succeeding” under conventional standards, I was never forced to confront my problems head on. Seattle changed that as it forced me to rebuild from ground zero.

Landing in Seattle. Some trepidation, but more excitement.

As I re-launched the job search, the simplest yet most difficult question glared at me judgingly — what is it that I want to do? It seemed like everyone around me had a well-thought out answer to that. I did too, to fit in and do interviews, but truly I didn’t know. “Let’s start with the basics,” said a friend, “Why did you study International Relations and Economics in the first place?” Well, that was part of the problem — I’d studied Economics because I wanted a more marketable degree to “get a job,” and one that would grant me two additional years of work authorization on my student visa, thereby giving me three shots at the coveted H1B work visa lottery instead of one. I truly loved International Relations, but I didn’t give myself the opportunity to explore it in depth and develop a niche — forcing in a second major along with a year-long study-abroad pursuit, the lack of pre-matriculation credits coming into college, and a year-long, off-campus internship did not leave me much room to explore freely instead of just cramming together any schedule that would allow me to graduate. I had a maddening schedule to make sure I would have a job, but my approach was one of risk mitigation and not of potential maximization. In the end, all that effort did get me a decent job, but I’d lost sight of what truly mattered, I no longer had a calling that was my own. Without a purpose grounding myself firmly, the whirlwind of coronavirus disruptions exposed the shallow roots underneath.

I thought back to my 17-year-old self, defying my family’s education plans for me to chase what I truly wanted — going to an elite US college and then taking advantage of one of the highest starting salaries in the world. I achieved that not by placating my family’s wishes and preparing for the French admissions process at the same time, but by putting my own dreams first. I wasn’t concerned about the consequences of failure because I had that confidence deep down that I wouldn’t fail, that I could achieve anything I wanted because of who I am.

Fast forward to my time in the US. These years I’ve been so focused on minimizing my chances of failure that I’d neglected prioritizing my pursuit of passion, happiness, and success as defined by myself. I’d been guarding my “bottom-line” so ferociously that I’d forgotten to reach for the stars – the true reason why I’m here. It shocked myself, that as someone known for zestful joie-de-vivre and adventure, I’d taken such a detrimentally conservative approach to my career/life. Perhaps it was because of the uncertainty of being an immigrant; perhaps it was because I’d fought so hard to get here that my tolerance of failure plummeted once I arrived. Regardless, none of that matters anymore.

The last few weeks in Seattle were characterized by painstakingly torturous waiting to hear back from a job I’d thought I was entitled to. As of now, I still haven’t gotten a concrete response yet. But what I have realised is that while that job checks all the boxes of my bottom line (well-paying, sponsors a work visa, “intellectual,” in the US, tech-related), it would not solve my fundamental existential crisis of who I am and what I want. My time in Seattle has been stressful, because I’d been working a demanding job while searching for the “dream job” without knowing what dreams were anymore. I didn’t have the courage to be unemployed with my limited allocation of unemployment days on my visa ticking, and fully focus on figuring out what I wanted and how to get there no matter the risk of failure.

The other lesson I learnt from 2020 is that there is no price on happiness. Initially I believed that the financial gain of sticking out a few years in an unsatisfying but well-paying job would be worth the sacrifice. After all, doesn’t everyone complain about their job at some point? Once I actually started working, I realised that if a job demands 40–50 hours a week, that’s half of one’s waking hours. Imagine spending half your time doing stressful work you don’t care about simply because you have to. The mental toll would weigh down even the strongest people. Money is just a hygiene factor as Harvard Business School professor Clayton Christensen categorized in the book How Will You Measure Your Life (an excerpt of which was included in Managing Yourself, which I’d also referenced in this post), as opposed to a motivation factor. Read more about the differences here.

“Do what you love, love what you do.” What seems like the most straightforward saying can be the hardest to implement, because we overthink it. The complexity of life lies in its simplicity, so simple we don’t even recognize it. Life isn’t about constructing safety nets in case we fall, but about leaping as high as we can.

In a few days, I’m packing up the life I’d built in America, loading it all into a one-way rental car, and driving up to Vancouver, Canada. Is it farewell for now or farewell forever, I truly will not know. But from my Boston-Seattle move, I’d learnt not to take anything for granted — I thought I’d be back in Boston in no time this fall, as it turned out I stayed in Seattle for the rest of the year. However, I’d also learnt that no matter what, everything’s going to be fine. Seattle ended up being a fun experience, I’d developed new routines, explored new wonders, and met awesome people. I know that Vancouver, Calgary… whatever comes next will be the same. I’ll be fine and find fun.

One of the many incredible hikes I did in Washington.

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Jennifer Wang
Wangdering Ruminations

YVR 🇨🇦, TPE 🇹🇼,📍BOS🇺🇸, CDG 🇫🇷 | Tufts '20 | Live, Laugh, Learn :)