Reflections on Career Change

Around two years ago, I finally committed to a decision that I had been contemplating for the better part of a decade beforehand. I would retire from the tech industry and pursue a brand-new career in urban planning, a field that had piqued my interest ever since high school. (Yes, I did stereotypically play a lot of SimCity back then.) With enough prodding from close friends and signs from the universe (a global pandemic was actually a blessing in this case), I took the plunge and started graduate school in Fall 2020.

One semester into the program, my good friend Aswath reached out to do an interview about my career change. This turned out to be an enlivening 1.5+ hour conversation about life, work, passions, personal finance, and so much more. Now that I’ve graduated from my Master’s in Urban Planning program, this seems like the perfect moment to reflect on this and everything I’ve learned over the past few years.

Full video with chapter markers covering various topics

I was pleasantly surprised to see that a remarkable amount of what I said then still matches my thinking today, and I’m even more grateful Aswath had the idea to record this for posterity. So, then the question becomes – now that I have nearly completed my career transition, what would I have done differently? I believe I only have three main “regrets” (if they can be called that): worrying too much about which school to attend, not networking enough beforehand, and not making the career shift sooner.


Worrying about which school to attend

I spent an inordinate amount of time during the first year of my graduate program at San Jose State University considering whether it was actually the right one for me. This is because I had applied and received admission to several more “prestigious” universities in other cities (e.g., NYU, the University of Melbourne) but ultimately declined their offers due to travel restrictions in 2020. Even so, I kept thinking I might collect some credits and then transfer in hopes of ending up with a more esteemed degree in the end. (I now consider this line of thinking part of the lasting negative influence of Lowell High School.)

It turns out that all this stressing over the reputation of my degree was quite needless. The opportunities I have been able to secure in research and industry have been as good or arguably even better than those found by peers at other universities. For example, the Mineta Transportation Institute was an endless source of research experience that gave preference to San Jose State graduate students. My work there directly led to internships with well-known public transit agencies and consulting firms, where I have worked alongside colleagues from even more elite schools (e.g., Berkeley, MIT). So, in the end, I finally learned the lesson that every student eventually realizes: it’s not your degree that counts – it’s what you do with it!

Not enough networking

I did attempt to do some informational interviews with urban planners in my network before diving into graduate school, but in retrospect my questions only scratched the surface of the field (and were too heavily focused on which school I should attend 😔). I also failed to expand my network from those conversations (i.e., asking to connect to more planners as part of the interviews and following up), which would have opened up even more opportunities down the road.

Fortunately, I’ve met so many amazing people through my various internships and am beyond grateful to have their support as this new career takes off. I look forward to running into them again, returning the favors, and connecting with even more planners in the field for years to come. As they say, planners are in a relatively tight-knit community and reputations matter!

Not leaving tech sooner

When people have asked me how the career transition is going, I have often responded “I wish I started sooner!” This sentiment seems common for many people making major life changes, and it makes me contemplate what holds us all back from pursuing these kinds of dreams.

For me, I believe it was mostly my fiscally conservative and risk-averse nature. In my conversation with Aswath, I mentioned I calculated a 10-year runway for myself to make this career sustainable before I would run out of money. In retrospect, this was grossly excessive – I’ve barely consumed any of my savings thanks to the low cost of tuition of San Jose State University, scholarships, and income from my various internships. Even if I didn’t have the savings, U.S. federal student loans have had 0% interest rates for the past two years and could even be forgiven after 10 years of working in public service if I needed that.

All this is to say I could have left the tech industry much sooner. (Though it probably would have made my research harder…) I’m hardly alone, however – the industry is rife with stories about golden handcuffs that keep people in cushy but stagnant roles for far too long. For those still in tech but wanting a change: you don’t need to wait for yet another bonus or stock refresh – just make a move already and you’ll be fine! And if you don’t know exactly what you want to do, I recommend taking the time to explore new fields during your unlimited PTO. 😉

Looking ahead

I owe an immense debt of gratitude to everyone and everything that has enabled my progress in this career change so far. From my family and friends who supported all my decisions, to the sinuous circumstances that landed me at San Jose State University and led to all the learning and growth opportunities that have sprung from here. The past two years have really been a series of miracles in many ways.

As I leverage my new Master’s degree to delve even deeper into the professional world of planning, I’m filled with a renewed and unbridled sense of optimism – it’s the very same feeling you get when you first graduate from high school or college! Would highly recommend doing something like this every decade or so. 😄

Classic illustration of the concept that every day is the first step of the rest of your life. Coincidentally, Tim Urban also has a fantastic post about how to choose a career that fits you.

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