Why I quit my job at Instagram on my 30th birthday

Jacky Wang
The Startup
Published in
7 min readJul 20, 2021

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After almost 5 years of being a software engineer at Instagram, I find it too magical of a time in my life to not reflect upon meaningfully. I’ve previously written, “4 Lessons From My 4 Years at Instagram & Facebook as a Software Engineer” which all still holds true. It has all the context on how I joined IG, what I worked on and learned so I won’t repeat myself here. I’ll focus on my favorite memories, what I would have done differently, why I’ve quit, and what that lies ahead.

My last time in the office

Favorite memories

I had a heck of a time there! Nothing but a euphoric experience full of learning and excitement. Seeing how many people used our products, how fast we can move, the quality of craft, and how ruthless we can prioritize is truly inspiring.

Other than working on cool features on explore, search, hashtag, save, collections, and shopping search, I loved our hackathons the most. We would try out all these ambitious ideas, things we saw other apps do much better than us, and try to innovate and fill the gaps. Even if some ideas don’t ship, the contagious passion and brilliance from people I get to work with give me a huge spark from the normal routine of work.

2 things I would have done differently

  • I worked on iOS this entire time — I became very efficient and fast at it, but I wish I had stepped out of my comfort zone a bit more and picked up a completely different stack such as backend or data engineering. I’ve seen how amazing engineers can come up with an idea and implement everything from back end to client on both platforms and it’s so impressive! Our managers always encouraged and supported us to try other tech stacks, but I’ve always found an excuse to stick to what I’m good at knowing I can be the most efficient that way. Whether it be for performance review, wanting a promotion sooner or complacency, things that don’t really matter outside of FB
  • I worked on the same problem space of social media — I’ve worked on messenger for a bit when I first started, but quickly switched to Instagram and stayed there the remaining 4 years among different teams in the same product space. I loved the Instagram culture, the people, the swag, the office space, and the product so I never wanted to go anywhere else within the company, either feeling like it’s not as “cool/sexy” or “fun” to work on. In retrospect, blockchain, VR/AR, and even hardware there are so many fascinating problem spaces that would’ve been fun to explore! No regrets here though since I really enjoyed my time anyway!

The People

One thing I think I absolutely did right during my time there was assuming every person I’ve come across to be a potential lifelong meaningful relationship. You won’t stay in touch with everyone you meet but leaving the possibility open and being your true authentic self will make your days at work much simpler and happier, and you might actually walk away with a few lifelong friends, which I am so grateful to say I have!

Left: More than half of our eng team at the time celebrating NYE in Taiwan! | Middle: Mostly IG colleagues playing basketball at 5:30 AM every week! These people are crazy! | Right: Traveling through Patagonia and Salar de Uyuni with my brother Jesse LOL

Why I’m quitting

5 years is a long time for working on any product or technology. I looked around internally but felt like even if I switched teams, I’d still be within the Facebook way of doing things and not be exposed to other technologies, methodologies, and learnings. I was starting to become aware of the limiting career dependency I had with the same company.

During the pandemic, I spent a couple of months in Taiwan working remotely which I enjoyed. However, we were forced to return to the US by 2021 despite Taiwan having no covid and the US with surging cases before vaccines were available. I’m still super grateful to have spent such a long time in Taiwan, a luxury most people around the world or other companies didn’t have at all. I ended up taking all my PTO and more to extend my stay from January to early March in order to attend my brother’s wedding the day before my flight.

I would have preferred to keep working remotely, but during this time I wasn’t allowed to work due to company policy, I tried to maximize the sudden freedom and free time to try new things. More notable ones were putting on my own painting & photography exhibition and starting a podcast in Taiwan that has grown a lot since — I wrote about how that year in Taiwan changed my perspectives forever in more detail here.

I’m a huge believer in “Discipline equals Freedom”. Not working gave me more freedom and required even more discipline to make the most out of the time and flexibility I have. I was amazed at how productive I can be when not bound by time and location. How I can prioritize the highest leverage points that maximize my impact and fulfillment — whether that be coding, writing, painting, learning, or creating — whatever, whenever, wherever my heart desired.

Perhaps the riskiest thing a company can give its employee is extended freedom, forcing highly motivated individuals to find new things to dive into. All these life-changing experiences in the face of a pandemic while not working made me realize that life is full of endless possibilities. The liberating feeling of working on things of your own complete ownership and consequences— the creative freedom to dare and to try. It made me more aware of the more dependencies I had coupled myself with, my time and location.

After 5 years at IG, you build deep relationships, trust, and love with your team, product, and people you worked with, which makes it very hard to leave, not to mention the juicy perks and nice paychecks, aka the beautiful “golden handcuffs.” — more dependencies.

30

I decided to give my notice on my 30th birthday.

30 is not old, but not exactly youthful either, a matter of perspective. It’s nothing but a number, but I still fancied the ceremonial idea of making that huge decision on that day. I also ordered a car on that day as the cherry on top.

What’s next?

I want to experience complete absolute total freedom for the first time in my life without any dependencies.

I want a car I can sleep in, put my bike on a bike rack, and perhaps road trip across the US, with an ambitious and ambiguous goal of exploring all the national parks and major cities I pass on my bike.

Other than this rough idea, I have absolutely no idea what I will do next. The plan is to have no plan. This is the first time in my life where there is so much ambiguity with everything up in the air, yet so much clarity in who I am, what I want, and what drives me — and I think that’s a beautiful dilemma to be in.

A lot of time I will spend alone on the road, which I am very excited about. I believe only in solitude can we hear the voices buried deep in our hearts. I’ll learn a lot about myself and everything I see and experience around me. Every major change in my life has been the biggest point of growth and learning and I expect nothing less from this one.

Maybe the happiest people out there don’t have “real jobs”, maybe they do, I will find what makes me the happiest. I will keep the podcast running! It’s my precious baby at this point and I love it. I’ve also been fascinated by Defi, “Decentralized Finance” / crypto, so will dig deeper into learning in this area and maybe do something in this space in the future.

My work badge | My dear NYC apartment of 3 years I will be giving up | A car I can sleep in

Conclusion

This is a big decision, but the risks look a lot smaller than they actually are. My skill and experiences are still with me, I can always go back to a tech job if I end up not liking this lifestyle or I don’t find anything else interesting. And knowing this is not for me will in itself be worthwhile learning of self-discovery.

So this point, I have absolutely nothing to lose. The only thing I might lose is the time and freedom to do things my way — the number 1 thing hospice patients regret in their lives.

One of my favorite quotes ever from the book “Gentlemen of Moscow” really resonates with me, especially at this precise moment:

Our lives are steered by uncertainties, many of which are disruptive or even daunting, but that if we persevere and remain generous of heart, we may be granted a moment of supreme lucidity — a moment in which all that has happened to us suddenly comes into focus as a necessary course of events, even as we find ourselves on the threshold of a bold new life that we had been meant to lead along.

Thank you for reading! Follow along the journey here!

Thank you Justin Kong, Jesse Hendrickson, and Stepan Parunashvili for reviewing this essay

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