Quitting Stripe and Leaving Singapore—now what?

by thefanggirl

After two years and a half, I am leaving Singapore and have quit my tech job—why and what’s next 

Thursday: August 4, 2022 

What a strange feeling it is to be seated in a cushy ergonomic chair, in an air-conditioned WeWork whose temperature was perfectly adjusted by employee feedback on Slack, and the rows of identical massive LG desktops seated perfectly in rows of eight—I am leaving this company today and I know the world here will continue to go on in this well-oiled machine. I know I am not that important and I am easily replaceable. 

I sit here, sipping a cup of coffee and I listen. I listen to the sounds of mouses impatiently being clicked, subtle sighs as the nearby engineers try to fix their code, and the murmur of employees discussing recurring account issues. Surrounding me are my colleagues, some I knew since I joined the company and some I never took the time to meet due to the remote nature the company took when covid was rampant. Working remote made me enjoy my alone time and I loved that I wasn’t forced to spend time in the office on social encounters and obligations with colleagues. 

I am a bag of mixed emotions though. Today would be my last day at Stripe and in 12 days, I’ll be leaving Singapore to take a career break whilst building on my creative passion projects. 

I, being the person that I am, had a tendency to change things if I was unhappy or bored; I would get stuck on it and I’d be quick to fix that. It was that mentality of “I need to live my most authentic self and do whatever I want at all costs.” Sometimes, I hated this specific quality of mine because I wondered if there was something wrong with me and that I would eventually get bored of all things, but I also relished it. I was also kind of proud of it. It was a quality that got me further and pushed me harder in my own lane. 

Garry Tan, a venture capitalist once shared this piece of career advice on Twitter – “At every job you should either learn or earn. Either is fine. Both is best. But if it’s neither, quit.

Today embarks a pretty pivotal moment in my life

I wonder if I’ll ever regret leaving Stripe or miss the undeniable envy and undeserving respect from others when they find out I worked there. Some of my brightest, capable friends have been rejected from working there and I had made it in. It was like touting a prestigious MBA around, but it didn’t mean anything if I wasn’t building something I was excited about—I wanted to try for myself.

The career coaching session that woke me up and got me to quit the next day

Backtrack a month ago, I was sniffling and crying seated on the wooden floors of my condo while my older sister in San Francisco FaceTimed me. I teary-eyed told her that I felt lost in all aspects of my life and didn’t know where to head towards—she was also the only person whose advice I trusted at this point. She was normally objective, precise, and non-prescriptive.

I wailed, “Should I stay in my job? Should I leave Singapore? Should I try building my own thing while juggling a full time job?”

My sister, being the hard ass that she was, barely batted an eye and got to asking me defining questions that made me think hard about what I wanted. These were questions I had personally avoided and did not know how to address by myself.

What if you quit your job tomorrow? How would you feel? What about a month for now?

Would you regret this five years from now?

What does five years look like for you? 

Imagine yourself a year from now and five years from now if you still had that job. What would that look like? Would you be happy?

What are the things you’re doing to get yourself to the life you want?

These were a couple of questions she shot at me, which I painstakingly answered them. It had stirred up a lot of insecurities in myself; my analysis paralysis was due to fear, my lack of confidence in myself, and in what I thought I could produce. 

So we talked it out and my sister softened up.

I ultimately decided that I would take the next six months to take a career break, but work on my side projects. I could treat this as rest and also crash with my sister while building. She had added a level of security I didn’t have, and now it was up to me to tell myself say that I too believed in me.

The different scenarios played out in my own head

Option A

  • Go to my sister’s place in San Francisco since she’s agreed I can use the space as an incubator until I build up projects and/or find part-time consulting or freelancing work

Option B 

  • Come back to live in Southeast Asia next year to travel around while I can and build my businesses up 

Option C

  • I put this one last because I will do my best to avoid this one. Option C is if I am unable to build anything up and it doesn’t go according to plan with anything. I would admit defeat for a bit and then go back to looking for a tech job.

My personal reflections: I personally think being “too comfortable” is a bad thing at this age of mine

I was living in a paradise in a paradise. I worked at a well-known fintech company valued at billions, living in a first world country (Singapore) that had taken me under its wing during covid. Everything was safe, comfortable, and stable. I am and was grateful for everything. I’ve built up a whole life here and even built a massively well-connected network for overseas Asians to soft land in Singapore, but felt like everything I was doing was not working towards the life I actually wanted. I felt like my growth was stagnating and my own drive and tenacity was being dulled; just like a warm lull of climbing back into your bed or snoozing the alarm, I felt I was doing that with my life.

I wanted work flexibility, to choose my own projects, to travel wherever I wanted, and to be around people I liked and wanted to learn from.

Instead, I was resolving user issues and high profile escalations on social media; on top of that, I was getting a daily blast of negativity which gave me anxiety each morning and the constant various touch points drove me crazy.

I wasn’t doing what I wanted, which was to build community and eventually, a multi-media company. I personally felt that Emily at 28 shouldn’t settle—it just didn’t feel right and I wanted to live outside the box and take risks for the Emily I wanted to become. 

So I left and I am only looking forward now. After two years and a half in Singapore, I am leaving to take a personal career break, and will build up my online community and side projects. 

I know I’m privileged and I wouldn’t have gotten this far without my family and community in San Francisco and Singapore

This entire article may flabbergast you. It may seem like I’m ungrateful or irrational. Maybe, maybe I’m all of those things, but I am authentic to myself and I am unafraid to pursue the life that I want. This path I chose is like taking the red pill and it’s not for everyone. Hell, I don’t even know if it’s for me, but I am willing to try it out.

However, I know a lot of people probably feel the same way, stuck in their hamster ball, but paralyzed with the fear and because you haven’t had exposure to other people who have lived outside the box. Through Asian Wander Women, I’ve met so many incredible women who have done exactly that. They’ve all paved their own path in doing so, whether it is living in a camper van while career coaching or staying at their parents’ home while building a six figure business or taking a year off to travel and reset. I’ve been hyper exposed to all the ways one can live a life up close.

Once you are inspired multiple times and you realize life can be lived in so many ways, you start to challenge and redefine what a life could look like—so that’s what I’m doing.

Sometimes you see other people and think, “Wow—if she could live a life like that, why can’t I?”

So this is me taking a long overdue leap of faith for myself.

If you ever want to chat or partner on projects, feel free to email me at efangily@gmail.com.

For now, I will be continuing to write on my blog The Fang Girl and share my thoughts while I take a career break from tech and figure how I’m going to build out various businesses. You can follow along my personal journey on YouTube and on Instagram. If you’d like to support the blog, you can drop off a virtual coffee to my Ko-Fi. Cheers!

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