Hi—if you’re reading this, it’s probably because you’ve googled how to moved from the Bay Area to Singapore and you fit a similar archetype that we both have. I have a lot of thoughts on this, especially since I spent three years there in my mid-20s. For context: I’m a Taiwanese American female and currently 28 that has worked in tech the past 5+ years. I bounced around from Booking.com, Google, Stripe, and startups. I am not a software engineer and I don’t have technical skills, but being from the Bay Area has its own advantages—we’re just molded differently and we can bring a lot of value to new markets if you’ve worked in Silicon Valley for a while.
I am going to be brutally honest and upfront in my experiences here. Take what you need with a grain of salt…
and read on, playah.
- Why I personally left the Bay Area
- Pros of living in Singapore
- Cons of living in Singapore
- 5 big questions to ask yourself for those really considering the move:
- Career trajectory and progression—does being in SEA make you more valuable?
- The Journey Back to the Bay Area if You decide to Come Home
- In my Opinion, this is the Demographic Sweet spot
- [General advice for men] My brutal personal advice for men who are doing this whole SEA thing and perhaps traveling around Asia
- [Real talk for women] Other random shits and giggles—men, keep scrolling because this won’t apply to you. Women, stay on.
- I couldn’t find anyone who just “got it.”
- Coming to a decision to leave
- My lingering thoughts and what’s next for me
- Get in touch with me
Why I personally left the Bay Area
For context, I have high risk tolerance. This is because I’ve taken a lot of risk when I was younger and I’ve always made it work, even though it doesn’t. Take a lot of risks when you’re younger because life is more forgiving at that time and you don’t have that many responsibilities. No kids, no mortgage, and nothing really tying me down at that time.
I like to think I take the red pill a lot and break out of my matrix whenever I think I am in one.
Like any other city, if you stay too long, you live in a bubble. I wanted different exposure—to different minds, way of life, way of thinking, and environmental changes. I popped that bubble and decided to venture out after being burnt out in my tech job and feeling like my life was the same shit every day. I also just felt like the world was a lot larger and I didn’t want to spend all of my 20s in San Francisco. The interest in Asia came from my Taiwanese heritage, study abroad experiences, and my brother-in-law who worked in Singapore before.
Nothing is ever as terrible as it seems if you know you can change your own fate. In an odd sentimental way, I am like my baba 爸爸, like how he mustered the courage and left Taiwan 台灣 in search for a better world out there. For all the adventurers and pioneers that I respect and see out there, they have this quirky, overly confident personality that they are prepared for anything life throws at them. The average person gets stuck in “what-if” and never attempts to make changes to their lives, sinking into complacency or getting so wound up in their own head that they don’t even try.
I left the burbs of Los Angeles for San Francisco, then left San Francisco for Singapore, and then left Singapore to become location independent. Every environmental change has taught me valuable life lessons and I have not regretted one single thing.
Pros of living in Singapore
- Living and being in Singapore is just like one long study abroad year for adults. I’ve had the pleasure of meeting people from all walks of life—not Bay Area intelligent, but worldly intelligent. Those who were well-traveled, moved around to various cities in their life, knew culture and actually cared, as well as led very interesting lives. For example, I met a founder who built his own Saas tool and his entire family is nomadic. They travel everywhere and eventually landed in Singapore for the kid.
- Singapore has their shit together. Seriously, I have not seen any other country that is as efficient, process driven, and forward-thinking. If it fits into their box, it’ll always work.
- Exposure to the diverse cultures that Singapore has to offer makes you a worldly and better person. Seriously, you’re less of an asshole for understanding the world a bit better, but don’t stick to just hanging out in expat areas. You should try to meet people outside your sphere.
Cons of living in Singapore
- You may begin to resent rules and how suffocating it makes you feel, but because you can travel outwards all the time, you might not feel it as much as when I felt it during the pandemic. But the rules are also there to make things work and to keep you safe. It’s a double edged sword, but after a while, I was just tired of feeling like I always had to watch out, otherwise I’d end up on the news somewhere. There’s a big tattle tale culture and fomo culture. I remember being shocked about reading the news about a young girl and her boyfriend doing PDA on the bus. Yes, maybe it was cringey, but not newsworthy enough to blast them across the country.
5 big questions to ask yourself for those really considering the move:
1. Why are you really wanting to move overseas? Is this because you want a change of scenery or you just saw a cool TikTok video that made you want to uproot your life?
2. Are you prepared to reinvent your own identity and life in a new place?
3. Are you prepared to work really hard to make the move overseas and plan accordingly?
4. What are you hoping to find in Singapore when you make the move?
5. Would you be okay if this journey ended up being something you hated? What if you hated all of it and wanted to leave?
Career trajectory and progression—does being in SEA make you more valuable?
The truth is that you can climb a lot faster in Singapore than San Francisco.
This is my own speculation, but there’s somewhat of a gap—there’s a lack of middle management of those who worked in tech for 5+ years, who can build and run a team, as well as sustain one. This is just what I perceive, but as more interest grows towards tech, there may be more seasoned and employable techies. Given Bay Area experience, your personal network, and added value, you could actually climb a lot faster.
The Journey Back to the Bay Area if You decide to Come Home
There becomes a real fear of coming back to the states because no one understands you. You’re different and that’s okay. There is that sinking realization that you’d probably be more successful in Singapore than Bay Area, but not so much when you come back unless you are catering to the SEA market and it’s part of your job scope.
If you were to return, people think it’s cool you’ve been in Southeast Asia the past couple of years; similar minded folks in tech will want to reach out and talk to you, and then the conversation moves on. No one really understands you and your experiences, but you hold onto it because it’s changed you. But Bay Area people don’t really care for that; they’re too busy trying to buy a multi-million dollar home in South Bay, raising their families, and driving their new Tesla to Napa Valley. Why should they care?
In my Opinion, this is the Demographic Sweet spot
1. If you’re in your early 20s and have a good paying job
2. If you’re a married couple with a young toddler
3. If you’re a single 20-30s man who is financially stable, nomadic, and having an existential life crisis
[General advice for men] My brutal personal advice for men who are doing this whole SEA thing and perhaps traveling around Asia
- Take this time to redefine yourself and build up your confidence. I’m not sure why I say this, but this seems to come to mind. It’s not that we are all fleeing America to avoid something, but I do believe we are all missing something inside of us when we leave the states. We’re in search of something new and building yourself up in Asia is a great place to do so. I won’t go heavy into detail here, but take more risks in this controlled environment. Build up your social skills, try new sports, learn new ideas, and jot them down—become more interesting and dynamic. We all gravitate towards people with confidence.
- Have fun, but be respectful. You will have more dating opportunities in Asia than the US most likely because you’re new, shiny, and interesting. Define what you’re doing with the people you’re dating. If it’s fun, be clear about it and don’t break hearts on the road. Your ego will get inflated and it’ll be nice to go on many dates; you’ll most likely spend a lot of money if you’re taking women out for drinks and dinner. Drinks are expensive in Singapore. Don’t get a fuckboi reputation because again, women will talk behind your back and this kind of reputation will follow you wherever you go. Asia is smaller than you think it is—seriously. As your self-appointed older sister telling you this, just be a good human being.
- Save while you can. You’d be surprised by how many bachelors out there are throwing money to the wind, spending the majority of their paycheck on club tables, partying, drinks, etc. and they don’t save a lot in their 20s. I found out that one friend (who made good money) was not saving at all and I was shocked. Like damn, I thought we were all Asians and knew how to save money. If you’re okay living paycheck to paycheck, that’s your call to make. Yea sure, YOLO but when you’re older with no 401K and have no savings, it’s going to bite you in the ass. Then I can say, “The Fang Girl told you so.”
- This one sucks (I know), but if you’re still 35+ and single in Asia, women will wonder what’s wrong with you. Our thoughts are normally 1) he got out of a recent relationship and is not ready mentally 2) he’s a shit boyfriend and no one wants him 3) he works really hard and focuses too much on his career 4) he’s not stable and cannot provide. You didn’t think there was a thing called leftover men too, huh? Well, there is.
Dating is great for Westernized men, especially if you’re financially stable, work out, speak Mandarin, have a good job in tech or finance (don’t forget the pedigree), and are culturally competent.
[Real talk for women] Other random shits and giggles—men, keep scrolling because this won’t apply to you. Women, stay on.
I left because I wanted to be closer to family, I wanted to start my own media company, I didn’t want to work in operations anymore, and I didn’t want to be tied down to one location anymore. I most commonly get asked about dating, which is also one of the reasons (but not main reason) I left Singapore in the end. I just wanted to find my lifelong partner and unfortunately, I did not think I could find one in Singapore.
Reader, please note: I don’t want your complaints or advice here, I’m just speaking my truth. Seriously, your unwarranted advice will irritate me here if you tell me how to properly date in Singapore.
I spent being 26-28 there and met many older, but accomplished women who were still single in my network.
A lot of older capable, globally-minded women I knew would complain about this over and over again; one was a senior manager at LinkedIn while another was running programs at an innovation lab—these were two incredibly bright, high-earning women and they couldn’t find anyone. Both were in their late 30s, and recently career focused turned dating focused. Both kept lamenting of the quality of men in Singapore; all the good ones were married, the dating pool was small, many divorcees in Singapore, or the men were too boring. Their high caliber personalities demanded high caliber men, and many of them were already taken.
It was honestly a bit alarming and they kept warning me to start dating earlier. I really hate that I acquiesced to societal ideology of women needing to run on a timeline, but in some ways, I do believe it because hello, children? I had my fun being single, but online dating was starting to suck in Singapore and I’d personally rather find my guy than continue the endless swiping. It gets exhausting and it’s not fun anymore. I didn’t meet a single person in Singapore who could meet those expectations nor pique and hold my interest.
Honestly, in hindsight, I think I just wanted someone like me—someone who was Asian American, torn and catering to two sides of their identity and understanding all of the cultural contexts, memes, inside jokes, and regional quirks and nuances.
We’re talking about someone who grew under an Asian household in America, who witnessed the struggles and tribulations of their immigrant parents making it out of their homeland, who had to make it out in this white society, and who never really felt in their skin and always out of their skin at the same time. Even better if they could also speak Mandarin and could fit into my life while getting along with my family and friends. Why is it so hard to find someone well traveled, open-minded, and appreciative of all the things I could share with him? To be frank, I don’t fall in love easily so I just realized I had to go to the ocean rather than stay in a puddle for dating.
I couldn’t find anyone who just “got it.”
This is purely based on my own experiences, but I’ve dated expats and locals alike, and there was something there that just kept missing the mark. Most expats were having a grand old time—many of them in their mid 20s who were making above way average salaries in SEA and only saw themselves there for 2-3 years while exploring the fun party nightlife; they were there for a good time, not a long time. Locals were on a particular track to get married, buy an HDB flat, stick with the same social group since uni, and settle down in Singapore close to their parents.
To be fair, I was living there during the pandemic, there was a lack of newcomers, and I was frustrated by the incestuous pool, so I refused to date after a while. There were too many dinner parties where my girlfriends were talking about a guy and it ended up being the “same” guy—awkward silence ensues and growing animosity sits at the table. There was another time where a friend I brought to a web3 meetup found out that her ex had been cheating on her through another attendee and tears ensued.
While I loved my social life in Singapore, I hated the dating life there and refused to partake in this messy twisted game of online dating where everyone seemed to have dated the same person before and airing their dating secrets. Trust me—I know far too many things I didn’t want to know about people in my social circles. People talk, and they talk mad shit.
Coming to a decision to leave
Leaving Singapore was really a tough decision. I dragged it out for a very long time. It seriously didn’t come easy because it felt like I was throwing an entire life away, but I soon shifted my mindset and told myself that this chapter was just closing and a new one was beginning. It’s funny because in Asia, quitting a stable job is unheard of, especially at a tech company that pays well—I think a lot of people in my network thought I got let go, but I quit my job because it just wasn’t serving me anymore.
My sister once asked me if I wanted my manager’s job and it was a flat-out no. I wanted to be an entrepreneur, build my own thing, and control my own time.
I also wanted to sharpen my focus and isolate myself from distractions; I wanted to focus on my media company Asian Wander Women and build multiple streams of income. My gut told me that I had to leave in order to do this.
As of now, I am consulting part-time (15-20 hours) for a tech company in San Francisco and now make more than I was making in Singapore, but without benefits. My niche speciality is valued more here in the Bay Area and I can charge more, while working on my side projects.
My lingering thoughts and what’s next for me
To me: the most ideal situation I could have seen myself in was to be in Singapore with a partner, live there for 2-3 years, fully take in and enjoy what the city-state has to offer whilst traveling around SEA, and then eventually settle down somewhere God-knows-where to get my own place in a high rise luxury apartment and adopt a dog.
In summary, you will have the best time of your life, but depending on your personal goals, your financial wants, and what you hope to get out of life, you’re in charge of your timeline and how much time you want to spend there.
Your entire life trajectory may or may not be turned upside down and the way you perceive life will definitely change.
Get in touch with me
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