Moving abroad: My path to Berlin

I'm writing this from a couch in my rented apartment in the centre of Berlin, ten thousand kilometres from the city I grew up in for my first 29 years of life. Living here, busy with the demands of the day-to-day, I often forget how remarkable being here is. How the heck is this even possible?

I'm writing for myself because I wonder, did I just luck out and found a secret path to moving abroad, or did I do something right and had agency in creating the opportunity for myself and my wife (and now, our very own little Berliner daughter)?

But that’s the smaller reason. I'm also writing this for you. Because I know a few people who might be considering a move away from Singapore and a few from other places they call home. I want to write this to help you feel validated about harbouring the desire to up and go. I want to help you feel less alone in your reasoning. And, in a forthcoming post, I want to give you ideas for approaching the landing of opportunities to move with your job.

I believe I can be most helpful by telling you the story of how I landed the opportunity and moved to Berlin - if not as a trusted person who's ahead on the path you're trying to embark on, at least as an anonymous data point you can jot down in your research note.

Why we moved abroad

I've actually written about this in a blog post in 2020, which I'll draw upon since that's two years less of memory fog.

From when I was very young, I knew I wanted to live abroad at least for a while.

Like most people who have gone to university, a 6-months exchange program would have been the best opportunity to experience life away from their home city. But I managed to screw up my exchange program application and lost that opportunity. Eventually, I managed to salvage a consolation prize and won a slot to spend an amazing month in London for summer school, but I wouldn’t describe that as really living abroad. It was just too short for a stay.

I wanted to live away from Singapore because movies and TV shows and… well, Google Maps told me that Singapore is a laughably small country. There was no way I going to knowingly limit my life experiences to that of a tiny dot on the map. Tragicomedy: you can’t even see the island that is Singapore on the world map. The letter “a” covers it.

But it’s not so much the size of my country that compelled me to move - intrinsically there is nothing wrong with spending one's days in a small community - it was the diversification of thought that I truly yearned for. I felt the need to see how other people lived, what kind of things they have access to that we don’t in Singapore, why, and what sort of rules, traditions, and ways of thinking govern their lives.

I was also starting to see the flaws of Singaporean society. In an honest sentence: stable and wealthy but lacking a soul. Every society has its strengths and weaknesses. I wanted to see if there were things I could learn from living abroad that I might eventually be able to apply to how I lived in Singapore when we go back.

I wrote it as if the decision to move was solely mine to make - it wasn't. I was already married when we were considering the move. Thankfully, my wife and I were completely aligned. We shared the same reasons for wanting to move: to see what we're missing.

Perhaps you have a similar reason. Perhaps it's completely different. Maybe you're from Singapore. Maybe you're from Australia, Canada, or Mexico. Does it matter? You have a desire to move away and you have your reasons that fuel that desire. The only person you need to convince now is yourself: do you believe, based on your acceptance criteria, that you can move given your current circumstances?

If your answer is yes, then it's all about the how. But if your answer is no (perhaps an ailing parent or a best friend in desperate need of your company or something like that), then you'll have to think hard before deciding to move, because living away from home means, well, losing stability, and that can be hard because it's like trying to tidy up your life on a boat that is perpetually in rather rough seas.

How we made the move to Berlin

Okay, here's the story of how I moved with my wife and dog to Berlin about 3 years ago.

Roughly 4 years ago, once I discussed with my wife and made up my mind that we were going to go for it, I started looking for ways to make our move.

Our context was that we had a very strong desire to live abroad, so we considered every option that was open to us. I googled a lot and read many threads on Quora and Reddit about how people moved abroad and that turned up some ideas here and there.

Before kicking into action, I had a list of options that looked like this:

• Ask friends for a referral to the companies based in San Francisco where they're working at. If not many, pull a favour or two from friends who know these people and ask for an introduction. Then try and interview well and land an offer with a relocation package.
• Make a trip down to San Francisco, meet current students from my university who are there on internships with startups, and ask for referrals.
• Cold apply to jobs in San Francisco and try and interview well and land an offer with a relocation package.

That was the list. My strategy could be summed up as "apply directly for jobs in San Francisco and do whatever it takes to make my application attractive."

For context, back then I'd only 3 years of work experience, partly as a software developer and partly as a programming bootcamp instructor and failed startup founder. Not a very attractive candidate even in my own eyes.

A friend, let's call him X to keep him anonymous, who studied computer science in San Francisco but had recently moved back to Singapore, made a tremendous effort in connecting me with his friends who were still there. He introduced me to his friends working at Dropbox, Google, Affirm, Peloton, and some other top-notch companies at the time. It was intimidating to talk to these folks even though they all turned out to be kind people (just like X). I was full of gratitude and felt indebted to X for doing this. I kept at this for a month or two, talking, getting a referral, and doing first-round interviews at these companies.

Right around this time, I discovered a different path serendipitously. I was teaching at General Assembly (a programming bootcamp) in Singapore when I left the classroom for a toilet break. The moment I stepped out of the classroom I saw a familiar face. It was JK.

JK was someone I knew from brief interactions when we both attended General Assembly as students. He graduated one cohort before me and I attended his graduation party in one of the classrooms one day after class. I remember having a beer and pizzas.

We talked a little and when he asked what I've been up to aside from teaching here, I told him about the quest of going abroad. Looking at San Francisco, applying directly to companies, referrals, all that.

At this point, JK looked at me with a smile and said calmly, "I'm working at a Finnish company now and we're looking for people like you to join the team I'm in. We also have an office in San Francisco, so maybe you can interview and ask if you can be relocated?"

He also told me to "go look at our Culture Handbook" on their website. I had to include this detail because had this weird handbook that piqued my interest and eventually convinced me about the quality of this Finnish startup, I probably would have kept my blinders on and not given it a shot. So I guess that's one point for companies to invest in a (well-produced, please) Culture Handbook for attracting people to work for them!

So I applied. I flunked the first round of technical interviews because I hadn't known how serious they were about testing me on Facebook advertising concepts. Luckily someone saw something in me and gave me a re-run. I did much better the second time once I knew what was important to them and when I didn't feel turned off by that (i.e. it made sense to focus on Facebook concepts in their context). Subsequent rounds of interviews went smoothly and I was given an offer by HR.

What's important to mention is that at the very beginning of the interviewing process, which is to say, before I proceeded to fail at meeting the interviewers' expectations, I laid bare my goals. I told them I wanted to be relocated to their San Francisco office. Was this possible? If not, I'm already interviewing at companies that are based there and I will not continue interviewing here.

The person who headed HR for the APAC region for this startup was sitting in my interview and she had the context and, I suppose, authority, to make a verbal promise to me that that would be possible. She gave me one condition: "We still need someone with your background to help in this office first. If your timeline is adjustable, let's say maybe you work 1 year here, and depending on your performance, we'll reopen the conversation for relocation then?"

I was very excited to hear this but I kept my composure. I felt like I still had to suss out their track record, so I asked the people in the room: "Has this relocation happened before in the company?" I was assured when I saw a few nodding heads and heard, "plenty."

And... that was that! I accepted their offer, stopped interviewing at SF-based companies, and eventually started working at Smartly.io. I joined when the startup had a global headcount of around 200; when I left about three and a half years later, we were close to 700. I knew more than a dozen colleagues who relocated during my time there.

I'd be remiss if I didn't mention that I did my best to make sure that my performance would be considered "good," or even better, "great," so that I would not squander my opportunity or delay my relocation. One of the splashier things I did was a project that I called the Tech AM Bootcamp, which was a 10-week programming course that I created from scratch to teach employees interested in becoming Technical Account Managers technical skills that would be helpful in their day-to-day work (full reflection in this post).

I ended up teaching 6 colleagues in the APAC offices and later, after I moved to Berlin, teaching 8 colleagues across our EMEA offices. I'm very proud of this project and the impact that it's had on the people I work with. Two have directly gained the confidence and skills to move to a technical role (one from Customer Success Manager to Technical Consultant, and another from Customer Success Manager to Technical Support Engineer and later, Team Lead).

That Tech AM Bootcamp project gave me a mark as a "good performer," I think, and secured my relocation.

A little over a year later, I nudged my colleague in HR (the one who interviewed me and made the verbal promise) to reopen the conversation formally. She went to talk to her counterparts in the various offices and came back to me with the news: "I know you originally wanted to relocate to San Francisco, but with Trump at the helm over there, realistically speaking, you're unlikely to get a work visa approved."

That was the bad news. Then came the good news: "So we can offer you relocation to either Helsinki or Berlin where we are more confident to be able to secure you a work visa. Let me know what you decide on."

I was bummed about SF, but I wasn't sad. I remember feeling incredible that evening as I commuted home, preparing to tell my wife about the first tangible relocation offers we've ever had.

We discussed our options that night. Helsinki was too cold for too many months each year for our liking (we'd both been there together once). Berlin felt much more manageable. Did you know that Berlin has more vegan restaurants than the woo-woo capital of the world, Los Angeles? Neither did we. We learned that from binge-watching YouTube videos about "living in Berlin." We hadn't an inkling of what it's like to live in Berlin before we moved. We'd never been and didn't know anyone based there.

In a matter of 3 months or so, our paperwork with the German Embassy in Singapore got approved fast and relatively painlessly, and we brought our luggages to the airport and flew to Berlin.

Regardless of how much more of our lives will be spent in Berlin, I'll say this about my experience living abroad: It has been the most transformative period of my life. I'm like a fish who can now recognise water.