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The perils of a suitcase life

“There’s nothing for you in Singapore.”

China was a huge market and we thought we had what it took to succeed in that market.

This was outside my comfort zone, not only in terms of the language but more so because the resources that I had mustered over the last 10+ years at that point of time were all within Southeast Asia - the connections, relationships and appreciation of the culturally diverse landscape.

I felt that I knew relatively better how to navigate in Southeast Asia as compared to China.

But China as an economy was the largest in Asia compared to the playing field in Southeast Asia. It was hard and impossible to ignore.

I made that decision not to re-locate, staying put in Singapore while spending the next 4 years shuttling in and out Shanghai and many other cities, making stopovers in Hong Kong.

By early 2020, our startup journey had taken us to Moscow, Saint Petersburg, Seoul, Riyadh, Astana, Budapest...the list goes on. As for the adventures we had over those 4 years, those stories are for another day.

I never posted any of those trips on social media. We had travelled to many exotic places and I got to know many people whom I would have not met if we never started this business.

More importantly for me, I succeeded in breaking away from the comfort zone I was in as an investment banker, the typical grunt of an employee.

While I had picked up most of my accounting knowledge, financial modelling and structuring skills in a formal professional setting, I really only learned how to set up meetings, present ideas and sell when I became a business owner.

These are lifelong skills that cannot be taught and follow you around for a long time.

Look, the point here is not about the fancy globetrotting or the invaluable lessons learned. There is also no success story to tell.

At the risk of being overly blunt and transactional: The business acquaintances and relationships acquired only make sense if you can convert them into fees at some point of time.

The cash flows (if any), only sustain you for a finite period, and then you have to look for the next elephant to bag, and the next, and so on and so forth.

The truth is we paid for many of these business expenses without getting anything in return. Many people choose to interpret and believe what they see on the outside.

It’s not as good as it sounds. There is no glamour in running your own business.

It is more like living life in a constant state of uncertainty. And when you are in a constant state of uncertainty, it gets difficult to plan for anything long term.

Then at the end of 2020, in a twist of an opportunity, I made the decision to relocate to Hong Kong, taking that uncertainty into a whole new dimension.


Over these last two years, many friends have asked me how I cope with living overseas for an extended period of time away from home.

All I can say is that it is not as easy as one might think, even for those who are accustomed to frequent traveling for business.

When I think about it, the people who travel and live overseas for work generally comes down to three buckets:

  1. Those who relocate early on in their lives either for study or upon graduation;

  2. Those in their mid-careers who relocate for work as a temporary arrangement and;

  3. Those in their mid-careers who relocate indefinitely.

I have many friends in the first bucket.

They had gone over mostly upon graduation and have called those cities home. Those I know have stayed overseas for easily more than ten years. They had built their social ecosystems and familial support there and did not have to uproot anything back home or had little to nothing to give up.

For them, life started overseas.


Those in the second bucket are slightly older and had more work experience. They had gone overseas midway into their careers or got seconded as part of a project.

In nearly all of the cases I knew, there was always clear visibility in terms of when they were going back home, be it two years, three years or five years.

There was always an end goal. Something to look forward to so to speak.


Then there are those in the third bucket.

I know of very few people who are in this bucket and they are mostly in C-suite positions. I sometimes wonder how they do it. How they manage their families at home is a miracle in itself. You can only truly empathise with this if you are in this bucket.


The thing is: When you already have a life back home, relocating overseas for work indefinitely is much harder than it sounds on paper and what you hear from others.

A lot of people take it for granted because they either feel that the remuneration package compensates for that inconvenience or they simply just think they are adaptable enough.

But when you take a step back and really evaluate the circumstances that could potentially impact you - the distance, the unfamiliar environment, the lack of social and familial support, there is always a chance that you over-estimate yourself.

The real question is: Money can only go so far in helping you settle the logistics of moving, but how does one psychologically prepare for and cope for the change to a new environment?


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