First Impressions From Our First Mentoring Session

I recently volunteered as a mentor with the Halogen Foundation and was paired with these two amazing young people: Joel and Steven

We had our first session together and enjoyed a really great time over dinner. On my way home, I found myself being rather contemplative and as I reflected on what we discussed, several themes emerged. I’m jotting them down here for posterity:  

Young people are amazing

I’ve always loved this exhortation: “Don’t let anyone look down on you because you are young but be an example…” It’s always been a good reminder to me that there is a lot more to young people than what we give them credit for (every generation is guilty of this). I wished I was as thoughtful and tenacious as these two when I was their age! Already, they are mindful enough to pursue great internships and part time jobs while having the self-awareness and grit to pick themselves up from the tough times they found themselves in. Their stories were truly invigorating and inspiring! 

There is victory in loss

We shared stories of losses and struggles; especially how we were trying to pick ourselves back up from difficult situations. Counterintuitively, these stories actually resolved our grit and determination; encouraging us and making us excited to witness what awaits on the other side as we press on through our current hardships. It took me back to one my favorite speeches on screen: 

Or, if you prefer, the text that inspired the words of the screenplay (emphasis mine):  

“And we shouldn’t be here at all, if we’d known more about it before we started. But I suppose it’s often that way. The brave things in the old tales and songs, Mr. Frodo: adventures, as I used to call them. I used to think that they were things the wonderful folk of the stories went out and looked for, because they wanted them, because they were exciting and life was a bit dull, a kind of a sport, as you might say. But that’s not the way of it with the tales that really mattered, or the ones that stay in the mind. Folk seem to have been just landed in them, usually – their paths were laid that way, as you put it. But I expect they had lots of chances, like us, of turning back, only they didn’t. And if they had, we shouldn’t know, because they’d have been forgotten.”

J.R.R. Tolkien, The Two Towers

Risk transparency

Our conversations readily leaned into transparency but at one point, I volunteered a particularly personal perspective that we had not discussed before. It immediately became an important pivotal moment that opened up an entirely new area of conversation and redefined how we understood one another. To be honest, I wasn’t entirely sure I wanted to share that view, but I risked it. I am now glad I did and that they both responded well to it!  

Be comfortable with questions as answers

For me, mentoring and coaching is less about providing The Answer™ but more about providing a safe space for mentees to explore their way into their own answers. So, as I reflect on the conversation flow over dinner, I want to remind myself to keep asking more thoughtful, probing questions as my responses to them; instead of just jumping in straight with my view, opinion, or experience. 

Serendipity plays a greater role than we realize

It’s a sober reminder to realize how much of life is beyond our direct ability to control it, despite everything we can do (and need to do) to influence outcomes or to prepare as much as possible. I was reminded about this when I recounted my journey-to-date: how serendipitous my career path has often been, for example. Many of my achievements have been thanks to the support of loved ones and friends around me; mentors and hiring managers who took chances on me; and sometimes just being at the right place and at the right time. So whether that’s thanks to coincidence, luck, privilege, the universe or an act of God, humility and gratefulness seem to be the best responses to life as we know it. 

One more quick point about serendipity: As our trio marveled at how well our life stories and outlooks clicked together (especially with that particularly personal perspective I alluded to earlier), we wondered whether the Halogen folks had matched our profiles so expertly, or… as life would have it, the three of us lucked out to have this mentoring journey together! However it happened, I am glad the three of us found each other in this group. 

I’m grateful for this opportunity and look forward to the inspiring mentoring journey ahead!

Earning My Fintech Stripe//s

I am excited to start my new role leading Asia Pacific Communications at Stripe; to help accelerate the region’s online economy and the commercial agility of APAC businesses with one of the world’s most ambitious and fastest growing technology companies. 

Stripe is a technology company that builds economic infrastructure for the internet. You might have heard how the company helps businesses from all over the world access the global online commerce market with sophisticated software tools. In fact, many exciting Asian and global organizations are powered by Stripe – such as Amazon,, Facebook, FashionValet, Grab, Khan Academy, Kickstarter, Klook, Shopify, Slack, Spotify, UNICEF, Zoom Video Communications and many more. Stripe’s products are helping them quickly expand globally and build new kinds of revenue models. 

So, why Stripe? 

Well, throughout my career, I have been privileged to enjoy front-row seats at some of the most revolutionary companies during truly transformative times. It’s where I honed my love for the sense of adventure that comes from working towards an inspiring, yet challenging, future vision. At Stripe, I look forward to building what we’re calling a “global payments and treasury network” – creating the infrastructure that will make it possible for hundreds of millions of businesses to participate in global commerce via the internet, regardless of where they come from. 

You’d think that much of this has been solved but only a tiny fraction of global commerce is happening online (~6-7%) and the financial services space is changing faster than it ever has. There are so many gaps to close to make it really easy for a company to do business wherever they want: accepting payments and understanding how consumer behaviours differ around the world is one of them. Being compliant is another. And keeping up with the fast pace of innovation in technology simply makes it incredibly costly and time-consuming for businesses to be competitive. If you’re a small business, a century old institution or a startup, how are you supposed to keep up? All this has become even more vital in a post-COVID-19 era, now that the whole world has come to rely on the internet to buy and sell goods and services. 

Besides Stripe’s mission, I was also drawn to the company by the people I’ve encountered at the company. Speaking with them, I often walked away from each conversation feeling like I wanted to continue the conversation further with whom I felt were very gracious, bright, engaging people; clearly a great reflection of the company culture as well as the talent Stripe brings on board. 

I also love how Stripe is committed to the APAC region. We are building out local engineering capabilities, with our hub in Singapore and our new engineering office in Japan, to ensure locally relevant solutions that help businesses grow further. Tens of thousands of businesses in Australia and New Zealand rely on Stripe since we launched in 2014 and 2017, respectively. We’re also available in Malaysia, Hong Kong, and are eyeing to expand into many more countries (stay tuned!). 

All this is certainly a lot, but we’re only getting started! Some consider Stripe “the internet’s most undervalued company,” so there is still much more to do. 

Wish me luck as I take on this new challenge! 

(Or join me – we’re still growing the team!)