could you provide a brief overview of your career progression in the legal field?
My family first immigrated to Canada in 1990 from Hong Kong. My parents had left behind a humble life, a cozy shoebox apartment, and stable jobs as a nurse and a taxi driver. Shortly after, I graduated from the University of Toronto with a Honors Bachelor of Arts in Political Science and Criminology.
When I entered law school, in order to make my skeptical Asian parents proud and to not waste expensive international tuition fees, I felt incredibly pressured to be the best law student and lawyer that I could be. I later received my Legal Practice Course diploma from the City University in London UK, as well as my Master of Laws from the University of Toronto.
The first few years after law school were tough for me. It took me 5 years after law school to qualify as a lawyer. After returning to Canada from the UK and a long year of studying for my Master of Laws degree in securities regulation, I finally felt like I had the right credentials to apply for legal roles. This was after a previous year of 100% application rejections. Soon after I secured and completed my articling and practiced one year at an international law firm in Calgary, Dentons, I left Canada and came to Asia, landing in Hong Kong initially and now in Singapore, working in the asset management and private equity industry in both law firm and in-house settings. It has been the most fun but also the most uncomfortable professional and personal experiences of my life so far. From learning to navigate in a fast paced East Asian work environment to nurturing a new network of friends and colleagues again, it’s pretty exhausting.
These past few years of exploration have been transformative for me, recently I have been able to combine my growing interest in crypto with my career. Today I am a digital assets lawyer and have joined Cake DeFi as their general counsel. Couldn’t be happier to be transitioning from asset management to digital assets with this young and dynamic crypto DeFi company based in Singapore.
Pivoting into the world of Web3 and crypto while suddenly becoming the primary source of legal advice in a company is both exciting and surprising to me as I honestly did not think that I would stick it out with law this long. It’s been 4 months since I dove into crypto, and it’s been a whirlwind as I learn about things like custodial wallets, liquidity mining, staking, token burning, travel rules.
what ultimately made you decide to pursue a career in law? and what drives you to continue your career in law today?
After taking “Canadian law and society” in Grade 11, I decided that I was going to be a lawyer, partly because I never found math or science interesting, but also because every time a lawyer introduced themselves as one, they would get the “ooh ahh” astonishment response — I wanted that too. My motivation these days are two fold: (1) provide my colleagues with the most commercial legal advice and make sure the company is well protected, and (2) become a mentor to law students and junior lawyers so that they will reap the most benefit out of their legal career like I have.
how would you describe a typical day in your life as a lawyer? how do you find a healthy work/life balance?
My typical day involves work in a number of areas, including regulatory, IP, corporate governance, transactions, marketing and products. My mornings consist of replying to overnight emails and slack messages, afternoons involve a quick trip to the gym and then jumping into work calls until dinner time. Every day is different as we may be gearing up for a new product launch or looking to review our terms and conditions. The variety is what I love the most about my day to day.
First and foremost, it seems like no matter the situation, law students and lawyers will always find time to flex and compete with each other on their suffering and sacrifices for this career. In my junior years, I was so scared to tell anyone that I was having a slow month or be seen away from my desk in the fear of being judged as lazy and non-essential. That anxiety doesn’t go away, trust me. And I wonder what would happen if we stopped shaming those in law that prioritize a more balanced career and healthy life? Perhaps we can tone down our glorification of martyrs in law.
Personally, I have always been a fan of entrepreneurial hustles, creating something from nothing is pretty cool. And I believe side passions are not distractions, the are part of who you are. Passions can complement your main career and allow you to stand out from the crowd. So, I think this is one way to find that healthy work/life balance all lawyers and legal professionals strive for.
how does our interview title, “life as a lawyer,” resonate with you?
Living the “life as a lawyer” means to hit the 3 major milestones of the lifecycle of being a lawyer, they are as follows:
The first milestone is when we qualify as a lawyer. The grind starts with law school applications, doing well enough to make the bell curve and graduating, and getting lucky enough to secure a trainee position. The journey to hitting this milestone is hard, but it is a well defined process with zero ambiguity.
The second milestone is when we realize that we're not completely useless after all. The journey to hitting this self competence and confidence milestone involves a lot of imposter syndrome. Commit enough time and effort and a will spark when we realize that we are resourceful enough to deal with most things. I only just hit this one, it feels great!
The third milestone is when we determine our career purpose. Now that we have the skills and experience, will money as a driver be enough? Mentorship or mind my own lane? Work-life balance or nah? I find that the most successful lawyers have all hit this milestone, and their purpose is inspiring and obvious. Hitting this milestone is rare as many just autopilot after qualifying. Only if you make career purpose a priority will you achieve it.
I emphasize all the time to law students and junior lawyers that we work to live, and not live to work. But with this career, it sometimes does become all encompassing and becomes an important part of your identity.
I proudly share that I am a lawyer, but I always keep in mind that the best lawyers are here to serve others.
what are some challenges you have faced in your career?
I was never an “A” student. At best, I was a B+ student and that was only well into the later years of my studies. In my first degree, I struggled to maintain a B average, and in my first year of law school in the UK I received a bunch of low 2:2s (equivalent to B-). I failed the administrative law NCA exam and even failed the Ontario solicitor bar exam the first time around. And it took me 5 years after law school to qualify as a lawyer. Everyone asked me "why are you wasting time, just get it done?!"
1st yr, I completed conversion law exams since moving back to Canada.
2nd yr, I completed my LLM in corporate law and securities reg.
3rd/4th yr, I worked at an investment bank to gain corporate work experience.
5th yr, I finally completed my articling/ training contract.
Was I worried that I wouldn’t become a lawyer, let alone be a good one? Of course, I still worry about that now.
Even though I was prolonging the start of my legal career, I was hesitant to just “get it done” because my end goal wasn’t to just qualify, but to qualify in the right firm and in a practice area that I genuinely was interested in. I knew I wanted and needed biglaw experience because that’s where I would get the best M&A deal exposure and also would set me up for an international career later. I set my sights on a big law articling/ training contract, fully knowing it won’t be easy.
This is not one of those “never give up” messages, I know I was lucky and it could have ended differently. This is more of a "know what you want and plan accordingly" and "who cares what others think, you do you" message.
Struggling and failing is part of life, you’ll experience it a lot. Don’t be ashamed of it. Show some grit, use it as fuel and keep pushing forward, you’ll be surprised where you may end up.
what ultimately motivates your decision to be a career strategist and to provide mentorship services?
As I shared above, the first few years after law school were tough for me. 100 job applications and no call backs, applied to pro bono clinics for experience but did not qualify as I wasn’t a law student anymore. I eventually landed a paralegal role at a small law firm through a friend’s recommendation; they also offered me an articling position if I wanted it. The catch: no salary, work wasn’t focused on M&A/ securities which I wanted, and this would probably hold me back from an international career later.
Frantic to get some advice, I reached out to an in-house counsel at the Ontario Securities Commission on a whim, luckily they had time for a coffee, that was enough for me. I shared with this lawyer that if I took this training contract, despite the drawbacks, at least I can be called a lawyer and can search for proper legal roles afterwards right?
His advice: "aim as high as you cant now, it will be east to scale back later but scaling up will be difficult". This made me think about what my rush was to get qualified, and also will this training contract propel me into the international career that I wanted or not. Because of that advice, I ended up leaving that training contract behind and went another 3 long years of studying and working before I secured a spot at an international law firm.
Fast forward and I am now in Singapore as a general counsel doing amazing legal work. Would this have been possible if I settled for that first opportunity? Maybe… but all I know is that those extra 3 years of up-skilling and the international training contract early on definitely made getting here much easier.
Career advice can come from anywhere, but it’s only useful if you listen and follow it.
So, last year, I opened up my calendar to 1 on 1 zoom calls with law students and lawyers that wanted to chat about their career journey and personal branding tips. I set out wanting to provide motivation and honest career advice to as many people as possible, with the hope that the trickle down effect will mean more people will benefit from my mistakes and be encouraged to start mentoring as well.
what are some things you wished you knew when you were thinking about a possible career in law? and if you could give your law-student-self any advice, what would it be?
I have been a “late bloomer” in my education and career for as long as I can remember.
In high school, I didn’t realize the value of extra-curricular activities for university applications until it was too late. I never studied and committed properly to my first degree until my final year of undergrad. My legal career only really kicked off in my late 20’s, and most of my friends were already established lawyers by then.
I have always felt self conscious about falling behind and never being ahead of the curve. Is it because I wasn’t smart enough? Maybe I’m just not meant to excel and be a leader?
What I have realized is that I just don’t want to rush into things until I’m mentally ready. I try to understand the pros and cons of what it is I’m “expected” to do, and I am constantly exploring what my purpose is and whether my life plan meshes with my life view.
All of this takes time. But once I find this clarity, I am committed to pushing through. I may not be the first one out of the gate, but I will definitely last the longest.