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The Singapore Law Gazette

Sizing Up the Law Firms

I have been in (practically) uninterrupted legal practice in the more than three decades since I was called to the Bar in 1990 focusing entirely on litigation work. In that period, I have moved from working in a large firm to a series of medium-sized firms and finally to operating my own firm (since 2015).

As I reflect on this year’s Mass Call, I wonder what advice I would have given my younger self in 1990 on selecting the most appropriate law firm to begin my career. That was one year after the fall of the Berlin Wall, when the Internet was in its nascent stage and when Tears For Fears still ruled the airwaves. What career advice can I give to rising young lawyers in 2022, which would not sound clichéd, out-of-date, or coming out of a Hallmark card? Shakespeare illustrates the enduring universality of the human experience, whatever the technological era. As such, I thought perhaps I should just share my own peripatetic practice experience, parts of which may resonate with readers, and from which some readers may draw their own lessons and advice. Different strokes for different folks, after all. 

But if you treat every step of the way as a learning experience, and remember that life is a marathon, not a sprint (thus keeping things in their proper perspective), you will find your way to what you are meant to be. 

Starting Out in a Big Firm

Having had the good fortune to have performed fairly decently academically, I naturally applied, and was accepted, to do my pupillage (a term which glaringly exposes my vintage) in a marquee firm. “Naturally” because in those days the large firms were actively courting those who appeared (at least on paper) to have the potential to be better lawyers. Thus, being accepted by a large firm was perceived to give you bragging rights, the “glamour” element if you like.

As it turned out, that is just about the worst reason to join a big firm. There was nothing glamorous about spending my entire pupillage with my face buried deep in musty and dusty law books doing research for the various partners on very narrow areas. Often, I was simply given a hypothetical situation without being told the full picture of what the case was about. While I accepted that was a necessary part of the process of being a lawyer, the situation did not change even in my first year of practice with the firm. I was not given the opportunity to handle my own matters, not even a simple PG case for a road traffic offence. I had seen my contemporaries in small firms arguing cases in the lower courts. I yearned to join them, to be at the forefront of the litigation process and it soon dawned on me that that was not about to happen for some time to come if I continued to remain in the firm. So, I decided to switch to a medium-sized firm.

But before delving into that, lest the reader erroneously thinks that my time spent in that firm did not contribute to what I am today, I would highlight two advantages of being in a big firm. The first is the diversity of work that big firms enjoy. This is important in assisting you to decide which area of the law you would like to specialise in. The second is that you have the opportunity to learn from various lawyers by simply reading their correspondence. Every lawyer has his or her own way of doing things and you learn soon enough to extract the best bits of each lawyer for your own development. To this day, I am not ashamed to say that some of my choice phrases in my correspondence are “borrowed” from what I read in 1990!

My Experience in Medium-sized Firms

After departing from the first firm, I joined a relatively new medium-sized firm. Its singular attraction to me was the fact that its litigation department was helmed by an up-and-coming female with more than 10 years’ experience. I reasoned that she would therefore understand my passion for litigation work.

True enough, she swiftly took me under her wing. I spent the first six months working closely with her on all her cases. During that period, I would frequently be sitting at her desk as she patiently pored over my drafts and explained the reasons for the changes she was making. I recall vividly how she mutilated my first draft such that only the inconsequential opening line “We refer to the telephone conversation …” survived! But instead of giving me a thoroughly-deserved lambasting, she was full of encouragement, pointing out the “good thinking” that had gone into the body of my draft. In that process of corrections and then (as I progressed) open discussions, I was expected to contribute to the overall strategy. I found her approach particularly refreshing as I was not treated as a “bit” player. She impressed upon me that I had to know every aspect of the case so that “if anything should happen to me on the day of the trial, you must be ready to step up to the plate and continue with the trial.” She inculcated in me a sense of responsibility as she geared me for the day that I would be standing in court on my own.

At the end of the six months, she decided that it was time to sever the apron string. Thus, with less than three years’ practice under my belt, I found myself flying solo before the learned Karthigesu J, and shortly after that, before the learned GP Selvam J. I won the civil trial in the High Court before Karthigesu J by dint of sheer persistence sprinkled with a good dose of luck. As for the latter case, a heavily contested High Court ancillaries, my divorce client, knowing my lack of seniority and experience, kept assuring me that she was praying for me. To this day, I am utterly convinced that her prayers must have been answered as I prevailed. It also helped that Selvam J, sensing that I was a greenhorn, was extremely patient, kind and forgiving. As litigators know, the “high” that one experiences in prevailing in court is a feeling that no amount of money can buy. I was hooked. More pertinently, from these two cases, I gained the necessary confidence to gradually come into my own as a litigator, with the help and guidance of my mentor.

It was her mentorship, the personal touch, which made all the difference. In a big firm, the senior partners, owing to their hectic schedule, are invariably through no fault of theirs unable to devote personal attention to those far down in the pecking order. I am also grateful to her for taking the bold step of allowing me to conduct a High Court trial and a High Court contested ancillaries during the infancy of my career. If you look around you, nowadays, it is not uncommon for lawyers in the big firms with 10 years’ practice not to have conducted a High Court trial on their own. Because of the faith she demonstrated in my ability, from my fifth year of practice onwards, I did all matters on my own. Incidentally, it should not come as a surprise that she went on to be appointed Senior Counsel.

Another pro of a smaller firm is that it might be more flexible in allowing you to get training and experience in different fields. As for the work exposure, I made it a point during my interview that I would not want to do debt collection work or too much personal injury work. Because the firm was up and coming, they agreed and to their credit, I ended up doing a fair bit of intellectually interesting stuff, especially in the banking field. 

Sadly, the medium sized firm broke up after I was there for about five years and I eventually ended up with another medium sized firm where I spent another five years. The big takeaway for me, from this second medium sized firm, was that lawyers MUST learn how to read financial statements too, and not shun away from numeracy. The managing partner of this firm walked the talk, and once again, I learned something new. 

However, because of the profile of the firm, I felt I did not get sufficient trial experience, as many of our cases ended up in negotiated settlements. So, I decided to join a Chambers arrangement, to get more involved in trial work. This is also one way to test your own “marketability” as an advocate, and is the typical jumping off point to setting up your own firm. I remained there for about 10 years. During that period, I was heartened that some of the clients from the medium-sized firms entrusted me with their legal matters. This is yet another advantage compared to working in a big firm. Unless you are a lawyer of exceptional quality, clients of big firms are generally reluctant to divert their work to a smaller outfit because it is the firm’s brand name that was the attraction to begin with.

Entering a Brave New World – Setting Up My Own Firm

In 2015, after having practised for 25 years, I decided to take the plunge in an attempt to answer the question that had been on my mind for a very long time: can I make it on my own? In the seven years since, I can confidently say (without sounding arrogant) that the answer is a resounding “yes”.

The biggest advantage of running your own firm is the independence. Because you only have to answer to yourself, you get to decide the type of cases you wish to do and how hard you want to push yourself. For example, on the former, I find it hugely satisfying to argue cases before the Court of Appeal as they usually involve points of law (this was before the establishment of the Appellate Division of the High Court). In that regard, I have been lucky to have been involved in a number of reported cases dealing with different areas of the law, including family and company law.

Needless to say, being a one-woman operation is not without its potential flipside. Chief among those is that there is no safety net. However, that should not be viewed as a deterrent to venturing out on your own. Rather, it should be regarded as an incentive for you to chart your own career path.

Money-wise, I can safely say that being in a small firm does not necessarily lead to a diminution in income. To the contrary, if you are willing to push yourself hard enough, you may find yourself being on par with those in the bigger firms. Sure, you may have to put in long hours to achieve that but if you do, you have the satisfaction of knowing that you were solely instrumental in that process. That knowledge is priceless.


Practice is not for everyone, and the high attrition rate that we constantly read about attests to that. But if you treat every step of the way as a learning experience, and remember that life is a marathon, not a sprint (thus keeping things in their proper perspective), you will find your way to what you are meant to be. 

As for money, practice is financially very rewarding, whether in a big, medium or small firm. Don’t join a firm for the salary, but for the opportunities to get good training – this is my only piece of one-size-fits-all advice!

LLB Hons 2nd Class, Upper Division, NUS Law (1989)
Josephine Chong LLC
E-mail: [email protected]

The writer is an experienced family lawyer who has been engaged in several landmark family cases in the apex court. In her 33 years of continuous legal practice, she has covered both family law as well as commercial law (including appearing in landmark cases in the apex court on commercial cases). Her straddling of both family and commercial cases enables her to discern the fine differences between property rights in both fields, and to see the cohesive interaction of both.