The Risk Of Quitting My Law Career

Aug 29, 2019

The risk of quitting my law career needed to be weighed against my chances of succeeding at my new business. Thankfully, that allowed me to avoid a hidden risk.


On Tuesday, Singapore welcomed 520 new lawyers.


In his speech, Singapore’s Chief Justice, Sunderesh Menon, said…


“Technology is already beginning to displace lawyers from areas of practice, especially those involving the more routine areas which are more susceptible to automation”…


“The future of the legal profession, like that of our nation, hangs on the ability and willingness of its members to reskill and relearn…


I’ve just written a futurist article, so I won’t put you through that again.


Generally speaking, I dislike futurist articles that are fear mongering.  My take is that we have a choice, and that’s what I wrote about earlier this week.


In this case, the Chief Justice’s speech hit very close to home for me, especially when he said, “due diligence and contract review… can now be conducted more quickly and accurately by natural language processing and machine learning tools.”


And so, I thought I’d write about it, but avoid the futurist spin.


You see, that last quote from him was the exact scenario that got me worried.  As a Corporate Lawyer for 20 years, that formed the bulk of the work that I did.


I knew little else besides being a corporate lawyer.


I had a great 20 year career.  But I was seriously worried what the next 20 years would look like.


Having reached the very peak of my career as the top lawyer and one of the top global brands, I knew that I would not have the same growth trajectory I had in the earlier years when my career was climbing rapidly.


So I started worrying about my expenses, which were high, retirement, how to maintain my family’s lifestyle…


My choices were to do nothing, and continue worrying; or to “reskill and relearn”, as Chief Justice Menon said.


And so I weigh up the risk of “reskilling and relearning”, because I would be doing something completely new, against the risk of doing nothing.


The cost of reskilling and relearning for me, would be the cost of the courses, the cost of starting a new business, but mostly, it was the opportunity cost of not being a lawyer.


Alot of people have said, “Tim you were a well paid lawyer, the cost of starting a business and paying for the training was nothing to you.”


That’s true to an extent.  


Because I was a well paid lawyer, the cost of stopping that work was massive.  The certainty of making multiple six figures a year was what I was giving up.


But I had to weigh that against the cost of doing nothing.


Of letting the world pass me by, while I did my best not to worry.


In his speech on Tuesday, Chief Justice Menon gave examples of how a bank had automated a process for creating wills, eating into the wills, probate, and estates portion of legal work.


He also spoke of how the Federal Court in Australia had developed a program with IBM that assists parties in a divorce with asset division, with “obvious” implications for family law practitioners.


All these examples made me realize that while it certainly wasn’t obvious at the time, the greatest risk was indeed for me to do nothing.


The risk of giving up my legal career, which was what I thought, at the time, was the biggest risk, could be weighed against the chances of me succeeding at a new business.


The risk of me doing nothing, needed to be weighed against the certainty of progress.


When we realize that progress is certain, doing nothing to stay on par with that progress, must therefore be the biggest risk.



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