A Passionate Programmer, a Passionate Lawyer?

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While learning how to write computer programs after stepping away from practice, I discovered something odd about the legal profession. There are books for the legal profession on how to write a good submission, structure deals, and run a law firm. But there aren't any books on how to love being a lawyer.

Oddly, such books are more common for programmers. Maybe it's because programmers are more likely to share their knowledge with others. Or maybe there are far more programmers than lawyers.

This post is essentially a book review about The Passionate Programmer (2nd Edn). This is the third book about programmers I've read so far. The first two were The Developer's Codeand The Agile Samurai.

The Passionate Programmer (2nd edition)We improve the lives of professional developers. We create timely, practical books on classic and cutting-edge topics to help you learn and practice your craft, and accelerate your career. Come learn with us.Chad Fowler

I enjoyed reading such books. I wanted to learn more about how programmers think and what software development practices should look like.

Transfer learning for your career

But wait a second? Am I seriously considering changing my career from a lawyer to a programmer? No more crappy contracts to read. Let's switch to reading crappy code?

One of the subplots in The Passionate Programmer was how the author, Chad Fowler, managed to turn his experiences as a jazz musician (see the saxophone on the cover?) into insights to advance his career as a programmer. Such insights include hanging out with people who challenge you to do better, the value of mentorship, and what you should be looking for when practising coding or music.

In a world where books on how to develop your legal career are non-existent, transferring your learning from one sector to another is your best bet. With a bit of imagination, I started to see parallels between the advice being doled out to programmers and things I should have done as a young lawyer. In those dark days when I had no idea what to do after leaving legal practice, some light in a different colour was better than none.

Most, if not all, lawyers are intelligent. I am sure many young lawyers would have figured out some, if not most, of the things in the book. Ultimately though, one lifetime is too short to figure out everything on your own. You have to enjoy your career as well!

Here are three lessons I learned from the book which surprised me:

Tip 49: Fat man in the mirror

Like Chad Fowler, I found myself getting fat lately. The experience, as lucidly explained in the book, is as follows:

I can’t tell, because I see me too often. If you’re constantly exposed to something, it’s hard to see it changing unless change happens rapidly. If you sit and watch a flower bloom, it will take a long time to notice that anything has happened. However, if you leave and come back in two days, you’ll see something very noticeably different from when you left.

Our careers are very much like this. Did I find myself leaving the profession after one lousy hearing? Or one bad experience with my bosses? Maybe this is how I would like to remember it. But it doesn't explain why I left this time when I was resilient in others.

It turns out that frustration and unhappiness build up over time. One fine day you decide to take a hard look at yourself and realise this is not how you want your life to be. It happens quickly, and you can't stop or control it. Not a good way to go.

One of my strangest experiences going into the corporate world was performance reviews. I had no such thing in my law firms. The only indicator I had that I was doing a good job in a law firm was my pay raises and title changes. Without regular performance reviews, you don't check whether you are doing any good work. You don't even check on whether you are doing yourself any good.

It's essential to check on yourself regularly, and Chad Fowler suggests that you should do something more concrete, like putting your objectives in writing. You might suddenly find a fat man in the mirror if you don't.

Tip 50: The South Indian Monkey Trap

Photo by Jamie Haughton / Unsplash

Here's a funny story from the book.

A town in South India had a monkey problem 🐒. To cull the population, they designed a trap. Monkeys love snatching food from the townsfolk. So, they dug a hole in the ground and put some rice there, but made the entrance narrow. A monkey would stick its hand into the hole to grab the rice, making a fist. However, due to the narrowness of the opening, the fist could not come out of the hole, and the monkey was stuck. The trap works because the monkey refuses to open its fist of rice to escape—game over for the monkey.

The story tells us that there are some ideas we refuse to let go of, even though they would help us to escape our traps. Here's how the concept is described in the book:

Value rigidity is what happens when you believe in the value of something so strongly that you can no longer objectively question it. The monkeys valued the rice so highly that when forced to make the choice between the rice and captivity or death, they couldn’t see that losing the rice was the right thing to do at the time. The story makes the monkeys seem really stupid, but most of us have our own equivalents to the rice.

I started wondering what my equivalent to the rice was.

One of them is that even when I became in house counsel, I still cling to the idea that I am and will become a lawyer. My mid-term goal is to head a legal department and, at some time, maybe be a general counsel.

However, is this what my company needs? Am I only good at doling out legal advice, or did I develop leadership and other skills which would be beneficial in other areas? Or is this really about what my comfort zones are?

There's nothing wrong with having fixed goals, of course. However, you're probably doing yourself a disservice if they become a quagmire or restrict your imagination of what you could become.

Tip 51: Don't Plan your career like a Waterfall

Photo by Timothy Meinberg / Unsplash

Here's a sign of how much agile software development practices have held nowadays: You have no idea what “waterfall” is.

The book describes “waterfall” software development as a “top-down, heavily planned, rigorous process”. It's usually used in a pejorative sense.

Most young Singaporeans have probably developed their career ideas using a “waterfall”. Requirements are designed right from the start and handed to you to implement. To be a lawyer, you must get a law degree from NUS. To be a good lawyer, you need to join a big law firm.

I have to admit that the plan sounds natural, almost a responsible way to achieve your goals. However, the best laid plans are often laid to waste.

According to the Passionate Programmer , agile software practices work because changing code is, in its nature, cheap. Agile responds to that by developing processes that react well to constant change. The focus is not on thorough documentation or grand designs but on what users want.

Some people might baulk at the idea that changing careers is as cheap as changing code. Of course, going from lawyer to actor is a huge change, but other changes are less extreme, such as legal support or in house counsel. Instead, it's essential to develop processes for your career that react well to constant change.

Set big goals and make constant corrections along the way.

Such corrections were necessitated by life changes too. One of the prime reasons I had to leave the profession was to care for my young family. They needed me around more at this point. However, I also recognised the need to keep an eye on the profession. Maybe there's a day I would go back, but it's got to fit my ultimate goals.

There's another thing about planning your career like a waterfall. Very often, these grand plans are imposed by others. I learnt that the hard way. Of course, your bosses want a good associate. Of course, the legal profession wants more lawyers in practice. But those were other people's goals, not mine, and I was following their plans.

I didn't know what I wanted at the time (or even at this time), so going with the flow is a workable option. However, this is your career — being successful is great for others, but is it at your expense? Having a career plan that reacts quickly to change will be fantastic if you have no idea.


The 3 tips I shared were the ones I found more meaningful, but there are many others ideas big and small that are easy to understand and get to the action. As a book for programmers, it certainly is not one where a lawyer can apply straight away. However, it is written in an encouraging and insightful way. So, as I wondered about my own situation, I felt that I do have options in my current station. It’s a wonderful feeling.

#BookReview #Lawyers #Programming

Author Portrait Love.Law.Robots. – A blog by Ang Hou Fu