As with most meetings, any reasonable person would expect the other party to be on time.

But for lawyer Darren Tan, being on time probably doesn’t cut it. (He was 25 minutes early for our appointment. How about that?)

After all, he spent over a decade of his life trying to be on the right side of time.

He had spent his teenage days mired in drug addiction and gang activities, smuggling drugs from across the causeway and eventually committing armed robbery at the age of 18 after a drug deal went wrong.

More than 10 years of his youth were spent behind bars, with a total of 19 strokes of the cane.

But time is definitely not a flat circle, at least not for him.

After taking his A-Levels in prison, he eventually went on to be the first student with a criminal past to be admitted to the National University of Singapore law school, and is now a civil litigation lawyer who takes on pro-bono cases.

It’s tempting to tell his story linearly as a prison inmate turned law student and finally, a civil litigation lawyer who also does pro-bono work.

But to really see who Darren Tan really is, we have to go back in time to the 80s.

A latchkey kid

The son of a coffee shop assistant dad and a stay at home mum turned food stall assistant, Tan grew up in a neighbourhood he described as one of the poorest in Singapore and one that was “infested with gangs and drugs”.

As both parents had to work to make ends meet, Tan was often left to his own devices at home. A latchkey kid since eight, he had “very, very little interaction” with his father.

“My father worked long hours after the coffee shop closed. So he would come back, usually about two or 3am. He worked very hard, the only days off were the first two days of Chinese New Year. So my mode of communication was usually to write a note on the table. He would answer the request when he came back,“ says the 41-year-old.

“I actually looked up to the gangsters. They seemed to have everything going for them.”

Everywhere he turned, he saw gang members -- even in school. One would be spoilt for choice, so to speak.

“There were many gangs in school. I just needed to choose one. It was actually not that difficult to be in contact with gang elements during my growing up years,” the self-proclaimed teacher’s nightmare explains.

You see, he had a problem with authority.

“Law enforcement officers, teachers, persons in a position of authority. Even my parents… I played truant, I actually got my friends to join the same gang as me. I didn't really attend classes and even when I did stay in the classroom I will be a troublemaker. So, I wasn't a good student ”

Ironically, given his poor attitude toward school and how he “hated going to school”, studying came naturally to him, especially for subjects such as science and mathematics. He recounted how he topped the standard for a physics test even without really studying for it, something he attributed to studying at his own pace, away from the classroom setting.

But surrounded by vices with minimal supervision, it didn’t take long for Tan to self-destruct.

Getting into fights and committing petty crimes like stealing game consoles, sweets, cigarettes, were a major part of his formative years.

And it didn't take him long till he graduated to more serious offences, which ultimately landed him behind bars for more than a decade, with stints at the maximum security prison.

“Life is made up of time”

Perhaps a regret for the 41-year-old is to have let time slip by over the years.

He never once explicitly articulates this, but throughout this interview, one gets the sense that he is a stickler of time, hoping to spend every minute purposefully.

He has a keen awareness of time’s passage, heightened by the wasted days of his youth, the hours spent under the influence of drugs, and the excruciating seconds counting down to his release in a solitary cell.

Today, as a father of two young girls, one witnesses his steely determination to make up for lost time.

Besides being a director and head of law practice at his own Invictus Law Corporation, he also spends time doing pro-bono work for the underprivileged, especially for the migrant worker community.

After a brief contemplative silence, he tells us:

“It was also in prison that I realised that life is made up of time. So if I value life, I will value time.”

Behind bars

To understand how he became the man he is today, one needs to get a glimpse into the years he spent behind bars.

With the four walls of a solitary cell caving in on you for months, the past hurts a lot less than the present.

He was locked up in solitary confinement a total of six times, with the longest stint being around two months for fighting with another inmate.

A tad embarrassed by the number of times he got into fights, Tan elaborates that there are a variety of reasons an inmate may be thrown into solitary confinement: from minor things like disobeying instructions to having contraband or fighting.

The length of stay, naturally, depends on the severity of the offence.

“Your experience in a punishment cell also very much depends on your mentality. When I was in a punishment cell in a reformatory when I was younger, I took that as a badge of honour. Didn't really change me a bit and I wasn't really affected by it. But later on when I was in maximum security and I was a bit more mature, I got really depressed.”

The solitary cell he stayed in, he describes, had only one small window for ventilation and a lamp that is on 24/7.

One can only imagine how the mind slowly melts away for an inmate slowly losing track of time and space.

“Honestly, I felt like even if I were to disappear, no one really cared. And I did contemplate taking my life there and then because there’s really not much hope to look forward to.”

Thankfully, after the suicidal thoughts dissipated, being alone with his thoughts also brought him much clarity.

Methodically, he illustrates that the path he had chosen would invariably end up in either of these three endings: constantly on the run, constantly imprisoned, or dead.

In this rare occurence of absolute clarity, he decided to reinvent himself: to take the A levels in prison and enter law school and hopefully become a lawyer.

School redux

“It took me nine months to do the A levels but five years to prepare for it.”

For someone who hated going to school and had a penchant for violence, any reasonable person would have serious doubts about this man’s motives.

According to Tan, prison school during his time was a new concept and there were stringent admission requirements. As the main goal was to provide basic education to inmates, more resources were allocated to N- and O-Levels, as well as technical education.

But his opening came serendipitously in the form of a NITEC course in electronics and computer networking.

“I managed to get into prison school because it needed to fill a quota [for the NITEC course],” he says matter of factly.

The completion of his NITEC course was quite the accomplishment, proving his application to the cause. With the technical course in the bag, he went to the principal seeking permission to do the A levels.

You would think he had proven himself, but yet again, time was not on his side.

Tan was due to be released in nine months and that was his only window of opportunity to study and complete his As. The principal was hesitant that Tan could take his As in just nine months -- given that the national standard is two years, based on the junior college system.

But by now, you should know that when Tan sets his mind to something, the only person who can stop him is himself. Truth be told, his preparations for the As started the day he made up his mind to be a lawyer in the confinement cell.

“I was really obsessed with studying. So, when I make a decision to want to be a lawyer. I became so obsessed with it that even bathing and eating were like distractions to me.”

An inmate, according to Tan, could borrow three books for two weeks. Determined to read and absorb as much as he could, he even asked his cell mates to borrow books for him just to satiate his thirst for knowledge.

Being in prison school also gave him the chance to be with a different set of inmates, away from the gang-stricken subculture of misplaced bravado and false fraternity in the main prison.

Spending a decade in prison, with the lingua franca being Hokkien and Malay, made him lose the ability to communicate in English.

In fact, he says sheepishly that his English still has a strong Hokkien accent now. (This writer disagrees, by the way.)

In order to brush up on the English language, he voraciously consumed whatever books he could get his hands on.

“So I would read all the reading materials that I could get my hands on. It could be the more erudite. I read Nietzsche’s Beyond Good and Evil, volumes of Adam Smith’s The Wealth of Nations. Well, in addition to the more mundane, like cook books, tabloid magazines, anything that I could get my hands on. I will read the newspapers from cover to cover.”

His obsession took him further than some students who had the comfort of studying in a bright, airy room with aircon and other creature comforts to boot.

At 26, he took the A levels. He scored 4As and 1B.

A life less ordinary

Armed with an A level certificate, things were looking up for him upon release.

But this isn’t a typical story. His path to redemption was only half done.

“One thing I didn't change about my life after the second imprisonment was that I still kept in contact with certain friends. And of course, ultimately this decision was up to me, but I reoffended again.”

Just six months after his second imprisonment, he found himself back in prison for drug offences for the third and last time.

Looking back, he admits that there were a few regrets.

“I regretted doing certain things, especially drug trafficking, which harmed a lot of people and their families.”

But does he regret spending, as he put it, the “best days of his life” behind bars?

On the contrary, he was grateful for the experience.

“Without that, I wouldn’t be who I am today. Prison afforded me the time and space to really think about my life, to contemplate to learn to be a mature person. Even simple things like dealing with another individual, living, coexisting with other people. I had a huge problem when I was younger, very abrasive.”

And with that, the two hours flew by.

As with most meetings, the ending is always the most awkward. Do I thank him first? Do I wait for him to stand up?

But for Darren Tan, there’s no hemming and hawing. He stands up, bids goodbye, and exits.

For he has no time to lose.

You can also listen to Darren Tan's story via our podcast:

Top photos courtesy of Darren Tan and by Lauren Choo